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Synlett 1999; 1999(12): 1954-1956
DOI: 10.1055/s-1999-2977
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1,3,4,5-Tetrahydroazepin-2-ones by Dearomatising Anionic Cyclisation of N-Allyl-1-Naphthamides

Anjum Ahmed* , Jonathan Clayden, Michael Rowley
  • *Department of Chemistry, University of Manchester, Oxford Rd., Manchester M13 9PL, U.K.; E-mail: j.p.clayden@man.ac.uk
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Publication Date:
31 December 1999 (online)

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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.

amide - cyclization - lithium - azepin - dearomatisation

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