Switchable Synthesis of 4,5-Functionalized 1,2,3-Thiadiazoles and 1,2,3-Triazoles from 2-Cyanothioacetamides under Diazo Group Transfer Conditions / Filimonov V.O., Dianova L.N., Galata K.A., Beryozkina T.V., Novikov M.S., Berseneva V.S., Eltsov O.S., Lebedev A.T., Slepukhin P.A., Bakulev V.A. // Journal of Organic Chemistry. - 2017. - V. 82, l. 8. - P. 4056-4071.

ISSN:
00223263
Type:
Article
Abstract:
High yield solvent-base-controlled, transition metal-free synthesis of 4,5-functionalized 1,2,3-thiadiazoles and 1,2,3-triazoles from 2-cyanothioacetamides and sulfonyl azides is described. Under diazo transfer conditions in the presence of a base in an aprotic solvent 2-cyanothioacetamides operating as C-C-S building blocks produce 5-amino-4-cyano-1,2,3-thiadiazoles exclusively. The use of alkoxide/alcohol system completely switches the reaction course due to the change of one of the reaction centers in the 2-cyanothioacetamide (C-C-N building block) resulting in the formation of 5-sulfonamido-1,2,3-triazole-4-carbothioamide sodium salts as the only products. The latter serve as good precursors for 5-amino-1,2,3-thiadiazole-4-carboximidamides, the products of Cornforth-type rearrangement occurring in neutral protic medium or under acid conditions. According to DFT calculations (B3LYP/6-311+G(d,p)) the rearrangement proceeds via intermediate formation of a diazo compound, and can be catalyzed by acids via the protonation of oxygen atom of the sulfonamide group. © 2017 American Chemical Society.
Author keywords:
Index keywords:
Salts; Sulfur compounds; 1 ,2 ,3-triazoles; Aprotic solvents; Building blockes; DFT calculation; Intermediate formation; Metal-free synthesis; Reaction center; Reaction course; Transition metals
DOI:
10.1021/acs.joc.6b02736
Смотреть в Scopus:
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85018498803&doi=10.1021%2facs.joc.6b02736&partnerID=40&md5=e06a3ae5901dae6de1f441d7c82484a5
Соавторы в МНС:
Другие поля
Поле Значение
Link https://www.scopus.com/inward/record.uri?eid=2-s2.0-85018498803&doi=10.1021%2facs.joc.6b02736&partnerID=40&md5=e06a3ae5901dae6de1f441d7c82484a5
Affiliations Ural Federal University Named after the First President of Russia B. N. Yeltsin, 19 Mira st., Yekaterinburg, Russian Federation; Institute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg, Russian Federation; Department of Chemistry, Lomonosov Moscow State University, Moscow, Russian Federation; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, 20 S. Kovalevskaya st., Yekaterinburg, Russian Federation
Funding Details RSF, Russian Science Foundation
Funding Text We gratefully acknowledge financial support of this work by the Russian Science Foundation (15-13-10031). This research was carried out using resources of the Computer Centre of St. Petersburg State University.
