Bronsted Acid-Catalyzed Tandem Pinacol-Type Rearrangement for the Synthesis of α-(3-Indolyl) Ketones by Using α-Hydroxy Aldehydes

被引：25

作者：

Kundu, Samrat ^{[1
]}

Banerjee, Ankush ^{[1
]}

Maji, Modhu Sudan ^{[1
]}

机构：

[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 24期

关键词：

SEMIPINACOL REARRANGEMENT; ANTIFUNGAL ACTIVITY; CARBONYL-COMPOUNDS; INDOLES; FUNCTIONALIZATION; CONSTRUCTION; CARBOLINES; EFFICIENT; ALKALOIDS; ALCOHOLS;

D O I：

10.1021/acs.joc.9b02474

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Bronsted acid-catalyzed pinacol-type rear-rangement pathway is reported here to synthesize various substituted alpha-(3-indolyl) ketones by employing unprotected indoles and alpha-hydroxy aldehydes as coupling partners. Utilization of economic and readily available Bronsted acid catalyst and use of simple starting precursors exemplify the economic viability of this method. Under this developed protocol, selective migration of aryl over alkyl or a second aryl group is observed depending upon the migratory aptitude of the substituents. Applicability of this method was further demonstrated by synthesizing highly substituted carbazoles through a simple extension of this method to one-pot cascade annulation strategy.

引用

页码：16003 / 16012

页数：10

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