- Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2- bromotrifluoroacetanilides
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(Chemical Equation Presented) Cross-coupling of 1-alkynes with vinyl iodides occurs at 80°C in dioxane catalyzed by CuI/N,N-dimethylglycine to afford conjugated enynes in good to excellent yields. Heating a mixture of 2-bromotrifluoroacetanilide, 1-alkyne, 2 mol % of CuI, 6 mol % of L-proline, and K2CO3 in DMF at 80 °C leads to the formation of the corresponding indole. This conversion involves a CuI/L-proline-catalyzed coupling between aryl bromide and the 1-alkyne followed by a CuI-mediated cyclization process. An ortho-substituent effect directed by NHCOCF3 enables me reaction to proceed under these mild conditions. Both aryl acetylenes and O-protected propargyl alcohol can be applied, leading to 5-, 6-, or 7-substituted 2-aryl and protected 2-hydroxymethyl indoles in good yields. With simple aliphatic alkynes, however, lower yields were observed.
- Liu, Feng,Ma, Dawei
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- Synthesis and preliminary evaluation of 3-thiocyanato-1H-indoles as potential anticancer agents
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A novel series of twenty 3-thiocyanato-1H-indoles, carrying diversification at positions N-1, C-2 and C-5 of the heterocyclic core, were synthesized; their antiproliferative activity against four human cancer cell lines (HL60, HEP-2, NCI-H292 and MCF-7) was evaluated, employing doxorubicin as positive control. Indole, N-methylindole and 2-(4-chlorophenyl)-N-methylindole demonstrated to be essentially inactive, whereas several of their congener 3-thiocyanato-1H-indoles displayed good to excellent levels of potency (IC50 ≤ 6 μM), while being non-hemolytic. N-Phenyl-3-thiocyanato-1H-indole and 1-methyl-2-(4-chlorophenyl)-3-thiocyanato-1H-indole showed good to high potency against all the cell lines. On the other side, the N-(4-chlorophenyl)-, 2-(4-chlorophenyl)- and 2-phenyl- 3-thiocyanato-1H-indole derivatives were slightly less active against the test cell lines. Overall, these results suggest that the indole-3-thiocyanate motif can be suitably decorated to afford highly cytotoxic compounds and that the substituted indole can be employed as a useful scaffold toward more potent compounds.
- Fortes, Margiani P.,Da Silva, Paulo B.N.,Da Silva, Teresinha G.,Kaufman, Teodoro S.,Milit?o, Gardenia C.G.,Silveira, Claudio C.
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- Discovery of indole-based tetraarylimidazoles as potent inhibitors of urease with low antilipoxygenase activity
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A series of tetraarylimidazoles (5A-5O) were prepared by one pot four component condensation reactions of 2-arylindole-3-carbaldehydes, substituted anilines, benzil and ammonium acetate in acetic acid. The synthesized compounds exhibited potent antiurease
- Naureen, Sadia,Chaudhry, Faryal,Asif, Nadia,Munawar, Munawar Ali,Ashraf, Muhammad,Nasim, Faizul Hassan,Arshad, Humera,Khan, Misbahul Ain
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- Gold-catalyzed synthesis of 2-substituted, 2,3-disubstituted and 1,2,3-trisubstituted indoles in [bmim]BF4
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Cyclization of 2-alkynylanilines in the presence of NaAuCl 4·H2O using [bmim]BF4 as the reaction medium afforded 2-substituted indoles in high yields. The catalyst system was best recycled using n-Bu4NAuCl4. 2,3-Disubstituted indoles could be prepared from 2-alkynylanilines and 3-buten-2-one through a one-flask annulation-alkylation sequence and 1,2,3-trisubstituted indoles were obtained from the same starting materials via an aza-Michael addition-annulation- alkylation process. Georg Thieme Verlag Stuttgart.
- Ambrogio, Ilaria,Arcadi, Antonio,Cacchi, Sandro,Fabrizi, Giancarlo,Marinelli, Fabio
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- Iron-Catalyzed Reductive Cyclization of o-Nitrostyrenes Using Phenylsilane as the Terminal Reductant
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Using microscale high-throughput experimentation, an efficient, earth-abundant iron phenanthroline complex was discovered to catalyze the reductive cyclization of ortho-nitrostyrenes into indoles via nitrosoarene reactive intermediates. This method requires only 1 mol % of Fe(OAc)2 and 1 mol % of 4,7-(MeO)2phen and uses phenylsilane as a convenient terminal reductant. The scope and limitations of the method were illustrated with 21 examples, and an investigation into the kinetics of the reaction revealed first-order behavior in catalyst and silane and zero-order behavior with respect to nitrostyrene.
- Shevlin, Michael,Guan, Xinyu,Driver, Tom G.
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- Catalytic Tandem Friedel-Crafts Alkylation/C4-C3 Ring-Contraction Reaction: An Efficient Route for the Synthesis of Indolyl Cyclopropanecarbaldehydes and Ketones
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A general strategy for the synthesis of indolyl cyclopropanecarbaldehydes and ketones via a Br?nsted acid-catalyzed indole nucleophilic addition/ring-contraction reaction sequence has been exploited. The procedure leads to a wide panel of cyclopropyl carbonyl compounds in generally high yields with a broad substrate scope.
