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Nitrile oxide cycloaddition routes to 2‐(isoxazolyl)‐benzoates and 2‐(1,2,4‐oxadiazol‐3‐yl)benzoates
Author(s) -
Howe Robert K.,
Schleppnik Frances M.
Publication year - 1982
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.5570190404
Subject(s) - benzoates , nitrile , chemistry , aryl , medicinal chemistry , methyl benzoate , organic chemistry , oxide , alkyl
Cycloaddition of aromatic nitrile oxides to methyl o ‐vinylbenzoate produced methyl 2‐(3‐aryl‐2‐isoxazolin‐5‐yl)benzoates; the isoxazolines were converted to methyl 2‐(3‐arylisoxazol‐5‐yl)benzoates. Reaction of the nitrile oxide from o ‐methoxycarbonylbenzohydroximinoyl chloride ( 11 ) with phenylacetylene, styrenes, and aromatic nitriles resulted in methyl 2‐(5‐phenylisoxazol‐3‐yl)benzoate, methyl 2‐(5‐aryl‐2‐isoxazolin‐3‐yl)‐benzoates ( 15 ), and methyl 2‐(5‐aryl‐1,2,4‐oxadiazol‐3‐yl)benzoates, respectively. The isoxazolines 15 were converted to the corresponding isoxazoles 16 .