- 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
-
supporting information
p. 9610 - 9616
(2021/12/09)
-
- 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
-
supporting information
p. 1096 - 1102
(2021/01/26)
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- DFT-Guided Phosphoric-Acid-Catalyzed Atroposelective Arene Functionalization of Nitrosonaphthalene
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Guided by computational design, Tan and colleagues disclose a chiral phosphoric-acid-catalyzed asymmetric functionalization of naphthalenes with nitroso as the activating and directing group. This nucleophilic aromatic substitution reaction allows divergent access to two types of axially chiral arylindole frameworks with wide substrate generality under excellent enantiocontrol and, more importantly, offers a facile approach to the privileged NOBIN (2-amino-2′-hydroxy-1,1′-binaphthyl) structures. DFT calculations illustrate the plausible reaction pathway and provide additional insights into the origins of enantioselectivity.Functionalization of arenes represents the most efficient approach for constructing a core backbone of important aryl compounds. Compared with the well-developed electrophilic aromatic substitution and transition-metal-catalyzed C–H activation, nucleophilic aromatic substitution remains challenging because of the lack of a convenient route for rapid conversion of the σH adduct to other stable and versatile intermediates in situ. Guided by computational design, we were able to realize asymmetric nucleophilic aromatic substitution by introducing a nitroso group on naphthalene via chiral phosphoric acid catalysis. This strategy enables efficient construction of atropisomeric indole-naphthalenes and indole-anilines with excellent stereocontrol. Density functional theory (DFT) calculations provide further insights into the origins of enantioselectivity and the reaction mechanisms. The successful application in the synthesis of NOBINs (2-amino-2′-hydroxy-1,1′-binaphthyl) extends the utility of this strategy.Highly efficient conversion of inexpensive and readily available arene materials into high-value-added chiral molecules is of great importance in modern synthetic chemistry given the enormous potential of such structures in functional materials, pharmaceuticals, and other relevant chemical industries. Organocatalytic nucleophilic aromatic substitution enabled by an azo group offers an effective approach to enantioselective functionalization of naphthalene C–H bonds featuring an intramolecular oxidation of an unstabilized σH adduct. Premised on density functional theory (DFT) calculations, nitroso has emerged as another promising activating and oxidative group, whose synthetic potential is substantiated in the atroposelective synthesis of several groups of representative biaryl atropisomers processed by a chiral phosphoric acid catalyst. The success of this reaction explicitly exemplifies the ability of computational tools to streamline organic synthesis with intensified robustness in the disclosed strategy.
- Ding, Wei-Yi,Yu, Peiyuan,An, Qian-Jin,Bay, Katherine L.,Xiang, Shao-Hua,Li, Shaoyu,Chen, Ying,Houk,Tan, Bin
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p. 2046 - 2059
(2020/07/13)
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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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- Highly Efficient Synthesis of Hindered 3-Azoindoles via Metal-Free C-H Functionalization of Indoles
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Although 3-azoindoles have recently emerged as an appealing family of photoswitch molecules, the synthesis of such compounds has been poorly covered in the literature. Herein a high-yielding and operationally simple protocol is reported allowing the synthesis of 3-azoindoles, featuring important steric hindrance around the azo motif. Remarkably, this C-H coupling is characterized by excellent atom economy and occurs under metal-free conditions, at room temperature, and within few minutes, delivering the expected products in excellent yields (quantitatively in most of the cases). Accordingly, a library of new molecules, with potential applications as photochromic compounds, is prepared.
- Guillemard, Lucas,Jacob, Nicolas,Wencel-Delord, Joanna
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supporting information
p. 574 - 580
(2020/02/13)
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- Selective Inhibition of Histone Deacetylase 10: Hydrogen Bonding to the Gatekeeper Residue is Implicated
-
The discovery of isozyme-selective histone deacetylase (HDAC) inhibitors is critical for understanding the biological functions of individual HDACs and for validating HDACs as drug targets. The isozyme HDAC10 contributes to chemotherapy resistance and has
- Géraldy, Magalie,Morgen, Michael,Sehr, Peter,Steimbach, Raphael R.,Moi, Davide,Ridinger, Johannes,Oehme, Ina,Witt, Olaf,Malz, Mona,Nogueira, Mauro S.,Koch, Oliver,Gunkel, Nikolas,Miller, Aubry K.