- Turnu, Francesca,Luridiana, Alberto,Cocco, Andrea,Porcu, Stefania,Frongia, Angelo,Sarais, Giorgia,Secci, Francesco
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- Pd-Catalyzed cascade reaction for the synthesis of 2-substituted indoles
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An efficient cascade methodology toward the synthesis of 2-substituted indoles has been developed. The transformation proceeds via a palladium-catalyzed cross-coupling reaction of o-nitrobenzyl cyanides with boronic acids. The use of Fe as co-catalyst during the course of reaction employs significant enhancement in reaction rates. The developed protocol allows for the unprecedented use of arylboronic acids as coupling partners for constructing 2-substituted indoles.
- Jadhav, Jagannath,Gaikwad, Vipul,Kurane, Rajanikant,Salunkhe, Rajashri,Rashinkar, Gajanan
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- Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors
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New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized 5. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCI/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.
- La Regina, Giuseppe,Bai, Ruoli,Rensen, Whilelmina Maria,Di Cesare, Erica,Coluccia, Antonio,Piscitelli, Francesco,Famiglini, Valeria,Reggio, Alessia,Nalli, Marianna,Pelliccia, Sveva,Da Pozzo, Eleonora,Costa, Barbara,Granata, Ilaria,Porta, Amalia,Maresca, Bruno,Soriani, Alessandra,Iannitto, Maria Luisa,Santoni, Angela,Li, Junjie,Miranda Cona, Marlein,Chen, Feng,Ni, Yicheng,Brancale, Andrea,Dondio, Giulio,Vultaggio, Stefania,Varasi, Mario,Mercurio, Ciro,Martini, Claudia,Hamel, Ernest,Lavia, Patrizia,Novellino, Ettore,Silvestri, Romano
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- Preparation of some novel imidazopyridine derivatives of indole as anticancer agents: one-pot multicomponent synthesis, biological evaluation and docking studies
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A series of novel imidazopyridine derivatives of indole has been synthesized. All the synthesized derivatives were evaluated for their antiproliferative activity against A-549, T-47D, Hep-G2 and MCF-7 human cancer cell lines. The results demonstrated that some of these derivatives exhibited moderate to excellent cytotoxic activities. Compounds 7a having a cyclohexyl ring substituted to the second amine of imidazopyridyl moiety and phenyl ring of the C-2 indole ring and 7f with a para-methylphenyl ring at the same position exhibited the highest activity against the A-594 cell line with IC50 of 11.48?μM and 10.66?μM, respectively. The results indicate that compounds 7a and 7f are more cytotoxic towards cancer cell lines compared with etoposide in vitro. In addition, compounds, 7d and 7j showed the most potent activity against Hep-G2, equal to etoposide as the standard drug. Also, most of the compounds were inactive against the T-47D and MCF-7 cell lines. The morphological analysis by the acridine orange/ethidium bromide double-staining test and flow cytometry analysis indicated that compounds 7a and 7f induced apoptosis in A-549 cells. Furthermore, in silico and in vitro results of the synthesized compounds showed good correlation with each other. Molecular docking results of the compounds of the 7a–k series with the cyclohexyl ring substituted to the second amine of the imidazopyridyl moiety compared with the 7l–t members with the t-butyl group at the same position confirmed the effect of the higher lipophilicity on hydrophobic interactions with the studied enzymes. Moreover, all the compounds showed higher affinity to tubulin than topoisomerase IIα enzyme.
- Bakherad, Zohreh,Safavi, Maliheh,Sepehri, Saghi,Fassihi, Afshin,Sadeghi-Aliabadi, Hojjat,Bakherad, Mohammad,Rastegar, Hossein,Larijani, Bagher,Saghaie, Lotfollah,Mahdavi, Mohammad
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- Synthesis of indoles: Sulfur-assisted reaction of 2-nitrostilbenes with carbon monoxide
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When 2-nitrostilbenes were treated with carbon monoxide in the presence of elemental sulfur, the reductive N-heterocyclization of the 2-nitrostilbenes smoothly proceeded to give the corresponding indoles in moderate to good yields.
- Umeda, Rui,Nishimoto, Yuuta,Mashino, Tsukasa,Nishiyama, Yutaka
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- Well-defined (NHC)Pd(N–heterocyclic carboxylate)(OAc) complexes-catalyzed direct C2-arylation of free (NH)-indoles with arylsulfonyl hydrazides
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A series of well-defined (NHC)Pd(N–heterocyclic carboxylate)(OAc) complexes (N–heterocyclic carboxylate = pyridine-2-carboxylate, quinoline-2-carboxylate and isoquinoline-1-carboxylate) were synthesized and fully characterized by NMR spectra, HR-MS and X-ray single crystal diffraction. The obtained complexes were then used for direct C2-arylation of free (NH)-indoles with arylsulfonyl hydrazides. With low catalyst loading, all complexes exhibited high catalytic activities for the arylation reactions.
- Yang, Jin,Zong, Ling-Li,Zhu, Xiao-Ting,Zhu, Xin-Ying,Zhao, Jian-Yi
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- 2-Phenylindole derivatives as anticancer agents: synthesis and screening against murine melanoma, human lung and breast cancer cell lines
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Indole derivatives have attractive anticancer properties and may be a future hope for better anticancer drug(s) of low toxicity and high potency. In this paper, syntheses of 2-phenylindole derivatives have been described via Fischer indole synthesis through a one-pot solvent-free method. The synthesized compounds were screened for anticancer potential in vitro against murine melanoma (B16F10), human lung cancer (A549), and human breast cancer (MDA-MB-231) cell lines. The results highlighted that 2-phenylindole derivatives are also promising anticancer agents in case of melanoma and lung cancer along with the breast cancer. Molecular docking analyses with possible targets for melanoma (NEDD4-1) and lung cancer (EGFR) were also performed to understand specific interactions of 2-phenylindole derivatives with the amino acid residues of the receptors.
