Chemistry of 5(2 H )‐isoxazolones: Novel conversion of positional isomers | Zendy

Batra Sanjay | Zendy; Akhtar Mohammad Shamim | Zendy; Seth Manju | Zendy; Bhaduri Amiya Prasad | Zendy

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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.

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