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Chemistry of 5(2 H )‐isoxazolones: Novel conversion of positional isomers
Author(s) -
Batra Sanjay,
Akhtar Mohammad Shamim,
Seth Manju,
Bhaduri Amiya Prasad
Publication year - 1990
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.5570270242
Subject(s) - chemistry , pyridinium chlorochromate , methyl iodide , medicinal chemistry , pyridinium , nucleophile , iodide , organic chemistry , catalysis
Reactions of 4‐arylidene‐3‐methyl‐5(4 H )‐isoxazolones with nucleophiles lead to 4‐substituted‐benzyl‐3‐methyl‐5(2 H )‐isoxazolones. Formation of 5(4 H )‐ and 5(2 H )‐isoxazolone derivatives have been observed when 4‐substituted‐arylidene‐3‐rriethyl‐5(4 H )‐isoxazolones are reacted with methyl magnesium iodide. Oxidation of 4‐substituted‐benzyl‐3‐methyl‐5(2 H )‐isoxazolones with manganic acetate and pyridinium chlorochromate, gives 4,4′‐bis[4‐substituted‐benzyl‐3‐methyl‐5(4 H )‐isoxazolone]. Oxidation of 4‐substituted‐benzyl‐3‐methyl‐5(2 H )‐isoxazolones with metachloroperbenzoic acid gives 4‐hydroxy‐4‐substituted‐benzyl‐3‐methyl‐5(4 H )‐isoxazolones and reactions of the same substrates with N ‐bromosuccinimide furnish 4‐bromo‐4‐substitutedbenzyl‐3‐methyl‐5(4 H )isoxazolones.