Abstract
IT has been observed that the hydrogenation of 3-phenyl-5-acetamidoisooxazole (I; R = Me)1 in ethanol using platinum or Raney nickel catalysts gives rise to a mixture of 2-methyl-4-phenyl-6-hydroxy pyrimidine (II) and N(β-aminocinnamoyl) acetamide (III), melting point 136°. When the latter compound (readily hydrolysed by cold dilute acid to (IV), melting point 105°) was melted, or when its aqueous solution was v armed, a facile cyclization to (II) occurred; taking this reaction into account, the final yield of the pyrimidine is almost quantitative. An intermediate in the hydrogenation may be the isooxazolin (V), by analogy with the products of hydrogenation of isooxazolones2. A similar series of compounds was obtained from (I; R = Ph).
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References
Burns, J., prakt. chim., (2), 47, 126 (1893). Auwers and Wunderling, Ber., 67, 640 (1934).
Shaw, J. Chem. Soc., 1017 (1951).
Lythgoe, Quart. Rev. Chem. Soc., 3, 184 (1949).
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SHAW, G., SUGOWDZ, G. A New Synthesis of Pyrimidines. Nature 172, 955 (1953). https://doi.org/10.1038/172955a0
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DOI: https://doi.org/10.1038/172955a0
