Hydrolytic cleavages of 7‐nitro‐2‐phenyl‐1,2‐benzisoxazol‐3‐one. Evidence for the occurrence of a benzidine‐like rearrangement of  N,O ‐diphenylhydroxylamines | Zendy

Sheradsky Tuvia | Zendy; AvramoviciGrisaru Schely | Zendy

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Hydrolytic cleavages of 7‐nitro‐2‐phenyl‐1,2‐benzisoxazol‐3‐one. Evidence for the occurrence of a benzidine‐like rearrangement of N,O ‐diphenylhydroxylamines

Author(s) -

Sheradsky Tuvia,

AvramoviciGrisaru Schely

Publication year - 1980

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.5570170137

Subject(s) - benzidine , chemistry , hydrolysis , nitro , cleavage (geology) , amide , bond cleavage , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl , geotechnical engineering , fracture (geology) , engineering

Preparation of the title compound 1 is described. Its treatment with base caused hydrolysis of the amide bond and subsequent benzidine‐like rearrangement to give 4′‐amino‐3‐carboxy‐4‐hydroxy‐5‐nitrobiphenyl (4) . Acid treatment caused cleavage of the nitrogen‐oxygen bond and rearrangement to 7‐nitro‐3‐phenylbenzoxazol‐2‐one (6) .

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