Synthesis and properties of azoles and their derivatives

Abstract

The reaction of 4,4-dinitrovaleronitrile with hydrogen chloride and methanol gives the hydrochloride of the methyl imino ester of 4,4-dinitrovaleric acid. The latter is converted to the free imino ester, amide, and methyl ester of 4,4-dinitrovaleric acid. The same hydrochloride readily condenses with ethylenediamine, o-phenylenediamine, or o-aminophenol to give, respectively, imidazoline, benzimidazole, or benzoxazole, which contain aγ,γ-dinitrobutyl radical in the 2-position. The methyl imino ester of 4,4-dinitrovaleric acid is rapidly converted to 2,4,6-tris(γ,γ-dinitrobutyl)-1,3,5-triazine at room temperature.