Synthesis of fused 1, 2, 5-triazepine-1, 5-diones and some N 2-and N 3-substituted derivatives: potential conformational mimetics for cis-peptidyl prolinamides1

MM Lenman, A Lewis, D Gani

Index: Lenman, Morag M.; Lewis, Arwel; Gani, David Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 16 p. 2297 - 2311

Full Text: HTML

Citation Number: 47

Abstract

The synthesis of a new fused 1, 2, 5-triazepine-1, 5-dione heterocycle, which is expected to mimic structural features of cis-peptidyl prolinamides, is described. The required parent heterocycle, corresponding to cis-glycyl-(2S)-prolinamide, has been prepared in good yield by the cyclisation of N-(2-bromoacetylprolyl) hydrazine which is itself generated in situ from the bromoacetyl proline methyl ester. Analogues corresponding to cis-(2R)-alanyl-and cis- ...