- Gaikwad, Ruchi,Bobde, Yamini,Ganesh, Routholla,Patel, Tarun,Rathore, Anju,Ghosh, Balaram,Das, Kalpataru,Gayen, Shovanlal
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- Merging Visible Light Photocatalysis and l-/d-Proline Catalysis: Direct Asymmetric Oxidative Dearomatization of 2-Arylindoles to Access C2-Quaternary Indolin-3-ones
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A mild and effective method for asymmetric synthesis of C2-quaternary indolin-3-ones directly from 2-arylindoles by combining visible light photocatalysis and organocatalysis is described. In this reaction, 2-substituted indoles undergo photocatalyzed oxidative dearomatization, followed by an organocatalyzed asymmetric Mannich reaction with ketones or aldehydes. Products with opposite configurations are easily obtained in satisfactory yields with excellent enantio- A nd diastereoselectivity by employing readily available l- A nd d-proline as chiral organocatalysts.
- Dong, Chun-Lin,Ding, Xuan,Huang, Lan-Qian,He, Yan-Hong,Guan, Zhi
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- Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones
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A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochemistry and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combination with asymmetric proline-catalyzed alkylation in an undivided cell under constant-current conditions.
- Chen, Yu-Jue,Chen, Yuan,Ding, Xuan,Guan, Zhi,He, Yan-Hong,Lu, Fo-Yun
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- One-Pot Asymmetric Oxidative Dearomatization of 2-Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2-Tetrasubstituted Indolin-3-Ones
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A one-pot approach for the asymmetric synthesis of C2-tetrasubstituted indolin-3-ones from 2-substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2-substituted indoles using O2 as green oxidant, and followed by an proline-promoted asymmetric Mannich reaction with ketones or aldehydes. A series of C2-tetrasubstituted indolin-3-ones were obtained in 35–86% yields, 2:1->20:1 dr and 48–99% ee. Moreover, the synthetic 2-tetrasubstituted indolin-3-ones could be easily transformed into 1H-[1,3] oxazino [3,4-a]indol-5(3H)-ones via a [4+1] cyclization process. In addition, the synthetic compound 3 s show certain antibacterial activity against S. aureus ATCC25923 and multi-drug resistance bacterial strain of S. aureus (20151027077) and its MIC values up to 8 μg/mL and 16 μg/mL, respectively. (Figure presented.).
- Zhao, Yong-Long,An, Jian-Xiong,Yang, Fen-Fen,Guan, Xiang,Fu, Xiao-Zhong,Li, Zong-Qin,Wang, Da-Peng,Zhou, Meng,Yang, Yuan-Yong,He, Bin
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p. 1277 - 1285
(2022/03/14)
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- Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones
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A simple and efficient strategy for iron-catalysed cascade radical cyclization was developed, by which an array of germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones were obtained in one pot with germanium hydrides as radical precursors. A rapid intramolecular radical trapping mode enabled the selective arylgermylation of alkenes over the prevalent hydrogermylation reaction.
- Li, Zhiping,Luo, Yani,Lv, Leiyang,Nishihara, Yasushi,Tian, Tian
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supporting information
p. 9276 - 9279
(2021/09/20)
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- B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions
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An efficient B(C6F5)3-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.
- Yuan, Wenkai,Huang, Jie,Xu, Xin,Wang, Long,Tang, Xiang-Ying
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supporting information
p. 7139 - 7143
(2021/09/14)
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- Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis
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Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.
- Chen, Shaomin,Gu, Yanlong,Li, Minghao
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supporting information
p. 10431 - 10434
(2021/10/12)
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- An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives
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We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is
- Chen, Wei-Li,Li, Kun,Liang, Cui,Liang, Wang-Fu,Liao, Wei-Cong,Mo, Dong-Liang,Qiu, Pei-Wen,Su, Gui-Fa
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supporting information
p. 9610 - 9616
(2021/12/09)
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- Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors
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The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.
- Chen, Zhe-Sheng,Dai, Qing-Qing,Li, Guo-Bo,Liu, Hong-Min,Liu, Hui,Wang, Bo,Wang, Shaomeng,Yu, Bin,Yuan, Shuo,Zhang, Jing-Ya,Zhang, Xiao-Nan,Zuo, Jia-Hui
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p. 14895 - 14911
(2021/10/12)
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- Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics
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Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.
- Wan, Jin-Lin,Cui, Jian-Feng,Zhong, Wei-Qiang,Huang, Jing-Mei
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supporting information
p. 10242 - 10245
(2021/10/12)
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- Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents
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The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de
- Liang, Hao,Zhu, Guoxun,Pu, Xiaoyun,Qiu, Liqin
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p. 9246 - 9250
(2021/12/06)
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- Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature
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Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.
- Kandasamy, Jeyakumar,Lee, Yong Rok,Singh, Adesh Kumar,Venkatesh, Rapelly
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supporting information
p. 7832 - 7837
(2021/09/28)
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- Modular counter-Fischer?indole synthesis through radical-enolate coupling
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A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.
- Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
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supporting information
p. 1096 - 1102
(2021/01/26)
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- Aniline-initiated and Br?nsted acid-catalyzed one-pot reaction toward 2-aryl-3-sulfenylindoles by using α-aminocarbonyl compounds and primary amines with RSSR
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A highly novel method of direct synthesis of 2-aryl-3-sulfenylindoles in moderate to good yields was developed via one-pot tandem reaction of readily available α-aminocarbonyl compounds and catalytic amount of benzenamines with RSSR.
- Chen, De,Cheng, Chaozhihui,Deng, Wei,Guan, Wenjian,Liu, Yuxuan,Luo, Yongyue,Xiang, Jiannan,Zhang, Jiajia
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- Regioselective Direct C2 Arylation of Indole, Benzothiophene and Benzofuran: Utilization of Reusable Pd NPs and NHC-Pd@MNPs Catalyst for C–H Activation Reaction
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Abstract: A regioselective C2 arylation of indoles, benzothiophene and benzofuran without directing group has been accomplished using economically cheap Pd NPs and NHC-Pd@MNPs catalyst. The reusable catalyst is efficiently employed to access C2 arylated heterocycles in good to excellent yield. The reusability of the catalyst is studied up to five cycles and a gram-scale synthesis has been achieved. The reaction mechanism is well supported by control experiments and literature precedents. Grapic Abstract: [Figure not available: see fulltext.]
- Hegde, Rajeev V.,Ong, Tiow-Gan,Ambre, Ram,Jadhav, Arvind H.,Patil, Siddappa A.,Dateer, Ramesh B.
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p. 1397 - 1405
(2020/10/02)
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- Pd/β-cyclodextrin-catalyzed C-H functionalization in water: A greener approach to regioselective arylation of (NH)-indoles with aryl bromides
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A greener and more practical strategy for the site-selective C-H arylation of (NH)-indoles via coupling of (hetero)aryl bromides was developed, in which β-cyclodextrin, acting as both a ligand for Na2PdCl4 and a host for indoles, enables the reactions to occur easily in water. The key advantage of this method is the ingenious merging of aqueous homogeneous catalysis and ligand mediation, leading to the highly regioselective formation of C3-arylindoles with a broad substrate scope and functional-group tolerance. Moreover, the regioselectivity can be switched from the C3 to the C2-position by varying the nature of the base without recourse to employing ArI as substrates.
- Duan, Xin Hong,Xu, Peng
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supporting information
p. 19425 - 19431
(2021/11/09)
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- Discovery of novel multi-substituted benzo-indole pyrazole schiff base derivatives with antibacterial activity targeting DNA gyrase
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The design and synthesis of novel multi-substituted benzo-indole pyrazole Schiff base derivatives of potent DNA gyrase inhibitory activity were the main aims of this study. All the novel synthesized compounds were examined for their antibacterial activities against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella. In addition, we selected 20 compounds for the in vitro antibacterial activities assay of 6 drug-resistant bacteria strains. The result revealed compound 8I-w exhibited excellent antibacterial activity against 4 drug-resistant E. coli bacteria strains with IC50 values of 7.0, 17.0, 13.5, and 1.0 μM, respectively. In vitro enzyme inhibitory assay showed that compound 8I-w displayed potent inhibition against DNA gyrase with IC50 values of 0.10 μM. The molecular docking model indicated that compounds 8I-w can bind well to the DNA gyrase by interacting with various amino acid residues. This study demonstrated that the compound 8I-w can act as the most potent DNA gyrase inhibitor in the reported series of compounds and provide valuable information for the commercial DNA gyrase inhibiting bactericides.
- Cao, Hai-Qun,Chu, Zhi-Wen,Liu, Hao,Lv, Xian-Hai,Xia, Dong-Guo
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- Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes
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A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed. Various tetraarylstannanes can be employed as aryl sources for 2-arylation of indoles in up to 89% yield, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.
- Liu, Yuxia,Wang, Chao,Huang, Linjuan,Xue, Dong
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supporting information
p. 1613 - 1618
(2020/09/15)
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- α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles
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Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).
- Burtoloso, Antonio C. B.,Caiuby, Clarice A. D.,De Jesus, Matheus P.
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p. 7433 - 7445
(2020/06/27)
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- Anti-cancer, anti-oxidant and molecular docking studies of thiosemicarbazone indole-based derivatives
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Based on the structural elements of bioactive 3-substituted indoles, a new series of indole–thiosemicarbazone hybrid derivatives were designed, synthesized, and well-characterized using different spectral techniques. The intended scaffolds were screened for their in vitro anti-proliferative activities against breast cancer (MCF-7), lung cancer (A-549), and liver cancer (Hep-G2) cell lines, as well as their anti-oxidant properties. Cytotoxicity studies revealed that compound 6n was the most potent, at least threefold more potent than the commercially available reference drug etoposide, against A-549. In addition, morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis confirmed induction of apoptosis in the A-549 cells by compound 6n. In order to validate the experimental results, molecular studies were performed to achieve the possible binding interactions of the most potent compound (6n) and colchicine with tubulin as well as ANP with ATPase domain of topoisomerase IIα active sites. Moreover, the radical scavenging potential of the final derivatives was found to be excellent with the range of 0.015–0.630?μM, comparable to the standard ascorbic acid (0.655?μM).
