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The unexpected rearrangement of 1,5-benzodiazepin-2,4-dione to a benzimidazol-2-one derivative during N,N'-diglucosylation

✍ Scribed by Brahim Lakhrissi; Mohamed Massoui; El Mokhtar Essassi; Vincent Lequart; Nicolas Joly; Patrick Martin; Gérard Goethals

Publisher: Journal of Heterocyclic Chemistry
Year: 2004
Tongue: English
Weight: 74 KB
Volume: 41
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570410627

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✦ Synopsis

Abstract

Reaction of 1,5‐benzodiazepin‐2,4‐dione with 3‐O‐substituted‐5,6‐anhydro‐1,2‐isopropylidene‐α‐D‐glucofuranose gave the unexpected N,N'‐di‐glucofuranosyl benzimidazol‐2‐one by a novel rearrangement and ring closure reaction. A mechanism is proposed.

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