Skip to main content
SpringerLink
Log in

Synthesis of 6-R-5-aryl-1,3-dioxo-1,2,3,4-tetrahydro-[1]benzothieno[3',2':4,5]pyrido[2,3-d]pyrimidin-5-ium salts and 6-R-5-aryl-5,6-dihydro[1]benzothieno-[3',2':4,5]pyrido[2,3-d]pyrimidine-1,3(2H,4H)-diones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Acylation of 5-(benzothiophen-3-yl)pyrimidine-2,4,6(1H,3H,5H)-trione using acetic and propionic anhydride in the presence of 70% perchloric acid gave the 6-methyl(ethyl)-1,3-dioxo-1,2,3,4-tetra-hydro[1]benzothieno[3',2':4,5]pyrano[2,3-d]pyrimidin-5-ium perchlorates. Hydrolysis of the pyrano[2,3-d]pyrimidin-5-ium salts in aqueous alcohol solution gave 5-(2-acylbenzothiophen-3-yl)-pyrimidine-2,4,6(1H,3H,5H)-triones. Cyclocondensation of the latter with aromatic amine hydrochlorides produced 6-R-5-aryl-1,3-dioxo-1,2,3,4-tetrahydro[1]benzothieno[3',2':4,5]pyrido[2,3-d]-pyrimidin-5-ium chlorides. 6-R-5-Aryl-5,6-dihydro[1]benzothieno[3',2':4,5]pyrido[2,3-d]pyrimidine-1,3(2H,4H)-diones were synthesized by reduction of the pyrimidinium chlorides using sodium borohydride.

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

Notes

  1. In the 1H NMR spectra of compounds 4a-i the 2-NH group was found to exchange with water and appeared in the region 3.20-3.60 ppm.

  2. In the 1H NMR spectra of compounds 5b,d,f,g the 2-NH exchanged with water and appeared in the range of 3.00-3.40 ppm.

Reference

  1. K. A. Krasnov, in: V. G. Kartsev (editor), Selected Methods for the Synthesis and Modification of Heterocycles [in Russian], Vol. 1, InterBioScreen Press, Moscow (2003), p. 314.

    Google Scholar 

  2. K. A. Krasnov, in: V. G. Kartsev (editor), Selected Methods for the Synthesis and Modification of Heterocycles [in Russian], Vol. 2, InterBioScreen Press, Moscow (2003), p. 258.

    Google Scholar 

  3. L. W. Deady, A.-M. Ganakas, and B. H. Ong, Aust. J. Chem., 42, 1029 (1989).

    Article  CAS  Google Scholar 

  4. E. D. Edstrom and W. Yuan, Tetrahedron Lett., 32, 323 (1991).

    Article  CAS  Google Scholar 

  5. V. S. Tolkunov, Yu. B. Vysotsky, O. A. Gorban’, S. V. Shiskhina, O. V. Shishkin, and V. I. Dulenko, Khim. Geterotsikl. Soedin., 601 (2005). [Chem. Heterocycl. Compd., 41, 515 (2005)].

    Google Scholar 

  6. V. I. Dulenko, S. V. Tolkunov, and N. N. Alekseev, Khim. Geterotsikl. Soedin., 1351 (1981). [Chem. Heterocycl. Compd., 17, 1010 (1981)].

    Google Scholar 

  7. S. V. Tolkunov, A. I. Khizhan, S. I. Simonova, N. S. Semenov, and S. N. Lyashchuk, Khim. Geterotsikl. Soedin., 321 (1994). [Chem. Heterocycl. Compd., 30, 283 (1994)].

    Google Scholar 

  8. S. V. Tolkunov and A. I. Khizhan, Khim. Geterotsikl. Soedin., 624 (2003). [Chem. Heterocycl. Compd., 39, 539 (2003)].

    Google Scholar 

  9. M. A. Kruchkov, R. I. Zubatyuk, I. F. Perepichka, O. V. Shishkin, and S. V. Tolkunov, Monatsh. Chem., 141, 35 (2010).

    Article  Google Scholar 

  10. Y. P. Stradiņš, Khim. Geterotsikl. Soedin., 1412 (1981).

Download references

Author information

Authors and Affiliations

  1. L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 70 R. Luxemburg St., Donetsk, 83114, Ukraine

    V. S. Tolkunov, A. B. Eresko & S. V. Tolkunov

  2. A. V. Bogatsky Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 6 Lyustdorfsky St., Odessa, 65080, Ukraine

    A. V. Mazepa

Authors
  1. V. S. Tolkunov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. B. Eresko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Mazepa
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. V. Tolkunov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. S. Tolkunov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp 1007-1014, June 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tolkunov, V.S., Eresko, A.B., Mazepa, A.V. et al. Synthesis of 6-R-5-aryl-1,3-dioxo-1,2,3,4-tetrahydro-[1]benzothieno[3',2':4,5]pyrido[2,3-d]pyrimidin-5-ium salts and 6-R-5-aryl-5,6-dihydro[1]benzothieno-[3',2':4,5]pyrido[2,3-d]pyrimidine-1,3(2H,4H)-diones. Chem Heterocycl Comp 49, 941–948 (2013). https://doi.org/10.1007/s10593-013-1329-7

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1329-7

Keywords

Search

Navigation