- SYNTHESIS OF INDOLES FROM PYRIDINIUM SALTS
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The detailed analysis of the products of the interaction of nitropyridinium salts with ketones and alkylamines resulted in new data testifying in favor of the previously proposed scheme for the formation of indoles from pyridinium salts.
- Gromov, S. P.,Bkhaumik, M. M.,Bundel, Yu. G.
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- SYNTHESIS OF INDOLES FROM PYRIDINIUM SALTS. 1. RECYCLIZATION OF 4-ALKYL-2,6-DIMETHYL-3-NITROPYRIDINE METHIODIDES IN THE PRESENCE OF KETONES
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A method for the synthesis of 4-alkylpolymethylindoles by recyclization of 4-alkyl-2,6-dimethyl-3-nitropyridine methiodides in the presence of ketones was developed.A method for establishing the structures of the polyalkylindoles on the basis of data from the PMR spectra and the proton-coupled 13C NMR spectra is proposed.
- Yurovskaya, M. A.,Chertkov, V. A.,Afanas'ev, A. Z.,Ienkina, F. V.,Bundel', Yu. G.
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- Cobalt-Catalyzed Enantioselective C–H Arylation of Indoles
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Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C–H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate- and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene ligand bearing an essential remote substituent. Attractive dispersion interactions along with positive C–H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.
- Ackermann, Lutz,Jacob, Nicolas,Oliveira, Jo?o C. A.,Wencel-Delord, Joanna,Zaid, Yassir
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supporting information
p. 798 - 806
(2022/02/03)
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- Copper-Catalyzed Synthesis of Indolyl Benzo[b]carbazoles and Their Photoluminescence Property
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A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.
- Hao, Tonggang,Huang, Long,Wei, Yin,Shi, Min
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supporting information
p. 5133 - 5137
(2021/07/19)
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- Assembly of polycyclic N-heterocycles: Via copper-catalyzed cycloamination of indolylquinones and aromatic amines
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The copper-catalyzed cycloamination of indolylquinones and various (hetero)aromatic amines under ligand-free conditions for the synthesis of polycyclic N-heterocycles has been developed. This method allows facile access to polycyclic N-heterocycles with the tolerance of chloride, bromide, amino, thio, etc. groups in moderate to high yields (60-89%).
- Dong, Yu,Mei, Ting,Ye, Ji-Xian,Chen, Xiang-Long,Jiang, Hui,Chang, Bo,Wang, Zhi-Fan,Shi, Zhi-Chuan,Li, Zhong-Hui,He, Bing
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supporting information
p. 4593 - 4598
(2021/05/31)
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- Visible-Light-Induced Carbonylation of Indoles with Phenols under Metal-Free Conditions: Synthesis of Indole-3-carboxylates
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A visible-light-induced carbonylation of indoles with phenols for the synthesis of indole-3-carboxylates has been developed. The reaction proceeded via a radical carbonylation process in which elementary I2 was used as an effective photosensitive initiator and, thus, avoided the use of transition metal catalysts. A series of different aryl indole-3-carboxylates were prepared in moderate to good yields. The broad applicability of this methodology was further highlighted by the late-stage functionalization of several phenol-containing natural products and pharmaceuticals.
- Qi, Zhuang,Li, Lin,Liang, Ying-Kang,Ma, Ai-Jun,Zhang, Xiang-Zhi,Peng, Jin-Bao
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supporting information
p. 4769 - 4773
(2021/06/28)
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- Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue
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A cobalt-catalyzed annulation of the C(sp2)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist.
- Huang, Mao-Gui,Shi, Shuai,Li, Ming,Liu, Yue-Jin,Liu, Yue-Jin
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supporting information
p. 7094 - 7099
(2021/09/14)
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- Straightforward access to novel indolo[2,3-: B] indoles via aerobic copper-catalyzed [3+2] annulation of diarylamines and indoles
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Herein, we report an unprecedented aerobic copper-catalyzed [3+2] annulation reaction of diarylamines with indoles, which allows direct access to novel 2-diarylaminoindolo[2,3-b]indoles, a class of potential photoelectric device molecules. The developed transformation proceeds with broad substrate scope, good functional group tolerance, high chemo-selectivity, and no need for pre-preparation of specific agents, which offers a practical route for diverse and atom-economic synthesis of the desired products that are difficult to prepare with the conventional approaches.
