A three-component cyclocondensation reaction for the synthesis of new triazolo[1,5-a]pyrimidine scaffolds using 3-aminotriazole, aldehydes and ketene N,S-acetal.

Karami, Solmaz; Bayat, Mohammad; Nasri, Shima; Mirzaei, Faezeh

This study describes the use of 3-aminotriazole, different aldehydes and N-methyl-1-(methylthio)-2-nitroethenamine as a ketene N,S-acetal in a three-component condensation for the synthesis of a novel library of triazolo[1,5-a]pyrimidine scaffolds. The presence of trichloroacetic acid as a Brønsted-Lowry acidic promoter in acetonitrile or water solvent and room temperature condition resulting novel triazolo[1,5-a]pyrimidine systems named N-methyl-6-nitro-5-aryl-3,5-dihydro-[1, 2, 4]triazolo[1,5-a]pyrimidine-7-amine. The structure of products and direction of the N-cyclization could be confirmed using spectral data. The effect of various solvents on the progress of process was investigated in the paper. The presence of five nitrogen heteroatoms, the use of various aldehydes affording a range of skeletally distinct triazolo[1,5-a]pyrimidine-based heterocycles, the potency to create numerous hydrogen bonds in the product structure, and direction of cyclization are attractive features of this reaction.