6-chloro-spirocyclohexenindol-2-ones: an unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates.

被引：12

作者：

Beccalli, EM ^{[1
]}

Clerici, F ^{[1
]}

Gelmi, ML ^{[1
]}

机构：

[1] Univ Milan, Fac Farm, Ist Chim Organ, I-20133 Milan, Italy

来源：

TETRAHEDRON | 1999年 / 55卷 / 28期

关键词：

Diels-Alder; chloromethylen-2-indolone; (cyclohexadienyl)phenylcarbamates; 2-aminobiphenyl; phenanthridone;

D O I：

10.1016/S0040-4020(99)00475-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder cycloaddition reaction of 3-chloromethylen-2-indolones 1 with a series of dienes 2 was studied in order to synthesize spirocyclohexenindolones 3 and 4. The reaction proceeded with good diastereoselectivity and regioselectivity. Chloro spirocyclohexenindolones 3 and 4 were transformed into 2-aminobiphenyl derivatives 5 by reacting with sodium ethoxide. Starting from the indolone 1c and 2,3-dimethylbutadiene the spiro compounds 3f and 4e were obtained. On treatment with sodium ethoxide, 3f was transformed into the phenanthridone derivatives 7 and 8. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：8579 / 8586

页数：8

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