Pyrimidines. 54. Ring transformation of 5-(2-carbamoylvinyl) uracil derivatives to 5-carbamoylpyridin-2-ones

K Hirota, Y Kitade, K Shimada…

Index: Hirota, Kosaku; Kitade, Yukio; Shimada, Kaoru; Maki, Yoshifumi Journal of Organic Chemistry, 1985 , vol. 50, # 9 p. 1512 - 1516

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Citation Number: 22

Abstract

Reaction of 5-formyluracil derivatives 1 with (carbamoylmethy1ene) triphenylphosphorane led to the formation of both the corresponding (2)-and (E)-5-(2-carbamoylvinyl) uracil derivatives 2 and 3. Upon treatment of the 2 isomers 2 with ethanolic sodium ethoxide, a mononuclear heterocyclic rearrangement occurred easily to give 3-(ethoxycarbamoyl) pyridin-6-ones (4) and 3-(N-substituted carbamoyl) pyridin-6-ones (5). Under the ...