- Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate
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An intermolecular asymmetric cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71–86 %) with excellent enantioselectivity (91–96 % ee) and chemoselectivity (3/4>19:1 in most cases).
- Ding, Lu,Gao, Run-Duo,You, Shu-Li
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supporting information
p. 4330 - 4334
(2019/02/25)
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- Divergent synthesis of indole-2-carboxylic acid derivatives via ligand-free copper-catalyzed ullmann coupling reaction
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— This article describes a ligand-free copper-catalyzed Ullmami coupling reaction for the preparation of divergent indole-2-carboxylic acid derivatives including esters, amides and anhydrides. Various compounds 3, which could be synthesized from aldehydes conveniently, were used as substrate to provide the corresponding indole-2-carboxylic acid derivatives in moderate to good vields.
- Zhou, Jiadi,Chen, Yongjian,Huang, Junsong,Li, Jianjun
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p. 904 - 915
(2019/08/21)
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- A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger–Knittel Indole Synthesis
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The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.
- Baykal, Aslihan,Plietker, Bernd
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supporting information
(2020/02/20)
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- A porous metal-organic cage constructed from dirhodium paddle-wheels: Synthesis, structure and catalysis
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Self-assembly of dirhodium(ii) tetraacetate (Rh2(OAc)4) with a dicarboxylic acid 3,3′-(1,3-phenylenebis(ethyne-2,1-diyl))dibenzoic acid (H2pbeddb) gives rise to a metal-organic cage (MOC) containing Rh-Rh bonds with the formula of [Rh4(pbeddb)4(H2O)2(DMAC)2] (MOC-Rh-1). Single-crystal X-ray diffraction analysis reveals that MOC-Rh-1 shows a lantern-type cage structure, in which a pair of Rh2(CO2)4 paddlewheels is linked by four diacid ligands. The dimensions of the inner cavity of MOC-Rh-1 are 9.5 × 14.8 ?2 (atom-to-atom distances across opposite metal and phenyl groups of pbeddb2-). In the solid phase, the cages are aligned by π-π stacking to form one-dimensional channels (9.5 × 11.1 ?2) through cage windows. Therefore, the crystalline samples of MOC-Rh-1 are porous with the inner and outer cavities of the cages accessible under the heterogeneous condition. MOC-Rh-1 has been fully characterized by EA, TGA, PXRD, IR, UV-vis and XPS measurements. The catalytic tests disclose that activated MOC-Rh-1 is effective in the intramolecular C-H amination of vinyl, dienyl and biaryl azides, leading to the formation of indoles, pyrroles and carbazoles, respectively, and the porous catalyst can be recycled easily and used for at least nine runs without significant loss of activity. In the nine runs, the conversions were in the range of 93-99%, whereas in the tenth run, the conversion was reduced to 78%.
- Chen, Lianfen,Yang, Tao,Cui, Hao,Cai, Tao,Zhang, Li,Su, Cheng-Yong
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supporting information
p. 20201 - 20209
(2015/10/19)
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- Design, synthesis, and biological evaluation of novel trifluoromethyl indoles as potent HIV-1 NNRTIs with an improved drug resistance profile
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A novel series of trifluoromethyl indole derivatives have been designed, synthesized and evaluated for anti-HIV-1 activities in MT-2 cells. The hydrophobic constant, acute toxicity, carcinogenicity and mutagenicity were predicted. Trifluoromethyl indoles 10i and 10k showed extremely promising activities against WT HIV-1 with IC50 values at the low nanomolar level, similar to efavirenz, better than nevirapine, and also possessed higher potency towards the drug-resistant mutant strain Y181C than nevirapine. Preliminary SAR and docking studies of detailed binding mode provided some insights for discovery of more potent NNRTIs. the Partner Organisations 2014.
- Jiang, Hai-Xia,Zhuang, Dao-Min,Huang, Ying,Cao, Xing-Xin,Yao, Jian-Hua,Li, Jing-Yun,Wang, Jian-Yong,Zhang, Chen,Jiang, Biao
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p. 3446 - 3458
(2014/05/20)
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- CuI-catalyzed intramolecular cyclization of 3-(2-aminophenyl)-2- bromoacrylate: Synthesis of 2-carboxyindoles
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A new approach was described for the synthesis of substituted 2-carboxyindole using 3-(2-aminophenyl)-2-bromo-acrylates through a CuI-catalyzed intramolecular coupling. The reactions were mild, rapid and with good to excellent yields.
