Skip to main content
SpringerLink
Log in

Synthesis of 2,3-dihydro-1,4-benzoxathiine derivatives

  • REVIEWS
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

2,3-Dihydro-1,4-benzoxathiine derivatives are important biologically active heterocyclic compounds. Approaches toward synthesis of 2,3-dihydro-1,4-benzoxathiine derivatives are summarized in this minireview, covering most important synthetic methods that might be gathered in six distinct categories: the intermolecular cyclizations of o-mercaptophenols, 2-mercaptoethanols, and their equivalents, cyclizations, cycloadditions, ring contractions and expansions, and reduction of 2,3-dihydro-1,4-benzoxathiine 4-oxides.

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

Figure 1.

Similar content being viewed by others

References

  1. Viglianisi, C.; Menichetti, S. Curr. Med. Chem. 2010, 17, 915.

    Article  CAS  Google Scholar 

  2. Kim, S.; Wu, J. Y.; Birzin, E. T.; Frisch, K.; Chan, W.; Pai, L.-Y.;Yang, Y. T.; Mosley, R. T.; Fitzgerald, P. M. D.; Sharma, N.; Dahllund, J.; Thorsell, A.-G.; DiNinno, F.; Rohrer, S. P.; Schaeffer, J. M.; Hammond, M. L. J. Med. Chem. 2004, 47, 2171.

    Article  CAS  Google Scholar 

  3. Buzzini, P.; Menichetti, S.; Pagliuca, C.; Viglianisi, C.; Branda, E.; Turchetti, B. Bioorg. Med. Chem. Lett. 2008, 18, 3731.

    Article  CAS  Google Scholar 

  4. Parham, W. E.; Jones, J. D. J. Am. Chem. Soc. 1954, 76, 1068.

    Article  CAS  Google Scholar 

  5. Martin, A. R.; Caputo, J. F. J. Org. Chem. 1974, 39, 1811.

    Article  CAS  Google Scholar 

  6. Cabiddu, S.; Floris, C.; Melis, S.; Sotgiu, F.; Cerioni, G. J. Heterocycl. Chem. 1986, 23, 1815.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  8. Hu, F. D.; Zhao, X.; Li, Y. Q.; Feng, L.; Ma, C. Synthesis 2013, 966.

  9. Bankar, S. K.; Shirke, R. P.; Ramasastry, S. S. V. Adv. Synth. Catal. 2015, 357, 3284.

    Article  CAS  Google Scholar 

  10. Dormer, P. G.; Kassim, A. M.; Leazer, J. L.; Lang, F.; Xu, F.; Savary, K. A.; Corley, E. G.; DiMichele, L.; DaSilva, J. O.; King, A. O.; Tschaen, D. M.; Larsen, R. D. Tetrahedron Lett. 2004, 45, 5429.

