Reactions of 5-dialkylamino-1,2,3-thiadiazole-4-carbaldehydes with amines as a method for the synthesis of 1,2,3-triazole-4-carbothioamides / Glukhareva T.V., Morzherin Yu.Yu., Dyudya L.V., Malysheva K.V., Tkachev A.V., Padva A., Bakulev V.A. // Russian Chemical Bulletin. - 2004. - V. 53, l. 6. - P. 1311-1317.

ISSN:
10665285
Type:
Article
Abstract:
A method for the synthesis of previously inaccessible 5-dialkylamino- substituted 1,2,3-thiadiazole-4-carbaldehydes was developed. Ring transformation in these compounds induced by primary aliphatic and aromatic amines, hydroxylamines, and N-substituted hydrazines resulted in the synthesis of a broad range of 1,2,3-triazole-4-carbothioamide.
Author keywords:
1,2,3-thiadiazole; 1,2,3-triazole; Cornfort rearrangement; nucleophilic substitution; oxidation; reduction; thioamides
Index keywords:
aldehyde derivative; amine; thioamide; triazole derivative; article; chemical reaction kinetics; drug synthesis; substitution reaction
DOI:
10.1023/B:RUCB.0000042292.1911
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https://www.scopus.com/inward/record.uri?eid=2-s2.0-4644245422&doi=10.1023%2fB%3aRUCB.0000042292.19119.3d&partnerID=40&md5=110c361bca84a785525040bb80040c42
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Affiliations Urals State Technical University, 19 Ul. Mira, 620002 Ekaterinburg, Russ. Fed., Russian Federation; N. N. Vorozhtsov Novosibirsk I., Siberian Br. Russ. Acad. of Sci., 9 Prosp. Akad. Lavrenteva, 630090 N., Russian Federation; Emory University, Department of Chemistry, 1515, Pierce Dr., Atlanta G., United States
Author Keywords 1,2,3-thiadiazole; 1,2,3-triazole; Cornfort rearrangement; nucleophilic substitution; oxidation; reduction; thioamides
References Jagodzinski, T.S., (2003) Chem. Rev., 103, p. 197; Zacharie, B., Lagraoui, M., Dimarco, M., Penney, C.L., Gagnon, L., (1999) J. Med. Chem., 42, p. 2046; Arnaud-Neu, F., Barrett, G., Corry, D., Cremin, S., Ferguson, G., Gallagher, J.F., Harris, S.J., Schwing Weill, M.J., (1997) J. Chem. Soc., Perkin Trans. 2, p. 575; Dankova, E.F., Bakulev, V.A., Grishakov, A.N., Mokrushin, V.S., (1988) Izv. Akad. Nauk SSSR. Ser. Khim., p. 1126; (1988) Bull. Acad. Sci. USSR, Div. Chem. Sci., 37, p. 987. , Engl. Transl; Dankova, E.F., Bakulev, V.A., Mokrushin, V.S., Shafran, Yu.M., (1985) Khim. Geterotsikl. Soedinen., p. 1429; Chem. Heterocycl. Compd., p. 1985. , Engl. Transl; Morzherin, Yu.Yu., Bakulev, V.A., Dankova, E.F., Mokrushin, V.S., (1994) Khim. Geterotsikl. Soedinen., p. 548; (1994) Chem. Heterocycl. Compd., 30, p. 483. , Engl. Transl; L'abbé, G., D'hooge, B., Dehaen, W., (1996) Molecules, p. 190; Rosenau, T., Potthast, A., Ebner, G., Hofinger, A., Kosma, P., (2002) Org. Lett., 4, p. 1257; Glukhareva, T.V., Morzherin, Yu.Yu., Mokrushin, V.S., Tkachev, A.V., Bakulev, V.A., (2000) Khim. Geterotsikl. Soedinen., p. 707; (2000) Chem. Heterocycl. Compd., 36, p. 626. , Engl. Transl; L'abbé, G., Vanderstede, E., Dehaen, W., Delbeke, P., Toppert, S., (1991) J. Chem. Soc., Perkin Trans. 1, p. 607; L'abbé, G., Verbeke, M., Dehaen, W., Toppet, S., (1993) J. Chem. Soc., Perkin Trans. 1, p. 1719; Shafiee, A., (1976) J. Heterocycl. Chem., 13, p. 301; Dehaen, W., Voets, M., Bakulev, V.A., (2000) Adventure in Nitrogen Heterocycles, 4, p. 37. , JAI Press Inc. Stamford, Connecticut; Goerdeler, J., Gnad, G., (1966) Chem. Ber., 99, p. 1618; L'abbé, G., Vanderstede, E., (1989) J. Heterocycl. Chem., 26, p. 1811; Morzherin, Yu.Yu., Tarasov, E.V., Bakulev, V.A., (1994) Khim. Geterotsikl. Soedinen., p. 554; (1994) Chem. Heterocycl. Compd., , Engl. Transl; Soai, K., Oyamada, H., Ookawa, A., (1982) Synth. Commun., 12, p. 463; Pain, D.L., Slack, R., (1965) J. Chem. Soc., p. 5166; Katritzky, A.R., Sobiak, S., Marson, C.M., (1978) Magn. Reson. Chem., 87, p. 293; Glukhareva, T.V., Morzherin, Yu.Yu., Savel'eva, E.A., Rozin, Yu.A., Tkachev, A.V., Bakulev, V.A., (2001) Izv. Akad. Nauk. Ser. Khim., p. 258; (2001) Russ. Chem. Bull., Int. Ed., 50, p. 268
Correspondence Address Urals State Technical University, 19 Ul. Mira, 620002 Ekaterinburg, Russ. Fed.Russian Federation; email: morjerine@htf.ustu.ru
Language of Original Document English
Abbreviated Source Title Russ. Chem. Bull.
Source Scopus