AMINOHALOBORANE IN ORGANIC-SYNTHESIS .2. SIMPLE SYNTHESIS OF INDOLES AND 1-ACYL-3-INDOLINONES USING SPECIFIC ORTHO-ALPHA-CHLOROACETYLATION OF ANILINES

被引:114
作者
SUGASAWA, T
ADACHI, M
SASAKURA, K
KITAGAWA, A
机构
[1] Shionogi Research Laboratory, Shionogi & Co., Ltd., Osaka 553, Fukushima-ku
关键词
D O I
10.1021/jo01318a021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general simple synthesis of 2, 3-unsubstituted indoles (5) and 1-acyl-3-indolinones (9 and 10) was performed from anilines in two steps. The general procedure involved (a) specific ortho chloroacetylation of anilines to give 2-amino-a-chloroacetophenones (4), and (b) reductive cyclization of 4 to produce 5 and dehydrochlorination of 2-(acylamino)-&-chloroacetophenones (7 and 8) to yield 9 and 10. © 1979, American Chemical Society. All rights reserved.
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页码:578 / 586
页数:9
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