- Gong, Lingzhen,Jiang, Huanfeng,Liang, Taoyuan,Zhang, Min,Zhao, He
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supporting information
p. 2807 - 2810
(2020/03/13)
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- Synthesis of Cyclopenta[b]indoles via a Formal [3+2] Cyclization of N-Sulfonyl-1,2,3-triazoles and Indoles
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Annulation of benzoxy-tethered N-sulfonyl-1,2,3-triazoles and indoles has been developed in this paper, providing an efficient and convenient access to valuable cyclopenta[b]indoles in moderate to good yields. α,β-Unsaturated imine, which generated in situ from denitrogenation and 1,2-OBz migration of triazole, provided three carbons for the formal [3+2] cyclization reaction for the first time. (Figure presented.).
- Duan, Shengguo,Zhang, Wan,Hu, Yuntong,Xu, Ze-Feng,Li, Chuan-Ying
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supporting information
p. 3570 - 3575
(2020/08/05)
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- Catalytic Aerobic Dehydrogenatin of N-Heterocycles by N-Hydoxyphthalimide
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Catalytic methods for the aerobic dehydrogenation of N-heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N-hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines. (Figure presented.).
- Chen, Weidong,Tang, Hao,Wang, Weilin,Fu, Qiang,Luo, Junfei
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supporting information
p. 3905 - 3911
(2020/08/10)
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- Method for preparing indole compound through air oxidation catalyzed by N-hydroxyphthalimide
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The invention discloses a method for preparing an indole compound through non-transition metal catalyzed air oxidation. According to the method, the low-cost N-hydroxyphthalimide is used as a catalystand air is used as an oxidizing agent, wherein indoline compounds are oxidized in an organic solvent, and synthesis of the indoline compounds is achieved. The method has the advantages of simple reaction operation, low reaction cost, high yield, mild conditions, no heavy metal pollution and the like.
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Paragraph 0065-0067
(2020/11/23)
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- Cobalt-Catalyzed Cycloamination: Synthesis and Photophysical Properties of Polycyclic N-Heterocycles
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The first earth-abundant cobalt-catalyzed cycloamination of indolylquinones and various (hetero)aromatic amine under ligand-free conditions for the synthesis of polycyclic N-heterocycles has been developed. The process allows facile access to polycyclic N-heterocycles with tolerance of chloride, bromide, amino, thio, etc. groups in moderate to high yields (up to 89percent). In addition, The photophysical properties of the synthesized products were evaluated. These products exhibit interesting fluorescence properties, which is promising for fluorescent probes.
- Dong, Yu,He, Shuai,Shi, Zhi-Chuan,Wang, Ji-Yu,Yang, Jian,Zhan, Xiao-Yu,Zhang, Hua,Zhang, Xiao-Mei
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supporting information
(2020/07/15)
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- Exhaustive Reduction of Esters Enabled by Nickel Catalysis
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We report a one-step procedure to directly reduce unactivated aryl esters into their corresponding tolyl derivatives. This is achieved by an organosilane-mediated ester hydrosilylation reaction and subsequent Ni/NHC-catalyzed hydrogenolysis. The resulting conditions provide a direct and efficient alternative to multi-step procedures for this transformation that often require the use of hazardous metal hydrides. Applications in the synthesis of -CD3-containing products, derivatization of bioactive molecules, and chemoselective reduction in the presence of other C-O bonds are demonstrated.
- Cook, Adam,Prakash, Sekar,Zheng, Yan-Long,Newman, Stephen G.
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supporting information
p. 8109 - 8115
(2020/05/20)
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- Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes
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Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step - the C-N bond cleavage of the Mannich product - was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical molecules.
- Yang, Liquan,Liu, Zhaoran,Li, Yujun,Lei, Ning,Shen, Yanling,Zheng, Ke
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supporting information
p. 7702 - 7707
(2019/10/19)
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- Method for methylation reaction
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The invention relates to a method for a methylation reaction. The method is characterized in that a reaction substrate is reacted in an organic solvent in the presence of an alkali with methyl trifluoroacetate as a methylation reagent to obtain a corresponding methylated product. The method is a new methylation method, and has the advantages of cheapness, easiness in operation, mild reaction conditions, wide application range of the substrate, avoiding of dimethyl sulfate, iodomethane and other highly toxic methylation reagents, and obtaining of the methylated product with a high yield.
