A series of C-amino-1,2,4-triazoles, substituted with methyl, dimethylamino, methoxy, and methylthio groups, was prepared from the appropriate JV-cyanoazomethines and either hydrazine or methylhydrazine (eq 1). C-Azido-1,2,4-triazoles were prepared from the corresponding amines by diazotization followed by reaction with azide ion. When these diazotization reactions were carried out, the C-amino-1,2,4-triazoles derived from methylhydrazine, unlike those derived from hydrazine, yielded varying quantities of products depending on the acidity of the reaction media. Ir and proton nmr spectra of the C-azido-1,2,4-triazoles in various solvents indicated that none of them participates in imidoyl azide-tetrazole tautomerism, even at -82°.

A study of low resolution mass spectra of 1,2,4-triazoles shows that fragmentations of C-amino-l,2,4-triazole nuclei are analogous to the three fragmentation modes reported for pyrrole. The extent to which these fragmentations account for the peaks in the mass spectra depends on the substituents of the 1,2,4-triazoIes. Mass spectra of C-azido-l,2,4-triazoles cannot be interpreted by the three modes found for pyrrole. Without exception, their mass spectra contain a base peak which is shown, with the aid of deuterium labeling, to represent an ion formed by the loss of four nitrogen atoms plus the substituent on the endocyclic nitrogen atom.

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Aus den N‐Cyano‐azomethinen (I) und den Hydrazinen (II) entstehen die isomeren C‐Amino‐l ,2,4‐triazole (III) bzw. (IV).