Skip to main content
SpringerLink
Log in

Synthesis, Crystal Structure, and DFT Study of (5-Bromo-2-fluorophenyl)-2-pyrazinylmethanone

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

Abstract

(5-Bromo-2-fluorophenyl)-2-pyrazinylmethanone is an important organic intermediate in medicinal chemistry. The title compound was obtained herein by an unreported synthetic method. Structure of the compound was confirmed by 1H NMR, 13C NMR, MS, FT-IR, and single crystal X-ray diffraction methods. To further study of the molecular electrostatic potential and frontier molecular orbitals of the title compound to understand the physicochemical properties of the compound was used density functional theory.

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

Scheme
Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.

REFERENCES

  1. Casuscelli, F., Ardini, E., Avanzi, N., Casale, E., Cervi, G., D’Anello, M., Donati, D., Faiardi, D., Ferguson, R.D., Fogliatto, G., Galvani, A., Marsiglio, A., Mirizzi, D.G., Montemartini, M., Orrenius, C., Papeo, G., Piutti, C., Salom, B., and Felder, E.R., Bioorg. Med. Chem., 2013, vol. 21, p. 7364. https://doi.org/10.1016/j.bmc.2013.09.054

    Article  CAS  PubMed  Google Scholar 

  2. Moravcová, Š., Fiedlerová, V., Tůma, J., Musil, K., and Tůmová, L., Nat. Prod. Commun., 2016, vol. 11, p. 457. https://doi.org/10.1177/1934578x1601100409

    Article  CAS  PubMed  Google Scholar 

  3. Heravi, M.M., Feiz, A., and Bazgir, A., Curr. Org. Chem., 2019, vol. 23, p. 2635. https://doi.org/10.2174/1385272823666191106101954

    Article  CAS  Google Scholar 

  4. Fontes, F.L., Peters, B.J., Crans, D.C., and Crick, D.C., ACS. Infect. Dis., 2020, vol. 6, p. 3004. https://doi.org/10.1021/acsinfecdis.0c00507

    Article  CAS  PubMed  Google Scholar 

  5. González, S.M., Rodríguez-Arístegui, S., Hernández, A.I., Varela, C., González Cantalapiedra, E., Álvarez, R.M., Hergueta, A.R., Bischoff, J.R., Albarrán, M.I., Cebriá, A., Cendón, E., Cebrián, D., Alfonso, P., and Pastor, J., Bioorg. Med. Chem. Lett., 2017, vol. 27, p. 2536. https://doi.org/10.1016/j.bmcl.2017.03.090

    Article  CAS  Google Scholar 

  6. Chen, M., Qin, A., Lam, J.W.Y., and Tang, B.Z., Coord. Chem. Rev., 2020, vol. 422, p. 213472. https://doi.org/10.1016/j.ccr.2020.213472

    Article  CAS  Google Scholar 

  7. Mąkosza, M., Lobanova, O., and Kwast, A., Tetrahedron, 2004, vol. 60, p. 2577. https://doi.org/10.1016/j.tet.2004.01.038

    Article  CAS  Google Scholar 

  8. Schultz, T.W., Ralston, K.E., Roberts, D.W., Veith, G.D. and Aptula, A.O., Sar. Qsar. Environ. Res., 2007, vol. 18, p. 21. https://doi.org/10.1080/10629360601033424

    Article  CAS  PubMed  Google Scholar 

  9. Dyk, K., Baran, Ł., Rżysko, W., Stankevič, M., and Kamiński, D.M., CrystEngComm, 2021, vol. 23, p. 2683. https://doi.org/10.1039/d0ce01673j

    Article  CAS  Google Scholar 

  10. Wang, L., Azizi, A., Xu, T., Kirk, S.R., and Jenkins, S., Chem. Phys. Lett., 2019, vol. 730, p. 206. https://doi.org/10.1016/j.cplett.2019.06.015

    Article  CAS  Google Scholar 

  11. Deppmeier, B.J. and Driessen, A.J., The Chemist’s Companion, Irvine: Wavefunction Inc., 2009, p. 123.

  12. Taha, D.K., Hilal, I.H., and Jabbar, R.H., J. Phys. Conf. Ser., 2021, vol. 1818, p. 012054. https://doi.org/10.1088/1742-6596/1818/1/012054

    Article  CAS  Google Scholar 

  13. Smirnova, I.E., Gatilov, Y.V., and Bagryanskaya, I.Y., Russ. J. Org. Chem., vol. 2021, 57, p. 671. https://doi.org/10.1134/S1070428021040266

  14. Politzer, P. and Driessen, J.S., In: Theoretical Biochemistry and Molecular Biophysics: A Comprehensive Survey. New York: Schenectady Adenine Press, 1990, p. 45.