    Article  CAS  Google Scholar 

  11. Alom, N.-E.; Kaur, N.; Wu, F.; Saluga, S. J.; Li, W. Chem.– Eur. J. 2019, 25, 6902.

  12. Kanemoto, K.; Sakata, Y.; Hosoya, T.; Yoshida, S. Chem. Lett. 2020, 49, 593.

    Article  CAS  Google Scholar 

  13. Liu, N.; Chao, F.; Yan, J. Y.; Huang, N.-Y.; Ren, Z.-L.; Wang, L. ChemistrySelect 2019, 4, 11177.

    Article  CAS  Google Scholar 

  14. Chao, F.; Xu, W.-H.; Ren, Z.-L.; Wang, L. Russ. J. Gen. Chem. 2019, 89, 2558.

    Article  CAS  Google Scholar 

  15. Yu, C. M.; Hu, G. B.; Zhang, C. L.; Wu, R.; Ye, H. W.; Yang, G. H.; Shi, X. J. J. Fluorine Chem. 2013, 153, 33.

    Article  CAS  Google Scholar 

  16. Zhao, P.; Yin, H.; Gao, H. X.; Xi, C. J. J. Org. Chem. 2013, 78, 5001.

    Article  CAS  Google Scholar 

  17. Gattaiah, D.; Reddy, A. S.; Khan, S. A.; Kumara Swamy, K. C. J. Organomet. Chem. 2019, 889, 33.

    Article  CAS  Google Scholar 

  18. Mühlstädt, M.; Kuhl, P. J. Prakt. Chem. 1978, 320, 873.

    Article  Google Scholar 

  19. Shevchenko, N. E.; Nenajdenko, V. G.; Balenkova, E. S. Synthesis 2003, 1191.

  20. Bürger, M.; Loch, M. N.; Jones, P. G.; Werz, D. B. Chem. Sci. 2020, 11, 1912.

    Article  Google Scholar 

  21. Xu, X.-B.; Liu, J.; Zhang, J.-J.; Wang, Y.-W.; Peng, Y. Org. Lett. 2013, 15, 550.

    Article  CAS  Google Scholar 

  22. Huang, C.; Qian, X.-Y.; Xu, H.-C. Angew. Chem., Int. Ed. 2019, 58, 6650.

    Article  CAS  Google Scholar 

  23. Liu, N. Chao, F.; Huang, Y.; Wang, Y. L.; Meng, X.; Wang, L.; Liu, X. Tetrahedron Lett. 2019, 60, 151259.

    Article  CAS  Google Scholar 

  24. Nagarjuna Reddy, M.; Kumara Swamy, K. C. Org. Biomol. Chem. 2013, 11, 7350.

    Article  CAS  Google Scholar 

  25. Sakairi, M.; Kogami, M.; Torii, M.; Kataoka, H.; Fujieda, H.; Makino, M.; Kataoka, D.; Okamoto, R.; Miyazawa, T.; Okabe, M.; Inoue, M.; Takahashi, N.; Harada, S.; Watanabe, N. Bioorg. Med. Chem. Lett. 2012, 22, 5123.

    Article  CAS  Google Scholar 

  26. Bosset, C.; Lefebvre, G.; Angibaud, P.; Stansfield, I.; Meerpoel, L.; Berthelot, D.; Guérinot, A.; Cossy, J. J. Org Chem. 2017, 82, 4020.

    Article  CAS  Google Scholar 

  27. Kim, S.; Wu, J. Y.; Chen, H. Y.; DiNinno, F. Org. Lett. 2003, 5, 685.

    Article  CAS  Google Scholar 

  28. Franzmann, P.; Beil, S. B.; Schollmeyer, D.; Waldvogel, S. R. Chem.–Eur. J. 2019, 25, 1936.

    Google Scholar 

  29. Kenis, S.; D'Hooghe, M.; Verniest, G.; Reybroeck, M.; Thi, T. A. D.; The, C. P.; Pham, T. T.; Törnroos, K. W.; Nguyen, V. T.; De Kimpe, N. Chem.–Eur. J. 2013, 19, 5966.

  30. (a) Capozzi, G.; Falciani, C.; Menichetti, S.; Nativi, C. J. Org. Chem. 1997, 62, 2611. (b) Capozzi, G.; Menichetti, S.; Nativi, C.; Simonti, M. C. Tetrahedron Lett. 1994, 35, 9451. (c) Capozzi, G.; Falciani, C.; Menichetti, S.; Nativi, C.; Franck, R. W. Tetrahedron Lett. 1995, 36, 6755. (d) Richichi, B.; Imberty, A.; Gillon, E.; Bosco, R.; Sutkeviciute, I.; Fieschi, F.; Nativi, C. Org. Biomol. Chem. 2013, 11, 4086.

  31. (a) Nair, V.; Mathew, B.; Menon, R. S.; Mathew, S.; Vairamani, M.; Prabhakar, S. Tetrahedron 2002, 58, 3235. (b) Nair, V.; Mathew, B. Tetrahedron Lett. 2000, 41, 6919.

  32. Nair, V.; Mathew, B.; Thomas, S.; Vairamani, M.; Prabhakar, S. J. Chem. Soc., Perkin Trans. 1 2001, 3020.

  33. Viglianisi, C.; Menichetti, S.; Piantini, S.; Tofani, L. Eur. J. Org. Chem. 2016, 5386.

  34. Menichetti, S.; Amorati, R.; Bartolozzi, M. G.; Pedulli, G. F.; Salvini, A.; Viglianisi, C. Eur. J. Org. Chem. 2010, 2218.