- Xiao, Xiong,Chen, Tian-Qi,Ren, Jiangmeng,Chen, Wei-Dong,Zeng, Bu-Bing
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p. 2056 - 2060
(2014/04/03)
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- Gold(I)-catalyzed rearrangement of alkynylaziridine indoles for the synthesis of spiro-tetrahydro-β-carbolines
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Functionalized spiro-tetrahydro-β-carbolines were formed by an efficient gold(I)-catalyzed rearrangement reaction of alkynylaziridine indoles. The reaction involved a Friedel-Crafts type intramolecular reaction of alkynylaziridine indoles, following by hydroamination of aminoallene intermediate.
- Yang, Yan-Fang,Li, Lian-Hua,He, Yu-Tao,Luo, Jian-Yi,Liang, Yong-Min
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supporting information
p. 702 - 707
(2014/02/14)
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- Optimization of chemical functionalities of indole-2-carboxamides to improve allosteric parameters for the cannabinoid receptor 1 (CB1)
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5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (1; ORG27569) is a prototypical allosteric modulator for the cannabinoid type 1 receptor (CB1). Here, we reveal key structural requirements of indole-2-carboxamides for allosteric modulation of CB1: a critical chain length at the C3-position, an electron withdrawing group at the C5-position, the length of the linker between the amide bond and the phenyl ring B, and the amino substituent on the phenyl ring B these significantly impact the binding affinity (KB) and the binding cooperativity (α). A potent CB1 allosteric modulator 5-chloro-N-(4-(dimethylamino)phenethyl)-3-propyl-1H-indole- 2-carboxamide (12d) was identified. It exhibited a KB of 259.3 nM with a strikingly high binding α of 24.5. We also identified 5-chloro-N-(4-(dimethylamino)phenethyl)-3-hexyl-1H-indole-2-carboxamide (12f) with a KB of 89.1 nM, which is among the lowest KB values obtained for any allosteric modulator of CB1 these positive allosteric modulators of orthosteric agonist binding nonetheless antagonized the agonist-induced G-protein coupling to the CB1 receptor, yet induced β-arrestin mediated ERK1/2 phosphorylation.
- Khurana, Leepakshi,Ali, Hamed I.,Olszewska, Teresa,Ahn, Kwang H.,Damaraju, Aparna,Kendall, Debra A.,Lu, Dai
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p. 3040 - 3052
(2014/05/06)
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- Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry
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Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chemistry, allowing formation of peptide adducts which can be subsequently labeled with fluorine tags.
- Ranasinghe, Nadeesha,Jones, Graham B.
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p. 1740 - 1742
(2013/04/10)
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- Iron(II) triflate as a catalyst for the synthesis of indoles by intramolecular C-H amination
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A practical iron-catalyzed intramolecular C-H amination reaction and its application in the synthesis of indole derivatives are presented. As a catalyst, commercially available iron(II) triflate is used.
- Bonnamour, Julien,Bolm, Carsten
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p. 2012 - 2014
(2011/06/28)
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- [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source
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The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones have been accomplished in moderate to excellent yields via [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation using aryl azides as nitrogen source.
- Liu, Yungen,Wei, Jinhu,Che, Chi-Ming
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supporting information; experimental part
p. 6926 - 6928
(2010/11/16)
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- Intramolecular Ir(I)-catalyzed benzylic C-H bond amination of ortho-substituted aryl azides
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Image Persented Iridium(I) catalyzes the intramolecular benzylic C-H bond amination of ortho-homobenzyl-substituted aryl azides to produce indolines at 25 °C.
- Sun, Ke,Sachwani, Rachna,Richert, Kathleen J.,Driver, Tom G.
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scheme or table
p. 3598 - 3601
(2011/02/23)
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- Rapid and easy access to indoles via microwave-assisted Hemetsberger-Knittel synthesis
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Hemetsberger-Knittel indole synthesis can be carried out under microwave activation. The optimum reaction conditions were found by using different solvents and by varying irradiation times and temperature. After 10 min of microwave irradiation, high conversion into the corresponding indole products was achieved without formation of any side products.
