Issue 0, 1981

Photochemical ring opening of 1-arylpyrimidin-2(1H)-ones

Abstract

The photochemical reactions of 1-arylpyrimidin-2(1H)-ones have been examined. Irradiation of the 1-arylpyrimidin-2(1H)-ones (3a–f) in benzene–methanol gave 1-alkoxycarbonylamino-3-aryliminoprop-1-enes (4), (6), and (7), which were hydrolysed to give the corresponding 3-alkoxycarbonylaminoprop-2-enal (5), in 45–55% yield. The formation of the N-arylimine products (4), (6), and (7) was presumed to arise from an unstable isocyanate intermediate (8) formed initially by Type I cleavage of the 1-arylpyrimidin-2(1H)-one (3).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 943-946

Photochemical ring opening of 1-arylpyrimidin-2(1H)-ones

T. Nishio, K. Katahira and Y. Omote, J. Chem. Soc., Perkin Trans. 1, 1981, 943 DOI: 10.1039/P19810000943

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