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Synthesis of 1,2,3‐Triazole Substituted Isoxazoles via Copper (I) Catalyzed Cycloaddition
Author(s) -
Ramana P. Venkata,
Reddy A. Ram
Publication year - 2012
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.837
Subject(s) - chemistry , isoxazole , hydroxylamine , cycloaddition , hydrolysis , catalysis , copper , organic chemistry , carboxylic acid , triazole , medicinal chemistry , condensation , physics , thermodynamics
The synthesis of a series of 3,5‐disubstituted isoxazole‐4‐carboxylic esters containing N ‐substituted 1,2,3‐triazoles ( V ) starting from various benzaldehydes ( I ) is reported. Benzaldehydes undergo oximation with hydroxylamine hydrosulfate. Later, chlorination followed by condensation with methylacetoacetate and the hydrolysis of the resulting ester afforded respective carboxylic acid ( II ), which on chlorination with PCl 5 gave the corresponding acid chlorides ( III ). The coraboxylic acid chlorides ( III ) on propargylation gave propargylic esters ( IV ) and these on click reaction gave the title compounds ( V ).