C. Kashima, M. Uemori, Y. Tsuda
Aug 1, 1976
Citations
0
Influential Citations
6
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The reaction product of 3,5-dimethylisoxazole (1) with methyl benzoate was found to be 3-methyl-5-(benzoylmethyl)isoxazole in the presence of sodium amide in liquid ammonia. On the other hand, the reaction of 1 with ethyl acetate did not give 3-methyl-5-acetonylisoxazole under similar conditions. The latter reaction product was, however, obtained in a good yield in the presence of lithium amide in liquid ammonia. The reaction of 1 with ketones and aldehydes was proved to give 3-methyl-5-(2-hydroxyalkyl)isoxazoles regiospecifically in the presence of alkali amide. In the above reactions, further alkylation gave 3-methyl-5-(2-alkoxyalkyl)isoxazoles in moderate yields. Compound 1 reacted with acrylaldehyde, crotonaldehyde, and cinnamaldehyde to give 1,2-addition products, 3-methyl-5-(2-hydroxyalkenyl)isoxazoles, exclusively, but methyl cinnamate and cinnamic acid gave only Michael addition products, 4-(3-methyl-5-isoxazolyl)butanoic acid derivatives.