RESEARCH ARTICLE

 

Ionic liquid 3-methyl-1-sulphonic acid imidazolium chloride {[Msim]Cl}: A highly efficient, mild and green catalyst for the synthesis of β-acetamido ketones

 

 

Abdolkarim Zare^{I, *}; Tahereh Hekmat-Zadeh^I; Setareh Mirzaei-Monfared^II; Maria Merajoddin^I; Hossein Torabi-Monfared^I; Mohammad Ali Zolfigol^{III, *}; Ahmad Reza Moosavi-Zare^III; Esmael Rostami^I; Mohammad Mokhlesi^III; Fatemeh Derakhshan-Panah^III; Saeedeh Porbahi^I; Samira Balandeh^I

^IDepartment of Chemistry, Payame Noor University, P.O. Box 19395-4697, Tehran, Iran
^IIDepartment of Chemistry, Yasouj University, Yasouj, 75914-35, Iran
^IIIFaculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

 

 

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ABSTRACT

Bronstedacidic ionic liquid 3-methyl-1-sulphonic acid imidazolium chloride {[Msim]Cl} is utilized as a highly efficient, inexpensive, mild and green catalyst for the synthesis of β-acetamido ketones by the one-pot multi-component coupling between acetophenones, arylaldehydes, acetonitrile and acetyl chloride at room temperature. Under these conditions, the title compounds are produced in high to excellent yields and in relatively short reaction times. In addition, this method is superior to reported methods, for the synthesis of β-acetamido ketones and is applicable for the synthesis of tris(β-acetamido ketone).

Keywords: 3-Methyl-1-sulphonic acid imidazolium chloride {[Msim]Cl}, β-acetamido ketone, Bronsted acidic catalyst, ionic liquid, one-pot multi-component reaction, acetophenone

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Acknowledgements

The authors gratefully acknowledge financial support of this work by the Research Affairs Office of Payame Noor University andBu-Ali Sina University (Grant number 32-1716 entitled development of chemical methods, reagents and molecules), and Center of Excellence in Development of Chemical Method (CEDCM), Hamedan, Iran.

 

References

1 I.-T. Horvath and P.-T. Anastas, Chem. Rev., 2007, 107, 2167-2168.         [ Links ]

2 S.-L.Schreiber, Nature, 2009, 457, 153-154.         [ Links ]

3 P. Wasserscheid and T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2008.         [ Links ]

4 S. Toma, M. Meciarová and R. Sebesta, Eur. J. Org. Chem., 2009, 321-327.         [ Links ]

5 R.-D. Rogers and K.-R. Seddon, Ionic Liquids: Industrial Applications to Green Chemistry, American Chemical Society, Washington, DC, 2002.         [ Links ]

6 V-I. Parvulescu and C. Hardacre, Chem. Rev.,2007, 107, 2615-2665.         [ Links ]

7 A. Zare, A. Hasaninejad, A. Parhami, A.-R. Moosavi-Zare, F. Khedri, Z. Parsaee, M. Abdolalipoor-Saretoli, M. Khedri, M. Roshankar and H. Deisi, J. Serb. Chem. Soc., 2010, 75, 1315-1324.         [ Links ]

8 A. Zare, A. Hasaninejad, A. Salimi Beni, A.-R. Moosavi-Zare, M. Merajoddin, E. Kamali, M. Akbari-Seddigh and Z. Parsaee, Sci. Iran. C, 2011, 18, 433-438.         [ Links ]

9 J.-A. Brito, S. Ladeira, E. Teuma, B. Royo and M. Gómez, Appl. Catal. A: Gen., 2011, 398, 88-95.         [ Links ]

10 H. Valizadeh, M. Amiri, A. Shomali and F. Hosseinzadeh, J. Iran. Chem. Soc., 2011, 8, 495-501.         [ Links ]

11 A. Zare, A.-R. Moosavi-Zare, A. Hasaninejad, A. Parhami, A. Khalafi-Nezhad and M.-H. Beyzavi, Synth. Commun., 2009, 39, 3156-3165.         [ Links ]

12. A. Zare, A. Parhami, A.-R. Moosavi-Zare, A. Hasaninejad, A. Khalafi-Nezhad and M.-H. Beyzavi, Can. J. Chem., 2009, 87, 416-421.         [ Links ]

13 A. Hasaninejad, A. Zare, M. Shekouhy and J.Ameri Rad, J. Comb. Chem., 2010, 12, 844-849.         [ Links ]

14 R. Giernoth, Angew. Chem., Int. Ed., 2010, 49, 2834-2839.         [ Links ]

15 B. Wu, W.-W. Liu, Y. Zhang and H. Wang, Chem. Eur. J., 2009, 15, 1804-1810.         [ Links ]

16 P.-N. Sibiya and N. Deenadayalu, S. Afr. J. Chem., 2009, 62, 20-25.         [ Links ]

17 M.-I. Ikhile, M.-D. Bala and V.-O. Nyamori, S. Afr. J. Chem., 2011, 64, 101-104.         [ Links ]

18 C.-X. Miao, L.-N. He, J.-Q. Wang and J.-L. Wang, Adv. Synth. Catal., 2009, 351, 2209-2216.         [ Links ]

19 M.-A. Zolfigol, A. Khazaei, A.-R. Moosavi-Zare and A. Zare, Sci. Iraw. C, 2010, 17, 31-36.         [ Links ]

20 M.-A. Zolfigol, A. Khazaei, A.-R. Moosavi-Zare, A. Zare and V. Khakyzadeh, Appl. Catal. A: Gew., 2011, 400, 70-81.         [ Links ]