References Bakulev, V.A., Dehaen, W., (2004) The Chemistry of 1,2,3-Thiadiazoles, p. 384. , John Wiley & Sons Inc. Hoboken, Heidelberg, New York, Dordrecht, London; Bakulev, V., Dehaen, W., Beryozkina, T., Thermal rearrangements and transformations of 1,2,3-triazoles (2015) Chemistry of 1,2,3-triazoles, pp. 1-50. , Dehaen, W. Bakulev, V. Springer-Verlag: Berlin Heidelberg; Tomé, A.C., (2004) 1,2,3-Triazoles. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, 13, pp. 415-601. , Georg Thieme Verlag KG; Vol; Rachwal, S., Katritzky, A.R., 1,2,3-Triazoles (2008) Comprehensive Heterocyclic Chemistry III, 501, pp. 1-158. , Katritzky, A. R. Ramsden, C. A. Scriven, E. F. V. Taylor, R. J. K. Pergamon Press: Oxford; Bakulev, V.A., Tarasov, E.V., Morzherin, Y.Y., Luyten, I., Toppet, S., Dehaen, W., (1998) Tetrahedron, 54, p. 8501; L'Abbé, G., (1990) Bull. Soc. Chim. Belg., 99, p. 281; L'Abbé, G., Vercauteren, K., Dehaen, W., (1994) Bull. Soc. Chim. Belg., 103, p. 321; L'Abbé, G., Vanderstede, E., (1989) J. Heterocycl. Chem., 26, p. 1811; L'Abbé, G., Verbeke, M., Dehaen, W., Toppet, S., (1993) J. Chem. Soc., Perkin Trans. 1, p. 1719; L'Abbé, G., (1984) J. Heterocycl. Chem., 21, p. 627; Dankova, E.F., Bakulev, V.A., Grishakov, A.N., Mokrushin, V.S., (1988) Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 37, p. 987; (1988) Izv. Akad. Nauk SSSR, Ser. Khim., p. 1450; Meza-Avina, M.E., Patel, M.K., Croatt, M.P., (2013) Tetrahedron, 69, p. 7840; Rao, V.V.R., Wentrup, C., (1998) J. Chem. Soc., Perkin Trans. 1, p. 2583; Chattopadhyay, B., Gevorgyan, V., (2012) Angew. Chem., Int. Ed., 51, p. 862; Bora, P.P., Luo, Z.-L., Chen, L., Kang, Q., (2016) Tetrahedron, 72, p. 1467; Burdzinski, G., Luk, H.L., Reid, C.S., Zhang, Y., Hadad, C.M., Platz, M.S., (2013) J. Phys. Chem. A, 117, p. 4551; Kurandina, D., Gevorgyan, V., (2016) Org. Lett., 18, p. 1804; Amirhamzeh, A., Vosoughi, M., Shafiee, A., Amini, M., (2013) Med. Chem. Res., 22, p. 1212; Balasankar, T., Gopalakrishnan, M., Nagarajan, S., (2005) Eur. J. Med. Chem., 40, p. 728; Dahlgren, M.K., Zetterstrom, C.E., Gylfe, A., Linusson, A., Elofsson, M., (2010) Bioorg. Med. Chem., 18, p. 2686; Hayat, F., Salahuddin, A., Zargan, J., Azam, A., (2010) Eur. J. Med. Chem., 45, p. 6127; Wu, M.J., Sun, Q.M., Yang, C.H., Chen, D.D., Ding, J., Chen, Y., Lin, L.P., Xie, Y.Y., (2007) Bioorg. Med. Chem. Lett., 17, p. 869; Zhan, P., Liu, X., Fang, Z., Li, Z., Pannecouque, C., De Clercq, E., (2009) Eur. J. Med. Chem., 44, p. 4648; Zhan, P., Liu, X., Li, Z., Fang, Z., Li, Z., Wang, D., Pannecouque, C., De Clercq, E., (2009) Bioorg. Med. Chem., 17, p. 5920; Li, Z., Wu, Z., Luo, F., (2005) J. Agric. Food Chem., 53, p. 3872; Zheng, Q., Mi, N., Fan, Z., Zuo, X., Zhang, H., Wang, H., Yang, Z., (2010) J. Agric. Food Chem., 58, p. 7846; Wang, Z.H., Guo, Y.Z., Zhang, J., Ma, L., Song, H.B., Fan, Z.J., (2010) J. Agric. Food Chem., 58, p. 2715; Zhao, W.