A novel protocol for catalyst-free synthesis of fused six-member rings to triazole and pyrazole

Mol Divers. 2020 Feb;24(1):225-231. doi: 10.1007/s11030-019-09944-5. Epub 2019 Apr 1.

Abstract

Herein, an effectual, quick and novel method is described for the synthesis of new triazolo[1,5-a]pyrimidine, triazolo[5,1-b][1,3] thiazine and pyrazolo[1,5-a]pyrimidine derivatives. This series of fused six-member rings to triazole and pyrazole was prepared via the catalyst-free reaction of dialkyl acetylenedicarboxylates and 3-substituted 1H-1,2,4-triazole or 3-amino-1H-pyrazole-4-carbonitrile. The structures of the prepared products were deduced from their Fourier-transform infrared, elemental analysis and proton and carbon-13 nuclear magnetic resonance spectral data. A novel and green method is described for the synthesis of new triazolo[1,5-a]pyrimidine, triazolo[5,1-b][1,3] thiazine and pyrazolo[1,5-a]pyrimidine derivatives.

Keywords: 3-Amino-1H-1,2,4-triazole; 3-Amino-1H-pyrazole-4-carbonitrile; Dialkyl acetylenedicarboxylates; Pyrazolo[15-a]pyrimidine; Triazolo[1,5-a]pyrimidine; Triazolo[5,1-b][1,3] thiazine.

MeSH terms

  • Chemistry Techniques, Synthetic*
  • Molecular Structure
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Spectrum Analysis
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • Pyrazoles
  • Triazoles