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p. 4426 - 4443
(2019/05/17)
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- Synthesis of Indoles through Domino Reactions of 2-Fluorotoluenes and Nitriles
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Indoles are essential heterocycles in medicinal chemistry, and therefore, novel and efficient approaches to their synthesis are in high demand. Among indoles, 2-aryl indoles have been described as privileged scaffolds. Advanced herein is a straightforward, practical, and transition-metal-free assembly of 2-aryl indoles. Simply combining readily available 2-fluorotoluenes, nitriles, LiN(SiMe3)2, and CsF enables the generation of a diverse array of indoles (38 examples, 48–92 % yield). A range of substituents can be introduced into each position of the indole backbone (C4 to C7, and aryl groups at C2), providing handles for further elaboration.
- Mao, Jianyou,Wang, Zhiting,Xu, Xinyu,Liu, Guoqing,Jiang, Runsheng,Guan, Haixing,Zheng, Zhipeng,Walsh, Patrick J.
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supporting information
p. 11033 - 11038
(2019/07/08)
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- Cp*IrIII-Catalyzed [3+2] Annulations of N-Aryl-2-aminopyrimidines with Sulfoxonium Ylides to Access 2-Alkyl Indoles Through C–H Bond Activation
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The iridium-catalyzed aromatic C–H alkylation followed by intramolecular annulation reactions between N-aryl-2-aminopyridines and sulfoxonium ylides for the synthesis of 2-alkyl indoles is described. This highly efficient and step-economical cyclization r
- Luo, Yi,Guo, Lingmei,Yu, Xinling,Ding, Haosheng,Wang, Huijing,Wu, Yong
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p. 3203 - 3207
(2019/06/08)
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- Synthetic method of 2-substituted indoles compounds
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The invention discloses a synthetic method of 2-substituted indoles compounds, and belongs to the organic synthesis field. 2-fluorotoluene compound shown in formula 1 and nitrile compound shown in formula 2 mix with an organic solvent in the presence of strong alkali and cesium salt additives, and react to synthesize the 2-substituted indoles compounds shown in formula 3. The synthesis method of 2-substituted indoles compounds is simple, economical and has wider applicability, is suitable for large-scale production, and has a very important influence on the synthesis of indoles compounds.
- -
-
Paragraph 0010; 0035-0037; 0041; 0043; 0055
(2019/05/02)
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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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- Method for synthetizing axial chirality aryl indole through organocatalysis
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The invention discloses a method for synthetizing axial chirality aryl indole through organocatalysis. The method is characterized in that chiral phosphoric acid is used as a catalyst; a compound 1 and a compound 2 react: the chemical formula is shown as the description, wherein R is hydrogen; R is selected from tertiary butyl, 1-methyl cyclopropyl, 1-methyl cyclobutyl, tertiary pentyl, aryl and heteroaryl; R represents any substituent group; n represents an integer being 1 to 4, and when n is greater than 2, existent two or greater R are identical or different; R selects CO2R, and R is alkyl or benzyl; R represents any substituent group; m represents an integer being 1 to 4, and when m is greater than 2, existent two or greater R are identical or different. The synthesis method is applicable to azobenzene derivatives of various kinds of ester; the axial chirality aryl indole is obtained at good yield and excellent enantioselectivity; the reaction conditions are mild. The method opens up a novel path for organocatalysis of asymmetrical aromatic functionalization.
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-
Paragraph 0106; 0107; 0108
(2018/01/11)
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- URAZOLE COMPOUNDS
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The present invention relates to a compound of formula (I) or a stereoisomer, enantiomer, racemic, or tautomer thereof, (I) wherein R1, R2, R3, R4, R5, R6, R7, L1 and Q1 have the meaning defined in the claims and the description. The present invention also relates to a process for the preparation of the compound of formula (I). The present invention also relates to the use of a compound of formula (I) as an in situ precursor of a triazolinedione reagent for the functionalization of enes, dienes, aryl and heteroaryl systems via the ene reactions, Diels-Alder reactions, and electrophilic aromatic substitution reactions of said reagent. The present invention also relates to the use of a compound of formula (I) in polymers, membranes, adhesives, foams, sealants, molded articles, films, extruded articles, fibers, elastomers, polymer based additives, pharmaceutical and biomedical products, varnishes, paints, coatings, inks, composite material, organic LEDs, organic semiconductors, conducting organic polymers, or 3D printed articles. The present invention also relates to article comprising said compound of formula (I) and to a process for reshaping and/or repairing said article.
