Tetrahedron

A novel convenient synthesis of 5-acyl-1, 2-dihydropyrimidin-2-ones via 4-trichloromethyl-1, 2, 3, 4-tetrahydropyrimidin-2-ones

AA Fesenko, PA Solovyev, AD Shutalev

Index: Fesenko, Anastasia A.; Solovyev, Pavel A.; Shutalev, Anatoly D. Tetrahedron, 2010 , vol. 66, # 4 p. 940 - 946

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Citation Number: 17

Abstract

A novel four-step methodology for the synthesis of 5-acyl-1, 2-dihydropyrimidin-2-ones has been developed. The reaction of readily available N-[(1-acetoxy-2, 2, 2-trichloro) ethyl] ureas with Na-enolates of 1, 3-diketones or β-oxoesters followed by heterocyclization–dehydration of the oxoalkylureas formed gave 5-acyl-4-trichloromethyl-1, 2, 3, 4-tetrahydropyrimidin-2- ones. The latter, in the presence of NaH, eliminate CHCl3 to give the target compounds.