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5‐Oxazolones, IV. Reactions of 5(4 H )‐oxazolones with triphenylphosphonium methylides
Author(s) -
Erba Emanuela,
Gelmi Maria Luisa,
Pocar Donato
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881210828
Subject(s) - chemistry , ylide , wittig reaction , oxazolone , medicinal chemistry , oxazole , yield (engineering) , stereochemistry , organic chemistry , materials science , metallurgy
The Wittig reaction of ethyl (triphenylphosphoranylidene)acetate ( 2a ) with the carbonyl group of trisubstituted 5(4 H )‐oxazolones 1a – c afforded ethyl 5(4 H )‐oxazolylideneacetates 3a – c and triphenylphosphane oxide. Starting from oxazolones 1d – i and ylide 2a , methyleneoxazoles 3d, e and ethyl 5‐oxazoleacetates 4a – f were obtained besides ylides 5a – e deriving from the nucleophilic attack of the ylide at 1 and subsequent opening of the oxazole ring. Oxazolones 1a – c reacted also with triphenylphosphonium phenylmethylide ( 2b ) to yield methyleneoxazoles 3f,g and ylides 5f – h . By treating triphenylphosphonium methylide ( 2c ) and ‐methoxymethylide ( 2d ) with 1a – c only open‐chain compounds 5i – k and 5l – n , respectively, were obtained.