Various 4‐substituted 1,2,3‐benzotriazines (2, 6, 7) have been prepared and of particular interest was the 4‐azido derivative (11) as a potential azidotetrazolo tautomerism exhibiting compound. However, no such interconversion could be established and this compound exists exclusively in the azido form. 2,5‐bis‐(Arylamino)‐1,3,4‐thiadiazoles (9) have been found to result from the reaction between 4‐hydrazino‐1,2,3‐benzotriazine and aryl isothiocyanates. In addition, a ring opening reaction between 4‐hydrazino‐1,2,3‐benzotriazine gave 2‐(tetrazol‐5″‐yl)‐2′,4′‐dihy‐droxyazobenzene (10) and photochemical conversion of the 4‐azido derivative gave s‐tetrazino‐[2,3‐b:5,6‐b′]diindazole(12).
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Stanovnik et al. (1971) studied this question.