A GENERAL APPROACH TO 4-UNSUBSTITUTED AND 4-ALKYL-SUBSTITUTED 5-ACYL-1,2,3,4-TETRAHYDROPYRIMIDINE-2-THIONES(ONES) <i>VIA</i> α-(THIO)UREIDOALKYLATION OF 1,3-DIKETONES OR β-OXOESTERS

Authors

  • Anatoly D. Shutalev N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Anastasia A. Fesenko N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Elena D. Strel'tsova N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

DOI:

https://doi.org/10.1007/6772

Keywords:

5-acyl-1, 2, 3, 4-tetrahydropyrimidine-2-thiones(ones), N-[alkyl(tosyl)methyl](thio)ureas, Biginelli compounds, 1, 3-diketones, β-oxoesters, α-(thio)ureidoalkylation

Abstract

A new general approach to a large variety of hitherto hardly accessible 4-unsubstituted and 4-alkyl-substituted 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones(ones) has been developed. The approach is based on the reaction of enolates of various 1,3-diketones or β-oxoesters with readily available N-[alkyl(tosyl)methyl]thioureas, N-(azidomethyl)thiourea, and N-[alkyl(tosyl)methyl]ureas followed by TsOH-catalyzed dehydration of the intermediate 4-hydroxyhexahydropyrimidine-2-thiones(ones) without or with isolation of the latter.

Author Biography

Anatoly D. Shutalev, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

Кафедра органической химии, заведующий

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Published

2022-12-20

Issue

Vol. 58 No. 12 (2022)

Section

Original Papers