Skip to main content
SpringerLink
Log in

An expedient one-pot tandem method for the synthesis of 3-(2-(phenylamino)thiazol-4-yl)-2H-chromen-2-ones under green conditions

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

This paper describes a facile pathway for the one-pot three-component synthesis of 3-(2-(phenylamino)thiazol-4-yl)-2H-chromen-2-ones starting from ethyl-4-chloroacetoacetate by treating it with equimolar amounts of various phenylthioureas independently reaction with Salicylaldehyde. Use of biosynthetically prepared l-proline as an efficient catalyst and naturally extracted renewable poly(ethylene) glycol-600(PEG-600) as an effective green reaction media are the added advantages of this method. Alternatively, tandem, stepwise methods have been proposed and isolated the intermediate, to study the possible reaction mechanism. These reactions are very simple, rapid, cost effective, industrially viable, which would be applied for various biomass conversions.

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

Fig. 1
Fig. 2
Fig. 3
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7

Similar content being viewed by others

References

  1. F. Belluti, G. Fontana, L.B. Dal, L. Dal Bo, N. Carenini, C. Giommarelli, F. Zunino, Bioorg. Med. Chem. 18, 3543 (2010)

    Article  CAS  PubMed  Google Scholar 

  2. M. Cacic, M. Trkovnik, F. Cacic, E. Has-Schon, Molecules 11, 134 (2006)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Y. Kashman, K.R. Gustafson, R. Fuller, J.H. Cardellina, J.B. McMohan, M.J. Currens, R.W. Buckheit, S.H. Hughes, G.M. Cragg, R. Boyd, J. Med. Chem. 35, 2735 (1992)

    Article  CAS  PubMed  Google Scholar 

  4. Z. Ye, Z. Biqun, C. Zhenfeng, Z. Chen, Y. Pan, H. Wang, H. Liang, X. Yi, Bioorg. Med. Chem. Lett. 21, 6811 (2011)

    Article  CAS  Google Scholar 

  5. M. Atul, A. Malde, J. Verma, V. Virsodia, A. Mishra, K. Upadhyay, H. Acharya, E. Coutinho, A. Shah, Eur. J. Med. Chem. 43, 2395 (2008)

    Article  CAS  Google Scholar 

  6. L. Gang, W. Dongmei, S. Mingna, L. Guangyan, H. Jinfeng, Y. Zhang, Y. Yuan, J. Haijie, C. Naihong, L. Gang, J. Med. Chem. 53, 1741 (2010)

    Article  CAS  Google Scholar 

  7. K.M. Amin, E.A.R. Doaa, A.A.E. Yasmin, Bioorg. Med. Chem. 16, 5377 (2008)

    Article  CAS  PubMed  Google Scholar 

  8. L. Racane, V. Tralic-Kulenovic, L. Fiser-Jakic, D. Boykin, G.Z. Karminski, Heterocycles 55, 2085 (2001)

    Article  CAS  Google Scholar 

  9. I. Hutchinson, M.S. Chua, H.L. Browne, V. Trapani, T.D. Bradshaw, A.D. West Well, M.F. Stevens, J. Med. Chem. 44, 1446 (2001)

    Article  CAS  PubMed  Google Scholar 

  10. M.L. Sassiver, R.G. Shepherd, J. Med. Chem. 9, 541 (1966)

    Article  CAS  PubMed  Google Scholar 

  11. B.S. Holla, K. Malini, B.S. Rao, B.K. Sarojini, N.S. Kumari, Eur. J. Med. Chem. 38, 313 (2003)

    Article  CAS  PubMed  Google Scholar 

  12. N. Siddiqui, W. Ahsan, Eur. J. Med. Chem. 45, 1536 (2010)

    Article  CAS  PubMed  Google Scholar 

  13. A. Tsuruoka, Y. Kaku, H. Kakinuma, I. Tsukada, M. Yanagisawa, K. Nara, T. Naito, Chem. Pharm. Bull. (Tokyo) 46, 623 (1998)

