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1-Methylimidazolium trifluoroacetate [Hmim]Tfa: Mild and efficient Brønsted acidic ionic liquid for Hantzsch reaction under microwave irradiation

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Abstract

One pot synthesis of 1,4-dihydropyridine derivatives was achieved via condensation of various β-ketoesters with aromatic/aliphatic aldehydes and ammonium acetate. The reaction was catalysed by a stable and reusable Brønsted acidic ionic liquid (IL), 1-methyl-imidazolium trifluoroacetate ([Hmim]Tfa), under microwave (MW) irradiation. The synergistic combination of MW with IL can potentially go a long way to meet the increasing demand for chemical processes. This homogeneous catalytic procedure is simple and efficient. The catalyst can be reused at least four times with almost complete retention in its activity.

The synthesis of 1,4- dihydropyridine derivatives via Hantzsch reaction induced by combination of microwave energy and ionic liquid is reported. This new protocol requires very mild reaction conditions with water as the only byproduct. The process proved to be simple, environmentally friendly, economic and high yielding.

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References

  1. Polshettiwar V and Varma R S 2008 Acc. Chem. Res. 41 629

    Article  CAS  Google Scholar 

  2. Santagada V, Perissutti E and Caliendo G 2002 Curr. Med. Chem. 9 1251

    CAS  Google Scholar 

  3. Kappe C O 2002 Curr. Opin. Chem. Biol. 6 314

    Article  CAS  Google Scholar 

  4. Cole A C, Jensen J L, Ntai I, Tran K L T, Weaver K J, Forbes D C and Davis Jr J H 2002 J. Am. Chem. Soc. 124 5962

    Article  CAS  Google Scholar 

  5. Ranu B C and Banerjee S 2005 Org. Lett. 7 3049

    Article  CAS  Google Scholar 

  6. Wilkes J S 2004 J. Mol. Catal. A: Chem. 214 11

    Article  CAS  Google Scholar 

  7. Garuti L, Roberti M and Pizzirani D 2007 Mini-Rev. Med. Chem. 7 481

    Article  CAS  Google Scholar 

  8. Bossert F, Meyer H and Wehinger E 1981 Angew. Chem. Int. Ed. 20 762

    Article  Google Scholar 

  9. Shan R, Velazquez C and Knaus E E 2003 J. Med. Chem. 47 254

    Article  Google Scholar 

  10. R Abeles R H, Hutton R F and Westheimer F H 1957 J. Am. Chem. Soc. 79 712

    Article  CAS  Google Scholar 

  11. Mauzerall D and Westheimer F H 1955 J. Am. Chem. Soc. 77 2261

    Article  CAS  Google Scholar 

  12. Triggle D J, Langs D A and Janis R A 1989 Med. Res. Rev. 9 123

    Article  CAS  Google Scholar 

  13. Hantzsch A 1882 Justus Liebigs Ann. Chem. 215 1

    Article  Google Scholar 

  14. Loev B and Snader K M 1965 J. Org. Chem. 30 1914

    Article  CAS  Google Scholar 

  15. Cherkupally S R and Mekala R 2008 Chem. Pharm. Bull. 56 1002

    Article  CAS  Google Scholar 

  16. Reddy C S and Raghu M 2008 Chin. Chem. Lett. 19 775

    Article  CAS  Google Scholar 

  17. Pasunooti K K, Nixon Jensen C, Chai H, Leow M L, Zhang D-W and Liu X-W 2010 J. Comb. Chem. 12 577

    Article  CAS  Google Scholar 

  18. Lei M, Ma L and Hu L H 2011 Synth. Commun. 41 1969

    Article  CAS  Google Scholar 

  19. Wang L-M, Sheng J, Zhang L, Han J-W, Fan Z-Y, Tian H and Qian C-T 2005 Tetrahedron 61 1539

    Article  CAS  Google Scholar 

  20. Debache A, Ghalem W, Boulcina R, Belfaitah A, Rhouati S and Carboni B 2009 Tetrahedron Lett. 50 5248

