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Diastereoselective nitrilimine cycloaddition to the CN bond of enantiopure 1,4-benzodiazepinones

✍ Scribed by Giorgio Molteni; Gianluigi Broggini; Tullio Pilati

Book ID: 104359501
Publisher: Elsevier Science
Year: 2002
Tongue: English
Weight: 255 KB
Volume: 13
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(02)00663-8

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✦ Synopsis

Enantiopure 1,4-benzodiazepin-4-one 1 and 1,4-benzodiazepin-6-ones 2 were reacted with hydrazonoyl chloride 8 in the presence of various basic agents. The diastereoselective 1,3-dipolar cycloaddition between the C N double bond of 1 or 2 and the nitrilimine intermediate 9 gave the enantiopure [1,2,4]triazolo [4,3-a][1,4]benzo diazepinones 10-13.

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