Russian Journal of Organic Chemistry

, Volume 51, Issue 6, pp 864–868 | Cite as

Multicomponent synthesis of 2-(alkylsulfanyl)-4-[furan-2-yl-(or thiophen-2-yl)]-5,6,7,8-tetrahydroquinoline-3-carbonitriles

  • V. D. Dyachenko
  • V. N. Nesterov
  • S. V. Dyachenko
  • A. V. Chernykh
Article
  • 52 Downloads

Abstract

Substituted 2-(alkylsulfanyl)-4-[furan-2-yl(or thiophen-2-yl)]-5,6,7,8-tetrahydroquinoline-3-carbonitriles were synthesized by condensation of furfural or thiophene-2-carbaldehyde with 2-cyanoethanethioamide, 1-(cyclohex-1-en-1-yl)pyrrolidine, and alkyl halides. The structure of methyl 2-{[3-cyano-4-(thiophen-2-yl)-5,6,7,8-tetrahydroquinolin-2-yl]sulfanyl}acetate was determined by X-ray analysis.

Keywords

Yellow Powder Alkyl Halide Sulfanyl Methylsulfanyl Fluoroacetic Acid 

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References

  1. 1.
    Shestopalov, A.M., Shestopalov, A.A., and Rodinovskaya, L.A., Synthesis, 2008, p. 1.Google Scholar
  2. 2.
    Orru, R.V.A., Book of Abstracts, VIth Int. Conf. “Chemistry of Nitrogen-Containing Heterocycles,” Kharkiv, 2012, L-1.Google Scholar
  3. 3.
    Tietze, L.F., Brasche, G., and Gericke, K.M., Domino Reactions in Organic Synthesis, Weinheim: Wiley-VCH, 2006.CrossRefGoogle Scholar
  4. 4.
    Litvinov, V.P., Russ. Chem. Rev., 2003, vol. 72, no. 1, p. 69.CrossRefGoogle Scholar
  5. 5.
    Ugi, I., Abstracts of Papers, III Vserossiiskii simpozium po organicheskoi khimii “Strategiya i taktika organicheskogo sinteza” (IIIrd All-Russian Symp. on Organic Chemistry “Strategy and Tactics of Organic Synthesis”), Yaroslavl, 2001, p. 2.Google Scholar
  6. 6.
    Dyachenko, V.D. and Krasnikov, D.O., Ukr. Khim. Zh., 2005, vol. 71, no. 6, p. 86.Google Scholar
  7. 7.
    Dyachenko, V.D., Russ. J. Org. Chem., 2011, vol. 47, p. 1535.CrossRefGoogle Scholar
  8. 8.
    Dyachenko, A.D., Desenko, S.M., and Dyachenko, V.D., Chem. Heterocycl. Compd., 2002, vol. 38, no. 6, p. 747.CrossRefGoogle Scholar
  9. 9.
    Dyachenko, V.D., Nesterov, V.N., and Dyachenko, I.V., Russ. J. Gen. Chem., 2011, vol. 81, p. 751.CrossRefGoogle Scholar
  10. 10.
    Nesterov, V.N., Dyachenko, V.D., Sharanin, Yu.A., and Struchkov, Yu.T., Russ. Chem. Bull., 1996, vol. 45, no. 2, p. 420.CrossRefGoogle Scholar
  11. 11.
    Dyachenko, V.D., Roman, S.V., and Litvinov, V.P., Russ. Chem. Bull., 2000, vol. 49, no. 1, p. 125.CrossRefGoogle Scholar
  12. 12.
    Dyachenko, V.D., Tkacheva, V.P., Dyachenko, A.D., and Tkachev, R.P., Russ. J. Gen. Chem., 2010, vol. 80, p. 1034.CrossRefGoogle Scholar
  13. 13.
    Leon, R., Rios, C., Marco-Contelles, J., Lopez, M.G., Garcia, A.G., and Villaroga, M., Eur. J. Med. Chem., 2008, vol. 43, p. 668.CrossRefGoogle Scholar
  14. 14.
    Lockman, J.W., Reeder, M.D., Suzuki, K., Ostamin, K., Hoff, R., Bhoite, L., Austin, H., Baichwall, V., and Willadsen, A.J., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 2283.CrossRefGoogle Scholar
  15. 15.
    Stoltefuβ, J., Lögers, M., Schmidt, G., Brandes, A., Schmeck, C., Bremm, K.-D., Bischoff, H., and Schmidt, D., DE Patent Appl. no. 19 741 051, 1999; Ref. Zh., Khim., 2000, no. 19 O 37 P.Google Scholar
  16. 16.
    Sirkar, D.Ts., Kumar, S.K.Ts., and Yuing, V., RU Patent Appl. no. 2005128190/04, 2006; Ref. Zh., Khim., 2007, no. 19 O 107 P.Google Scholar
  17. 17.
    Izbrannye metody sinteza i modifikatsii geterotsiklov. Khinoliny: khimiya i biologicheskaya aktivnost’ (Selected Methods of Synthesis and Modification of Heterocycles. Quinolines: Chemistry and Biological Activity), Kartsev, V.G., Ed., Moscow: MBFNP (ICSPF), 2007, vol. 6.Google Scholar
  18. 18.
    Stork, G., Brizzolara, A., Landesman, H., Szmuszkovicz, J., and Terrell, R., J. Am. Chem. Soc., 1963, vol. 85, p. 207.CrossRefGoogle Scholar
  19. 19.
    March, J., Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, New York: Wiley, 1985. Translated under the title Organicheskaya khimiya. Reaktsii, mekhanizmy i struktura, Moscow: Mir, 1987, vol. 3, p. 25.Google Scholar
  20. 20.
    Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, no. 12, p. S1–S19.Google Scholar
  21. 21.
    Bruker APEX2, Madison, WI: Bruker Advanced Analytical X-ray Systems, 2007.Google Scholar
  22. 22.
    Bruker SADABS, Madison, WI: Bruker Advanced Analytical X-ray Systems, 2007.Google Scholar
  23. 23.
    SHELXTL Version 6.14, Madison, WI: Bruker Advanced Analytical X-ray Systems, 2003.Google Scholar
  24. 24.
    Dyachenko, V.D. and Litvinov, V. P., Chem. Heterocycl. Compd., 1997, vol. 33, no. 10, p. 1203.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2015

Authors and Affiliations

  • V. D. Dyachenko
    • 1
  • V. N. Nesterov
    • 2
  • S. V. Dyachenko
    • 1
  • A. V. Chernykh
    • 3
  1. 1.Taras Shevchenko Lugansk National UniversityLuganskUkraine
  2. 2.University of North TexasDentonUSA
  3. 3.Institute of Organic ChemistryNational Academy of Sciences of UkraineKievUkraine

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