Synthesis and properties of 1-arylsulfonyl-1,2,3-triazol-5-olates / Morzherin Yu.Yu., Rozin Yu.A., Vorob'eva E.A., Bakulev V.A. // Chemistry of Heterocyclic Compounds. - 2001. - V. 37, l. 5. - P. 560-566.

ISSN:

00093122

Type:

Article

Abstract:

A series of 1-arylsulfonyl-4-carbamoyl-1,2,3-triazol-5-olates has been synthesized. The cyclization of diazoacetamides by the action of base has been shown to be reversible for the first time. 1-Arylsulfonyl-1,2,3-triazol-5-olates undergo rearrangement upon heating to give isomeric N-sulfonylcarbamoyldiazoacetimidolates. An equilibrium exists between these isomers in DMSO solution, which is shifted toward the acyclic derivative.

Author keywords:

Diazo transfer reaction; Diazomalonimidolates; Ring-chain isomerization; Thermodynamic stability

Index keywords:

нет данных

DOI:

10.1023/A:1011648303788

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0347238239&doi=10.1023%2fA%3a1011648303788&partnerID=40&md5=7dfc608810b934a4724d4d6ca213b993

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0347238239&doi=10.1023%2fA%3a1011648303788&partnerID=40&md5=7dfc608810b934a4724d4d6ca213b993
Affiliations	Ural State Technical University, 620002 Yekaterinburg, Russian Federation
Author Keywords	Diazo transfer reaction; Diazomalonimidolates; Ring-chain isomerization; Thermodynamic stability
References	Doyle, M.P., (1995) Diazo Chemistry II: Aliphatic, Inorganic and Organometallic Compounds, p. 522. , VCH, New York; Padwa, A., Curtis, E.A., Sandanayaka, V.P., (1996) J. Org. Chem., 61, p. 73; Manitto, P., Monti, D., Zanzola, S., Speranza, G., (1997) J. Org. Chem., 62, p. 6658; Maseras, F., Lockwood, M.A., Eisenstein, O., Rothwell, I.P., (1998) J. Am. Chem. Soc., 120, p. 6598; Sakaguchi, K., Tsujino, M., Mizuno, K., Hayano, K., (1975) Cancer Res., 38, p. 1643; Lebedev, A.T., Bakulev, V.A., Kolobov, M.Yu., (1991) Organic Mass Spectrometry, 26, p. 789; Kolobov, M.Yu., Morzherin, Yu.Yu., Bakulev, V.A., Mokrushin, V.S., (1991) Khim. Geterotsikl. Soedin., p. 1521; 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; Kolobov, M.Yu., Bakulev, V.A., Mokrushin, V.S., (1992) Khim. Geterotsikl. Soedin., p. 1208; Regitz, M., (1977) Diazoalkane: Eigenschaften und Synthesen, p. 245. , Thieme, Stuttgart; Sander, W., Kirschfeld, A., Halupka, M., (1997) J. Am. Chem. Soc., 119, p. 981; Bakulev, V.A., Tarasov, E.V., Morzherin, Yu.Yu., Luyten, I., Toppet, S., Dehaen, W., (1998) Tetrahedron, 54, p. 8501
Correspondence Address	Morzherin, Yu.Yu.; Ural State Technical University, 620002 Yekaterinburg, Russian Federation; email: morjerine@htf.ustu.ru
CODEN	CHCCA
Language of Original Document	English
Abbreviated Source Title	Chem. Heterocycl. Compd.
Source	Scopus