Abstract
Multicomponent condensation of acetaldehyde, cyanothioacetamide, 1-(but-2-en-2-yl)pyrrolidine, and alkyl halides afforded 2-alkylsulfanyl-4,5,6-trimethylnicotinonitriles. Their structure was confirmed by IR, 1H NMR spectroscopy, and chromatography-mass spectrometry.
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Morioka, M., Ikegami, H., Jakiyama, M., Hayashi, M., Ooike, S., Fujino, Y., Abe, D., Tomozane, H. EP Patent 1876178, 2008.
Krauze, A., Baumane, L., Sile, L., Chernova, L., Vilums, M., Vitolina, R., Duburs, G., and Stradins, J., Chem. Heterocycl. Compd., 2004, vol. 40, no. 7, p. 876. DOI: 10.1023/B:COHC.0000044570.13567.74.
Elkholy, Y.M., Chem. Heterocycl. Compd., 2002, vol. 38, no. 11, p. 1342. DOI: 10.1023/A:1022126409122.
Darvesh, S., Magee, D., Valenta, Z., and Martin, E., US Patent 6436972, 2002.
Schmidt, U. and Kubitzek, H., Chem. Ber., 1960, vol. 93, nos. 7–9, p. 1559.
Wagner, G., Vieweg, H., Leistner, S., Bohm, N., Krasselt, Hanfeld, V., and Prantz, J., Pharmazie, 1990, vol. 45, no. 2, p. 102.
Elgemeie, G.E.H., Ali, H.A., and Eid, M.M., J. Chem. Res. Miniprint, 1993, no. 7, p. 1517.
Elgemeie, G.E.H., Ali, H.A., and Eid, M.M., J. Chem. Res. Synop., 1993, no. 7, p. 256.
Dyachenko, V.D., Russ. J. Gen. Chem., 2005, vol. 75, no. 10, p. 1537. DOI: 10.1007/s11176-005-0463-z.
Shelyakin, V.V., Dyachenko, V.D., and Sharanin, Yu.A., Chem. Heterocycl. Compd., 1995, vol. 31, no. 2, p. 239. DOI: 10.1007/BF01169689.
Dyachenko, V.D., Krivokolysko, S.G., and Litvinov, V.P., Russ. Chem. Bull. Int. Ed., 1997, vol. 46, no. 11, p. 1909. DOI: 10.1007/BF02503784.
Dyachenko, V.D., Russ. J. Gen. Chem., 2005, vol. 75, no. 3, p. 440. DOI: 10.1007/s11176-005-0247-5.
Stork, G., Brizzolara, A., Landesman, H., Szmuszkovich, J., and Terrell, R., J. Am. Chem. Soc., 1963, vol. 85, no. 2, p. 207. DOI: 10.1021/ja00885a021.
Shainyan, B.A., Izv. Sib. Otd. Akad. Nauk SSSR, 1990, no. 4, p. 137.
Rappoport, Z., Acc. Chem. Res., 1992, vol. 25, no. 10, p. 474. DOI: 10.1021/ar00022a007.
Litvinov, V.P., Yakunin, Ya.Yu., and Dyachenko, V.D., Chem. Heterocycl. Compd., 2001, vol. 37, no. 1, p. 37. DOI: 10.1023/A:1017536700235.
Pretch, E., Bühlmann, P., and Affolter, C., Structure Determination of Organic Compounds: Tables of Spectral Data, Berlin: Springer, 2000.
Dyachenko, V.D., Russ. J. Gen. Chem., 2012, vol. 82, no. 5, p. 906. DOI: 10.1134/S1070363212050180.
Abdel-Fattah, A.M., Phosphorus, Sulfur, Silicon, Relat. Elem., 2000, vol. 156, no. 1, p. 53. DOI: 10.1080/10426500008044993.
El-Neairy, M.A.A., Phosphorus, Sulfur, Silicon, Relat. Elem., 1999, vol. 148, no. 1, p. 189. DOI: 10.1080/10426509908037010.
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Original Russian Text © I.V. Dyachenko, V.D. Dyachenko, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 7, pp. 1146–1151.
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Dyachenko, I.V., Dyachenko, V.D. New approach to the synthesis of 2-alkylsulfanyl-4,5,6-trimethylnicotinonitriles. Russ J Gen Chem 85, 1668–1672 (2015). https://doi.org/10.1134/S1070363215070166
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DOI: https://doi.org/10.1134/S1070363215070166