Abstract
Knoevenagel condensation of N-hetaryl-substituted cyanoacetamides with aldehydes gave the corresponding (E)-N-hetaryl-2-cyanoacrylamides which were converted into (E)-N-alkyl-N-hetaryl-2-cyanoacrylamides and 6-amino-2-oxo-4-phenyl-1-(pyridin-2-yl)-1,2-dihydropyridine-3,5-dicarbonitriles. The structure of (E)-N-(pyridin-2-yl)-2-cyano-3-phenylprop-2-enamide was determined by X-ray analysis.
Similar content being viewed by others
References
Dyachenko, V.D., Tkachov, R.P., and Dyachenko, O.D., Ukr. Khim. Zh., 2004, vol. 70, p. 49; Dyachenko, V.D. and Tkachev, R.P., Khim. Geterotsikl. Soedin., 2005, p. 589; Metwally, N.H. and Abdelrazek, F.M., J. Prakt. Chem., 1998, vol. 340, p. 676; Ismail, A.H. and Hwatta, M., Kogaku to Kogyo (Osaka), 1997, vol. 71, p. 102; Chem. Abstr., 1997, vol. 126, no. 330573g.
Khalifa, M.A.E., Tammam, G.H., and Elbanany, A.A.A., Arch. Pharm., 1983, vol. 316, p. 822; Krasnikov, D.O. and Dyachenko, V.D., Abstracts of Papers, Ukrains’ka konferentsiya z organichnii khimii (Ukrainian Conf. on Organic Chemistry), Odessa: Astroprint, 2004, part II, p. 510; Abed, N.M., Hafez, E.A.A., Elsakka, I., and Elnagdi, M.N., J. Heterocycl. Chem., 1984, vol. 21, p. 1261; Hamed, A.A., Hashem, A.I., Salem, M.A., and Madkour, H.F., Egypt. J. Chem., 1986, vol. 29, p. 89.
Abdel-Latif, F.F. and Mahgoub, S.A., Egypt. J. Chem., 1990, vol. 33, p. 83; Abdel-Latif, F.F., Rev. Roum. Chim., 1990, vol. 35, p. 679.
Peseke, K., Bartroli, R.M., and Quincoces, S.J., Naturwissenschaften (R.), 1988, vol. 37, p. 46; Ref. Zh., Khim., 1991, no. 7Zh198.
Peseke, K., Suarez, J.Q., and Bartroli, R.M., Naturwissenschaften (R.), 1987, vol. 36, p. 70; Ref. Zh., Khim., 1990, no. 24Zh217.
Dorokhov, V.A., Baranin, S.V., Stashina, G.A., and Zhulin, V.M., Izv. Akad. Nauk SSSR, Ser. Khim., 1989, p. 211.
Borisov, V.N., Sovremennye problemy organicheskoi khimii (Current Problems in Organic Chemistry), Ogloblin, K.A., Ed., Leningrad: Leningr. Gos. Univ., 1975, p. 89.
Krivokolysko, S.G., Dyachenko, V.D., Nesterov, V.N., and Litvinov, V.P., Khim. Geterotsikl. Soedin., 2001, p. 929.
Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, p. S1.
Tietze, L.F., Chem. Rev., 1996, vol. 96, p. 115; Gorobets, E.V., Miftakhov, M.S., and Valeev, F.A., Usp. Khim., 2000, vol. 69, p. 1091.
Dyachenko, V.D. and Rusanov, E.B., Khim. Geterotsikl. Soedin., 2003, p. 745.
Yano, T., Isivatari, T., Torisu, I., Matsuo, N., and Tikho, S., JPN Patent no. 232804, 1991; Ref. Zh., Khim., 1994, no. 8O312P; Balicki, R., Sobotka, W., and Ejmocki, Z., Pol. J. Chem., 1991, vol. 65, p. 1049; Malhotra, S.K., Dripps, J., Bradfisch, G.A., Wollavitz, S., and Knax, I.L., US Patent no. 4 931 452, 1990; Ref. Zh., Khim., 1991, no. 21O380P.
Sheldrick, G.M., SHELXS-97. Program for the Solution of Crystal Structures, Göttingen: University of Göttingen, 1997.
Sheldrick, G.M., SHELXL-97. Program for the Refinement of Crystal Structures, Göttingen: University of Göttingen, 1997.
Author information
Authors and Affiliations
Additional information
Original Russian Text © I.V. Dyachenko, V.D. Dyachenko, E.B. Rusanov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 1, pp. 81–86.
Rights and permissions
About this article
Cite this article
Dyachenko, I.V., Dyachenko, V.D. & Rusanov, E.B. N-hetaryl-2-cyanoacetamides in the synthesis of substituted (E)-N-hetaryl-2-cyanoacrylamides, (E)-N-alkyl-N-hetaryl-2-cyanoacrylamides, and 6-amino-2-oxo-4-phenyl-1-(pyridin-2-yl)-1,2-dihydropyridine-3,5-dicarbonitriles. Russ J Org Chem 43, 83–89 (2007). https://doi.org/10.1134/S1070428007010101
Received:
Issue Date:
DOI: https://doi.org/10.1134/S1070428007010101