    Article  CAS  Google Scholar 

  21. Ko S, Sastry M N V, Lin C and Yao C-F 2005 Tetrahedron Lett. 46 5771

    Article  CAS  Google Scholar 

  22. Sabitha G, Reddy G S K K, Reddy C S and Yadav J S 2003 Tetrahedron Lett. 44 4129

    Article  CAS  Google Scholar 

  23. Shaabani A, Rezayan A H, Rahmati A and Sharifi M 2006 Monatsh. Chem. 137 77

    Article  CAS  Google Scholar 

  24. Li M, Guo W-S, Wen L-R, Li Y-F and Yang H-Z 2006 J. Mol. Catal. A: Chem. 258 133

    Article  CAS  Google Scholar 

  25. Dadhania A N, Patel V K and Raval D K 2011 J. Braz. Chem. Soc. 22 511

    Article  CAS  Google Scholar 

  26. Dadhania A N, Patel V K and Raval D K 2012 C. R. Chim. 15 378

    Article  CAS  Google Scholar 

  27. Dabiri M, Baghbanzadeh M and Arzroomchilar E 2008 Catal. Commun. 9 939

    Article  CAS  Google Scholar 

  28. Crowhurst L, Mawdsley P R, Perez-Arlandis J M, Salter P A and Welton T 2003 Phys. Chem. Chem. Phys. 5 2790

    Article  CAS  Google Scholar 

  29. Anderson J L, Ding J, Welton T and Armstrong D W 2002 J. Am. Chem. Soc. 124 14247

    Article  CAS  Google Scholar 

  30. Liu Q, Janssen M H A, van Rantwijk F and Sheldon R A 2005 Green Chem. 7 39

    Article  CAS  Google Scholar 

  31. Suresh Kumar D and Sandhu J S 2009 Synth. Commun. 39 1957

    Article  Google Scholar 

  32. Salehi H and Guo Q X 2004 Synth. Commun. 34 4349

    Article  CAS  Google Scholar 

  33. Sharma M, Agarwal N and Rawat D S 2008 J. Heterocycl. Chem. 45 737

    Article  CAS  Google Scholar 

  34. Ghorbani-Choghamarani A, Zolfigol M A, Salehi P, Ghaemi E, Madrakian E, Nasr Isfahani H and Shahamirian M 2008 Acta Chim. Slov. 55 644

    CAS  Google Scholar 

  35. Khadilkar B M, Jaisinghania H G, Saraf M N and Desai S K 2001 Indian J. Chem. B. 40 82

    Google Scholar 

  36. Khadilkar B M, Gaikar V G and Chitnavis A A 1995 Tetrahedron Lett. 36 8083

    Article  CAS  Google Scholar 

  37. Hernández-Gallegos Z, Lehmann F P A, Hong E, Posadas F and Hernández-Gallegos E 1995 Eur. J. Med. Chem. 30 355

    Article  Google Scholar 

  38. Akbari J D, Tala S D, Dhaduk M F and Joshi H S 2008 Arkivoc 126

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Acknowledgements

Authors thank Head, Department of Chemistry, Sardar Patel University for providing necessary research facilities. DKR is grateful to authorities of Sardar Patel University, Vallabh Vidyanagar for allocation of research funding in the form of seed grant-2011.

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Authors and Affiliations

  1. Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, 388 120, India

    JEMIN R AVALANI, DEVJI S PATEL & DIPAK K RAVAL

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  1. JEMIN R AVALANI
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  2. DEVJI S PATEL
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  3. DIPAK K RAVAL
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Correspondence to DIPAK K RAVAL.

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AVALANI, J.R., PATEL, D.S. & RAVAL, D.K. 1-Methylimidazolium trifluoroacetate [Hmim]Tfa: Mild and efficient Brønsted acidic ionic liquid for Hantzsch reaction under microwave irradiation. J Chem Sci 124, 1091–1096 (2012). https://doi.org/10.1007/s12039-012-0306-5

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