Novel ring enlargement of lactams via quinazolinone annelation. A facile route to benzoannelated large-membered cyclic 1, 5-diamines

H Takeuchi, Y Matsushita, S Eguchi

Index: Takeuchi, Hisato; Matsushita, Yuji; Eguchi, Shoji Journal of Organic Chemistry, 1991 , vol. 56, # 4 p. 1535 - 1537

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Citation Number: 38

Abstract

A novel route to benzoannelated large-membered cyclic 1, 5-diamines from lactams is described. Thus, n-membered lactams 1 were N-acylated by o-azidobenzoyl chloride 5 to afford the corresponding imides 4. These were treated with tributylphosphine and underwent an intramolecular aza-Wittig reaction to give n-membered ring-fused quinazolinones 2 in 8446% yleld. By reductive cleavage of 2 with BH,. THF,(n+ 4)-membered cyclic diamines 3 ...