- Bakherad, Zohreh,Safavi, Maliheh,Fassihi, Afshin,Sadeghi-Aliabadi, Hojjat,Bakherad, Mohammad,Rastegar, Hossein,Ghasemi, Jahan B.,Sepehri, Saghi,Saghaie, Lotfollah,Mahdavi, Mohammad
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p. 2827 - 2854
(2019/03/13)
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- Design and Synthesis of Novel Cytotoxic Indole-Thiosemicarbazone Derivatives: Biological Evaluation and Docking Study
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In this work, two novel series of indole-thiosemicarbazone derivatives were designed, synthesized, and evaluated for their cytotoxic activity against MCF-7, A-549, and Hep-G2 cell lines in comparison to etoposide and colchicine as the reference drugs. Generally, the synthesized compounds showed better cytotoxicity towards A-549 and Hep-G2 than MCF-7. Among them, (2E)-2-{[2-(4-chlorophenyl)-1H-indol-3-yl]methylidene}-N-(4-methoxyphenyl)hydrazinecarbothioamide (8l) was found to be the most potent compound against A-549 and Hep-G2, at least three times more potent than etoposide. The morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that compound 8l induced apoptosis in A-549 cells. Moreover, molecular docking methodology was exploited to elucidate the details of molecular interactions of the studied compounds with putative targets.
- Bakherad, Zohreh,Safavi, Maliheh,Fassihi, Afshin,Sadeghi-Aliabadi, Hojjat,Bakherad, Mohammad,Rastegar, Hossein,Saeedi, Mina,Ghasemi, Jahan B,Saghaie, Lotfollah,Mahdavi, Mohammad
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- A Three-Component Strategy for Benzoselenophene Synthesis under Metal-Free Conditions Using Selenium Powder
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An efficient three-component benzoselenophenes formation has been developed from substituted indoles, acetophenones, and selenium powder under metal-free conditions. 2-Aryl indoles played an important role to promote benzoselenophene formation from acetophenone derivatives and selenium powder. One C-C and two C-Se bonds were selectively formed to provide 40 new benzoselenophenes in good yields.
- Ni, Penghui,Tan, Jing,Zhao, Wenqi,Huang, Huawen,Xiao, Fuhong,Deng, Guo-Jun
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supporting information
p. 3518 - 3522
(2019/05/24)
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- Green approach for the synthesis of 3-methyl-1-phenyl-4-((2-phenyl-1H-indol 3-yl)methylene)-1H-pyrazole-5(4H)-ones and their DNA Cleavage, antioxidant, and antimicrobial activities
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3-Methyl-1-phenyl-4-((2-phenyl-1H-indol-3-yl)methylene)-1H-pyrazol-5(4H)-ones (5a-i) was prepared by the condensation reaction of different 3-formyl-2-phenylindole derivatives (2a-i) and 3-methyl-1-phenyl-2-pyrazoline-5-one in quantitative yield by applying various green synthetic methods as grinding, microwave irradiation using different catalysts under solvent-free mild reaction conditions with high product yields. The structures of the synthesized compounds were characterized on the basis of elemental analysis, infrared, 1HNMR, 13C NMR, and mass spectral data. The synthesized compounds were screened for free radical scavenging, antimicrobial, and DNA cleavage activities. Most of the tested compounds belonging to the 3-methyl-1-phenyl-4-((2-phenyl-1H-indol-3-yl)methylene)-1H-pyrazol-5(4H)-ones series exhibited promising activities.
- Modi, Madhuri,Jain, Meenakshi
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p. 3303 - 3312
(2019/11/03)
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- Palladium-Catalyzed C–C Ring Closure in α-Chloromethylimines: Synthesis of 1H-Indoles
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The C-C ring closure of α-chloromethyl alkyl or aryl N-aryl imines catalyzed with 1 to 10 % Pd(OAc)2/P(p-tolyl)3 afford efficiently 2-aryl- and 2-alkyl-1H-indoles. The heterocyclization reaction involves the initial formation of [2-(arylimino)ethyl]palladium(II) chloride complexes with subsequent C-H activation of the aromatic amine ring. Readily or commercially available α-chloromethyl-aryl or -alkyl ketones are used as the precursors. Functionalized indoles at the benzene ring are obtained when the imines are derived from substituted anilines.
- Bellezza, Delia,Noverges, Bárbara,Fasano, Francesco,Sarmiento, Jeymy T.,Medio-Simón, Mercedes,Asensio, Gregorio
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p. 1229 - 1235
(2019/01/04)
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- Supported dual-acidic 1,3-disulfoimidazolium chlorozincate@HZSM-5 as a promising heterogeneous catalyst for synthesis of indole derivatives
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HZSM-5-supported Br?nsted and Lewis acidic ionic solid 1,3-disulfoimidazolium chlorozincate materials ([dsim]2[ZnCl4]@HZSM-5) were synthesized with various ratios (3, 6, 9, 17 and 50% w/w). The heterogeneous materials were characterized via a variety of spectroscopic techniques. Dual acidity of these materials was determined using specified techniques. These acidic solids were examined as stable heterogeneous catalysts for the Fischer indole reaction of equimolar amounts of phenylhydrazine hydrochloride and various aliphatic or aromatic ketones at 80–90°C in neat condition to produce substituted indole derivatives. The efficient 17% ionic salt-loaded HZSM-5 composite was easily reused for ten consecutive cycles with a slight loss of its activity. The recycled catalyst was further analysed using powder X-ray diffraction and inductively coupled plasma optical emission spectrometric techniques.
