Skip to main content
SpringerLink
Log in

Synthesis of dithienoquinazolines from pyrimidines via intramolecular nucleophilic aromatic substitution of hydrogen

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The possibility of intramolecular nucleophilic aromatic substitution of hydrogen in the series of 5-[2-(het)aryl-1-benzothiophen-3-yl]-pyrimidines was explored. A convenient method for the synthesis of [1]benzothieno-[3,2-f]thieno[2,3-h]quinazoline and [1]benzothieno-[3,2-f]thieno[3,2-h]quinazoline based on the developed SN H protocol was proposed. The energy parameters (width of the band gap, the energy of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbitals (LUMO)) of benzothieno[3,2-f]-thieno[2,3-h]quinazoline synthesized for the first time were determined based on the data of the absorption spectra and cyclic voltammetry.

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

Figure 1.
Scheme 1.
Fig. 2.
Scheme 2.
Figure 3.
Figure 4.
Figure 5.

Similar content being viewed by others

References

  1. (a) Thompson, M. E.; Saris, P.; Djurovich, P. I.; Chen, S. H.-F. WO Patent 2015066244. (b) Hara, T.; Inoue, H.; Takahashi, T.; Hamada, T.; Seo, S. US Patent 2016190479. (c) Yamada, Y.; Inoue, H.; Seo, H.; Takahashi, T. US Patent 2016181550. (d) Jang, J. W.; Jung, H. Y.; Kim, S.-G.; Kim, W. S.; Byun, J. H.; Park, J. H.; Hwang, S. P. WO Patent 2016032150.

  2. Verbitskiy, E. V.; Slepukhin, P. A.; Valova, M. S.; Cheprakova, E. M.; Schepochkin, A. V.; Rusinov, G. L.; Charushin, V. N. Eur. J. Org. Chem. 2014, 8133.

  3. Verbitskiy, E. V.; Cheprakova, E. M.; Makarova, N. I.; Dorogan, I. V.; Metelitsa, A. V.; Minkin, V. I.; Slepukhin, P. A.; Svalova, T. S.; Ivanova, A. V.; Kozitsina, A. N.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. Eur. J. Org. Chem. 2016, 1420.

  4. Verbitskiy, E. V.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. ARKIVOC 2016, (iv), 204.

  5. (а) Chupakhin, O. N.; Charushin, V. N. Tetrahedron Lett. 2016, 57, 2665. (b) Charushin, V. N.; Chupakhin, O. N. Top Heterocycl. Chem. 2014, 37, 1. (c) Mąkosza, M. Chem. Soc. Rev. 2010, 39, 2855.

  6. Verbitskiy, E. V.; Rusinov, G. L.; Charushin, V. N.; Chupakhin, O. N.; Cheprakova, E. M.; Slepukhin, P. A.; Pervova, M. G.; Ezhikova, M. A.; Kodess, M. I. Eur. J. Org. Chem. 2012, 6612.

  7. Costa, J. C. S.; Taveira, R. J. S.; Lima, C. F. R. A. C.; Mendes, A.; Santos, L. M. N. B. F. Opt. Mater. (Amsterdam, Neth.) 2016, 58, 51.

    CAS  Google Scholar 

  8. Cardona, C. M.; Li, W.; Kaifer, A. E.; Stockdale, D.; Bazan, G. C. Adv. Mater. 2011, 23, 2367.

    Article  CAS  Google Scholar 

  9. Verbitskiy, E. V.; Cheprakova, E. M.; Slepukhin, P. A.; Kravchenko, M. A.; Skornyakov, S. N.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. Eur. J. Med. Chem. 2015, 97, 225.

    Article  CAS  Google Scholar 

  10. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

  11. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

Download references

The work was supported by the grant of the Russian Science Foundation (project no 16-13-10435).

Author information

Authors and Affiliations

  1. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoy/20 Akademicheskaya St., Yekaterinburg, 620219, Russia

    Egor V. Verbitskiy, Ekaterina M. Dinastiya, Gennady L. Rusinov, Oleg N. Chupakhin & Valery N. Charushin

  2. Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    Egor V. Verbitskiy, Anna A. Baranova, Oleg S. Eltsov, Gennady L. Rusinov, Oleg N. Chupakhin & Valery N. Charushin

Authors
  1. Egor V. Verbitskiy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ekaterina M. Dinastiya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Anna A. Baranova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Oleg S. Eltsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Gennady L. Rusinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Oleg N. Chupakhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Valery N. Charushin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Egor V. Verbitskiy.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1156–1160

Electronic supplementary material

ESM 1

(PDF 841 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Verbitskiy, E.V., Dinastiya, E.M., Baranova, A.A. et al. Synthesis of dithienoquinazolines from pyrimidines via intramolecular nucleophilic aromatic substitution of hydrogen. Chem Heterocycl Comp 53, 1156–1160 (2017). https://doi.org/10.1007/s10593-017-2188-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2188-4

Keywords

Search

Navigation