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

Anjum Ahmed, Jonathan Clayden*, Michael Rowley

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

28 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)1954-1956
Number of pages3
Issue number12
Publication statusPublished - 1999


  • Amide
  • Azepin
  • Cyclization
  • Dearomatisation
  • Lithium


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