Skip to main content
Log in

Cationic ring contraction of seven-membered cycle of 3,4-dihydro-2H-1,5-benzoxathiepine derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A number of 1,4-benzoxathiine derivatives was obtained using ring contraction of seven-membered cycle of 3,4-dihydro-2H-1,5-benzoxathiepin-3-ol derivatives. This synthetic approach allowed to obtain the corresponding alkene, alcohol, nitrile, chloride, bromide, azide, and amine.

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 1.
Scheme 2.
Scheme 3.

Similar content being viewed by others

References

  1. Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.

    Article  CAS  PubMed  Google Scholar 

  2. Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Pustenko, A.; Žalubovskis, R. Chem. Heterocycl. Compd. 2017, 53, 1283. [Khim. Geterotsikl. Soedin. 2017, 53, 1283.]

    Google Scholar 

  4. Tarasiuk, T. M.; Shyshkina, O. O. Chem. Heterocycl. Compd. 2016, 52, 999. [Khim. Geterotsikl. Soedin. 2016, 52, 999.]

    Article  CAS  Google Scholar 

  5. Tarasiuk, T. M.; Shyshkina, O. O.; Volovenko, Y. M.; Medviediev, V. V.; Volovnenko, T. A.; Shishkin, O. V. Monatsh. Chem. 2015, 146, 1733.

    Article  CAS  Google Scholar 

  6. Vacher, B.; Pignier, C.; Létienne, R.; Verscheure, Y.; Le Grand, B. Br. J. Pharmacol. 2009, 156, 214.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Pignier, C.; Rougier, J.-S.; Vié, B.; Culié, C.; Verscheure, Y.; Vacher, B.; Abriel, H.; Le Grand, B. Br. J. Pharmacol. 2010, 161, 79.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Mahfoudh, N.; Marín-Ramos, N. I.; Gil, A. M.; Jiménez, A. I.; Choquesillo-Lazarte, D.; Kawano, D. F.; Campos, J. M.; Cativiela, C. Arabian J. Chem. 2018, 11, 426.

    Article  CAS  Google Scholar 

  9. Díaz-Gavilán, M.; Conejo-García, A.; Cruz-López, O.; Núñez, M. C.; Choquesillo-Lazarte, D.; González-Pérez, J. M.; Rodríguez-Serrano, F.; Marchal, J. A.; Aránega, A.; Gallo, M. A.; Espinosa, A.; Campos, J. M. ChemMedChem 2008, 3, 127.

    Article  CAS  PubMed  Google Scholar 

  10. Kimatrai, M.; Conejo-García, A.; Ramírez, A.; Andreolli, E.; Da Silveira-Gomes, A.; García, M. A.; Aránega, A.; Marchal, J. A.; Campos, J. M. ChemMedChem 2011, 6, 1854.

    Article  CAS  PubMed  Google Scholar 

  11. Donald, J. R.; Unsworth, W. P. Chem.–Eur. J. 2017, 23, 8780.

    Article  CAS  PubMed  Google Scholar 

  12. Abdel-Wahab, B. F.; Shaaban, S.; El-Hiti, G. A. Mol. Diversity 2018, 22, 517.

    Article  CAS  Google Scholar 

  13. Kirmse, W. Eur. J. Org. Chem. 2002, 2193.

  14. Silva, L. F. Tetrahedron 2002, 58, 9137.

    Article  CAS  Google Scholar 

  15. Song, Z.-L.; Fan, C.-A.; Tu, Y.-Q. Chem. Rev. 2011, 111, 7523.

    Article  CAS  PubMed  Google Scholar 

  16. García-Rubiño, M. E.; Núñez-Carretero, M. C.; Choquesillo-Lazarte, D.; García-Ruiz, J. M.; Madrid, Y.; Campos, J. M. RSC Adv. 2014, 4, 22425.

    Article  Google Scholar 

  17. García-Rubiño, M. E.; Núñez, M. C.; Gallo, M. A.; Campos, J. M. RSC Adv. 2012, 2, 12631.

    Article  CAS  Google Scholar 

  18. Casiraghi, A.; Valoti, E.; Suigo, L.; Artasensi, A.; Sorvillo, E.; Straniero, V. J. Org. Chem. 2018, 83, 13217.

    Article  CAS  PubMed  Google Scholar 

  19. Mühlstädt, M.; Stransky, N.; Seifert, A.; Kleinpeter, E.; Meinhold, H. J. Prakt. Chem. 1978, 320, 113.

    Article  Google Scholar 

  20. Pigini, M.; Brasili, L.; Giannella, M.; Giardina, D.; Gulini, U.; Quaglia, W.; Melchiorre, C. J. Med. Chem. 1988, 31, 2300.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Taras M. Tarasiuk.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(4/5), 416–420

Electronic supplementary material

ESM 1

(PDF 6877 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tarasiuk, T.M., Shyshkina, O.O., Potikha, L.M. et al. Cationic ring contraction of seven-membered cycle of 3,4-dihydro-2H-1,5-benzoxathiepine derivatives. Chem Heterocycl Comp 55, 416–420 (2019). https://doi.org/10.1007/s10593-019-02474-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02474-w

Keywords

Navigation