  15. Sandhu, B., McLean, A., Sinha, A.S., Desper, J., Sarjeant, A.A., Vyas, S., Reutzel-Edens, S.M., and Aakeröy, C.B., Cryst. Growth. Des. 2018, vol. 18, p. 466. https://doi.org/10.1021/acs.cgd.7b01458

  16. Kotan, G., Gökce, H., Akyıldırım, O., Yüksek, H., Beytur, M., Manap, S., and Medetalibeyoğlu, H., Russ. J. Org. Chem. 2020, vol. 56, p. 1982. https://doi.org/10.1134/S1070428020110135

  17. Liao, T.H., Ye, W.J., Chen, D.M., Qin, Y.M., Chen, Y.M., Liao, W.K. and Zhou, Z.X., J. Heterocycl. Chem., 2022, vol. 59, p. 137. https://doi.org/10.1002/jhet.4373

    Article  CAS  Google Scholar 

  18. Chen, D.M., Chen, Y.M., Yang, D., Zheng, Z.P., and Zhou, Z.X., J. Heterocycl. Chem., 2021, vol. 58, p. 1628. https://doi.org/10.1002/jhet.4287

    Article  CAS  Google Scholar 

  19. Zhao, X., Chen, C.F., Sun, Q., Li, Y.C., and Yu, H.B., Appl. Surf. Sci., 2019, vol. 494, p. 895, https://doi.org/10.1016/j.apsusc.2019.07.248

    Article  CAS  Google Scholar 

  20. Wu, Q., Li, J.D., Liu, F.X., Xiao, J.C., Tang, Y.F., and Zi, Q.L., Russ. J. Coord. Chem., 2020, vol. 46, p. 137. https://doi.org/10.1134/S1070328420020086

    Article  CAS  Google Scholar 

  21. Yankova, R., Dimov, M., Dobreva, K., and Stoyanova, A., J. Chem. Res., 2019, vol. 43, p. 9, https://doi.org/10.1177/1747519819863957

    Article  CAS  Google Scholar 

  22. Sun, H., Deng, L.Y., Hu, W.Y., Liao, T.H., Liao, W.K., Chai, H.F. and Zhao, C.S., J. Mol. Struct., 2021, vol. 1248, p. 131395. https://doi.org/10.1016/j.molstruc.2021.131395

  23. Mıhçıokur, Ö. and Özpozan, T., J. Mol. Struct., 2017, vol. 1149, p. 27. https://doi.org/10.1016/j.molstruc.2017.07.064

    Article  CAS  Google Scholar 

  24. Sivaprakash, S., Prakash, S., Mohan, S. and Jose, S.P., J. Mol. Struct., 2017, vol. 1149, p. 835. https://doi.org/10.1016/j.molstruc.2017.08.060

  25. Lübben, J., Wandtke, C.M., Hübschle, C.B., Ruf, M., Sheldrick, G.M. and Dittrich, B., Acta Crystallogr. (A), 2019, vol. 75, p. 2053. https://doi.org/10.1107/s2053273318013840

    Article  CAS  Google Scholar 

Download references

Funding

This work was awarded the Guizhou Provincial Natural Science Foundation ([2020]1Y393).

Author information

Authors and Affiliations

  1. School of Pharmaceutical Sciences, Guizhou University, 550000, Guiyang, China

    P.-C. Shi, J.-L. Xiao, W.-F. Deng, Q. Guo, L. Jin, Z.-X. Zhou & C. Ji

  2. Guizhou Engineering Laboratory for Synthetic Drugs, 550000, Guiyang, China

    P.-C. Shi, J.-L. Xiao, W.-F. Deng, Q. Guo, L. Jin, Z.-X. Zhou & C. Ji

Authors
  1. P.-C. Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J.-L. Xiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. W.-F. Deng
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Q. Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. Jin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Z.-X. Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. C. Ji
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to C. Ji.

Ethics declarations

No conflict of interest was declared by the authors.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shi, PC., Xiao, JL., Deng, WF. et al. Synthesis, Crystal Structure, and DFT Study of (5-Bromo-2-fluorophenyl)-2-pyrazinylmethanone. Russ J Gen Chem 93, 91–96 (2023). https://doi.org/10.1134/S1070363223010139

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363223010139

Keywords:

Search

Navigation