N -Alkylation of 4-Trichloromethylpyrimidinones: Synthesis of Some New and Interesting Modified Nucleoside Analogues
Nilo Zanatta, Patrícia B. Brondani, Simone S. Amaral, Taritza D. Oliveira, Helio G. Bonacorso and Marcos A.P. Martins
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97.105-900, Santa Maria, RS, Brazil.
Abstract
The N1-alkylation of 4-(trichloromethyl)pyrimidin-2(1H)-one, 4-methoxy-4-(trichloromethyl)-3,4-dihydropyrimidin- 2(1H)-one, and 5-bromo-4-methoxy-4-(trichloromethyl)-3,4-dihydropyrimidin-2(1H)-one with selected alkylating agents such as 2-chloroacetamide, diethyl 2-bromomalonate, and 5-bromo-1,1,1-trichloro-4-methoxypent-3-en-2-one, is presented. Further reactions of 1-[5,5,5-trichloro-2-methoxy-4-oxo-penten-2-yl]4-trichloromethyl-pyrimidin-2(1H)-one with primary amines and aminoalcohols furnished a series of unexpected new acyclic nucleoside analogues.
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