Catalyst-free Synthesis of 6-Hydroxy Indoles via the Condensation of Carboxymethyl Cyclohexadienones and Amines

被引：9

作者：

Reddy, Reddy Rajasekhar ^{[1
]}

Adlak, Komalkant ^{[1
]}

Ghorai, Prasanta ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 16期

关键词：

C-N BONDS; ASYMMETRIC DEAROMATIZATION; BIOLOGICAL EVALUATION; DERIVATIVES; ACID; ALKYLATION; ARYL; DESYMMETRIZATION; INTERMEDIATE; DUOCARMYCIN;

D O I：

10.1021/acs.joc.7b01136

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient catalyst-free synthesis of 6-hydroxy indoles from carboxymethyl cyclohexadienones and primary amines has been developed. The aza-Michael addition of the in situ formed enamine, generated through the condensation of carboxymethyl unit of the substrates with an external amine, to cyclohexadienone moiety followed by rearomatization reaction to provide such indoles. Anilines, aliphatic amines, alpha-chiral aliphatic amines, or even ammonia were used as amine counterpart. Some of the cyclohexadienones gave 6-amino indoles instead of 6-hydroxy indoles using the Re2O7 catalyst. Various post methodological transformations were performed to explore the synthetic utility of the synthesized hydroxy indoles.

引用

页码：8426 / 8437

页数：12

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