V. V. Pinson

Synthesis and structure of 1-methyl-2,3-dihydro-1,2,4-triazolium salts and their free bases

Abstract1-Methyl-2,3-dihydro-1,2,4-triazolium iodides can be obtained by reacting methylhydrazones with S-methylthioamide hydriodides, by condensing 2-methylamidrazone hydriodides with aldehydes and ketones, or by reacting methyl iodide with 1-alkylidene (or arylidene)benzamidrazones. In solutions these salts are capable of undergoing tautomerism to 1-alkylidene(or arylidene)-2-methylamidrazone hydriodides. The influence of the structural factors on the position of the tautomeric equilibrium has been studied. The free bases obtained by neutralization of the respective salts by an alkali metal hydroxide are heretofore undescribed 1-alkylidene(or arylidene)-2-methylhydrazidoimines or 4-triazolines, depending on their structure. Under the action of oxygen, these compounds are readily oxidized to substituted 1-methyl-1,2,4-triazoles with heating.

Tautomerism of 1-methyl-5-amino-2,3-dihydro-1,2,4-triazolium-1-alkylidene(or arylidene)-2-methylaminoguanidinium iodide

Abstract1H and 13C NMR spectroscopy has been used to examine the structures of the products of the condensation of aldehydes and ketones with 1-methyl-1-aminoguanidinium iodide, which in some instances in solution are involved in a ring-chain tautomeric equilibrium between 1-methyl-5-amino-2,3-dihydro-1,2,4-triazolium iodide and 1-alkylidene(or arylidene)-2-methylaminoguanidinium iodide.