Skip to main content
SpringerLink
Log in

Cyclohexene-4-carbaldehyde in the Synthesis of 4-(Cyclohex-3-enyl)-Substituted 4H-Chromenes, 4H-Thiopyrans, 1,4,5,6,7,8-Hexahydroquinolines, 1,4-Dihydropyridines, Pyridines, and 6,7-Dihydro-5H-[1]pyrindines

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

Abstract

Cyclocondensation of cyclohexene-4-carbaldehyde in the presence of morpholine with CH acids [malonodinitrile, dimedone, 1,3-cyclohexanedione, ethyl acetoacetate, cyanothioacetamide, β-aminophenol, resorcinol, and 4-(cyclopent-1-enyl)morpholine] yields the corresponding 4-(cyclohex-3-enyl)-substituted 4H-chromenes, 4H-thiopyrans, 1,4,5,6,7,8-hexahydroquinolines, 1,4-dihydropyridines, and 6,7-dihydro-5H-[1]pyrindines.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Tietze, L.F., Chem. Rev., 1996, vol. 96, no.1, p. 115.

    Article  CAS  Google Scholar 

  2. Litvinov, V.P., Usp. Khim., 2003, vol. 72, no.1, p. 75.

    Google Scholar 

  3. Dyachenko, V.D., Doctoral (Chem.) Dissertation, Moscow, 1998.

  4. Gorobets, E.V., Miftakhov, M.S., and Valeev, F.A., Usp. Khim., 2000, vol. 69, no.12, p. 1091.

    Google Scholar 

  5. Ugi, I., Abstracts of Papers, III Vserossiiskii simpozium po organicheskoi khimii “Strategiya i taktika organicheskogo sinteza” (III Russian Symp. “Strategy and Tactics of Organic Synthesis”), Yaroslavl, 2001, p. 2.

  6. Smith, W.A., Bochkov, A.F., and Caple, R., Organic Synthesis: The Science behind the Art, London: Roy. Soc. Chem., 1998.

    Google Scholar 

  7. Dyachenko, V.D., in Novye dostizheniya v khimii karbonil'nykh soedinenii: Sbornik nauchnykh trudov (New Achievements in Chemistry of Carbonyl Compounds: Coll. of Scientific Papers), Saratov, 2000, p. 60.

  8. Dyachenko, A.D., Desenko, S.M., and Dyachenko, V.D., Khim. Geterotsikl. Soedin., 2002, no. 6, p. 845.

  9. Dyachenko, V.D., Nesterov, V.N., Krivokolysko, S.G., and Litvinov, V.P., Izv. Ross. Akad. Nauk, Ser. Khim., 1997, no. 1, p. 196.

  10. Dyachenko, V.D., Krivokolysko, S.G., and Litvinov, V.P., Khim. Geterotsikl. Soedin., 1998, no. 1, p. 81.

  11. Dyachenko, V.D., Nesterov, V.N., Krivokolysko, S.G., and Litvinov, V.P., Khim. Geterotsikl. Soedin., 1997, no. 6, p. 785.

  12. Comprehensive Organic Chemistry. The Synthesis and Reactions of Organic Compounds, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979.

    Google Scholar 

  13. Drabkina, A.A. and Tsizin, Yu.S., Zh. Obshch. Khim., 1974, vol. 44, no.2, p. 450.

    CAS  Google Scholar 

  14. Stork, G. and Landesman, H.K., J. Am. Chem. Soc., 1956, vol. 78, no.19, p. 5128.

    CAS  Google Scholar 

  15. Litvinov, V.P., Promonenkov, V.K., Sharanin, Yu.A., and Shestopalov, A.M., Itogi Nauki Tekh., Ser.: Org. Khim., 1989, vol. 17, p. 72.

    Google Scholar 

  16. Litvinov, V.P., Rodinovskaya, L.A., Sharanin, Yu.A., Schestopalov, A.M., and Senning, A., Sulfur Rep., 1992, vol. 13, no.1, p. 1.

    Article  CAS  Google Scholar 

  17. Kaigorodova, E.A., Vasilin, V.K., and Krapivin, G.D., Available from VINITI, Moscow, 2001, no. 1901-V; Ref. Zh. Khim., 2002, 02.04-19Zh213Dep.

