1.2.3- Triazole, 4-diazo-5-carboxamide

In the reaction of 4-diazotriazoles with morpholine, pyrrolidine [83DIS(B)(43)2557], and several other secondary amines (66JMC733), the corresponding triazenes 247 were obtained. Also, in the case of 4-diazo-l,2,3-triazole-5-carboxamide, these compounds could easily be obtained in organic solvents despite the competing intramolecular ring closure to 2,8-diazahypoxanthine. In aqueous media, the intermolecular coupling... 

Halotriazoles 249 (X = Cl, Br, I) were obtained by Sandmeyer reactions of 4-diazotriazoles [66JMC733 83DIS(B)(43)2557]. Reduction of 4-diazo-l,2,3-triazole-5-carboxamide with semicarbazide led to a mixture of the corresponding azido- and amino-triazoles (73JHC839). 

Diazonium salts (165), derived from 4- or 5-aminotriazoles (164), undergo ready displacement of the nitrogen like other aromatic diazonium salts. Thus, 5-diazo-l,2,3-triazole-4-carboxamide is rapidly converted into the corresponding iodide (166) (66JMC733). 

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