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-
Page/Page column 151-152
(2015/02/25)
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- Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
-
The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
- -
-
Paragraph 0408; 1756
(2015/09/22)
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- Probing the molecular and structural elements of ligands binding to the active site versus an allosteric pocket of the human farnesyl pyrophosphate synthase
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In order to explore the interactions of bisphosphonate ligands with the active site and an allosteric pocket of the human farnesyl pyrophosphate synthase (hFPPS), substituted indole and azabenzimidazole bisphosphonates were designed as chameleon ligands. NMR and crystallographic studies revealed that these compounds can occupy both sub-pockets of the active site cavity, as well as the allosteric pocket of hFPPS in the presence of the enzyme's Mg2+ ion cofactor. These results are consistent with the previously proposed hypothesis that the allosteric pocket of hFPPS, located near the active site, plays a feed-back regulatory role for this enzyme.
- Gritzalis, Dimitrios,Park, Jaeok,Chiu, Wei,Cho, Hyungjun,Lin, Yih-Shyan,De Schutter, Joris W.,Lacbay, Cyrus M.,Zielinski, Michal,Berghuis, Albert M.,Tsantrizos, Youla S.
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supporting information
p. 1117 - 1123
(2015/02/19)
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- Synthesis of indoles, benzofurans, and related heterocycles via an acetylene-activated SNAr/intramolecular cyclization cascade sequence in water or DMSO
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The synthesis of 2-substituted indoles and benzofurans was achieved by nucleophilic aromatic substitution, followed by subsequent 5-endo-dig cyclization between the nucleophile and an ortho acetylene. The acetylene serves the dual role of the electron withdrawing group to activate the substrate for SNAr, and the C1-C2 carbon scaffold for the newly formed 5-membered heteroaromatic ring. This method allows for the bond forming sequence of Ar-X-N/O-C1 to proceed in a single synthetic step, furnishing indoles and benzofurans in moderate to high yields. Since the method is not transition metal mediated, brominated and chlorinated substrates are tolerated, and benzofuran formation can be conducted using water or water-DMSO mixtures as solvent. This journal is
- Hudson,Bizier,Esdale,Katz
-
supporting information
p. 2273 - 2284
(2015/03/04)
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- MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS
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The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.
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-
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- COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
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The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
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- Domino sonogashira coupling/cyclization reaction catalyzed by copper and ppb levels of palladium: A concise route to indoles and benzo[b]furans
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Both indoles and benzo[b]furans can be obtained in high yield by the reactions of 2-iodoaniline derivatives and 2-iodophenols with terminal alkynes under mild conditions, namely in the presence of cuprous iodide (10-mol%) and a base in ethanol or 1,4-dioxane. Further investigation reveals that palladium contaminants as low as 100 ppb are responsible for these successful couplings. It is worth noting that simple aliphatic substituted terminal alkynes could be tolerated to smoothly produce indole and benzo[b]furan derivatives. Copyright
- Wang, Ruiping,Mo, Song,Lu, Yongzhong,Shen, Zengming
-
supporting information; experimental part
p. 713 - 718
(2011/05/15)
-
- One-Pot synthesis of indoles and aniline derivatives from nitroarenes under hydrogenation condition with supported gold nanoparticles
-
One-pot sequences of hydrogenation/hydroamination to form indoles from (2-nitroaryl)alkynes and hydrogenation/reductive amination to form aniline derivatives from nitroarenes and aldehydes were catalyzed by Au nanoparticles supported on Fe2O3. Nitro group selective hydrogenations and successive reactions were efficiently catalyzed under the conditions.
- Yamane, Yoshihiro,Liu, Xiaohao,Hamasaki, Akiyuki,Ishida, Tamao,Haruta, Masatake,Yokoyama, Takushi,Tokunaga, Makoto
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supporting information; experimental part
p. 5162 - 5165
(2009/12/28)
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- InBr3-promoted divergent approach to polysubstituted indoles and quinolines from 2-ethynylanilines: Switch from an intramolecular cyclization to an intermolecular dimerization by a type of terminal substituent group
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(Chemical Equation Presented) Use of a 2-ethynylaniline having an alkyl or aryl group on the terminal alkyne selectively produced a variety of polyfunctionalized indole derivatives in moderate to excellent yields via indium-catalyzed intramolecular cyclization of the corresponding alkynylaniline. In contrast, employment of a substrate with a trimethylsilyl group or with no substituent group on the terminal triple bond, exclusively afforded polysubstituted quinoline derivatives in good yields via indium-promoted intermolecular dimerization of the ethynylaniline. This indium catalytic system successfully accommodated the intramolecular cyclization of other arylalkyne skeletons involving a carboxylic acid and an amide group.
