Journal of the Chemical Society. Perkin transactions I p. 943 - 946 (1981)
Update date:2022-08-05
Topics:
Nishio, Takehiko
Katahira, Katsuhiro
Omote, Yoshimori
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).
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