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Paragraph 0013
(2019/01/21)
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- Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones
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A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series of tetrahydro-β-carbolinones in good yields under mild conditions. Gram-sca
- Zhang, Kaifan,Xu, Xiaoying,Zheng, Jiuan,Yao, Hequan,Huang, Yue,Lin, Aijun
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supporting information
p. 2596 - 2599
(2017/05/24)
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- Copper-mediated trifluoroacetylation of indoles with ethyl trifluoropyruvate
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Direct trifluoroacetylation of indoles with ethyl trifluoropyruvate as a trifluoroacetylating reagent has been developed. This novel protocol provides an attractive route for the preparation of 3-trifluoroacetylindole derivatives, due to its operational simplicity and practicability as well as mild reaction conditions.
- Yan, Guobing,Cao, Xihan,Zheng, Wanbin,Ke, Qiumin,Zhang, Jieyu,Huang, Dayun
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supporting information
p. 5904 - 5907
(2017/07/25)
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- CuCl2/TBHP-mediated direct chlorooxidation of indoles
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CuCl2/TBHP-mediated direct chlorooxidation of indole derivatives under simple aerobic conditions was reported, leading to facile preparations of a range of 3,3-disubstituted 3-chlorooxindoles in good yields and selectivities.
- Wang, Huifei,Liu, Dong,Chen, Huiyu,Li, Jing,Wang, David Zhigang
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supporting information
p. 7073 - 7076
(2015/08/19)
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- Acid-catalyzed acylation reaction via C-C bond cleavage: A facile and mechanistically defined approach to synthesize 3-acylindoles
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A facile acid-catalyzed acylation of indoles with 1,3-dione as an eco-friendly acylating agent was developed. This protocol combines C-C bond cleavage and heterocyclic C-H bond functionalization to form new C-C bonds. Based on the detailed mechanistic studies, a credible mechanistic pathway was proposed. This journal is
- Xing, Qi,Li, Pan,Lv, Hui,Lang, Rui,Xia, Chungu,Li, Fuwei
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supporting information
p. 12181 - 12184
(2014/12/11)
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- NOVEL IMIDAZOPYRIDINE COMPOUND
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For the prevention and/or treatment of chymase-mediated diseases such as skin diseases, circulatory diseases, digestive system diseases, respiratory diseases, liver diseases, ocular diseases or the like, a drug is provided having as an active ingredient a
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Page/Page column 20
(2012/04/23)
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- Cine substitution of arenes using the aryl carbamate as a removable directing group
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An efficient and controlled means to achieve a rare cine substitution of arenes is reported. The methodology relies on the strategic use of aryl O-carbamates as readily removable directing groups for arene functionalization. The removal of aryl carbamates is achieved by employing an air-stable Ni(II) precatalyst, along with an inexpensive reducing agent, to give synthetically useful yields across a range of substrates. The net cine substitution process offers a new strategy for analogue synthesis, which complements the well-established logic for achieving arene functionalization by ipso substitution.
- Mesganaw, Tehetena,Fine Nathel, Noah F.,Garg, Neil K.
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supporting information; experimental part
p. 2918 - 2921
(2012/07/28)
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- Benzimidazolone as potent chymase inhibitor: Modulation of reactive metabolite formation in the hydrophobic (P1) region
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A new class of chymase inhibitor featuring a benzimidazolone core with an acid side chain and a P1 hydrophobic moiety is described. Incubation of the lead compound with GSH resulted in the formation of a GSH conjugate on the benzothiophene P1 moiety. Replacement of the benzothiophene with different heterocyclic systems such as indoles and benzoisothiazole is feasible. Among the P1 replacements, benzoisothiazole prevents the formation of GSH conjugate and an in silico analysis of oxidative potentials agreed with the experimental outcome.
- Lo, Ho Yin,Nemoto, Peter A.,Kim, Jin Mi,Hao, Ming-Hong,Qian, Kevin C.,Farrow, Neil A.,Albaugh, Daniel R.,Fowler, Danielle M.,Schneiderman, Richard D.,Michael August,Martin, Leslie,Hill-Drzewi, Melissa,Pullen, Steven S.,Takahashi, Hidenori,De Lombaert, Stephane
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scheme or table
p. 4533 - 4539
(2011/09/12)
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- Synthesis of indole and biindolyl triflones: Trifluoromethanesulfonylation of indoles with Tf2O/TTBP (2,4,6-tri- tert -butylpyridine) system
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A convenient synthesis of indole triflones is reported. N-Alkyl, aryl and N-H indole triflones were obtained in 82-96% yields by the Tf2O/TTBP System. Biindolyl triflones were accessed in 51-81% yields for the first time by simple treatment of the resulting indole triflones with a base and without any use of organometallic chemistry. An environmentally friendly solvent, Solkane 365/227, can be substituted for this process without any loss of efficiency.
