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Synthesis of oxazirino[2,3-a][1,5]benzodiazepines by oxidation of 1H-1,5-benzodiazepines with m-chloroperbenzoic acid (MCPBA)

✍ Scribed by Jiaxi Xu; Liangbi Chen

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 145 KB
Volume: 11
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(2000)11:2<158::aid-hc12>3.0.co;2-g

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✦ Synopsis

2,4-Disubstituted 1-benzoyl-2,3-dihydro-1H-1,5-benzodiazepines were oxidized by m-chloroperbenzoic acid (MCPBA) to produce 1a, 3-disubstituted 4-benzoyl-1a,2,3,4-tetrahydro-oxazirino[2,3a][1,5]benzodiazepines, a novel tricyclic heterocyclic system. However, 2,4-disubstituted 2,3-dihydro-1H-1,5-benzodiazepines were oxidized by MCPBA under the same conditions to give a 2,4-disubstituted 2,3dihydro-2-hydroxy-1H-1,5-benzodiazepine or a 2,4-disubstituted 3H-1,5-benzodiazepine, respectively. We propose a hydroxylation mechanism of peracid oxidation.

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