Skip to main content
SpringerLink
Log in

Synthesis of Fused 2Н-Pyridin-2-ones under the Conditions of Multicomponent Hantzsch Reaction

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

Abstract

One-pot process was studied between a substituted 4-hydroxy-2Н-pyran-2-one and aromatic aldehydes and ammonium acetate in the conditions of modified Hantzsch reaction in acid environment under thermal and microwave activation. Arylmethylenebis-4-hydroxy-2Н-pyridin-2-ones, hydrochromenopyridinone, and their oxygen-containing heteroanalogs were isolated. A primary condensation was confirmed into bispyran-2-one adducts, and at the use of salicilaldehyde, into pyranochromene with subsequent recyclization of pyranone fragments in pyridinone ones.

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

References

  1. Armstrong, R.W., Combs, A.P., Tempest, P.A., Brown, S.D., and Keating, T.A., Acc. Chem. Res., 1996, vol. 29, p.123.

    Article  CAS  Google Scholar 

  2. Sha, F. and Huang, X., Angew. Chem., Int. Ed., 2009, vol. 48, p. 3458.

    Article  CAS  Google Scholar 

  3. Sausins, A. and Duburs, G., Heterocycles, 1988, vol. 27, p.269.

    Article  CAS  Google Scholar 

  4. Vara Prasad, J.V.N., Para, K.S., Lunney, E.A., Ortwine, D.F., Dunbar, J.B. Jr., Ferguson, D., Tummino, P.J., Hupe, D., Tait, B.D., Domagala, J.M., Humblet, C., Bhat, T.N., Liu, B., Guerin, D.M.A., Baldwin, E.T., Erickon, J.W., and Swayer, T.K., J. Am. Chem. Soc., 1994, vol. 116, p. 6989.

    Article  CAS  Google Scholar 

  5. Douglas, C.J., Sklenicka, H.M., Shen, H.C., Mathias, D.S., Degen, S.I., Golding, G.M., Morgan, C.D., Shih, R.A., Mueller, K.L., Seurer, I.M., Johnson, E.W., and Hsung, R.P., Tetrahedron, 1999, vol. 55, p. 13683.

    Article  CAS  Google Scholar 

  6. Hagen, S.E., Vara Prasad, J.V.N., Boyer, F.E., Domagala, J.M., Ellsworth, E.L., Gjda, C., Hamilton, H.W., Markkoski, L.J., Steinbangh, B.A., Tit, B.D., Lunney, E.A., Tummino, P.J., Fergnson, D., Hupe, D., Nouhan, C., Gracheck, S.J., Saunders, J.M., and Vander Roest, S., J. Med. Chem., 1997, vol. 40, p. 3707.

    Article  CAS  PubMed  Google Scholar 

  7. Claydon, N. and Allan, M., Trans. Br. Mycol. Soc., 1987, vol. 88, p.503.

    Article  CAS  Google Scholar 

  8. Fairlamb, I.J.S., Marrison, L.R., Dickinson, J.M., Lu, F.J., and Schmidt, J.P., Bioorg. Med. Chem., 2004, vol. 12, p. 4285.

    Article  CAS  PubMed  Google Scholar 

  9. Cervera, M., Moreno-Manas, M., and Pleixats, R., Tetrahedron, 1990, vol. 46, p. 7885.

    Article  CAS  Google Scholar 

  10. Jacinto Demuner, A., Moreira Valente, V.M., Almeida Barbosa, L.C., Rathi, A., Donohoe, T.J., and Thompson, A.L., Molecules, 2009, vol. 14, p. 4973.

    Article  CAS  Google Scholar 

  11. De March, P., Moreno-Manas, M., Pi, R., and Trius, A., J. Heterocycl. Chem., 1982, vol. 19, p.335.

    Article  Google Scholar 

  12. De March, P., Moreno-Manas, M., and Roca, J.L., J. Heterocycl. Chem., 1984, vol. 21, p. 1371.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chernyshevskii Saratov National Research State University, Astrakhanskaya ul. 83, Saratov, 410012, Russia

    I. V. Strashilina, E. M. Arzyamova & O. V. Fedotova

Authors
  1. I. V. Strashilina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. M. Arzyamova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. V. Fedotova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Strashilina.

Additional information

Original Russian Text © I.V. Strashilina, E.M. Arzyamova, O.V. Fedotova, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 8, pp. 1162–1167.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Strashilina, I.V., Arzyamova, E.M. & Fedotova, O.V. Synthesis of Fused 2Н-Pyridin-2-ones under the Conditions of Multicomponent Hantzsch Reaction. Russ J Org Chem 54, 1173–1178 (2018). https://doi.org/10.1134/S1070428018080092

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428018080092

Search

Navigation