- Saikia, Susmita,Puri, Krishna,Borah, Ruli
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- A Reusable MOF-Supported Single-Site Zinc(II) Catalyst for Efficient Intramolecular Hydroamination of o-Alkynylanilines
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The exploitation of new and active earth-abundant metal catalysts is critical for sustainable chemical production. Herein, we demonstrate the design of highly efficient, robust, and reusable ZnII-bipyridine-based metal–organic framework (MOF) catalysts for the intramolecular hydroamination of o-alkynylanilines to indoles. Under similar conditions homogeneous catalytic systems mainly provide hydrolysate. Our results prove that MOFs support unique internal environments that can affect the direction of chemical reactions. The ZnII-catalyzed hydroamination reaction can be conducted without additional ligands, base, or acid, and is thus a very clean reaction system with regard to its environmental impact.
- Li, Beibei,Ju, Zhanfeng,Zhou, Mi,Su, Kongzhao,Yuan, Daqiang
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supporting information
p. 7687 - 7691
(2019/05/15)
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- Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
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A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.
- Chen, Wei-Li,Wu, Si-Yi,Mo, Xue-Ling,Wei, Liu-Xu,Liang, Cui,Mo, Dong-Liang
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supporting information
p. 3527 - 3530
(2018/06/26)
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- Copper-Catalyzed Radical Sulfonylation of N-Propargylindoles with Concomitant 1,2-Aryl Migration
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A novel copper-catalyzed cascade radical sulfonylation of N-propargyl-substituted indoles with concomitant 1,2-aryl migration was described. The protocol, which has good functional-group tolerance, provides practical, versatile and atom-economical method of accessing a new class of fascinating 2-sulfonated pyrrolo[1,2-α]indole derivatives in moderate to good yields through the formation of the new C?S, C?C and C=O bonds in a one-step. (Figure presented.).
- Zhu, Xin-Yu,Han, Ya-Ping,Li, Ming,Li, Xue-Song,Liang, Yong-Min
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p. 3460 - 3465
(2018/05/30)
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- Design and applications of new phosphine-free tetradentate Pd-catalyst: Regioselective C–H activation on 1-substituted 1,2,3-triazoles and indoles(NH-Free)
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This article describes the synthesis of a new phosphine free tetradentate Pd catalyst using dl-2,3-diaminopropionic acid. The complex was characterized by Mass, IR, and 1H NMR. The catalyst is air stable at room temperature and non-hygroscopic. Application of this new catalyst to regioselective C–H activation on 1-substituted 1,2,3-triazole and indoles with aryl iodides to get corresponding C-5 and C-2 arylated products with satisfactory yields. All the products were characterized by spectroscopic studies.
- Markandeya, Sarma V.,Renuka, Ch.,Lakshmi, Parvathi K.,Rajesh,Sridhar, Chidara,Babu, Korupolu Raghu
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p. 135 - 145
(2017/12/28)
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- Alkyne Hydroamination Catalyzed by Silica-Supported Isolated Zn(II) Sites
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Hydroamination is an atom-economical reaction to form C-N bonds, which are ubiquitous in organic compounds. Hydroamination has seen prolific advancements and has mostly focused on the development of homogeneous catalysts based on lanthanides or transition metals. Here, we have developed silica-supported, site-isolated Zn(II) sites through a combined surface organometallic chemistry (SOMC) and thermolytic molecular precursor (TMP) approach and show that they catalyze the intramolecular hydroamination of alkynes. This material is applicable to a broad range of substrates. On the basis of kinetics and in situ IR spectroscopic studies, we propose that the mechanism involves coordination of the aminoalkyne onto Zn(II) followed by the heterolytic activation of the N-H bond and subsequent cyclization and proton transfer.
- Cook, Amanda K.,Copéret, Christophe
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supporting information
p. 1342 - 1345
(2018/05/24)
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- Regioselective Synthesis of 2-Substituted Indoles from Benzotriazoles and Alkynes by Photoinitiated Denitrogenation
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Herein, we describe a photoinitiated and regioselective synthesis of 2-substituted indoles under mild reaction conditions. This biologically privileged scaffold was accessed in good yields from N-aroylbenzotriazoles, a quencher class previously identified using our mechanism-based luminescence screening, and terminal alkynes in the presence of a photocatalyst and blue light irradiation. This straightforward protocol displays a broad substrate scope and functional group tolerance. Furthermore, the mildness and robustness of the reaction were assessed by the application of an additive-based robustness screen. The determination of the reaction quantum yield and Stern-Volmer studies support the proposed photoinitiated radical chain mechanism.
- Teders, Michael,Pitzer, Lena,Buss, Stefan,Glorius, Frank
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p. 4053 - 4056
(2017/06/19)
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- Gold(i)-catalyzed synthesis of 2-substituted indoles from 2-alkynylnitroarenes with diboron as reductant
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An efficient method for the synthesis of 2-substituted indoles via a diboron/base promoted tandem reductive cyclization of o-alkynylnitroarene under Au catalysis conditions has been disclosed. This reaction is efficient and convenient, affording 2-substituted indoles with broad functional groups tolerance and excellent yields.
- Fu, Wenqiang,Yang, Kai,Chen, Jinglong,Song, Qiuling
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p. 8354 - 8360
(2017/10/19)
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- Pd-PEPPSI-IPentCl: A new highly efficient ligand-free and recyclable catalyst system for the synthesis of 2-substituted indoles: Via domino copper-free Sonogashira coupling/cyclization
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A pyridine-containing decidedly resourceful Pd-N-heterocyclic carbene complex, Pd-PEPPSI-IPentCl (PEPPSI = pyridine enhanced precatalyst preparation, stabilization, and initiation), is used as a first class recyclable catalytic system for the synthesis of 2-substituted indoles via domino copper-free Sonogashira coupling/cyclization. The catalyst showed a greater performance in the cascade reaction of various 2-bromo anilines with different terminal acetylenes under mild (60 °C) and green conditions (ethanol:water) even in the absence of a copper catalyst and an inert atmosphere. The catalyst is used for the first time in these reactions. The findings suggest that 0.1 mol% of the catalyst is sufficient, and that the catalyst is recyclable and can be reused for up to six cycles.