    Article  CAS  Google Scholar 

  14. N. Siddiqui, M. Faizarshad, S.A. Khan, Acta Pol. Pharm. 66, 161 (2009)

    CAS  PubMed  Google Scholar 

  15. C.H.V.S. Rao, R.V. Rao, J. Chem. Res. 1, 50 (2010)

    Google Scholar 

  16. R.S. Koti, K. Gundurao, S.H. Vinayak, I.M. Khazi, Synth. Commun. 37, 99 (2007)

    Article  CAS  Google Scholar 

  17. K. Kavitha, P. Aparna, Res. J. Life Sci. Bioinf. Pharm. Chem. Sci. 4, 204 (2018)

    Google Scholar 

  18. K. Kavitha, D. Srikrishna, P.K. Dubey, P. Aparna, Int. J. Mod. Pharm. Res. 2, 84 (2018)

    Google Scholar 

  19. K. Kavitha, D. Srikrishna, P.K. Dubey, P. Aparna, Arkivoc vii, 172 (2018)

    Article  CAS  Google Scholar 

  20. K. Kavitha, D. Srikrishna, P.K. Dubey, P. Aparna, J. Sulfur Chem. 40, 195–208 (2018). https://doi.org/10.1080/17415993.2018.1556275

    Article  CAS  Google Scholar 

  21. K. Kavitha, D. Srikrishna, P. Aparna, J. Saudi Chem. Soc. 23, 325–337 (2019). https://doi.org/10.1016/j.jscs.2018.08.007

    Article  CAS  Google Scholar 

  22. K. Kavitha, D. Srikrishna, P.K. Dubey, P. Aparna, Lett. Org. Chem. https://doi.org/10.2174/1570178616666181224112851

  23. D. Srikrishna, P.K. Dubey, New J. Chem. 41, 5168 (2017)

    Article  CAS  Google Scholar 

  24. D. Srikrishna, P.K. Dubey, Tetrahedron Lett. 55, 6561 (2014)

    Article  CAS  Google Scholar 

  25. S.G. Shrikant, P.B. Babasaheb, D.K. Prasad, S.S. Shailesh, Green Chem. Lett. Rev. 3, 315 (2010)

    Article  CAS  Google Scholar 

  26. S. Chandrasekhar, Ch. Narsihmulu, S.S. Sultana, N. Ramakrishna Reddy, Org. Lett. 4, 4399 (2002)

    Article  CAS  PubMed  Google Scholar 

  27. R.T. Abhishek, M.B. Bhalchandra, Green Chem. 18, 144 (2016)

    Article  Google Scholar 

  28. J.M. Harris, H.N. Hundley, G.T. Shannon, E.C. Struck, J. Org. Chem. 47, 4789 (1982)

    Article  CAS  Google Scholar 

  29. P. Ferravoschi, A. Fiecchi, P. Grisenti, S. Trave, Synth. Commun. 17, 1569 (1987)

    Article  Google Scholar 

  30. N.F. Leininger, J.L. Gainer, D.J. Kirwan, AIChE J. 50, 511 (2004)

    Article  CAS  Google Scholar 

  31. E. Santaniello, A. Manzocchi, P. Sozzani, Tetrahedron Lett. 20, 4581 (1979)

    Article  Google Scholar 

  32. D. Badone, G. Jommi, R. Pagligrin, P. Tavecchia, Synthesis 10, 920 (1987)

    Article  Google Scholar 

  33. N.F. Leininger, R. Clontz, J.L. Gainer, D. Kirwan, Chem. Eng. Commun. 190, 431 (2003)

    Article  CAS  Google Scholar 

  34. K.V. Sashidhara, G.R. Palnati, S.R. Avula, A. Kumar, Synlett 23, 611 (2012)

    Article  CAS  Google Scholar 

  35. C. Su, Z.C. Chen, Q.G. Zhen, Synthesis 4, 555 (2003)

    Google Scholar 

  36. Z. Qiong, Y. Dehuan, D. Shuangshuang, G. Feng, Chem. Commun. 50, 14002 (2014)

    Article  CAS  Google Scholar 

  37. O.V. Khilya, M.S. Frasinyuk, A.V. Turov, V.P. Khilya, Chem. Heterocycl. Compd. 37, 1029 (2001)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are thankful to the authorities of Jawaharlal Nehru Technological University Hyderabad for providing laboratory facilities. One of the authors (KK) is thankful to the University for the financial support in the form of Lectureship.

Author information

Authors and Affiliations

  1. Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad College of Engineering, Kukatpally, Hyderabad, Telangana, 500 085, India

    K. Kavitha, D. Srikrishna, Pramod Kumar Dubey & P. Aparna

Authors
  1. K. Kavitha
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. Srikrishna
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pramod Kumar Dubey
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. P. Aparna
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to P. Aparna.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kavitha, K., Srikrishna, D., Dubey, P.K. et al. An expedient one-pot tandem method for the synthesis of 3-(2-(phenylamino)thiazol-4-yl)-2H-chromen-2-ones under green conditions. J IRAN CHEM SOC 16, 1913–1921 (2019). https://doi.org/10.1007/s13738-019-01661-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-019-01661-y

Keywords

Search

Navigation