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The reaction of carbanions from 3‐methyl‐5‐phenylisoxazole with electrophilic compounds
Author(s) -
Alberola Angel,
Calvo Luis,
Rodríguez Teresa Rodríguez,
Sañudo Carmen
Publication year - 1992
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.5570290225
Subject(s) - chemistry , electrophile , carbanion , alkylation , halide , alkyl , reactivity (psychology) , methyl group , medicinal chemistry , organic chemistry , catalysis , alternative medicine , medicine , pathology
The reactivity of 3‐methyl‐5‐phenylisoxazole against electrophilic compounds in the presence of different bases is studied. With n ‐BuLi, alkylated products at C‐4 position and C‐3 methyl group, and, in a few cases, dialkylated isoxazoles are obtained. When the reactions are carried out with LICA, the nature of the alkylated products depends on the alkyl halide used. By using LICA‐TMEDA, as deprotonating system, regio‐selective reaction at the C‐3 methyl group is found.