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

作者：Fesenko Anastasia A; Solovyev Pavel A; Shutalev Anatoly D^*

来源：Tetrahedron, 2010, 66(4): 940-946.

DOI：10.1016/j.tet.2009.11.099

• 1,2,3,4-Tetrahydropyrimidin-2-ones
• 1,2-Dihydropyrimidin-2-ones
• Ureidoalkylation
• Aromatization

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 beta-oxoesters followed by heterocyclization-dehydration of the oxoalkylureas formed gave 5-acyl-4-trichloromethyl-1,2,3,4-tetrahydtopyrimidin-2-ones. The latter, in the presence of NaH, eliminate CHCl(3) to give the target compounds.

• 出版日期2010-1-23