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Synthesis of 4-thioacetyl-1,2,3-thiadiazoles. Reversible rearrangement of N-Substituted 5-methyl-1,2,3-thiadiazole-4-carbothioamides

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Abstract

The equilibrium in the reversible rearrangement of 5-methyl-1,2,3-thiadiazole-4-carbothioamides into 5-amino-4-thioacetyl-1,2,3-thiadiazoles is displaced toward the former, and polar solvents favor increased fraction of the thioketone.

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References

  1. Bakulev, V.A. and Dehaen, W., The Chemistry of 1,2,3-Thiadiazoles, Hoboken, NJ: Wiley, 2004.

    Book  Google Scholar 

  2. Regitz, M. and Liedhegener, A., Justus Liebigs Ann. Chem., 1967, vol. 710, p. 118.

    Article  CAS  Google Scholar 

  3. Morzherin, Yu.Yu., Bakulev, V.A., Dankova, E.F., and Mokrushin, V.S., Khim. Geterotsikl. Soedin., 1994, p. 548.

  4. Reichardt, C., Solvents and Solvent Effects in Organic Chemistry, Weinheim: VCH, 1988, 2nd ed.

    Google Scholar 

  5. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr.,, Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision A.1, Wallingford CT: Gaussian, 2004.

    Google Scholar 

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Correspondence to Yu. Yu. Morzherin.

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Original Russian Text © P.E. Prokhorova, T.A. Kalinina, T.V. Glukhareva, Yu.Yu. Morzherin, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 10, pp. 1338–1341.

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Prokhorova, P.E., Kalinina, T.A., Glukhareva, T.V. et al. Synthesis of 4-thioacetyl-1,2,3-thiadiazoles. Reversible rearrangement of N-Substituted 5-methyl-1,2,3-thiadiazole-4-carbothioamides. Russ J Org Chem 48, 1333–1336 (2012). https://doi.org/10.1134/S1070428012100132

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  • DOI: https://doi.org/10.1134/S1070428012100132

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