16886-00-3Relevant articles and documents
Ir(iii)-Catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling for the synthesis of N-H indoles
Chang, Sukbok,Kim, Dongwook,Kim, Youyoung
, p. 12309 - 12312 (2021/12/07)
Herein, an iridium(iii)-catalysed electrooxidative intramolecular dehydrogenative C-H/N-H coupling of unprotected 2-alkenyl anilines is described. The developed method allows the synthesis of a variety of 3-substituted N-H indole scaffolds under undivided electrolytic conditions. Mechanistic studies suggest that the reaction proceeds through the electro-oxidation induced reductive elimination pathway.
Nickel-catalyzed C3-alkylation of indoles with alcohols: Via a borrowing hydrogen strategy
Hu, Miao,Jiang, Yong,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan,Jin, Liqun
, p. 10057 - 10062 (2021/06/15)
An efficient method for the Ni-catalyzed C3-alkylation of indoles using readily available alcohols as the alkylating reagents has been developed. The alkylation was addressed with an air and moisture-stable binuclear nickel complex ligated by tetrahydroquinolin-8-one as the effective pre-catalyst. The newly developed transformation could accommodate a broad substrate scope including primary/secondary benzylic and aliphatic alcohols and substituted indoles. Mechanistic studies suggested that the reaction proceeds through a borrowing hydrogen pathway.
Site-Specific Oxidation of (sp3)C-C(sp3)/H Bonds by NaNO2/HCl
Zhao, Jianyou,Shen, Tong,Sun, Zhihui,Wang, Nengyong,Yang, Le,Wu, Jintao,You, Huichao,Liu, Zhong-Quan
supporting information, p. 4057 - 4061 (2021/05/26)
A site-specific oxidation of (sp3)C-C(sp3) and (sp3)C-H bonds in aryl alkanes by the use of NaNO2/HCl was explored. The method is chemical-oxidant-free, transition-metal-free, uses water as the solvent, and proceeds under mild conditions, making it valuable and attractive to synthetic organic chemistry.
Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2- a]indoles
Xie, Tao,Sui, Qi-Bang,Qin, Lu-Zhe,Wen, Xiaoan,Sun, Hongbin,Xu, Qing-Long,Zhen, Le
supporting information, p. 5518 - 5529 (2021/05/04)
A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.
Constructing Saturated Guanidinum Heterocycles by Cycloaddition of N-Amidinyliminium Ions with Indoles
Allred, Tyler K.,Shaghafi, Michael B.,Chen, Pan-Pan,Tran, Quan,Houk,Overman, Larry E.
supporting information, p. 7618 - 7623 (2021/10/12)
We report that structurally complex guanidinium heterocycles can be prepared in one step by regio- and stereoselective [4 + 2]-cycloadditions of N-amidinyliminium ions with indoles or benzothiophene. In contrast to reactions of these heterodienes with alkenes, density functional theory (DFT) calculations show that these cycloadditions take place in a concerted asynchronous fashion. The [4 + 2]-cycloaddition of N-amidinyliminium ions (1,3-diaza-1,3-dienes) with indoles and benzothiophene are distinctive, as related [4 + 2]-cycloadditions of N-acyliminium ions (1-oxa-3-aza-1,3-dienes) are apparently unknown.
Manganese-Catalyzed Regioselective Dehydrogenative C-versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation
Borghs, Jannik C.,Zubar, Viktoriia,Zubar, Viktoriia,Azofra, Luis Miguel,Sklyaruk, Jan,Rueping, Magnus,Rueping, Magnus
supporting information, p. 4222 - 4227 (2020/06/04)
The first base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air-and moisture-stable manganese catalyst provides access to either C3-or N-alkylated indoles depending on the solvent used. Mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation and hydrogen autotransfer strategy.
Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-Pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis
Frison, Gilles,Guinchard, Xavier,Marinetti, Angela,Retailleau, Pascal,Smal, Vitalii,Voituriez, Arnaud,Zhang, Zhenhao
supporting information, p. 3797 - 3805 (2020/03/10)
Tethering a metal complex to its phosphate counterion via a phosphine ligand enables a new strategy in asymmetric counteranion-directed catalysis (ACDC). A straightforward, scalable synthetic route gives access to the gold(I) complex of a phosphine displaying a chiral phosphoric acid function. The complex generates a catalytically active species with an unprecedented intramolecular relationship between the cationic Au(I) center and the phosphate counterion. The benefits of tethering the two functions of the catalyst are demonstrated here in a tandem cycloisomerization/nucleophilic addition reaction, by attaining high enantioselectivity levels (up to 97% ee) at an unusually low 0.2 mol % catalyst loading. Remarkably, the method is also compatible with a silver-free protocol.
[1,2,4]TRIAZOLO[1,5-A]PYRIDINYL SUBSTITUTED INDOLE COMPOUNDS
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Page/Page column 364, (2018/02/28)
Disclosed are compounds of Formula (I) or a salt thereof, wherein R1, R2, R3, R4, R5, m, n, and p are defined herein. Also disclosed are methods of using such compounds as inhibitors of signaling through Toll-like receptor 7, or 8, or 9, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating inflammatory and autoimmune diseases.
Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines: Via the copper-catalyzed aerobic oxygenated CC bond of indoles
Yu, Lemao,Zhong, Yuan,Yu, Jicong,Gan, Lu,Cai, Zhengjun,Wang, Rui,Jiang, Xianxing
supporting information, p. 2353 - 2356 (2018/03/09)
Herein, a copper-catalyzed highly diastereoselective aerobic oxygenated [3+3] cyclization of 3-substituted indoles with C,N-cyclic azomethine imines using oxygen as the sole oxidant under mild conditions has been developed. This protocol provides a simple and convenient approach for constructing [2,3]-fused indoline O-heterocycles bearing two pharmaceutically intriguing parts, tetrahydroisoquinoline and indoline. Good yields and excellent diastereoselectivity under mild reaction conditions were observed.
Preparation method of 3-substituted oxidized indole and derivative
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Paragraph 0044; 0046; 0081, (2018/06/26)
The invention belongs to the technical field of organic chemistry and pharmaceutical chemistry and particularly relates to a method of preparing 3-substituted oxidized indole and a derivative. In themethod, with a 3-substituted indole derivative as a raw material and one or more of a tetrabutyl ammonium halide compound/sodium chloride/sodium iodide/potassium iodide as additives, and one or more of dichloromethane/1,2-dichloroethane/tetrahydrofurane/methylbenzene/1,4-dioxane/ethyl acetate/methanol are added as solvents; then one or more of [bis(trifluoroacetoxyl)iodine]benzene/iodosobenzene diacetate are added as oxidants in order to carry out a reaction with reaction temperature being controlled, thus producing the 3-substituted oxidized indole derivative. The method has gentle reaction conditions, simple operations, short reaction time and high yield, and is free of a metal catalyst and is environment-friendly.