21 M.-A. Zolfigol, A. Khazaei, A.-R. Moosavi-Zare and A. Zare, J. Iraw. Chem. Soc., 2010, 7, 646-651.         [ Links ]

22 M.-A. Zolfigol, A. Khazaei, A.-R. Moosavi-Zare and A. Zare, Org. Prep. Proced. Iwt., 2010, 42, 95-102.         [ Links ]

23 J. Montgomery, Acc. Chem. Res., 2000, 33, 467-473.         [ Links ]

24 A. Strecker, Liebigs Aww. Chem., 1850, 75, 27-45.         [ Links ]

25 J. Zhu and H. Bienayme (Eds), Multicompowewt Reactiows, Wiley, Weinheim, 2005.         [ Links ]

26 A. Khazaei, M.-A. Zolfigol, A.-R. Moosavi-Zare, A. Zare, A. Parhami and A. Khalafi-Nezhad, Appl. Catal. A: Gew., 2010, 386, 179-187.         [ Links ]

27 A. Fayol and J. Zhu, Org. Lett., 2005, 7, 239-242.         [ Links ]

28 J.-R. Casimir, C. Turetta, L. Ettouati and J.Paris, Tetrahedrow Lett., 1995, 36, 4797-4800.         [ Links ]

29 A.-G. Goodfrey, D.-A. Brooks, L.-A. Hay, M. Peters, J.-R. Mc Carthy and D. Mitchell, J. Org. Chem., 2003, 68, 2623-2632.         [ Links ]

30 D. Enders, M. Moser, G. Geibel and M.-C. Laufer, Sywthesis, 2004, 2040-2046.         [ Links ]

31 J. Barluenga, A.-L. Viado, E. Aguilar, S. Fustero and B. Olano, J. Org. Chem.,1993, 58, 5972-5975.         [ Links ]

32 K. Kobinata, M. Uramoto, M. Nishii, H. Kusakabe, G. Nakamura and K. Isono, Agric. Biol. Chem., 1980, 44, 1709-1711.         [ Links ]

33 U. Daehn, H. Hagenmaier, H. Hoehne, W.-A. Koenig, G. Wolf and H. Zaehner, Arch. Microbiol., 1976, 107, 249-256.         [ Links ]

34 H.-D. Dakin and R. West, J. Biol. Chem., 1928, 78, 745-756.         [ Links ]

35 I.-N. Rao, E.-N. Prabhakaran, S.-K. Das and J. Iqbal, J. Org. Chem.,2003, 68, 4079-4082.         [ Links ]

36 A.-T. Khan, T. Parvin and L.-H. Choudhury, Tetrahedrow, 2007, 63, 5593-5601.         [ Links ]

37 V-S. Shinu, P. Pramitha and D. Bahulayan,Tetrahedrow Lett., 2011, 52, 3110-3115.         [ Links ]

38 M.-A. Zolfigol, A. Khazaei, A. Zare, M. Mokhlesi, T. Hekmat-Zadeh, A. Hasaninejad, F. Derakhshan-Panah, A.-R. Moosavi-Zare, H. Keypour, A.-A. Dehghani-Firouzabadi and M. Merajoddin, J. Chem. Sci., in press.         [ Links ]

39 M.-M. Heravi, L. Ranjbar, F. Derikvand and F.-F. Bamoharram, Catal. Commuw., 2007, 8, 289-291.         [ Links ]

40 B.-F. Mirjalili, A. Bamoniri, M.-A. Karimi Zarchi and H. Emtiazi, J. Iraw. Chem. Soc., 2010, 7, 95-99.         [ Links ]

41 A.-R. Momeni and M. Sadeghi, Appl. Catal. A: Gew., 2009, 357, 100-105.         [ Links ]

42 M.-R. Nabid and S.-J.-T. Rezaei, Appl. Catal. A: Gew., 2009, 366, 108-113.         [ Links ]

43 V-S. Shinu, B. Sheeja, E. Purushothaman and D. Bahulayan, Tetrahedrow Lett., 2009, 50, 838-4843.         [ Links ]

44 M.-T. Maghsoodlou, A. Hassankhani, H.-R. Shaterian, S.-M. Habibi-Khorasani and E. Mosaddegh, Tetrahedrow Lett., 2007, 48, 1729-1734.         [ Links ]

45 G. Pandey,R.-P. Singh,A. Garg and V.-K. Singh, Tetrahedrow Lett., 2005, 46, 2137-2140.         [ Links ]

46 R. Ghosh, S. Maiti, A. Chakraborty, S. Chakraborty and A.-K. Mukherjee, Tetrahedrow, 2006, 62, 4059-4064.         [ Links ]

47 L. Nagarapu, S. Kantevari, V-N. Cheemalapati, S. Apuri and N.-V Kumari, J. Mol. Catal. A: Chem., 2007, 264, 22-25.         [ Links ]

48 X.-H. Zhang, J.-F. Yan, L. Fan, G.-B. Wang and D.-C. Yang, Acta Pharmaceutica Sinica B, 2011, 1, 100-105.         [ Links ]

49. M.-M. Heravi, L. Ranjbar, F. Derikvand and F.-F. Bamoharram, J. Mol. Catal. A: Chem., 2007, 271, 28-31.         [ Links ]

 

 

Received 17 January 2012
Revised 30 January 2012
Accepted 14 March 2012

 

 

* To whom correspondence should be addressed. E-mail: abdolkarimzare@yahoo.com or mzolfigol@yahoo.com