Skip to main content
SpringerLink
Log in

Nucleophilic Reactivity of a Novel 3-Chloro-3-(4,9-dimethoxy5-oxo-5H-furo[3,2-g]chromen-6-yl)prop-2-enal

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

Abstract

A novel 3-chloro-3-(4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromen-6-yl)prop-2-enal was synthesized from 6-acetyl-4,9-dimethoxy-5H-furo[3,2-g]chromen-5-one by the Vilsmeier–Haack reaction, and its chemical reactivity toward some mono- and di-nitrogen nucleophiles was investigated. The reactions of the synthesized enal with primary amines, specifically benzylamine and p-toluidine, gave novel enamines or enaminones, depending on the molar ratio of the reagents, and its reactions with 1,2- and 1,3-dinucleophiles produced some novel benzofuran derivatives bearing bipyrazole, pyrazolylisoxazole, and bipyrimidine substituents in the C6 position. The structures of the newly synthesized compounds waere elucidated on the basis of their analytical and spectral data.

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
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Abu-Hashem, A.A. and El-Shazly, M., Eur. J. Med. Chem., 2015, vol. 90, p. 633. https://doi.org/10.1016/j.ejmech.2014.12.001

    Article  CAS  PubMed  Google Scholar 

  2. Gammill, R.B., Day, C.E., and Schurr, P.E., J. Med. Chem., 1983, vol. 26, p. 1672. https://doi.org/10.1021/jm00366a002

    Article  CAS  PubMed  Google Scholar 

  3. Travaini, M.L., Sosa, G.M., Ceccarelli, E.A., Walter, H., Cantrell, C.L., Carrillo, N.J., Dayan, F.E., Meepagala, K.M., and Duke, S.O., J. Agric. Food Chem., 2016, vol. 64, p. 9475. https://doi.org/10.1021/acs.jafc.6b02462

    Article  CAS  PubMed  Google Scholar 

  4. Dewar, H.A. and Grimson, T.A., Br. Heart J., 1950, vol. 12, p. 54. https://doi.org/10.1136/hrt.12.1.54

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Sharma, R., Williams, I.S., Gatchie, L., Sonawane, V.R., Chaudhuri, B., and Bharate, S.B., ACS Omega, 2018, vol. 3, p. 8553. https://doi.org/10.1021/acsomega.8b01088

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Amr, A.E., Abdalla, M.M., Essaouy, S.A., Areef, M.M.H., Elgamal, M.H., Nassear, T.A., Haschich, A.E., and Al-Omar, M.A., Russ. J. Gen.Chem., 2017, vol. 87, p. 1591. https://doi.org/10.1134/S1070363217070246

    Article  CAS  Google Scholar 

  7. Reis, J., Gaspar, A., Milhazes, N., and Borges, F., J. Med. Chem., 2017, vol. 60, p. 7941. https://doi.org/10.1021/acs.jmedchem.6b01720

    Article  CAS  PubMed  Google Scholar 

  8. Frasinyuk, M.S., Gorelov, S.V., Bondarenko, S.P., and Khilya, V.P., Chem. Heterocycl. Compd., 2009, vol. 45, p. 1261. https://doi.org/10.1007/s10593-010-0417-1

    Article  CAS  Google Scholar 

  9. Ghate, M. and Kulkarni, M.V., Ind. J. Chem. B, 2005, vol. 44, p. 1674. http://nopr.niscair.res.in/handle/123456789/9154

    Google Scholar 

  10. Abu-Hashem, A.A. and Youssef, M.M., Molecules, 2011, vol. 16, p. 1956. https://doi.org/10.3390/molecules16031956

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Ali, T.E. and Ibrahim, M.A., J. Braz. Chem. Soc., 2010, vol. 21, p. 1007. https://doi.org/10.1590/S0103-50532010000600010

    Article  Google Scholar 

  12. Ali, T.E., Abdel-Aziz, S.A., El-Edfawy, S.M., Mohamed, E.A., and Abdel-Kariem, S.M., Synth. Commun., 2014, vol. 44, p. 3610. https://doi.org/10.1080/00397911.2014.948965

    Article  CAS  Google Scholar 

  13. Ali, T.E., Ali, M.M., Abdel-kariem, S.M., and Ahmed, M.M., Russ. J. Org. Chem., 2017, vol. 53, p. 904. https://doi.org/10.1134/S107042801706015X

    Article  CAS  Google Scholar 

  14. El-Gohary, N.M., Ibrahim, M.A., El-Sawy, E.R., and Abdel-Fatah, N.A., J. Heterocycl. Chem., 2017, vol. 54, p. 1467. https://doi.org/10.1002/jhet.2733

    Article  CAS  Google Scholar 

  15. Eiden, F. and Schuenemann, J., Arch. Pharm., 1983, vol. 316, p. 201. https://doi.org/10.1002/ardp.19833160304

    Article  CAS  Google Scholar 

  16. Sharma, A., Gudala, S., Ambati, S.R., Penta, S., Bomma, Y., Janapala, V.R., Jha, A., and Kumar, A., J. Chin. Chem. Soc., 2018, vol. 65, p. 810. https://doi.org/10.1002/jccs.201700340

    Article  CAS  Google Scholar 

  17. Saunders, R.A. and Williams, A.E., Mass Spectrometry of Organic Ions, McLafferty, F.W., Ed., New York: Academic Press, 1963, p. 343.

  18. Parella, T. and Espinosa, J.F., Prog. Nucl. Mag. Res. Sp., 2013, vol. 73, p. 17. https://doi.org/10.1016/j.pnmrs.2013.07.001

    Article  CAS  Google Scholar 

  19. Ibrahim, M.A. and El-Gohary, N.M., Tetrahedron, 2018, vol. 74, p. 512. https://doi.org/10.1016/j.tet.2017.12.030

    Article  CAS  Google Scholar 

  20. Ibrahim, M.A., Arkivoc, 2008, vol. xvii, p. 192. https://doi.org/10.3998/ark.5550190.0009.h18

  21. Ibrahim, M.A., Ali, T.E., El-Gohary, N.M., and El-Kazak, A.M., Eur. J. Chem., 2013, vol. 4, p. 311. https://doi.org/10.5155/eurjchem.4.3.311-328.815

    Article  CAS  Google Scholar 

Download references

Funding

The authors extend their appreciation to the Deanship of Scientific Research, King Khalid University, for funding this work through the General Research Project (no. R.G.P1./22/40).

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, King Khalid University, 61421, Abha, Saudi Arabia

    T. E. Ali & M. A. Assiri

  2. Department of Chemistry, Faculty of Education, Ain Shams University, 11711, Cairo, Egypt

    T. E. Ali & M. A. Ibrahim

  3. Department of Physics, Faculty of Science, King Khalid University, 61421, Abha, Saudi Arabia

    I. S. Yahia

Authors
  1. T. E. Ali
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. A. Assiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. A. Ibrahim
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. S. Yahia
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. E. Ali.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ali, T.E., Assiri, M.A., Ibrahim, M.A. et al. Nucleophilic Reactivity of a Novel 3-Chloro-3-(4,9-dimethoxy5-oxo-5H-furo[3,2-g]chromen-6-yl)prop-2-enal. Russ J Org Chem 56, 845–855 (2020). https://doi.org/10.1134/S1070428020050188

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020050188

Keywords:

Search

Navigation