  35. Viglianisi, C.; Di Pietro, L.; Meoni, V.; Amorati, R.; Menichetti, S. ARKIVOC 2019, (ii), 65.

    Article  Google Scholar 

  36. Viglianisi, C.; Sinni, A.; Menichetti, S. Heteroat. Chem. 2014, 25, 361.

    Article  CAS  Google Scholar 

  37. (a) Díaz-Gavilan, 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. (b) Núñez, M. C.; Díaz-Gavilan, M.; Conejo-García, A.; Cruz-López, O.; Gallo, M. A.; Espinosa, A.; Campos, J. M. Curr. Med. Chem. 2008, 15, 2614. (c) 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.

  38. Conejo-García, A.; García-Rubiño, M. E.; Marchal, J. A.; Núñez, M. C.; Ramírez, A.; Cimino, S.; García, M. A.; Aránega, A.; Gallo, M. A.; Campos, J. M. Eur. J. Med. Chem. 2011, 46, 3795.

    Article  Google Scholar 

  39. Tarasiuk, T. M.; Shyshkina, O. O.; Potikha, L. M.; Volovenko, Y. M. Chem. Heterocycl. Compd. 2019, 55, 416.

    Article  CAS  Google Scholar 

  40. Korupalli, C.; Dandapat, A.; Prasad, D. J. C.; Sekar, G. Org. Chem. Int. 2011, 980765.

  41. (a) Dong, J.; Xu, J. X. Org. Biomol. Chem. 2017, 15, 836. (b) Li, S. Q.; Chen, X. P.; Xu, J. X. Tetrahedron 2018, 74, 1613. (c) Chen, X. P.; Xu, J. X. Tetrahedron Lett. 2017, 58, 1651. (d) Dong, J.; Du, H. G.; Xu, J. X. J. Org. Chem. 2019, 84, 10724.

  42. (a) Dong, J.; Xu, J. X. Synthesis 2018, 2407. (b) Li, X. Y.; Xu, J. X. Tetrahedron 2011, 67, 1681. (c) Yu, H.; Cao, S. L.; Zhang, L. L.; Liu, G.; Xu, J. X. Synthesis 2009, 2205. (d) Huang, J. X.; Du, D.-M.; Xu, J. X. Synthesis 2006, 315. (e) Huang, J. X.; Wang, F.; Du, D. M.; Xu, J. X. Synthesis 2005, 2122.

  43. Dong, J.; Xu, J. X. New. J. Chem. 2018, 42, 9037.

    Article  CAS  Google Scholar 

  44. Satoh, J. Y.; Haruta, A. M.; Yokoyama, C. T.; Yamada, Y.; Hirose, M. J. Chem. Soc., Chem. Commun. 1985, 1645.

  45. Tani, H.; Irie, S.; Masumoto, K.; Ono, N. Heterocycles 1993, 36, 1783.

    Article  CAS  Google Scholar 

  46. Kong, Z. S.; Pan, C.; Li, M.; Wen, L. R.; Guo, W. S. Green Chem. 2021, 23, 2773.

    Article  CAS  Google Scholar 

Download references

Financial support by the National Natural Science Foundation of China (Nos. 21572017 and 21772010) is gratefully acknowledged.

Author information

Authors and Affiliations

  1. School of Chemistry and Environmental Engineering, Yancheng Teachers University, Yancheng, Jiangsu, China

    Jun Dong

  2. Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029, China

    Jiaxi Xu

Authors
  1. Jun Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jiaxi Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jiaxi Xu.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(6/7), 271–278

Rights and permissions

Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dong, J., Xu, J. Synthesis of 2,3-dihydro-1,4-benzoxathiine derivatives. Chem Heterocycl Comp 58, 271–278 (2022). https://doi.org/10.1007/s10593-022-03084-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-022-03084-9

Keywords

Search

Navigation