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Synthesis of a novel ring-expanded nucleoside analogue containing the imidazo[4,5-e][1,3]diazepine ring system with a guanidinocarbamoyl-substituted cyclopropylidene group in place of a sugar moiety

✍ Scribed by Huan-Ming Chen; Ramachandra S. Hosmane; Donna M. Baldisseri

Publisher: Journal of Heterocyclic Chemistry
Year: 2000
Tongue: English
Weight: 217 KB
Volume: 37
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570370444

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✦ Synopsis

Abstract

The synthesis of a novel ring‐expanded nucleoside analogue, (Z)‐1‐((2‐Guanidinocarbamoyl‐cyclopropylidene)methyl)‐4,5,7,8‐tetrahydro‐6__H__‐6‐iminoimidazo[4,5‐e][1,3]diazepine‐4,8‐dione (1) has been reported. It was prepared starting from methyl imidazole‐4,5‐dicarboxylate by sequential condensations with 2‐bromo‐2‐bromomethylcyclopropane‐1‐carboxylate and guanidine. The overall yield for the two‐step synthesis is 46%.

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