Skip to main content
SpringerLink
Log in

trans-Stereoselective Reduction of Hexahydroquinazoline-2(1H)-thione Derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Reduction of substituted 4-arylhexahydroquinazoline-2(1H)-thiones using NaBH4/CF3CO2H in chloroform gave the corresponding trans-fused octahydroquinazoline-2(1H)-thiones. The use of two reducing systems, NaBH4/CH3CO2H or NaBH4/CF3CO2H, permitted the consecutive trans-selective reduction of the endo- and exocyclic double bond in the case of 8-dithiomethylidene derivatives of hexahydroquinazoline-2(1H)-thiones.

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

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. T. Lorand, D. Szabo, A. Foldesi, and A. Neszmelyi, Acta Chim. Acad. Sci. Hung., 108, 197 (1981).

    CAS  Google Scholar 

  2. O. D. Kololeikina, I. M. Gella, and V. D. Orlov, Vestn. Khar'kovsk. Nats. Univ., No. 495, 50 (2000).

  3. A. V. Mirnyi, I. M. Gella, and V. D. Orlov, Zh. Org. Farm. Khim., 1, Nos. 3-4, 55 (2003).

    CAS  Google Scholar 

  4. W. L. F. Armarego and T. Kobayashi, J. Chem. Soc. C, 238 (1971).

  5. S. Mantegani, T. Bandiera, E. Brambilla, and G. Traquandi, J. Heterocycl. Chem., 29, 455 (1992).

    Article  CAS  Google Scholar 

  6. C. Kashima, A. Katoh, Y. Yokota, and Y. Omote, J. Chem. Soc., Perkin Trans.1, 162 (1981).

  7. N. M. Yousif, F. A. Gad, A. F. M. Fahmy, M. S. Amine, and H. H. Sayed, Phosphorus, Sulfur Silicon Relat. Elem., 117, 11 (1996).

    Article  CAS  Google Scholar 

  8. G. W. Gribble, Chem. Soc. Rev., 27, 395 (1998).

    Article  CAS  Google Scholar 

  9. J. J. P. Stewart, MOPAC2012, Stewart Computational Chemistry, Version12.239W, http://OpenMOPAC.net.

  10. S. I. Filimonov, S. A. Filimonova, A. S. Shashkov, S. I. Firgang, and G. A. Stashina, Izv. Akad. Nauk, Ser. Khim., 1456 (2005). [Russ. Chem. Bull., Int. Ed., 54, 1500 (2005)].

  11. B. A. Shainyan and A. N. Mirskova, Usp. Khim., 48, 201 (1979). [Russ. Chem. Rev., 48, 107 (1979)].

    Article  CAS  Google Scholar 

  12. O. D. Bui, I. M. Gella, S. V. Shishkina, O. V. Shishkin, V. I. Musatov, and V. D. Orlov, Zh. Org. Farm. Khim., 4, No. 2, 24 (2006).

    Google Scholar 

  13. C. S. Rao, R. T. Chakrasali, H. Ila, and H. Junjappa, Tetrahedron, 46, 2195 (1990).

    Article  CAS  Google Scholar 

  14. S. Yoshida, H. Yorimitsu, and K. Oshima, Org. Lett., 11, 2185 (2009).

    Article  CAS  Google Scholar 

  15. O. Cohen, Y. Hagooly, and S. Rozen, Tetrahedron, 65, 1361 (2009).

    Article  CAS  Google Scholar 

  16. G. M. Sheldrick, Acta Crystallogr., Sect.A, A64, 112 (2008).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Scientific-Technological Complex “Institute of Monocrystals”, National Academy of Sciences of Ukraine, 60 Lenina Ave., Kharkiv, 61001, Ukraine

    I. M. Gella, S. V. Shishkina & O. V. Shishkin

  2. V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61022, Ukraine

    O. D. Bui, A. V. Mirnyi & V. D. Orlov

Authors
  1. I. M. Gella
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. D. Bui
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Mirnyi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. V. Shishkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. V. Shishkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. D. Orlov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. D. Orlov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 327-334, February, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gella, I.M., Bui, O.D., Mirnyi, A.V. et al. trans-Stereoselective Reduction of Hexahydroquinazoline-2(1H)-thione Derivatives. Chem Heterocycl Comp 49, 302–309 (2013). https://doi.org/10.1007/s10593-013-1247-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1247-8

Keywords

Search

Navigation