Convenient Synthesis of [1,2,4]Triazolo[4,3-a][1,3,5]triazin-5-amines, [1,2,4]Triazolo[4,3-c][1,3,5]thiadiazine-5-thiones, and [1,2,4]Triazolo[4,3-c][1,3,5]thiadiazin-5-imines from N-(4H-1,2,4-Triazol-3-yl) Carboximidates

Abstract

The condensation of 4H-1,2,4-triazol-3-amine with ortho esters derived from acetic, propionic, and benzoic acids gave the corresponding N-(4H-1,2,4-triazol-3-yl) carboximidates which were treated with cyan-amide, carbon disulfide, and sodium thiocyanate to afford 7-substituted [1,2,4]triazolo[4,3-a][1,3,5]triazin-5-amines, [1,2,4]triazolo[4,3-c][1,3,5]thiadiazine-5-thiones, and [1,2,4]triazolo[4,3-c][1,3,5]thiadiazin-5-imines, respectively. The structures of the synthesized compounds were confirmed by IR, ¹H and ¹³C NMR, and mass spectra and elemental analyses.