A PASE Approach towards (Adamantyl-1)-, Alkyl- and (Het)Aryl-Substituted [1, 2,4]triazolo[1, 5-d][1, 2,4]triazines: A Sequence of Two Solvent-Free Reactions Bearing Lower E-Factors

Abstract

A Pot, Atom, Step Economic (PASE) approach is reported towards [1, 2,4]triazolo[1, 5-d][1, 2,4]triazines, substituted with the azole ring with pharmacophore residues, such as 1-adamantyl or 2-furanyl moieties, naproxen residues, as well aliphatic and (het)aromatic substituents, starting from easily available 1,2,4-triazine-5-carbonitriles and carboxylic acids hydrazides. This approach involves a sequence of two solvent-free reactions accompanied by the Dimroth rearrangement on the last step. The structures of the final Dimroth rearrangement products were confirmed based on the DFT studies as well as the single crystal X-ray analysis for the admantane-substituted product. In addition, this method possesses lower E-factors.