Skip to main content
Log in

Synthesis of 2-Aryl-5-oxo-5H-thiopyrano[4,3-b]pyridine-7-carboxylic Acids as the First Representatives of a New Heterocyclic System

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

Abstract

A series of ethyl 2-[(Z)-(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]-6-arylnicotinoates was obtained as a result of the reaction of 6-aryl-2-formylnicotinoates with rhodanine. Under alkaline conditions, they underwent recyclization to form 2-aryl-5-oxo-5H-thiopyrano[4,3-b]pyridine-7-carboxylic acids—the first representatives of new heterocyclic system.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme

REFERENCES

  1. Borges, F., Roleira, F., Milhazes, N., Santana, L., and Uriarte, E., Curr. Med. Chem., 2005, vol. 12, p. 887. https://doi.org/10.2174/0929867053507315

    Article  CAS  PubMed  Google Scholar 

  2. Napolitano, E., Org. Prep. Proc. Int., 1997, vol. 29, p. 631. https://doi.org/10.1080/00304949709355245

    Article  CAS  Google Scholar 

  3. Hill, R.A., Forschr. Chem. Naturst., 1986, vol. 49, p. 1.

    CAS  Google Scholar 

  4. Kaminskyy, D., Kryshchyshyn, A., Nektegayev, I., Vasylenko, O., Grellier, P., and Lesyk, R., Eur. J. Med. Chem., 2014, vol. 75, p. 57. https://doi.org/10.1016/j.ejmech.2014.01.028

    Article  CAS  PubMed  Google Scholar 

  5. Pokhodylo, N.T., Matiychuk, V.S., and Obushak, M.D., Chem. Heterocycl. Compd., 2010, vol. 46, p. 140. https://doi.org/10.1007/s10593-010-0484-3

    Article  CAS  Google Scholar 

  6. Pokhodylo, N.T., Matiychuk, V.S., and Obushak, M.D., Chem. Heterocycl. Compd., 2009, vol. 45, p. 121. https://doi.org/10.1007/s10593-009-0238-2

    Article  CAS  Google Scholar 

  7. Obushak, M.D., Matiychuk, V.S., and Turytsya, V.V., Tetrahedron Lett., 2009, vol. 50, no. 45, p. 6112. https://doi.org/10.1016/j.tetlet.2009.08.024

    Article  CAS  Google Scholar 

  8. Zelisko, N., Atamanyuk, D., Vasylenko, O., Bryhas, A., Matiychuk, V., Gzella, A., and Lesyk, R., Tetrahedron, 2014, vol. 70, no. 3, p. 720. https://doi.org/10.1016/j.tet.2013.11.083

    Article  CAS  Google Scholar 

  9. Pokhodylo, N.T. and Matiychuk, V.S., J. Heterocycl. Chem., 2010, vol. 47, no. 2, p. 415. https://doi.org/10.1002/jhet.321

    Article  CAS  Google Scholar 

  10. Zelisko, N., Atamanyuk, D., Ostapiuk, Y., Bryhas, A., Matiychuk, V., Gzella, A., and Lesyk, R., Tetrahedron, 2015, vol. 71, no. 50, p. 9501. https://doi.org/10.1016/j.tet.2015.10.019

    Article  CAS  Google Scholar 

  11. Bryhas, A.O., Horak, Y.I., Ostapiuk, Y.V., Obushak, M.D., and Matiychuk, V.S., Tetrahedron Lett., 2011, vol. 52, no. 18, p. 2324. https://doi.org/10.1016/j.tetlet.2011.02.081

    Article  CAS  Google Scholar 

  12. Gräf, E. and Troschütz, R., Synthesis, 1999, no. 7, p. 1216. https://doi.org/10.1055/s-1999-3532

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to T. I. Chaban.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chaban, T.I., Matiychuk, V.S. Synthesis of 2-Aryl-5-oxo-5H-thiopyrano[4,3-b]pyridine-7-carboxylic Acids as the First Representatives of a New Heterocyclic System. Russ J Gen Chem 90, 1578–1580 (2020). https://doi.org/10.1134/S1070363220080290

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363220080290

Keywords:

Navigation