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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 4–5, pp 416–420 | Cite as

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

  • Taras M. TarasiukEmail author
  • Olena O. Shyshkina
  • Lyudmila M. Potikha
  • Yulian M. Volovenko
Article
  • 9 Downloads

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.

Keywords

1,5-benzoxathiepine 1,4-benzoxathiine episulfonium intermediate medium-ring compounds rearrangement ring contraction 

Supplementary material

10593_2019_2474_MOESM1_ESM.pdf (6.7 mb)
ESM 1 (PDF 6877 kb)

References

  1. 1.
    Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.CrossRefGoogle Scholar
  2. 2.
    Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.CrossRefGoogle Scholar
  3. 3.
    Pustenko, A.; Žalubovskis, R. Chem. Heterocycl. Compd. 2017, 53, 1283. [Khim. Geterotsikl. Soedin. 2017, 53, 1283.]Google Scholar
  4. 4.
    Tarasiuk, T. M.; Shyshkina, O. O. Chem. Heterocycl. Compd. 2016, 52, 999. [Khim. Geterotsikl. Soedin. 2016, 52, 999.]CrossRefGoogle Scholar
  5. 5.
    Tarasiuk, T. M.; Shyshkina, O. O.; Volovenko, Y. M.; Medviediev, V. V.; Volovnenko, T. A.; Shishkin, O. V. Monatsh. Chem. 2015, 146, 1733.CrossRefGoogle Scholar
  6. 6.
    Vacher, B.; Pignier, C.; Létienne, R.; Verscheure, Y.; Le Grand, B. Br. J. Pharmacol. 2009, 156, 214.CrossRefGoogle Scholar
  7. 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.CrossRefGoogle Scholar
  8. 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.CrossRefGoogle Scholar
  9. 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.CrossRefGoogle Scholar
  10. 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.CrossRefGoogle Scholar
  11. 11.
    Donald, J. R.; Unsworth, W. P. Chem.–Eur. J. 2017, 23, 8780.CrossRefGoogle Scholar
  12. 12.
    Abdel-Wahab, B. F.; Shaaban, S.; El-Hiti, G. A. Mol. Diversity 2018, 22, 517.CrossRefGoogle Scholar
  13. 13.
    Kirmse, W. Eur. J. Org. Chem. 2002, 2193.Google Scholar
  14. 14.
    Silva, L. F. Tetrahedron 2002, 58, 9137.CrossRefGoogle Scholar
  15. 15.
    Song, Z.-L.; Fan, C.-A.; Tu, Y.-Q. Chem. Rev. 2011, 111, 7523.CrossRefGoogle Scholar
  16. 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.CrossRefGoogle Scholar
  17. 17.
    García-Rubiño, M. E.; Núñez, M. C.; Gallo, M. A.; Campos, J. M. RSC Adv. 2012, 2, 12631.CrossRefGoogle Scholar
  18. 18.
    Casiraghi, A.; Valoti, E.; Suigo, L.; Artasensi, A.; Sorvillo, E.; Straniero, V. J. Org. Chem. 2018, 83, 13217.CrossRefGoogle Scholar
  19. 19.
    Mühlstädt, M.; Stransky, N.; Seifert, A.; Kleinpeter, E.; Meinhold, H. J. Prakt. Chem. 1978, 320, 113.CrossRefGoogle Scholar
  20. 20.
    Pigini, M.; Brasili, L.; Giannella, M.; Giardina, D.; Gulini, U.; Quaglia, W.; Melchiorre, C. J. Med. Chem. 1988, 31, 2300.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Taras M. Tarasiuk
    • 1
    • 2
    Email author
  • Olena O. Shyshkina
    • 2
  • Lyudmila M. Potikha
    • 1
  • Yulian M. Volovenko
    • 1
  1. 1.Department of Organic ChemistryKyiv Taras Shevchenko National UniversityKyivUkraine
  2. 2.Enamine Ltd.KyivUkraine

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