Regiocontrolled synthesis of 3-substituted-6-trifluoromethyl-4(3H)-pyrimidinones
2001; Elsevier BV; Volume: 57; Issue: 14 Linguagem: Inglês
10.1016/s0040-4020(01)00042-4
ISSN1464-5416
AutoresColin M. Tice, Lois M. Bryman,
Tópico(s)Synthesis and Biological Evaluation
ResumoDirect reaction of a variety of N-monosubstituted benzamidines with 4,4,4-trifluoroacetoacetate esters substituted at the 2-position with methyl, ethyl or methoxy afforded moderate to good yields of herbicidal 3-substituted-6-trifluoromethyl-4(3H)-pyrimidinones. Lower yields were obtained with the corresponding 4,4-difluoroacetoacetate esters and the reaction failed with nonfluorinated β-ketoesters. In addition to benzamidines, 3- and 4-pyridylcarboxamidines reacted successfully. The reaction tolerated propyl, allyl, propargyl and phenyl substituents on the amidine nitrogen.
Referência(s)