- Lehmann, Frank,Holm, Melanie,Laufer, Stefan
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experimental part
p. 1708 - 1709
(2009/09/05)
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- Intramolecular C-H amination reactions: Exploitation of the Rh 2(II)-catalyzed decomposition of azidoacrylates
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Rhodium(II) perfluorobutyrate-mediated decomposition of vinyl azides provides a new, mild entry into Rh2(II) nitrenoid chemistry. This methodology allows rapid access to a variety of complex, functionalized N-heterocycles in two steps from commercially available starting materials. Copyright
- Stokes, Benjamin J.,Dong, Huijun,Leslie, Brooke E.,Pumphrey, Ashley L.,Driver, Tom G.
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p. 7500 - 7501
(2008/02/09)
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- Synthesis and structure-activity relationships of second-generation hydroxamate botulinum neurotoxin A protease inhibitors
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Botulinum neurotoxins are the most toxic proteins currently known. Based on a recently identified potent lead structure, 2,4-dichlorocinnamic acid hydroxamate, herein we report on the structure-activity relationship of a series of hydroxamate BoNT/A inhibitors. Among them, 2-bromo-4-chlorocinnamic acid hydroxamate, 2-methyl-4-chlorocinnamic acid hydroxamate, and 2-trifluoromethyl-4-chlorocinnamic acid hydroxamate displayed comparable inhibitory activity to that of the lead structure.
- Capkova, Katerina,Yoneda, Yoshiyuki,Dickerson, Tobin J.,Janda, Kim D.
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p. 6463 - 6466
(2008/04/02)
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- Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones
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A new approach is described for the synthesis of substituted indoles 5, through an intramolecular and regioselective Friedel-Crafts cyclization of enaminones 6a-h catalyzed by Lewis acids. Compounds 6 were prepared from the 2-anilinocarbonyl compounds 7, by treatment with DMFDMA under thermal or microwave (MW) irradiation conditions. An alternative and shorter one-pot two-step synthesis of indoles 5 was achieved starting from compounds 7 and promoted by MW radiation, including the elusive 2-acetylindoles 5i-m. Georg Thieme Verlag Stuttgart.
- Cruz, María Del Carmen,Jiménez, Fabiola,Delgado, Francisco,Tamariz, Joaquín
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p. 749 - 755
(2007/10/03)
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- Probing the subpockets of factor Xa reveals two binding modes for inhibitors based on a 2-carboxyindole scaffold: A study combining structure-activity relationship and X-ray crystallography
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Structure-activity relationships within a series of highly potent 2-carboxyindole-based factor Xa inhibitors incorporating a neutral P1 ligand are described with particular emphasis on the structural requirements for addressing subpockets of the factor Xa enzyme. Interactions with the subpockets were probed by systematic substitution of the 2-carboxyindole scaffold, in combination with privileged P1 and P4 substituents. Combining the most favorable substituents at the indole nucleus led to the discovery of a remarkably potent factor Xa inhibitor displaying a Ki value of 0.07 nM. X-ray crystallography of inhibitors bound to factor Xa revealed substituent-dependent switching of the inhibitor binding mode and provided a rationale for the SAR obtained. These results underscore the key role played by the P1 ligand not only in determining the binding affinity of the inhibitor by direct interaction but also in modifying the binding mode of the whole scaffold, resulting in a nonlinear SAR.
- Nazaré, Marc,Will, David W.,Matter, Hans,Schreuder, Herman,Ritter, Kurt,Urmann, Matthias,Essrich, Melanie,Bauer, Armin,Wagner, Michael,Czech, J?rg,Lorenz, Martin,Laux, Volker,Wehner, Volkmar
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p. 4511 - 4525
(2007/10/03)
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- Tricyclic compounds having fungicidal activity, their preparation and their use
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Compounds of formula (I): STR1 ?wherein: R1 represents halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, or cycloalkyloxy; R2 represents hydrogen or halogen; R3 represents hydrogen, alkyl, or cycloalkyl; and the dotted line represents a single or double carbon--carbon bond!; and salts thereof have valuable fungicidal activities which make them of considerable value in agriculture and horticulture.
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