Abstract
Monoacylketene aminals containing an unsubstituted NH2 group react as C-nucleophiles with benzoyl isothiocyanate to give the corresponding thioamides which undergo cyclization by sodium methoxide in methanol to afford 6-R-amino-5-acetyl-2-phenyl-3H-pyrimidine-4-thiones. A scheme for constructing the pyrido[2,3-d]pyrimidine system from keteneaminals is offered. The reaction of 6-R-amino-5-acetyl-2-phenyl-3H-pyrimidine-4-thiones with dimethylformamide dimethylacetal leads to 8-R-N-4-methylthio-8H-pyrido-[2,3-d]pyrimidine-5-ones. Cyclization of 5-acetyl-6-benzoylamino-4-methylthio-2-phenylpyrimidine by sodium methoxide yields N-unsubstituted 4-methylthio-8H-pyrido-[2,3-d]pyrimidine-5-one.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1932–1937, November, 1993
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Dorokhov, V.A., Komkov, A.V., Shashkova, E.M. et al. Synthesis of functionalized pyrimidine-4-thiones and derivatives of pyrido[2,3-d]pirimidine-5-one from monoacylketene aminals. Russ Chem Bull 42, 1848–1854 (1993). https://doi.org/10.1007/BF00699001
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DOI: https://doi.org/10.1007/BF00699001