Skip to main content
Log in

Synthesis of novel spiro-condensed 2-amino-4H-pyrans based on 1,2-benzoxathiin-4(3H)-one 2,2-dioxide

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A series of new spiro-condensed 2-amino-4H-pyrans were synthesized by three-component interaction of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide, malononitrile, and cyclic carbonyls in moderate to high yields. This is one of the first examples of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide application in multicomponent transformations.

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.
Scheme 4.
Scheme 5.
Figure 1.

Similar content being viewed by others

References

  1. Shalala, D. E.; Henney, J. E.; Woodcock, J. From Test Tube to Patient: Improving Health Through Human Drugs; U. S. Food and Drug Administration, 1999.

  2. DiMasi, J. A.; Hansen, R. W.; Grabowski, H. G. J. Health Econ. 2003, 22, 151.

    Article  PubMed  Google Scholar 

  3. Adams, C. P.; Brantner, V. V. Health Aff. 2006, 25, 420.

    Article  Google Scholar 

  4. Yang, S.-Y. Drug Discovery Today 2010, 15, 444.

    Article  CAS  PubMed  Google Scholar 

  5. Ehrlich, P. Ber. Dtsch. Chem. Ges. 1909, 42, 17.

    Article  CAS  Google Scholar 

  6. Rohini, K.; Agarwal, P.; Preethi, B.; Shanthi, V.; Ramanathan, K. Appl. Biochem. Biotechnol. 2019, 187, 194.

    Article  CAS  Google Scholar 

  7. Aswathy, L.; Jisha, R. S.; Masand, V. H.; Gajbhiye, J. M.; Shibi, I. G. In Silico Pharmacol. 2018, 6: 12.

    Article  PubMed  PubMed Central  Google Scholar 

  8. Ukrainets, I. V.; Petrushova, L. A.; Dzyubenko, S. P.; Sim, G. Chem. Heterocycl. Compd. 2014, 50, 103. [Khim. Geterotsikl. Soedin. 2014, 114.]

  9. Lega, D. A.; Filimonova, N. I.; Zupanets, I. A.; Shebeko, S. K.; Chernykh, V. P.; Shemchuk, L. A. J. Org. Pharm. Chem. 2016, 14(4), 3.

    CAS  Google Scholar 

  10. Mungra, D. C.; Patel, M. P.; Rajani, D. P.; Patel, R. G. Eur. J. Med. Chem. 2011, 46, 4192.

    Article  CAS  PubMed  Google Scholar 

  11. Amr, A.-G. E.; Mohamed, A. M.; Mohamed, S. F.; AbdelHafez, N. A.; Hammam, A. E.-F. G. Bioorg. Med. Chem. 2006, 14, 5481.

    Article  CAS  PubMed  Google Scholar 

  12. Pandeya, S. N.; Smitha, S.; Jyoti, M.; Sridhar, S. K. Acta Pharm. 2005, 55, 27.

    CAS  PubMed  Google Scholar 

  13. Souzangarzadeh, S.; Bazian, A.; Anaraki-Ardakani, H. J. Chem. Res. 2012, 36, 94.

    Article  CAS  Google Scholar 

  14. Lega, D. A.; Gorobets, N. Y.; Chernykh, V. P.; Shishkina, S. V.; Shemchuk, L. A. RSC Adv. 2016, 6, 16087.

  15. Shemchuk, L. A.; Lega, D. A.; Redkin, R. G.; Chernykh, V. P.; Shishkin, O. V.; Shishkina, S. V. Tetrahedron 2014, 70, 8348.

    Article  CAS  Google Scholar 

  16. Zhungietu, G. I.; Rehter, M. A. Isatin and its Derivatives [in Russian]; Shtiintsa: Kishinev, 1977.

  17. Brahmachari G. In Green Synthetic Approaches for Biologically Relevant Heterocycles; Brahmachari, G., Ed.; Elsevier: Boston, 2015, p. 185.

  18. Lega, D. A.; Chernykh, V. P.; Zaprutko, L.; Gzella, A. K.; Shemchuk, L. A. Chem. Heterocycl. Compd. 2017, 53, 219. [Khim. Geterotsikl. Soedin. 2017, 53, 219.]

  19. Grygoriv, G. V.; Lega, D. A.; Chernykh, V. P.; Zaprutko, L.; Gzella, A. K.; Pawełczyk A.; Shemchuk, L. A. RSC Adv. 2018, 8, 37295.

  20. CrysAlis PRO, Version 1.171.38.41; Rigaku Oxford Diffraction: Yarnton, 2015.

  21. Sheldrick, G. Acta Crystallogr. Sect. A: Found. Adv. 2015, A71, 3.

  22. Sheldrick, G. Acta Crystallogr. Sect. C: Struct. Chem. 2015, C71, 3.

  23. Farrugia, L. J. J. Appl. Crystallogr. 2012, 45, 849.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Leonid A. Shemchuk.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(3), 254–260

Electronic supplementary material

ESM 1

(PDF 1086 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Grygoriv, G.V., Lega, D.A., Zaprutko, L. et al. Synthesis of novel spiro-condensed 2-amino-4H-pyrans based on 1,2-benzoxathiin-4(3H)-one 2,2-dioxide. Chem Heterocycl Comp 55, 254–260 (2019). https://doi.org/10.1007/s10593-019-02450-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02450-4

Keywords

Navigation