Skip to main content
Log in

Synthesis and alkylation of new 3-functionally substituted carbo[c]fused pyridin-2-ones(thiones)

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. 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.

    Google Scholar 

  2. 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.

    CAS  Google Scholar 

  3. 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.

  4. Hunt, J.C.A., Briggs, E., Clarke, E.D., and Whittingham, W.G., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 5222.

    Article  CAS  Google Scholar 

  5. Issac, Y.A., Ali, M.S., and Eian, A.W., Sci. Pharm., 2000, vol. 68, p. 389.

    CAS  Google Scholar 

  6. 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.

    Article  CAS  Google Scholar 

  7. Elgemeie, G.E.H., Attia, A.M.E., and Fathy, N.M., Nucleosides, Nucleotides, 1997, vol. 16, p. 485.

    Article  CAS  Google Scholar 

  8. 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.

    Article  CAS  Google Scholar 

  9. 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.

    Article  CAS  Google Scholar 

  10. 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.

    Google Scholar 

  11. Gewald, K., Buchwalder, M., and Peukert, M., J. Pract. Chem., 1973, vol. 315, p. 679.

    Article  CAS  Google Scholar 

  12. 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.

    Article  Google Scholar 

  13. 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.

    Google Scholar 

  14. 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.

    Article  CAS  Google Scholar 

  15. Zhang, P. and Li, L. Synth. commun., 1986, vol. 16, p. 957.

    Article  CAS  Google Scholar 

  16. 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.

    Google Scholar 

  17. 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.

    CAS  Google Scholar 

  18. Organikum. Organisch-Chemisches Grundpraktikum, Berlin: VEB Deutscher Verlag der Wissenschaften, 1976.

  19. Dyachenko, V.D., Tkachev, R.P., Zh. Org. Khim., 2002, vol. 38, p. 765.

    Google Scholar 

  20. 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.

    Google Scholar 

  21. Sasse, K., Lieb. Ann. Chem., 1976, p. 768.

    Google Scholar 

  22. Schaper, W., Synthesis, 1985, p. 861.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. V. Dyachenko.

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

Reprints 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

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428013020139

Keywords

Navigation