Abstract
In reaction of tetracyanoethylene with ketones and HCl in 1,4-dioxane at 30–40°? 6-hydroxy-2-chloro-1,4,5,6-tetrahydropyridine-3,4,4-tricarbonitriles are formed.
References
Ershov, O.V., Ievlev, M.Yu., Tafeenko, V.A., and Nasakin, O.E., Green Chem., 2015, vol. 17, p. 4234. doi 10.1039/C5GC00909J
Ievlev, M.Yu., Ershov, O.V., Milovidova, A.G., Belikov, M.Yu., and Nasakin, O.E., Chem. Heterocycl. Compd., 2015, vol. 51, p. 457. doi 10.1007/s10593-015-1720-7
Eremkin, A.V., Ershov, O.V., Mol’kov, S.N., Sheverdov, V.P., Nasakin, O.E., Kayukov, Ya.S., and Tafeenko, V.A., Russ. J. Org. Chem., 2006, vol. 42, p. 193. doi 10.1134/S1070428002120060
Ershov, O.V., Eremkin, A.V., Kayukov, Ya.S., Nasakin, O.E., Tafeenko, V.A., and Nurieva, E.V., Tetrahedron Lett., 2017, vol. 48, p. 2803. doi 10.1016/j.tetlet.2007.01.138
Sheverdov, V.P., Ershov, O.V., Nasakin, O.E., Chernushkin, A.N., and Tafeenko, V.A., Russ. J. Org. Chem., 2002, vol. 38, p. 1001. doi 10.1023/A:1020801612443
Ershov, O.V., Lipin, K.V., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2009, vol. 45, p. 470. doi 10.1134/S1070428009030245
Nasakin, O.E., Sheverdov, V.P., Ershov, O.V., Moiseeva, I.V., Lyshchikov, A.N., Khrustalev, V.N., and Antipin, M.Yu., Mendeleev Commun., 1997, vol. 7, p. 112. doi 10.1070/MC1997v007n03ABEH000722
Bardasov, I.N., Alekseeva, A.U., Mihailov, D.L., Ershov, O.V., Nasakin, O.E., and Tafeenko, V.A., Tetrahedron Lett., 2014, vol. 55, p. 2730. doi 10.1016/j.tetlet.2014.03.056
Eremkin, A.V., Molkov, S.N., Ershov, O.V., Kayukov, Ya.S., Nasakin, O.E., Tafeenko, V.A., and Nurieva, E.V., Mendeleev Commun., 2006, vol. 15, p. 115. doi 10.1070/MC2006v016n02ABEH002206
Lu, S., Shao, X., Li, Zh., Xu, Zh., Zhao, Sh., Wu, Y., and Xu, X., J. Agric. Food Chem., 2012, vol. 60, p. 322. doi 10.1021/jf203068a
Carroll, W.A., Agrios, K.A., Altenbach, R.J., Buckner, S.A., Chen, Y., Coghlan, M.J., Daza, A.V., Drizin, I., Gopalakrishnan, M., Henry, R.F., Kort, M.E., Kym, P.R., Milicic, I., Smith, J.C., Tang, R., Turner, S.C., Whiteaker, K.L., Zhang, H., and Sullivan, J.P., J. Med. Chem., 2004, vol. 47, p. 3180. doi 10.1021/jm030357o
Kandil, S., Wymant, J.M., Kariuki, B.M., Jones, A.T., McGuigan, C., and Westwell, A.D., Eur. J. Med. Chem., 2016, vol. 110, p. 311. doi 10.1016/j.ejmech.2015.12.037
Iwasawa, T., Hooley, R.J., and Rebek, J., Science, 2007, vol. 317, p. 493. doi 10.1126/science.1143272
Sheldrick, G.M., Acta Cryst., Sect. A, 2008, vol. 64, p. 112. doi 10.1107/S0108767307043930
Brandenburg, K., DIAMOND, Release 2.1d, Germany, Bonn Crystal Impact, 2000.pb]Nauka/Interperiodica Moscow
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Original Russian Text © K.V. Ershov, K.V. Lipin, O.V. Eremkin, O.E. Nasakin, V.P. Sheverdov, P.I. Fedorov, V.E. Tafeenko, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 2, pp. 223–228.
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Ershov, O.V., Lipin, K.V., Eremkin, A.V. et al. Tricomponent domino synthesis of 6-hydroxy-2-chloro-1,4,5,6-tetrahydropyridine-3,4,4-tricarbonitriles. Russ J Org Chem 53, 215–221 (2017). https://doi.org/10.1134/S1070428017020129
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DOI: https://doi.org/10.1134/S1070428017020129