Palladium-Catalyzed Approach for the General Synthesis of (E)-2-Arylmethylidene-N-tosylindolines and (E)-2-Arylmethylidene-N-tosyl/nosyltetrahydroquinolines: Access to 2-Substituted Indoles and Quinolines

被引：38

作者：

Chowdhury, Chinmay ^{[1
]}

Das, Bimolendu ^{[1
]}

Mukherjee, Sanjukta ^{[1
]}

Achari, Basudeb ^{[1
]}

机构：

[1] Indian Inst Chem Biol, CSIR, Div Chem, Kolkata 700032, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 11期

关键词：

ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SUBSTITUTED QUINOLINES; CYCLIZATION REACTIONS; DOMINO REACTION; ARYL HALIDES; DERIVATIVES; EFFICIENT; AMINOPALLADATION; HYDROGENATION;

D O I：

10.1021/jo300458v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient method for the synthesis of (E)-2-arylmethylidene-N-tosylindolines and (E)-2-arylmethylidene-N-tosyl/nosyltetrahydroquinoline variants has been developed through palladium-catalyzed cyclocondensation of aryl iodides with readily available 1-(2-tosylaminophenyl)prop-2-yn-1-ols and their higher homologues, respectively. The proposed reaction mechanism invokes the operation of trans-aminopalladation during cyclization (5/6-exo-dig), which ensures exclusive (E)-stereochemistry in the products. The method is fast, operationally simple, totally regio- and stereoselective, and versatile enough to access a variety of 2-substituted indoles and quinolines. The reactions proceeded efficiently with a wide variety of substrates and afforded the corresponding products in moderate to excellent yields.

引用

页码：5108 / 5119

页数：12

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