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A new approach to 5-functionalized 1,2-dihydropyrimidin-2-ones/imines via base-induced chloroform elimination from 4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones/imines
1 , 2 , * 2
1  Russian Technological University, 86 Vernadsky Avenue, 119571 Moscow, Russian Federation
2  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation


A novel four-step methodology for the synthesis of 5-acyl- and 5-arylsulfonyl-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, beta-oxoesters, or alpha-arylsulfonylketones followed by heterocyclization-dehydration of the oxoalkylureas formed gave 5-acyl- or 5-arylsulfonyl-4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones. The latter, in the presence of strong bases, eliminate CHCl3 to give the target compounds. The above methodology was also used in the synthesis of 5-acyl-1,2-dihydropyrimidin-2-imines starting from N-[(1-acetoxy-2,2,2-trichloro)ethyl]-N′-guanidine.

Keywords: 1,2,3,4-Tetrahydropyrimidin-2-ones/imines; 1,2-Dihydropyrimidin-2-ones/imines; Amidoalkylation; Aromatization