- Kolli, Murali Krishna,Shaik, Nagul Meera,Chandrasekar, Govindasamy,Chidara, Sridhar,Korupolu, Raghu Babu
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p. 8187 - 8195
(2017/08/15)
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- Palladium-catalyzed tandem addition/cyclization in aqueous medium: Synthesis of 2-arylindoles
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An efficient protocol to construct 2-arylindoles was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover, the utility of this catalytic tandem transformation was also demonstrated in an efficient gram-scale synthesis. This method provides an alternative synthetic tool for accessing a more diverse array of 2-arylindoles.
- Yu, Shuling,Hu, Kun,Gong, Julin,Qi, Linjun,Zhu, Jianghe,Zhang, Yetong,Cheng, Tianxing,Chen, Jiuxi
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p. 4300 - 4307
(2017/07/10)
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- Palladium-catalyzed direct C2-arylation of free (N–H) indoles via norbornene-mediated regioselective C–H activation
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A palladium-catalyzed direct C2-arylation reaction of free (N–H) indoles has been developed. This reaction relies on a norbornene-mediated C–H activation process on the indole ring, which features high regioselectivity and excellent functional group tolerance.
- Gao, Yadong,Zhu, Wangying,Yin, Long,Dong, Bo,Fu, Jingjing,Ye, Zhiwen,Xue, Fengtian,Jiang, Chao
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supporting information
p. 2213 - 2216
(2017/05/16)
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- Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides
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Metal carbenes can undergo a myriad of synthetic transformations. Sulfur ylides are potential safe precursors of metal carbenes. Herein, we report cascade reactions that involve carbenoids derived from sulfoxonium ylides for the efficient and regioselective synthesis of indoles and pyrroles. The tandem action of iridium and Br?nsted acid catalysts enables rapid assembly of the heterocycles from unmodified anilines or readily accessible enamines under microwave irradiation. The key mechanistic steps are the catalytic transformation of the sulfoxonium ylide into an iridium–carbene complex, followed by N?H or C?H functionalization of an aniline or enamine, respectively, and a final acid-catalyzed cyclization. The present method was successfully applied to the synthesis of the densely functionalized pyrrole subunit of atorvastatin.
- Vaitla, Janakiram,Bayer, Annette,Hopmann, Kathrin H.
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p. 4277 - 4281
(2017/04/03)
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- The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons
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A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations thereby broadening the diversity of the products. Preliminary mechanistic experiments indicate that this transformation involves sequential nucleophilic addition followed by an intramolecular cyclization.
- Yu, Shuling,Qi, Linjun,Hu, Kun,Gong, Julin,Cheng, Tianxing,Wang, Qingzong,Chen, Jiuxi,Wu, Huayue
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p. 3631 - 3638
(2017/04/11)
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- Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1
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In our ongoing effort of discovering anticancer and chemopreventive agents, a series of 2-arylindole derivatives were synthesized and evaluated toward aromatase and quinone reductase 1 (QR1). Biological evaluation revealed that several compounds (e.g., 2d, IC50 = 1.61 μM; 21, IC50 = 3.05 μM; and 27, IC50 = 3.34 μM) showed aromatase inhibitory activity with half maximal inhibitory concentration (IC50) values in the low micromolar concentrations. With regard to the QR1 induction activity, 11 exhibited the highest QR1 induction ratio (IR) with a low concentration to double activity (CD) value (IR = 8.34, CD = 2.75 μM), while 7 showed the most potent CD value of 1.12 μM. A dual acting compound 24 showed aromatase inhibition (IC50 = 9.00 μM) as well as QR1 induction (CD = 5.76 μM) activities. Computational docking studies using CDOCKER (Discovery Studio 3.5) provided insight in regard to the potential binding modes of 2-arylindoles within the aromatase active site. Predominantly, the 2-arylindoles preferred binding with the 2-aryl group toward a small hydrophobic pocket within the active site. The C-5 electron withdrawing group on indole was predicted to have an important role and formed a hydrogen bond with Ser478 (OH). Alternatively, meta-pyridyl analogs may orient with the pyridyl 3′-nitrogen coordinating with the heme group.
- Prior, Allan M.,Yu, Xufen,Park, Eun-Jung,Kondratyuk, Tamara P.,Lin, Yan,Pezzuto, John M.,Sun, Dianqing
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supporting information
p. 5393 - 5399
(2017/11/20)
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- On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone Derivatives
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Silver-catalyzed on-water intramolecular cyclization of acetylenic free amines is reported, which affords 7-azaindoles in good to excellent yields. Neither strong base/acid catalysts nor N-substituted substrates are required to achieve this cycloisomerization. Hydrogen bonds between water medium and the substrates play an important role in improving chemical reactivity and regioselectivity. Furthermore, the on-water reaction is extendable to acetylenic amides for isoquinolone synthesis.
