Pyrimidine Derivatives and Related Compounds, V Synthesis of Some Isoxazolo [2,3-a] pyrimidines. A New Ring System

Abstract

3-Amino-5-phenyl-4-phenylazoisoxazole (1) reacts with ethyl acetoacetate to yield the corresponding ethyl isoxazolylaminocrotonate derivative (2) which could be thermally cyclized into the isoxazolopyrimidine derivative (4). On the other hand, condensation of 1 with ethoxymethylenemalononitrile has resulted in the formation of the aminoethylene derivative (5). Compound 1 reacted with acrylonitrile to yield the isoxazolo[2,3-a]pyrimidine derivative (6). The latter was converted into the corresponding exo derivative (8) by the action of acetic acid-hydrochloric acid mixture. Compound 1 also reacted with methoxycarbonyl-, ethoxycarbomyl- and benzoyl isothiocyanates to yield the isoxazolylthioureas (10a, b) and (11), respectively. The reaction of 2 with acetic acid-hydrochloric acid and with phenylhydrazine is reported.