Skip to main content
SpringerLink
Log in

Unexpected conversion of 4-oxo-4H-chromene-2-carboxylic acid to 2-(1,3-benzothiazol-2-yl)-4H-chromen-4-one and spiro[1,4-benzothiazine-2,2'-chromene]-3,4'(3'H,4H)-dione

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

2-(1,3-Benzothiazol-2-yl)-4H-chromen-4-one and spiro[1,4-benzothiazine-2,2'-chromene]-3,4'(3'H,4H)-dione have been synthesized from 4-oxo-4H-chromene-2-carboxylic acid. The course of the reaction that usually occurs between the activated carboxylic acid and aromatic amines was changed upon the use of different reaction conditions (acidic or basic) and 2-aminobenzenethiol. As a result, new heterocyclic derivatives were obtained. Structures of the compounds have been established on the basis of spectral (1D and 2D NMR spectra) and X-ray 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 1.
Scheme 2.
Scheme 3.
Figure 1.
Figure 2.

Similar content being viewed by others

References

  1. The Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones; Ellis, G. P., Ed.; John Wiley & Sons: New York, 1977, Vol. 31.

  2. Reis, J.; Gaspar, A.; Milhazes, N.; Borges, F. J. Med. Chem. 2017, 60, 7941.

    Article  CAS  Google Scholar 

  3. Gaspar, A.; Matos, M. J.; Garrido, J.; Uriarte, E.; Borges, F. Chem. Rev. 2014, 114, 4960.

    Article  CAS  Google Scholar 

  4. Li, N.-G.; Shi, Z.-H.; Tang, Y.-P.; Ma, H.-Y.; Yang, J.-P.; Li, B.-Q.; Wang, Z.-J.; Song, S.-L.; Duan, J.-A. J. Heterocycl. Chem. 2010, 47, 785.

    Article  CAS  Google Scholar 

  5. (a) Ghosh, K. C.; Khan, S. Synthesis 1981, 719. (b) Fillion, E.; Dumas, A. M.; Kuropatwa, B. A.; Malhotra, N. R.; Sitler, T. C. J. Org. Chem. 2006, 71, 409.

  6. Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606.

  7. Cagide, F.; Reis, J.; Gaspar, A.; Borges, F. Tetrahedron Lett. 2011, 52, 6446.

    Article  CAS  Google Scholar 

  8. (a) Gaspar, A.; Reis, J.; Matos, M. J.; Uriarte, E.; Borges, F. Eur. J. Med. Chem. 2012, 54, 914. (b) Gaspar, A.; Reis, J.; Kachler, S.; Paoletta, S.; Uriarte, E.; Klotz, K.-N.; Moro, S.; Borges, F. Biochem. Pharmacol. 2012, 84, 21. (c) Gaspar, A.; Silva, T.; Yáñez, M.; Vina, D.; Orallo, F.: Ortuso, F.; Uriarte, E.; Alcaro, S.; Borges, F. J. Med. Chem. 2011, 54, 5165. (d) Gaspar, A.; Reis, J.; Fonseca, A.; Milhazes, N.; Viña, D.; Uriarte, E.; Borges, F. Bioorg. Med. Chem. Lett. 2011, 21, 707. (e) Reis, J.; Cagide, F.; Chavarria, D.; Silva, T.; Fernandes, C.; Gaspar, A.; Uriarte, E.; Remião, F.; Alcaro, S.; Ortuso, F.; Borges, F. J. Med. Chem. 2016, 59, 5879. (f) Cagide, F.; Silva, T.; Reis, J.; Gaspar, A.; Borges, F.; Gomes, L. R.; Low, J. N. Chem. Commun. 2015, 51, 2832.

  9. Rigaku CrystalClear SM Expert 2.0 r13; Rigaku Corporation: Tokyo, 2011.

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

  11. Hübschle, C. B.; Sheldrick, G. M.; Dittrich, B. J. Appl. Crystallogr. 2011, 44, 1281.

    Article  Google Scholar 

  12. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Crystallogr. 2006, 39, 453.

    Article  CAS  Google Scholar 

  13. Mackay, A. L. Acta Crystallogr., Sect. A: Short Commun. 1984, A40, 165.

Download references

Author information

Authors and Affiliations

  1. CIQUP/Department of Chemistry and Biochemistry, Faculty of Science, University of Porto, Rua do Campo Alegre, 687, 4169-007, Porto, Portugal

    Fernando Cagide & Fernanda Borges

  2. Faculdade de Cíencias de Saúde, Escola Superior de Saúde, Universidade Fernando Pessoa, Praça de 9 de Abril, 349, 4249-004, Porto, Portugal

    Ligia R. Gomes

  3. Department of Chemistry, University of Aberdeen, Meston Building, Meston Walk, Aberdeen, AB24 3UE, Scotland, United Kingdom

    John N. Low

Authors
  1. Fernando Cagide
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ligia R. Gomes
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. John N. Low
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fernanda Borges
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Fernando Cagide or Fernanda Borges.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(1), 68–72

Supplementary Information

ESM 1

(PDF 953 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Cagide, F., Gomes, L.R., Low, J.N. et al. Unexpected conversion of 4-oxo-4H-chromene-2-carboxylic acid to 2-(1,3-benzothiazol-2-yl)-4H-chromen-4-one and spiro[1,4-benzothiazine-2,2'-chromene]-3,4'(3'H,4H)-dione. Chem Heterocycl Comp 58, 68–72 (2022). https://doi.org/10.1007/s10593-022-03058-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-022-03058-x

Keywords

Search

Navigation