Dihalotriphenylphosphoranes in heterocyclic synthesis. Part 8. Reactions of uracils. 6. New ring transformations of 6-aminouracils with acetylenedicarboxylates to …

H Wamhoff, W Schupp, A Kirfel…

Index: Wamhoff, Heinrich; Schupp, Winfried; Kirfel, Armin; Will, Georg Journal of Organic Chemistry, 1986 , vol. 51, # 2 p. 149 - 154

Full Text: HTML

Citation Number: 0

Abstract

Treatment of 6 4 (triphenylphosphoranylidene) amino]-l, 3-dimethyluracils 8 with dialkyl acetylenedicarboxylates in aprotic solvents affords zwitterionic pyridinedionates 12, involving a novel ring transformation reaction, via cleaving attack of a terminal carbanion to the 2-carbonyl of the uracil. In protic solvents 12 undergo a smooth heterocyclization reaction to give the pyrrolo [3, 4c] pyridies 14. The structures of 12b and 14b have been ...