Pyrimidine Derivatives and Related Compounds, V Synthesis of Some Isoxazolo [2,3-a] pyrimidines. A New Ring System
Open Access
- 1 March 1977
- journal article
- Published by Walter de Gruyter GmbH in Zeitschrift für Naturforschung B
- Vol. 32 (3) , 311-314
- https://doi.org/10.1515/znb-1977-0316
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.Keywords
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