-G., Wang, J.-G., Li, Z.-M., Yang, Z., (2006) Bioorg. Med. Chem. Lett., 16, p. 6107; Tornøe, C.W., Christensen, C., Meldal, M., (2002) J. Org. Chem., 67, p. 3057; Rostovtsev, V.V., Green, L.G., Fokin, V.V., Sharpless, B.K., (2002) Angew. Chem., Int. Ed., 41, p. 2596; Da Silva, F.G., Do Carmo Cardoso, M.F., Ferreira, G.P., Ferreira, V.F., Biological properties of 1H-1,2,3- and 2H-1,2,3-triazoles (2015) Chemistry of 1,2,3-triazoles, pp. 117-165. , Dehaen, W. Bakulev, V. Springer-Verlag: Berlin Heidelberg; Zheng, T., Rouhanifard, S.H., Jalloh, A.S., Wu, P., (2012) Top. Heterocycl. Chem., 28, p. 163; Watkinson, M., (2012) Top. Heterocycl. Chem., 28, p. 109; Crowley, J.D., McMorran, D.A., (2012) Top. Heterocycl. Chem., 28, p. 31; Lee, S., Flood, A.H., (2012) Top. Heterocycl. Chem., 28, p. 85; Stadler, D., Anschütz, W., Regit, M., Keller, G., Van Assche, D., Fleury, J.-P., (1975) Justus Liebigs Ann. Chem., 1975, p. 2159; Mignani, S., Zhou, Y., Lecourt, T., Micouin, L., (2012) Top. Heterocycl. Chem., 28, p. 185; Krivopalov, V.P., Shkurko, O.R., (2005) Russ. Chem. Rev., 74, p. 339; Dianova, L.N., Berseneva, V.S., El'Tsov, O.S., Fan, Z.-J., Bakulev, V.A., (2014) Chem. Heterocycl. Compd., 50, p. 972; Shafran, Yu.M., Bakulev, V.A., Mokrushin, V.S., Validuda, G.I., (1986) Chem. Heterocycl. Compd., 22, p. 567; (1986) Chem. Informationsdienst, 17, p. 691; Trost, B.M., (1995) Angew. Chem., Int. Ed. Engl., 34, p. 259; Clark, J.H., (1999) Green Chem., 1, p. 1; Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Fox, D.J., (2010) Gaussian 09, , Revision C.01; Gaussian: Wallingford CT; Bakulev, V.A., (1995) Russ. Chem. Rev., 64, p. 99; Birney, D.M., Wagenseller, P.E., (1994) J. Am. Chem. Soc., 116, p. 6262; Efimov, I., Bakulev, V., Beliaev, N., Beryozkina, T., Knippschild, U., Leban, J., Zhi-Jin, F., Dehaen, W., (2014) Eur. J. Org. Chem., 2014, p. 3684; Morzherin, Y.Y., Glukhareva, T.V., Bakulev, V.A., (2003) Chem. Heterocycl. Compd., 39, p. 679; Kosterina, M.F., Morzherin, Y.Y., Tkachev, A.V., Rybalova, T.V., Gatilov, Yu.V., Bakulev, V.A., (2002) Russ. Chem. Bull., 51, p. 653; Dankova, E.F., Bakulev, V.A., Kolobov, M.Y., Shishkina, V.I., Yasman, Ya.B., Lebedev, A.T., (1988) Chem. Heterocycl. Compd., 24, p. 1051; (1988) Eng. Trans.; Khim. Geterotsikl. Soedin., 20, p. 1269; Ransborg, L.K., Albrecht, Ł., Weise, C.F., Bak, J.R., Jørgensen, K.A., (2012) Org. Lett., 14, p. 724; Kang, T., Kim, H., Kim, J.C., Chang, S., (2014) Chem. Commun., 50, p. 12073
Correspondence Address Bakulev, V.A.; Ural Federal University Named after the First President of Russia B. N. Yeltsin, 19 Mira st., Russian Federation; email: v.a.bakulev@urfu.ru
Publisher American Chemical Society
CODEN JOCEA
Language of Original Document English
Abbreviated Source Title J. Org. Chem.
Source Scopus