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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) .