1,3,4,5-tetrahydroazepin-2-ones by dearomatising anionic cyclisation of N-allyl-1-naphthamides

被引：26

作者：

Ahmed, A

Clayden, J

Rowley, M

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

[2] Merck Sharp & Dohme Ltd, Neurosci Res Ctr, Harlow CM20 2QR, Essex, England

来源：

SYNLETT | 1999年 / 12期

关键词：

amide; cyclization; lithium; azepin; dearomatisation;

D O I：

10.1055/s-1999-2977

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On treatment with t-BuLi and DMPU, 1-naphthamides bearing N-allyl or N-prenyl substituents cyclise to give a mixture of products from which seven-membered lactams can be isolated in up to 73% yield - the first example of an organolithium-C=C cyclisation leading to a seven-membered ring.

引用

页码：1954 / 1956

页数：3

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