Abstract: 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. Key words: amide, cyclization, lithium, azepin, dearomatisation
