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Nucleophilic displacement of aromatic fluorine, part I, synthesis of benzisoxazoles
Author(s) -
Walser Armin,
Flynn Thomas,
Fryer R. Ian
Publication year - 1974
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.5570110608
Subject(s) - chemistry , aromatization , acetic anhydride , quinazoline , nucleophile , hydrolysis , hydride , organic chemistry , fluorine , hydrogen , catalysis
The quinazoline 3‐oxides 2 were found to convert to the benzisoxazoloquinazolines 3 by heating in acetic anhydride. The dihydroquinazoline 3‐oxides 1 underwent aromatization to 4 under the same conditions. Hydrolysis of 3 or 2 led to the 3‐(2‐aminophenyl)benzisoxazoles 8 which could be rearranged to the 3‐(2‐hydroxyphenyl)indazoles 11 by treatment with hydride. Possible mechanisms are discussed.