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The diazoimine/triazole equilibria of diazo substituted azoles are not well documented in the literature. Data have been reported for thiazoles,1.* thiadiazoles, 1 thiatriazoles3 and tetrazoles.4 but no information is available for oxazoles and oxadiazoles. In this investigation we wanted to fill this gap by considering some diazo derivatives of the title compounds.The diazoacyl substituted azoles 1 (281, mp 85°C from CHC13/Et20), 2 (65%, mp 58°C from CHCI,/Et20), 3 (36%, mp 71°C from EtOH) and 4 (48%, mp 142°C from CHCI,/Et20) were prepared I3C NMR spectrum (DMSO-d6). The triazole form 8 was not observed. Ph J 8 CONHPh L 7

5-Azidotriazoles bearing a thiazole, benzothiazole or pyridine ring at the 4-position were synthesized and thermolyzed at 60°C. Whereas the 5-azido-4-(thiazol-2-yl)triazole 4 decomposed with extrusion of nitrogen and formation of the triazene 5 as the sole reaction product, the 5-azido-4-(benzothiazol-2-yl)triazoles 1 la,b furnished mixtures of the triazenes 12a,b and the tetrazoles 14a,b. In the case of the 5-azido-4-(2-pyridyl)triazoles 17ad, the product distribution was found to depend strongly on the N-1 aryl substituent, favouring the tetrazole 20 by increasing the electron-withdrawing capacity of this group.

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