  18. Issac, Y.A., Ali, M.S., and Erian, A.W., Sci. Pharm., 2000, vol. 68, no.4, p. 389.

    Google Scholar 

  19. El-Abadehan, M.M., Sabri, S.S., Al-Ashqar, A., Mion, P., Bompart, J., and Calas, M., Phosphorus, Sulfur, Silicon, Relat. Elem., 1998, vols. 134–135, no.1, p. 21.

    Google Scholar 

  20. Attia, A., Abo-Ghalia, M.H., and El-Salem, O.I.A., Pharmazie, 1995, vol. 50, no.7, p. 455.

    CAS  ISI  Google Scholar 

  21. Hussein, A.M., Abu-Shanal, F.A., and Ishak, E.A., Phosphorus, Sulfur, Silicon, Relat. Elem., 2000, vol. 159, no.1, p. 55.

    CAS  Google Scholar 

  22. Mohareb, R.M., Hoda, H.Z., Elkhoyly, Y.M., and Rasha, R.A., Phosphorus, Sulfur, Silicon, Relat. Elem., 1999, vol. 155, no.1, p. 215.

    CAS  Google Scholar 

  23. US Patent 6 329 388, 2000, Ref. Zh. Khim., 2002, 02.20-19O73P.

  24. US Patent 5 656 638, 1997, Chem. Abstr., 1997, vol. 127, no. 16, 220 647x.

  25. GDR Patent 275 688, 1990, Ref. Zh. Khim., 1990, 22O60P.

  26. Sharanin, Yu.A., Shestopalov, A.M., Nesterov, V.N., Melenchuk, S.N., Promonenkov, V.K., Shklover, V.E., Struchkov, Yu.T., and Litvinov, V.P., Zh. Org. Khim., 1989, vol. 25, no.6, p. 1323.

    CAS  Google Scholar 

  27. Dyachenko, V.D., Krivokolysko, S.G., Sharanin, Yu.A., and Litvinov, V.P., Zh. Org. Khim., 1997, vol. 33, no.7, p. 1084.

    Google Scholar 

  28. Dyachenko, V.D. and Litvinov, V.P., Khim. Geterotsikl. Soedin., 1997, no. 7, p. 995.

  29. Dyachenko, V.D. and Litvinov, V.P., Zh. Org. Khim., 1998, vol. 34, no.4, p. 592.

    Google Scholar 

  30. Nakanishi, K., Infrared Absorption Spectroscopy, Tokyo: Nankido, 1962.

    Google Scholar 

  31. Sharanin, Yu.A., Shestopalov, A.M., Litvinov, V.P., Klokol, G.V., Mortikov, V.Yu., and Demerkov, A.S., Zh. Org. Khim., 1988, vol. 24, no.4, p. 854.

    CAS  Google Scholar 

  32. RF Patent 2 083 572, 1997, Ref. Zh. Khim., 1998, 6O50P.

  33. US Patent 5 514 706, 1996, Ref. Zh. Khim., 1998, 13O40P.

  34. Kartsev, V.G., in Izbrannye metody sinteza i modifikatsii geterotsiklov (Selected Methods for Synthesis and Modification of Heterocycles), Moscow: IBS, 2003, p. 534.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Shevchenko National Pedagogical University, Lugansk, Ukraine

    V. D. Dyachenko

Authors
  1. V. D. Dyachenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 10, 2005, pp. 1612–1619.

Original Russian Text Copyright © 2005 by Dyachenko.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dyachenko, V.D. Cyclohexene-4-carbaldehyde in the Synthesis of 4-(Cyclohex-3-enyl)-Substituted 4H-Chromenes, 4H-Thiopyrans, 1,4,5,6,7,8-Hexahydroquinolines, 1,4-Dihydropyridines, Pyridines, and 6,7-Dihydro-5H-[1]pyrindines. Russ J Gen Chem 75, 1537–1544 (2005). https://doi.org/10.1007/s11176-005-0463-z

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11176-005-0463-z

Keywords

Search

Navigation