Triple equilibrium in n′-aryl-n-tosyldiazomalonimidolates, 1-tosyl-1,2,3-triazol-5-olates, and 1-aryl-1,2,3-triazol-5-olates / Morzherin Yu.Yu., Rozin Yu.A., Savel'eva E.A., Bakulev V.A. // Chemistry of Heterocyclic Compounds. - 2003. - V. 39, l. 2. - P. 168-173.

ISSN:

00093122

Type:

Article

Abstract:

A series of 1-tosyl-substituted 4-arylcarbamoyl-1,2,3-triazol-2-olates, which can undergo rearrangement to isomeric 1-aryl-4-tosylcarbamoyl-1,2,3-triazol-5-olates and N-tosyl-N′-aryldiazomalonimidolates, were synthesized. An equilibrium between these compounds is observed in solutions in DMSO. The introduction of an electron-withdrawing substituent into the aryl residue increases the stability of the 1-tosyl-1,2,3-triazoles but reduces the stability of the 1-aryl-1,2,3-triazoles. π-Donating substituents increase the stability of the open-chain structure.

Author keywords:

1,2,3-triazoles; Diazo compounds; Diazo transfer reaction; Equilibrium; Sulfonamides

Index keywords:

1,2,3 triazole derivative; dimethyl sulfoxide; malonic acid derivative; triazole derivative; article; synthesis

DOI:

10.1023/A:1023756005530

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0037817844&doi=10.1023%2fA%3a1023756005530&partnerID=40&md5=9d07795359e7113710b7afa35a49dce4

Соавторы в МНС:

Другие поля

Поле	Значение
Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0037817844&doi=10.1023%2fA%3a1023756005530&partnerID=40&md5=9d07795359e7113710b7afa35a49dce4
Affiliations	Urals State Technical University, Ekaterinburg 620002, Russian Federation
Author Keywords	1,2,3-triazoles; Diazo compounds; Diazo transfer reaction; Equilibrium; Sulfonamides
Chemicals/CAS	1,2,3 triazole derivative, 53897-99-7; dimethyl sulfoxide, 67-68-5
References	Aran, V.J., Goya, P., Ochoa, C., (1988) Adv. Heterocycl. Chem., 44, p. 81; Gazieva, G.A., Kravchenko, A.N., Lebedev, O.V., (2000) Usp. Khim., 69, p. 239; Yanagisawa, Y., Hirata, Y., Ishii, Y., (1987) J. Med. Chem.,, 30, p. 1787; Ahija, P., Singh, J., Asthama, M.B., Sardana, V., Anand, N., (1989) Indian J. Chem., 28 B, p. 1034; Hamprecht, G., Köning, K.-H., Stubenrauch, G., (1981) Angew. Chem., 93, p. 151; Groutas, W.C., Kuang, R.Z., VenKataraman, R., (1994) Biochem. Biophys. Res. Commun., 198, p. 341; Lebedev, A.T., Bakulev, V.A., Kolobov, M.Yu., (1991) Org. Mass Spectrom., 26, p. 789; Morzherin, Yu.Yu., Rozin, Yu.A., Vorob'Eva, E.A., Bakulev, V.A., (2001) Khim. Geterotsikl. Soedin., p. 612; Kolobov, M.Yu., Bakulev, V.A., Mokrushin, V.S., (1992) Khim. Geterotsikl. Soedin., p. 1208
Correspondence Address	Morzherin, Yu.Yu.; Urals State Technical University, Ekaterinburg 620002, Russian Federation; email: morjerine@htf.usm.ru
CODEN	CHCCA
Language of Original Document	English
Abbreviated Source Title	Chem. Heterocycl. Compd.
Source	Scopus