Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids

The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation an...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2016-05, Vol.12 (1), p.874-881
Main Authors: Dzhons, Daria Yu, Budruev, Andrei V
Format: Article
Language:English
Subjects:
1,5-electrocyclization
2,1-benzisoxazolones
aryl azides
azepinones
Chemistry
Full Research Paper
nitrenes
photochemical cyclization
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Summary:The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation and photolysis of 2-azidobenzoate anions.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.12.86