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The unexpected rearrangement of 1,5‐benzodiazepin‐2,4‐dione to a benzimidazol‐2‐one derivative during N,N' ‐diglucosylation
Author(s) -
Lakhrissi Brahim,
Massoui Mohamed,
Essassi El Mokhtar,
Lequart Vincent,
Joly Nicolas,
Martin Patrick,
Goethals Gérard
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410627
Subject(s) - chemistry , derivative (finance) , ring (chemistry) , closure (psychology) , medicinal chemistry , stereochemistry , organic chemistry , economics , financial economics , market economy
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.