SYNTHESIS AND INVESTIGATION OF RING–CHAIN ISOMERISM OF THE DERIVATIVES OF N-AMINO-5-HYDROXY-1,2,3-TRIAZOLE-4-CARBOXYLIC ACID

Abstract

A series of sodium salts of 4-substituted 1-amino-5-hydroxy-1,2,3-triazoles was obtained by the "diazo transfer" reaction to arylmethylene-protected α-ethoxycarbonyl‑ and α-(methylcarbamoyl)-acetohydrazides. In DMSO solution the corresponding neutral hydroxytriazoles exist in equilibrium with the isomeric diazo compounds with an open chain. Electron-donating substituents stabilize the cyclic form. A good correlation was obtained between the equilibrium constants and the Hammett σ‑constants. During the diazotization of benzaldehyde α-amino-α-cyanoacetylhydrazone the initially formed diazo compound undergoes spontaneous cyclization in solution to hydroxytriazole. Removal of the arylmethylene protection leads to N-unsubstituted sodium salts of 1-amino-5-hydroxytriazoles, but acidification of the latter leads to diazoacetohydrazides with an open chain.

How to Cite
Rozin, Yu. A.; Vorob'ova, E. A.; Morzherin, Yu. Yu.; Bakulev, V. A. Chem. Heterocycl. Compd. 2001, 37, 294. [Khim. Geterotsikl. Soedin. 2001, 323.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1017598814562