- Xu, Xiu-Hua,Liu, Guo-Kai,Azuma, Ayaka,Tokunaga, Etsuko,Shibata, Norio
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supporting information; experimental part
p. 4854 - 4857
(2011/11/06)
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- 5-PYRIDIN-3-YL-1,3-DIHYDRO-INDOL-2-ON DERIVATIVES AND THEIR USE AS MODULATORS OF ALDOSTERONE SYNTHASE AND/OR CYP11B1
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The present invention provides a compound a formula (I); or a pharmaceutically acceptable salt thereof, wherein: X is CH2, O, S or-NR1; each R1 are independently C1-7alkyl or C3-8cycloalkyl; each of R
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Page/Page column 86
(2010/12/17)
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- Benzimidazole derivative
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The present invention is a thiobenzimidazole derivative represented by the following formula (1) or a medically acceptable salt thereof wherein said thiobenzimidazole derivative and a medically acceptable salt thereof have a potent activity of inhibiting human chymase. Thus, they are potential preventive and/or therapeutic agents clinically applicable to various diseases in which human chymase is involved.
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- Benzimidazole derivatives
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A benzimidazole derivative or its medically acceptable salt, represented by the following formula (1), that is a human chymase activity inhibitor capable of being applied clinically: 1wherein, R1 and R2 represent a hydrogen atom, an alkyl group or an alkoxy group, etc., A represents an alkylene group or an alkenylene group, E represents —COOR3, —SO3R3, —CONHR3 or —SO2NHR3, etc., G represents an alkylene group, M represents a single bond or —S(O)m. J represents a heterocyclic group, and X represents —CH= or a nitrogen atom.
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- BENZIMIDAZOLE DERIVATIVES
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A benzimidazole derivative or its medically acceptable salt, represented by the following formula (1), that is a human chymase activity inhibitor capable of being applied clinically: wherein, R1 and R2 represent a hydrogen atom, an alkyl group or an alkoxy group, etc., A represents an alkylene group or an alkenylene group, E represents -COOR3, -SO3R3, -CONHR3 or -SO2NHR3, etc., G represents an alkylene group, M represents a single bond or -S(O)m-, J represents a heterocyclic group, and X represents -CH= or a nitrogen atom.
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- Ortho-Vinylation reaction of anilines
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N-Alkylanilines and anilines are vinylated at the ortho-position with ethyne in the presence of SnCl4-Bu3N.
- Yamaguchi, Masahiko,Arisawa, Mieko,Hirama, Masahiro
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p. 1399 - 1400
(2007/10/03)
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- Scheme of transformation of 3-nitropyridinium salts into indoles
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A mechanistic scheme for the transformation of 3-nitropyridinium salt indoles by action of N-alkylketimines (or mixture of the corresponding ketones and amines) is discussed.
- Yurovskaya,Afanasyev,Maximova,Bundel
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p. 4945 - 4954
(2007/10/02)
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- Inhibitors of Protein Kinase C. 1. 2,3-Bisarylmaleimides
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The design and synthesis of a series of novel inhibitors of protein kinase C (PKC) is described.These 2,3-bisarylmaleimides were derived from the structural lead provided by the indolocarbazoles, staurosporine and K252a.Optimum activity required the imide NH, both carbonyl groups, and the olefinic bond of the maleimide ring. 2,3-Bisindolylmaleimides were the most active, and the potency of these was improved by a chloro substituent at the 5-position of one indole ring (compound 28, IC50 0.11 μM).In a series of (phenylindolyl)maleimides, nitro compound 74 was most active (IC50 0.67 μM).Naphthalene 19 and benzothiophene 21 showed greater than 100-fold selectivity for inhibition of PKC over the closely related cAMP-dependent protein kinase (PKA).
- Davis, Peter D.,Hill, Christopher H.,Lawton, Geoffrey,Nixon, John S.,Wilkinson, Sandra E.,et al.
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p. 177 - 184
(2007/10/02)
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