- Sakai, Norio,Annaka, Kimiyoshi,Fujita, Akiko,Sato, Asuka,Konakahara, Takeo
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p. 4160 - 4165
(2008/09/21)
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- Asymmetric synthesis of iridoid derivatives using resolved 2-phenylindoline as a chiral auxiliary
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An asymmetric synthetic route to cis,cis-nepetalactol (component of the sex pheromone for the hop aphid, Phorodon humuli) is presented. 2-Phenylindoline was resolved to provide a chiral auxiliary for the cycloaddition of oxocitral. The resolution was made by chromatographic separation of the diastereomers of the urea derivative made from 2-phenylindoline and with (R)-(+)-α- methylbenzyl isocyanate, followed by reductive cleavage of the isolated diasteromers using diborane. The cycloaddition of oxocitral using (S)-2-phenylindoline yielded an enantiopure product after chromatography. Hydrolysis of the cycloaddition adduct yielded gastrolactol (3). As gastrolactol is a versatile synthon for the synthesis of iridoids, the overall procedure provides a general asymmetric route to elaborated iridoids. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
- Santangelo, Ellen M.,Liblikas, Ilme,Mudalige, Anoma,Toernroos, Karl W.,Norrby, Per-Ola,Unelius, C. Rikard
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experimental part
p. 5915 - 5921
(2009/05/27)
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- Modulators of ATP-binding cassette transporters
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Compounds of the present invention and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTR”). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.
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Page/Page column 141
(2008/06/13)
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- A novel indole synthesis via conjugate addition of pyrrolidine to o-nitrophenylacetylenes
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A novel indole synthesis reaction by conjugate addition of pyrrolidine to o-nitrophenylacetylenes and subsequent reductive cyclization of o-nitroarylenamines was developed.
- Tokuyama, Hidetoshi,Makido, Takaki,Han-ya, Yuki,Fukuyama, Tohru
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p. 191 - 197
(2008/03/12)
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- InBr3-catalyzed intramolecular cyclization of 2-alkynylanilines leading to polysubstituted indole and its application to one-pot synthesis of an amino acid precursor
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We describe InBr3-catalyzed cyclization of 2-alkynylaniline derivatives having a variety of functional groups producing polysubstituted indoles. This methodology could be applied to the one-pot synthesis of an amino acid precursor by the addition of a catalytic amount of the indium salt, an imine, and TMSCl.
- Sakai, Norio,Annaka, Kimiyoshi,Konakahara, Takeo
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p. 631 - 634
(2007/10/03)
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- Carbonylation of various organolithium reagents. A novel approach to heterocycles via intramolecular trapping of aromatic acyllithiums
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Doubly lithiated N-pivaloylanilines react smoothly with carbon monoxide at 0°C to give 3-tert-butyl-3-hydroxy-2,3-dihydroindol-2-ones in good yields. Similarly, carbonylation of doubly lithiated 4-pivaloylamino- and 2-pivaloylaminopyridines at 0°C affords the corresponding 5-aza- and 7-aza-3-tert-butyl-3-hydroxy-2,3-dihydroindol-2-ones, respectively, in good yields. However, carbonylation of doubly lithiated N-pivaloyl-o-toluidines takes a different course due to direct intramolecular cyclisation of the dilithio reagents to afford 2-tert-butylindoles without uptake of carbon monoxide.
- Smith, Keith,El-Hiti, Gamal A.,Pritchard, Gareth J.,Hamilton, Anna
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p. 2299 - 2303
(2007/10/03)
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- Formation of Basic Compounds during the Indole Cyclization of Ketone Phenylhydrazones
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On the basis of previous occasional findings, the Fischer indole cyclization of ten ketone phenylhydrazones containing moieties of increasing bulkiness was investigated in order to isolate eventual side products. In the cases of the three 2-, 3- and 4-acetylpyridine phenylhydrazones the corresponding 2-pyridylindoles were the sole compounds so far isolated. In all the remaining cases, beside the indoles a mixture of basic compounds was obtained. In all cases aniline and a 2-substituted (2-methyl or 2-phenyl)benzimidazole were formed, the last resulting through an apparent ortho-semidinic rearrangements of phenylhydrazones. Starting from methyl isopropyl ketone phenylhydrazone a compound of formula C11H15NO was also isolated, to which the structure of 3-(4-aminophenyl)-3-methylbutanone was assigned on the basis of ir, nmr spectra and of the chemical reactivity. The formation of this compound seems related to a para-benzidine-like rearrangement of phenyl hydrazone.