- Sun, Hongpeng,Xiao, Li,Li, Wei,Xie, Qiong,Shao, Liming
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supporting information
p. 4845 - 4852
(2017/10/06)
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- Method of using deep eutectic solvent to prepare 2-arylindole compounds
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The invention discloses a method of using a deep eutectic solvent to prepare 2-arylindole compounds, and relates to the technical field of organic compound preparation. The deep eutectic solvent is environment-friendly and is taken as the reaction solvent and catalyst. 2-arylindole compounds are prepared through one-step reactions between phenyl hydrazine and substituted acetophenone. The method comprises the following steps: mixing choline chloride (ChCl) and zinc chloride (ZnCl2) according to a mole ratio of 1:4, slowly heating to a temperature of 95 to 100 DEG C, maintaining the temperature, stirring the mixture by magnetic force for 8 to 12 hours to obtain a deep eutectic solvent (ChCl+4ZnCl2); sequentially adding the prepared deep eutectic solvent, phenyl hydrazine, and substituted acetophenone into a reactor according to a mole ratio of 1:1:1, magnetically stirring the mixture for 70 to 90 minutes at a temperature of 120 to 125 DEG C, after reactions, cooling to the room temperature, adding water, stirring, carrying out vacuum suction filtration, washing the filter cake by polyphosphoric acid (10%) until the filter cake becomes neutral to obtain a coarse product, and further recrystallizing the coarse product by ethanol (95%) to obtain a pure crystalline product. The synthesis method is simple, the raw materials are easily available, the cost is low, and the method can be applied to massive production.
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Paragraph 0012
(2017/06/13)
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- 2-Amino-4-aryl thiazole: A promising scaffold identified as a potent 5-LOX inhibitor
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Human 5-lipoxygenase (5-LOX) is an important enzyme in the biosynthesis of leukotrienes and is a target for asthma and allergy treatment. Zileuton is the only drug currently marketed that targets this enzyme (IC50 ~ 1 μM). So, the development of novel lead compounds is highly desirable. A series of 2-aryl indole, thiazolopyrazole acid, oxadiazolobenzothiophene, 1,4-disubstituted-1,2,3-triazole, 2-amino-4-aryl thiazole and 4,4′-(1,4-phenylene)bis(1,3-thiazole) derivatives when tested against this enzyme resulted in the identification of a potent compound (1d), p-fluoro substituted 2-amino-4-aryl thiazole, with an IC50 of ~10 μM. Another lead compound identified is (4a), a thiazolopyrazole acid derivative (IC50 ~ 40 μM). All the compounds exhibit poor DPPH radical scavenging activity which suggests that their action occurs not due to the disruption of the redox cycle of iron present in the enzyme (unlike zileuton) but through competitive inhibition, since the Vmax remains constant but the Km increases with an increase in inhibitor concentration. Molecular docking of 1d and 4a to the active site of 5-LOX also supports the experimental data, and suggests that their possible mechanism of action is through competitive inhibition. The current study identifies a promising lead molecule which could be improved further to match the activity of the commercial drug.
- Sinha, Shweta,Sravanthi,Yuvaraj,Manju,Doble, Mukesh
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p. 19271 - 19279
(2016/03/01)
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- Palladium/Copper Cocatalyzed Coupling Reaction of Aroyl Hydrazides with Indoles
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An unprecedented palladium/copper cocatalyzed coupling reaction of indoles with simple aroyl hydrazides has been developed under aerobic conditions. A range of aroyl hydrazides underwent palladium/copper cocatalyzed oxidative arylation with indoles open to air in a 1:1 mixture of dimethyl sulfoxide and nitromethane to give structurally diverse 2-arylindoles or 3-arylindoles in moderate to good yields. The reaction well tolerates a wide variety of functional groups such as alkoxy, halo, ester.
- Liu, Congrong,Yang, Fulai
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supporting information
p. 1213 - 1217
(2016/12/28)
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- Access to 2-Arylindoles via Decarboxylative C?C Coupling in Aqueous Medium and to Heteroaryl Carboxylates under Base-Free Conditions using Diaryliodonium Salts
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Easily accessible heteroaromatic carboxylic acids and diaryliodonium salts were successfully employed to construct valuable 2-arylindoles and heteroaryl carboxylates in a regioselective fashion. C2-arylated indoles were produced using a Pd-catalyzed decarboxylative strategy in water without any base, oxidant, or ligand. Heteroaryl carboxylates were prepared under metal and base-free conditions. This protocol was successfully utilized to synthesize Paullone, a cyclin-dependent kinase (CDK) inhibitor.
- Arun, Velladurai,Pilania, Meenakshi,Kumar, Dalip
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supporting information
p. 3345 - 3349
(2016/12/14)
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- Iron-Catalyzed Intramolecular C(sp2)-H Amination
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The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C-H amination of α-azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional-group tolerance render this method a particularly attractive alternative to established noble-metal-based procedures.
- Alt, Isabel T.,Plietker, Bernd
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p. 1519 - 1522
(2016/02/14)
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- Palladium-catalyzed direct arylation of indoles with arylsulfonyl hydrazides
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A novel method to synthesise 2-arylindoles is demonstrated via direct arylation of indoles with arylsulfonyl hydrazides. Under the optimized reaction conditions, the reaction well tolerates a wide variety of functional groups to afford structurally diverse 2-arylindoles in good to excellent yields at 70 °C.
- Liu, Congrong,Ding, Lianghui,Guo, Guang,Liu, Weiwei,Yang, Fu-Lai
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supporting information
p. 2824 - 2827
(2016/03/12)
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