Pyrimidine Derivatives and Related Compounds. 39. A Novel Cycloaromatization Reaction of 5-Formyl-1,3-dimethyluracil with Three-Carbon Nucleophiles. Synthesis of Substituted 4-Hydroxybenzoates

Article abstract of DOI:10.1021/jo00333a003

Treatment of 5-formyl-1,3-dimethyluracil (1) with α-substituted acetone derivatives (C-C-C type nucleophiles) such as acetylacetone, acetoacetamide, ethyl acetoacetate, and phenylacetone in basic media affords the corresponding 4-hydroxybenzoates (4).On the other hand, treatment of 1 with cyanoacetamide, a C-C-N type nucleophile, gives the nicotinate 8.A mechanism for this cycloaromatization was proposed on the basis of reaction of 5-formyl-1,3-dimethyluracil-d1 (6) with acetylacetone.