DBU-catalyzed, aromatization-oriented, regioselective domino synthesis of 2-aminopyrimidines from β-dicarbonyl compounds, DMF-DMA, and cyanamide

Mol Divers. 2017 Nov;21(4):925-932. doi: 10.1007/s11030-017-9770-7. Epub 2017 Aug 1.

Abstract

A multicomponent domino synthesis has been developed for the preparation of 2-aminopyrimidines from β-dicarbonyl compounds, N,N-dimethylformamide dimethyl acetal, and cyanamide. The protocol was used for the regioselective preparation of 4-amide/ester/ketone substituted 2-aminopyrimidines. Twelve 2-aminopyrimidines were isolated in good yields (56-93%).

Keywords: -Dicarbonyl compound; 2-Aminopyrimidine; Cyanamide; DBU; Domino synthesis; Four-component; MCR.

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyanamide / chemistry*
  • Cyclization
  • Dimethylformamide / analogs & derivatives*
  • Dimethylformamide / chemistry
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry*
  • Stereoisomerism

Substances

  • Pyrimidines
  • 2-aminopyrimidine
  • Cyanamide
  • dimethylformamide-dimethylacetal
  • Dimethylformamide