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

  • K. Kavitha
  • D. Srikrishna
  • Pramod Kumar Dubey
  • P. AparnaEmail author
Original Paper


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.


Salicylaldehyde Ethyl-4-chloroacetoacetate Phenylthioureas l-Proline Environmentally benign conditions 



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.


  1. 1.
    F. Belluti, G. Fontana, L.B. Dal, L. Dal Bo, N. Carenini, C. Giommarelli, F. Zunino, Bioorg. Med. Chem. 18, 3543 (2010)CrossRefGoogle Scholar
  2. 2.
    M. Cacic, M. Trkovnik, F. Cacic, E. Has-Schon, Molecules 11, 134 (2006)CrossRefGoogle Scholar
  3. 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)CrossRefGoogle Scholar
  4. 4.
    Z. Ye, Z. Biqun, C. Zhenfeng, Z. Chen, Y. Pan, H. Wang, H. Liang, X. Yi, Bioorg. Med. Chem. Lett. 21, 6811 (2011)CrossRefGoogle Scholar
  5. 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)CrossRefGoogle Scholar
  6. 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)CrossRefGoogle Scholar
  7. 7.
    K.M. Amin, E.A.R. Doaa, A.A.E. Yasmin, Bioorg. Med. Chem. 16, 5377 (2008)CrossRefGoogle Scholar
  8. 8.
    L. Racane, V. Tralic-Kulenovic, L. Fiser-Jakic, D. Boykin, G.Z. Karminski, Heterocycles 55, 2085 (2001)CrossRefGoogle Scholar
  9. 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)CrossRefGoogle Scholar
  10. 10.
    M.L. Sassiver, R.G. Shepherd, J. Med. Chem. 9, 541 (1966)CrossRefGoogle Scholar
  11. 11.
    B.S. Holla, K. Malini, B.S. Rao, B.K. Sarojini, N.S. Kumari, Eur. J. Med. Chem. 38, 313 (2003)CrossRefGoogle Scholar
  12. 12.
    N. Siddiqui, W. Ahsan, Eur. J. Med. Chem. 45, 1536 (2010)CrossRefGoogle Scholar
  13. 13.
    A. Tsuruoka, Y. Kaku, H. Kakinuma, I. Tsukada, M. Yanagisawa, K. Nara, T. Naito, Chem. Pharm. Bull. (Tokyo) 46, 623 (1998)CrossRefGoogle Scholar
  14. 14.
    N. Siddiqui, M. Faizarshad, S.A. Khan, Acta Pol. Pharm. 66, 161 (2009)Google Scholar
  15. 15.
    C.H.V.S. Rao, R.V. Rao, J. Chem. Res. 1, 50 (2010)Google Scholar
  16. 16.
    R.S. Koti, K. Gundurao, S.H. Vinayak, I.M. Khazi, Synth. Commun. 37, 99 (2007)CrossRefGoogle Scholar
  17. 17.
    K. Kavitha, P. Aparna, Res. J. Life Sci. Bioinf. Pharm. Chem. Sci. 4, 204 (2018)Google Scholar
  18. 18.
    K. Kavitha, D. Srikrishna, P.K. Dubey, P. Aparna, Int. J. Mod. Pharm. Res. 2, 84 (2018)Google Scholar
  19. 19.
    K. Kavitha, D. Srikrishna, P.K. Dubey, P. Aparna, Arkivoc vii, 172 (2018)CrossRefGoogle Scholar
  20. 20.
    K. Kavitha, D. Srikrishna, P.K. Dubey, P. Aparna, J. Sulfur Chem. 40, 195–208 (2018). CrossRefGoogle Scholar
  21. 21.
    K. Kavitha, D. Srikrishna, P. Aparna, J. Saudi Chem. Soc. 23, 325–337 (2019). CrossRefGoogle Scholar
  22. 22.
    K. Kavitha, D. Srikrishna, P.K. Dubey, P. Aparna, Lett. Org. Chem.
  23. 23.
    D. Srikrishna, P.K. Dubey, New J. Chem. 41, 5168 (2017)CrossRefGoogle Scholar
  24. 24.
    D. Srikrishna, P.K. Dubey, Tetrahedron Lett. 55, 6561 (2014)CrossRefGoogle Scholar
  25. 25.
    S.G. Shrikant, P.B. Babasaheb, D.K. Prasad, S.S. Shailesh, Green Chem. Lett. Rev. 3, 315 (2010)CrossRefGoogle Scholar
  26. 26.
    S. Chandrasekhar, Ch. Narsihmulu, S.S. Sultana, N. Ramakrishna Reddy, Org. Lett. 4, 4399 (2002)CrossRefGoogle Scholar
  27. 27.
    R.T. Abhishek, M.B. Bhalchandra, Green Chem. 18, 144 (2016)CrossRefGoogle Scholar
  28. 28.
    J.M. Harris, H.N. Hundley, G.T. Shannon, E.C. Struck, J. Org. Chem. 47, 4789 (1982)CrossRefGoogle Scholar
  29. 29.
    P. Ferravoschi, A. Fiecchi, P. Grisenti, S. Trave, Synth. Commun. 17, 1569 (1987)CrossRefGoogle Scholar
  30. 30.
    N.F. Leininger, J.L. Gainer, D.J. Kirwan, AIChE J. 50, 511 (2004)CrossRefGoogle Scholar
  31. 31.
    E. Santaniello, A. Manzocchi, P. Sozzani, Tetrahedron Lett. 20, 4581 (1979)CrossRefGoogle Scholar
  32. 32.
    D. Badone, G. Jommi, R. Pagligrin, P. Tavecchia, Synthesis 10, 920 (1987)CrossRefGoogle Scholar
  33. 33.
    N.F. Leininger, R. Clontz, J.L. Gainer, D. Kirwan, Chem. Eng. Commun. 190, 431 (2003)CrossRefGoogle Scholar
  34. 34.
    K.V. Sashidhara, G.R. Palnati, S.R. Avula, A. Kumar, Synlett 23, 611 (2012)CrossRefGoogle Scholar
  35. 35.
    C. Su, Z.C. Chen, Q.G. Zhen, Synthesis 4, 555 (2003)Google Scholar
  36. 36.
    Z. Qiong, Y. Dehuan, D. Shuangshuang, G. Feng, Chem. Commun. 50, 14002 (2014)CrossRefGoogle Scholar
  37. 37.
    O.V. Khilya, M.S. Frasinyuk, A.V. Turov, V.P. Khilya, Chem. Heterocycl. Compd. 37, 1029 (2001)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  • K. Kavitha
    • 1
  • D. Srikrishna
    • 1
  • Pramod Kumar Dubey
    • 1
  • P. Aparna
    • 1
    Email author
  1. 1.Department of ChemistryJawaharlal Nehru Technological University Hyderabad College of EngineeringKukatpally, HyderabadIndia

Personalised recommendations