Abstract
By condensation of 2-acyl-1-(morpholin-4-yl)cycloalkenes with CH-acids new 3-functuinally substituted carbo[c]fused pyridin-2-ones(thiones) were synthesized. N, 1-Diphenyl-5, 6, 7, 8-tetrahydroisoquinoline-3-thione under the action of acrylonitrile and alkyl halides suffered a selective S-alkylation.
Similar content being viewed by others
References
Paronikyan, E.G., Noravyan, A.S., Akopyan, Sh.F., Dzhagatspanyan, I.A., Nazaryan, I.M., and Paronikyan, R.G., Khim.-Farm. Zh., 2007, vol. 41, no. 9, p. 14.
Faermark, I.F., Guss, L.T., Ershov, L.V., Shvarts, G.Ya., and Granik, V.G., Khim.-Farm. Zh., 1990, vol. 24, no 5, p. 27; Smetskaya, N.I., Mukhina, N.A., Granik, V.G., Shvarts, G.Ya., Syubaev, R.D., and Mashkovskii, M.D., Khim.-Farm. Zh., 1984, vol. 18, no. 8, p. 931.
Azotistye geterotsikly i alkaloidy (Nitrogen Heterocycles and Alkaloids), Kartsev, V.G. and Tolstikov, G.A., IBS, 2001, vol. 1, p. 435; Kaiho, T., San-nohe, K., Kajiya, S., Suzuki, T., Otsuka, K., Ito, T., Kamiya, J., and Maruyama, M., J. Med. Chem., 1989, vol. 32, p. 351.
Hunt, J.C.A., Briggs, E., Clarke, E.D., and Whittingham, W.G., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 5222.
Issac, Y.A., Ali, M.S., and Eian, A.W., Sci. Pharm., 2000, vol. 68, p. 389.
Chan, L., Stefanac, T., Turcotte, N., Hu, Z., Chen, Y., Bedard, J., May, S., and Jin, H., Bioorg. Med. Chem. Lett., 2000, vol. 10, p. 1477.
Elgemeie, G.E.H., Attia, A.M.E., and Fathy, N.M., Nucleosides, Nucleotides, 1997, vol. 16, p. 485.
Vernier, J.-M., Holsenback, H., Cosford, N.D.P., Whitten, J.P., Menzaghi, F., Reid, R., Rao, T.S., Sacaan, A.I., Lloyd, G.K., Suto, C.M., Chavez-Noriega, L.E., Washburn, M.S., Urrutia, A., and McDonald, I.A., Bioorg. Med. Chem. Lett., 1998, vol. 8, p. 2173.
Ashwell, G.J., Robinson, B.J., Amiri, M.A., Locatelli, D., Quici, S., and Roberto, D., J. Mater. Chem., 2005, vol. 15, p. 4203; Ashwell, G.J., Tyrrel, W.D., Whittem, A.J. J. Am. Chem. Soc., 2004, vol. 126, p. 7102.
Dyachenko, V.D., Sukach, S.M., Dyachenko, A.D., Zubatyuk, R.M., and Shishkin, O.V., Zh. Obshch.Khim., 2010, vol. 80, p. 1728; Lozinskii, M.O., Chernega, A.N., and Shelyakin, V.V., Zh. Org. Khim., 2002, vol. 38, p. 1718; Freeman, F., Farquhar, D.K., and Walker, R.L., J. Org. Chem., 1968, vol. 33, p. 3648.
Gewald, K., Buchwalder, M., and Peukert, M., J. Pract. Chem., 1973, vol. 315, p. 679.
Megm, A.M., El-Aaad, F.A.E.A., Hafez, E.A., Elnagdi, M.H., and Mostafa, Y.M.N. Phosph., Sulfur, Silicon. Relat. Elem., 1995, vol. 106, p. 1.
Fadda, A.A., Indian J. Chem., 1991, vol. 30, p. 28; El-Dead, A.M.K., Hafez, A.A.A., and Attallah, H.A., Phosph., Sulfur, Silicon. Relat. Elem., 1989, vol. 46, p. 1.
Elgemeie, G.E.H. and Fathy, N.M., Tetrahedron, 1995, vol. 51, p. 3345; Elgemeie, G.H., and Ahmed, M.A., Nucleosides, Nucleotides, Nucleic, acids., 2002, vol. 21, p. 837; Elgemeie, G.H., El-Enany, M.M., Ismail, M.M., and Ahmed, E.K., Nucleosides, Nucleotides, Nucleic Acids., 2002, vol. 21, p. 477.
Zhang, P. and Li, L. Synth. commun., 1986, vol. 16, p. 957.
March, J., Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, New York: Wiley-Interscience, 1985. Litvinov, V.P., Yakunin, Ya.Yu., and Dyachenko, V.D., Khim. Geterotsikl. Soedin., 2001, p. 41.
Stanetty, P., Purstinger, G. Monatsh. Chem., 1999, vol. 130, p. 441; Al-Omran, F., Elassar, A.-Z.A., and El-Khair, A.A., Tetrahedron, 2001, vol. 57, p. 10163.
Organikum. Organisch-Chemisches Grundpraktikum, Berlin: VEB Deutscher Verlag der Wissenschaften, 1976.
Dyachenko, V.D., Tkachev, R.P., Zh. Org. Khim., 2002, vol. 38, p. 765.
Dyachenko, V.D. and Kudryavtseva, A.G., Khim. Geterotsikl. Soedin., 2004, p. 1728; Klokol, G.V., Sharanina, L.G., Nesterov, V.N., Shklover, V.E., Sharanin, Yu.A., and Struchkov, Yu.T., Zh. Org. Khim., 1987, vol. 23, p. 412; Abd-El-Aziz, A.S., Egrody, A.M., Bedair, A.H., Corkery, T.C., and Ato, A. Hetrocycles, 2004, vol. 63, p. 1793; Al-Mousawi, S.M., Elkholy, Y.M., Mohammed, M.A., and Elnagdi, M.H. Org. Prep. Proc. Int., 1999, 31, p. 305.
Sasse, K., Lieb. Ann. Chem., 1976, p. 768.
Schaper, W., Synthesis, 1985, p. 861.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original English Text © I.V. Dyachenko, M.V. Vovk, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 2, pp. 268–275.
Rights and permissions
About this article
Cite this article
Dyachenko, I.V., Vovk, M.V. Synthesis and alkylation of new 3-functionally substituted carbo[c]fused pyridin-2-ones(thiones). Russ J Org Chem 49, 259–267 (2013). https://doi.org/10.1134/S1070428013020139
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428013020139