- Boido, Caterina Canu,Boido, Vito,Novelli, Federica,Sparatore, Fabio
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p. 853 - 858
(2007/10/03)
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- High-affinity inhibitors of dihydrofolate reductase: Antimicrobial and anticancer activities of 7,8-dialkyl-1,3-diaminopyrrolo[3,2-f]quinazolines with small molecular size
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A series of 7,8-dialkylpyrrolo[3,2-f]quinazolines were prepared as inhibitors of dihydrofolate reductase (DHFR). On the basis of an apparent inverse relationship between compound size and antifungal activity, the compounds were designed to be relatively small and compact. Inhibitor design was aided by a GRID analysis of the three-dimensional structure of Candida albicans DHFR, which suggested that relatively small, branched alkyl groups at the 7- and 8-positions of the pyrroloquinazoline ring system would provide optimal interactions with a hydrophobic region of the protein. The compounds were potent inhibitors of fungal and human DHFR, with K(i) values as low as 7.1 and 0.1 pM, respectively, and were highly active against C. albicans and an array of tumor cell lines. In contrast to known lipophilic inhibitors of DHFR such as trimetrexate and piritrexim, members of this series of pyrroloquinazolines were not susceptible to P-glycoprotein-mediated multidrug resistance and also showed significant distribution into lung and brain tissue. The compounds were active in lung and brain tumor models and displayed in vivo activity against Pneumocystis carinii and C. albicans.
- Kuyper, Lee F.,Baccanari, David P.,Jones, Michael L.,Hunter, Robert N.,Tansik, Robert L.,Joyner, Suzanne S.,Boytos, Christine M.,Rudolph, Sharon K.,Knick, Vince,Wilson, H. Robert,Caddell, J. Marc,Friedman, Henry S.,Comley, John C. W.,Stables, Jeremy N.
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p. 892 - 903
(2007/10/03)
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- N-nitrosodiphenylamine as an alternative nitrosating agent for indoles
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N-nitrosodiphenylamine reacts in the presence of catalytic amounts of trichloroacetic acid with indoles forming the corresponding nitroso and isonitroso derivatives in good yields.
- Cardellini,Greci,Stipa
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p. 677 - 682
(2007/10/02)
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- PALLADIUM CATALYZED REACTION OF 2-ALKYNYLANILINES WITH ALLYL CHLORIDES. FORMATION OF 3-ALLYLINDOLES
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Pd(II) catalyzed reaction of N-carbomethoxy-2-alkynylanilines with allyl chlorides produces 2-alkyl-3-allyl-N-carbomethoxyindoles in the presence of oxiranes; Aminopalladation of a N-carbomethoxy-2-alkynylaniline gives 3-(N-carbomethoxyindolyl)palladium intermediate, which regioselectively attacks on the γ position of allyl chlorides to give 3-allyl-2-alkylindoles with concurrent regeneration of Pd(II) catalyst.
- Iritani, Koji,Matsubara, Seijiro,Utimoto, Kiitiro
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p. 1799 - 1802
(2007/10/02)
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- Lithiation of N-(2-Alkylphenyl)alkanamides and Related Compounds. A Modified Madelung Indole Synthesis
-
A modified Madelung synthesis for the conversion of N-(alkylphenyl)alkanamides and related compounds to indoles, benzindoles, and azindoles has been developed.This procedure consists of treating the amide with 2 or 3 equiv of n-butyllithium or lithium diisopropylamide in tetrahydrofuran at temperatures from -20 to +25 deg C.Several examples where products other than indoles were formed from the starting amide are also reported.
- Houlihan, William J.,Parrino, Vincent A.,Uike, Yasuyuki
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p. 4511 - 4515
(2007/10/02)
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- Indole Synthesis via SRN1 Reactions
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o-Haloanilines react with ketone enolate ions in ammonia under irradiation to form indoles in good yields.
- Bard, Raymond R.,Bunnett, Joseph F.
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p. 1546 - 1547
(2007/10/02)
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- 2-Substituted indoles and process for their preparation
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Highly branched α-substituted indoles, e.g., 2-(1-methylcyclohexyl)-indole, are prepared by treating N-(α-branched carbonyl) toluidines with alkyl lithium. The reaction sequence may be illustrated as SPC1
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