Synthesis of tetrahydro-1-benzazocin-2(1H)-ones using 8-endo-trig radical cyclization of 2,2-bis(phenylthio)-N-[o-(prop-2-enyl)phenyl]acetamides?

被引：9
|
作者：
Ikeda, M
Obata, K
Oka, J
Ishibashi, H
Sato, T
机构：
[1] Kyoto Pharmaceutical University, Misasagi, Yamashina
来源：
HETEROCYCLES | 1997年 / 44卷
关键词：
D O I：
10.3987/COM-96-S8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The effects of N-substituents upon the 8-endo-trig radical cyclization of 2,2-bis(phenylthio)-N-[o-(prop-2-enyl)phenyl]acetamides (4) were examined. The N-(p-methoxybenzyl) (4a) and N-tosyl derivatives (4b), when treated with tributyltin hydride in the presence of a small amount of azoisobutyronitrile, gave regioselectively the corresponding 3,4,5,6-tetrahydro-3-phenylthio-1-benzazocin-2(1H)-ones (5a,b) (8-endo cyclization products) in 40 and 47% yields, respectively, while the N-unsubstituted derivative (4c) afforded the reduction products (6c) and (8) as the major products, Some chemical transformation reactions of 5a are also described.
引用
收藏
页码：203 / 212
页数：10
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