Synthesis and investigation of ring-chain isomerism of the derivatives of N-amino-5-hydroxy-1,2,3-triazole-4-carboxylic acid / Rozin Yu.A., Vorob'ova E.A., Morzherin Yu.Yu., Bakulev V.A. // Chemistry of Heterocyclic Compounds. - 2001. - V. 37, l. 3. - P. 294-304.

ISSN:

00093122

Type:

Article

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 aryhmethylene protection leads to N-unsubstituted sodium salts of 1-amino-5-hydroxytriazoles, but acidification of the latter leads to diazoacetohydrazides with an open chain.

Author keywords:

Diazo-transfer reaction; Diazomalonomonohydrazide; Equilibrium constants; Hammett equation; Ring-chain isomerism

Index keywords:

1,2,3 triazole derivative; acetohydrazide; carbenoid; dimethyl sulfoxide; n amino 5 hydroxy 1,2,3 triazole 4 carboxylic acid; unclassified drug; acidification; article; correlation analysis; cyclizati

DOI:

10.1023/A:1017598814562

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https://www.scopus.com/inward/record.uri?eid=2-s2.0-0035295947&doi=10.1023%2fA%3a1017598814562&partnerID=40&md5=059abe0118f4ebbdfb5580018ff62f8f

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Поле	Значение
Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0035295947&doi=10.1023%2fA%3a1017598814562&partnerID=40&md5=059abe0118f4ebbdfb5580018ff62f8f
Affiliations	Urals State Technical University, Ekaterinburg, Russian Federation
Author Keywords	Diazo-transfer reaction; Diazomalonomonohydrazide; Equilibrium constants; Hammett equation; Ring-chain isomerism
References	Wamhoff, H., (1984) Comprehensive Heterocyclic Chemistry, 5, p. 350. , (Ed. A. R. Katritzky and C. Rees), Pergamon, Oxford, Ch. 4.11; L'abbe, G., Bruynseels, M., Beenaerts, M., Vandendriessche, A., Delbelke, P., Toppet, S., (1989) Bull. Soc. Chim. Belg., 98, p. 343; Curtius, T., Jermias, B., (1926) J. Pr. Chem., 112, p. 88; Rosin, Yu.A., Vorob'eva, E.A., Morzherin, Yu.Yu., Yakimov, A.C., Dehaen, W., Bakulev, V.A., (1998) Mendeleev Commun., 6, p. 240; Bakulev, V.A., Kappe, C.O., Padva, A., (1996) Organic Synthesis: Theory and Applications, 3, p. 149. , JAI Press Inc., Greenwich, London; Bakulev, V.A., Morzherin, Yu.Yu., Lebedev, A.T., Dankova, E.F., Kolobov, M.Yu., Shafran, Yu.M., (1993) Bull. Soc. Chim. Belg., 102, p. 493; Bakulev, V.A., Tarasov, E.V., Morzherin, Yu.Yu., Luyten, I., Toppet, S., Dehaen, W., (1998) Tetrahedron, 54, p. 8501; Kolobov, M.Yu., Bakulev, V.A., Mokrushin, V.S., (1992) Khim. Geterotsikl. Soedin., p. 1208; Dimroth, O., (1904) Lieb. Ann. Chem., 335, p. 1; Huisgen, R., (1980) Angew. Chem. Int. Ed. Engl., 19, p. 947; Zhdanov, Yu.A., Minkin, V.I., (1966) Correlation Analysis in Organic Chemistry [in Russian], p. 470. , Izd. Rost. Un-ta, Rostov-on-Don; Curtius, T., Hochschwender, K., (1930) J. Pr. Chem., 125, p. 218; Kolobov, M.Yu., Bakulev, V.A., Mokrushin, V.S., Lebedev, A.T., (1987) Khim. Geterotsikl. Soedin., p. 1503
Correspondence Address	Rozin, Yu.A.; Urals State Technical University, Ekaterinburg, Russian Federation; email: vab@htf.ustu.ru
CODEN	CHCCA
Language of Original Document	English
Abbreviated Source Title	Chem. Heterocycl. Compd.
Source	Scopus