Abstract
Reaction of cyanoacetanilides with 3,3-bis(methylthio)-2-cyano-N-arylacrylamides proceeds to form isomeric N,1-diaryl-1,6-dihydropyridine-3-carboxamides. A single crystal consisting of 2-amino-4-methylthio-N-(2-methoxyphenyl)-6-oxo-1-phenyl-5-cyano-1,6-dihydropyridine-3-carboxamide and 2-amino-4-methylthio-1-(2-methoxyphenyl)-6-oxo-N-phenyl-5-cyano-1,6-dihydropyridine-3-carboxamide was studied by XRD.
Similar content being viewed by others
References
Litvinov, V.P., Yakunin, Ya.Yu., and Dyachenko, V.D., Khim. Geterotsikl. Soedin., 2001, no. 1, p.41.
Litvinov, V.P., Krivokolysko, S.G., and Dyachenko, V.D., Khim. Geterotsikl. Soedin., 1999, no. 5, p. 579.
Hirokawa, Y., Fujiwara, I., Suzuki, K., Horada, H., Yoshukawa, T., Yoshida, N., and Kato, S., J. Med. Chem., 2003, vol. 46, no. 5, p. 702.
Onnis, V., Cocco, M.T., Lilliu, V., and Congiu, C., Bioorg. Med. Chem., 2008, vol. 18, no. 5, p. 2367.
Michell, W.L., Giblin, G.M.P., Naylor, A., Eatherton, A.J., Slingsby, B.P., Rawlings, A.D., Jandu, K.S., Haslam, C.P., Brown, A.J., Goldsmith, P., Clayton, N.M., Wilson, A.W., Chessell, I.P., Green, R.H., Whittington, A.R., and Wall, I.D., Bioorg. Med. Chem. Lett., 2009, vol. 19, no. 1, p. 259.
Dneprovskii, A.S. and Temnikova, T.I., Teoreicheskie osnovy organicheskoi khimii (Theoretical Basis of Organic Chemistry), Leningrad: Khimiya, 1991, p. 468.
Zefirov, Yu.V., Kristallografiya, 1997, vol. 42, no. 5, p. 936.
Burgi, H-B. and Dunitz, J.D., Structure Correlations, vol. 2, Weinheim: VCH, 1994, p. 741.
Fischer, W. and Koch, E., Z. Krist., 1997, vol. 150, p. 245.
Espinosa, E., Souhassou, M., Lachekar, H., and Lecomite, C., Acta Crystallogr., Sect. B, 1999, 55, p. 563.
Grabowski S.J., J. Phys. Chem., A, 2001, vol. 105, p. 10739.
Zhikol, O.A., Shishkin, O.V., Lysenko, K.A., and Leszcynski, J., J. Chem. Phys., 2005, vol. 122, p. 144104.
Sheldrick, G., Acta Crystalligr., Sect. A, 2008, vol. 64, p. 112.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuceria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsui, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, Jr.J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Stariverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, N.J., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.I., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Caussian 09, Revision A.1., Gaussian Inc., Wallingford C.T., 2009.
Biegler-Kong, F., Sghonbohm, J., and Bayles, D., J. Comput. Chem., 2001, vol. 22, no. 5, p. 545.
Blatov, V.A., IUCr Commun Newsletter, 2006, no. 7, p. 4.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © V.D. Dyachenko, O.S. Bityukova, A.D. Dyachenko, O.V. Shishkin, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 5, pp. 857–868.
Rights and permissions
About this article
Cite this article
Dyachenko, V.D., Bityukova, O.S., Dyachenko, A.D. et al. Competing processes in condensation of 3,3-bis(methylthio)-2-cyano-N-arylacrylamides with cyanoacetanilides. Russ J Gen Chem 81, 944–955 (2011). https://doi.org/10.1134/S1070363211050185
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363211050185