Heterocyclization of compounds containing diazo and cyano groups. 6. Theoretical and experimental investigations of cyclization of 2-cyano-2-diazoacetamides to 5-hydroxy-1,2,3-triazole-4-carbonitriles / Morzherin Yu.Yu., Kolobov M.Yu., Mokrushin V.S., Brauer M., Anders E., Bakulev V.A. // Chemistry of Heterocyclic Compounds. - 2000. - V. 36, l. 1. - P. 22-36.

ISSN:

00093122

Type:

Article

Abstract:

A series of N-alkyl- and N-aryl-2-cyano-2-diazoacetamides was synthesized by the reaction of 2-amino-2-cyanoacetamides with sodium nitrite in hydrochloric acid. The mechanism of their heteroelectrocyclization to 5-hydroxy-1,2,3-triazoles was investigated kinetically and theoretically by the B3LYP/6-31 + G* method. The conclusion was made on the basis of the determined activation energy of the cyclization process, reaction parameters ρ, and kinetic isotope effects, that there is a difference between the mechanisms of cyclization of the N-alkyl and N-aryl derivatives of 2-cyano-2-diazoacetamide: cyclization of the N-alkyl derivatives takes place by a monorotatory mechanism, while cyclization of the N-aryl derivatives takes place by a mechanism where one of the stages is heteroelectrocyclization of 2-diazoacetimidates.

Author keywords:

1,2,3-triazoles; Diazo compounds; Heteroelectrocyclization; Kinetic isotope effect; Quantum-chemical calculations

Index keywords:

2 amino 2 cyanoacetamide derivative; 2 cyano 2 diazoacetamide derivative; 2 diazoacetimidate derivative; 5 hydroxy 1,2,3 triazole 4 carbonitrile derivative; acetamide derivative; azo compound; cyanide

DOI:

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0033992710&partnerID=40&md5=a5fa920811b3150ca5ed8e88c417cac2
Affiliations	Ural State Technical University, Ekaterinburg, Russian Federation; Institut für Organische Chemie und Makromolekulare Chemie, Friedrich-Schiller-Universität, Jena, Germany
Author Keywords	1,2,3-triazoles; Diazo compounds; Heteroelectrocyclization; Kinetic isotope effect; Quantum-chemical calculations
References	Kolobov, M.Yu., Bakulev, V.A., Mokrushin, V.S., Lebedev, A.T., (1987) Khim. Geterotsikl. Soedin., 11, p. 1503; Bakulev, V.A., Kartsev, V.G., Mokrushin, V.S., (1989) Khim. Geterotsikl. Soedin., 11, p. 1443; Padwa, A., Blacklock, T.J., Losa, R., (1982) J. Org. Chem., 47, p. 3712; Bakulev, V.A., Gloriozov, I.P., (1989) Khim. Geterotsikl. Soedin., 4, p. 504; Nguyen, M.N., Ha, T.K., O'Ferrall, R.A.M., (1990) J. Org. Chem., 55, p. 3251; Birney, D.M., (1996) Org. Chem., 61, p. 243; Fabian, W.M.F., Bakulev, V.A., Kappe, C.O., (1998) J. Org. Chem., 63, p. 5801; Huisgen, R., (1981) Khim. Geterotsikl. Soedin., 5, p. 579; Dimroth, O., (1904) Lieb. Ann. Chem., 335, p. 1; Barton, D., Ollis, W.D., (1983) General Organic Chemistry [Russian translation], 4, p. 728. , Khimiya, Moscow; Gordon, A.J., Ford, R.A., (1973) The Chemist's Companion, p. 541. , Wiley-Interscience; Hine, J., Hine, M., (1952) J. Am. Chem. Soc., 74, p. 5266; Perrin, C.L., Thoburn, J.D., (1989) J. Org. Chem., 54, p. 764; 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; Marvell, E.N., (1980) Thermal Electrocyclic Reaction, p. 422. , Wiley-Interscience, New York; Katritzky, A.R., Lagowski, J.M., (1986) Comprehensive Heterocyclic Chemistry. II, (PART 4A), p. 4. , Pergamon; Scheiner, S., Wang, L., (1993) J. Am. Chem. Soc., 115, p. 1958; Mikhailov, I.E., Ivashchenko, E.P., Shif, A.I., Feigel'man, V.M., Olekhnovich, L.P., (1989) Zh. Org. Khim., 59, p. 1416; Becke, A.D., (1988) Phys. Rev., 38, p. 3098; Becke, A.D., (1993) J. Chem. Phys., 98, p. 5648; Cox, B.G., (1994) Modern Liquid Phase Kinetics, p. 83. , Oxford University Press; Perrin, C.L., Thobum, J.D., Kresge, A.J., (1992) J. Am. Chem. Soc., 114, p. 8800; Shafran, Yu.M., Bakulev, V.A., Mokrushin, V.S., Alekseev, S.G., (1984) Khim. Geterotsikl. Soedin., 9, p. 1266
Correspondence Address	Morzherin, Yu.Yu.; Ural State Technical University, Ekaterinburg, Russian Federation; email: crocus@htf.ustu.ru
CODEN	CHCCA
Language of Original Document	English
Abbreviated Source Title	Chem. Heterocycl. Compd.
Source	Scopus