74442-97-0Relevant academic research and scientific papers
Heterocyclic transformations. Part 7. Unprecedented transformations of 1,3-dialkyl-5-formyluracils to 1,3-dialkyl-7-hydroxyquinazolines
Singh, Harjit,Singh, Palwinder,Chimni, Swapandeep Singh,Kumar, Subodh
, p. 2363 - 2368 (2007/10/02)
1,3-Dialkyl-5-formyluracil reacts with ethyl acetoacetate, acetylacetone, benzoylacetone, acetoacetamide and acetoacetanilide under phase transfer catalytic conditions to provide exclusively the annulation products: 6-substituted-1,3-dialkyl-7-hydroxyquinazolines or/and also 4-hydroxybenzamide derivatives.Similar reaction with cyanoacetamide provides 6-cyano-7-hydroxy-1,3-dimethylpyridopyrimidine.The reaction mechanism prevailing in these reactions has been rationalized.
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
Hirota, Kosaku,Kitade, Yukio,Senda, Shigeo
, p. 3949 - 3953 (2007/10/02)
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.
