Notes

1-Methylimidazolium Hydrogen Sulfate: An Efficient Catalyst for the Synthesis of Substituted Pyrroles

  • Wu Changchun ,
  • Zang Hongjun ,
  • Li Daqing ,
  • Yu Nianqin ,
  • Cheng Bowen ,
  • Yu Kai
Expand
  • a Department of Environmental and Chemistry Engineering, Tianjin Polytechnic University, Tianjin 300387;
    b Ganghua Gas Limited Company, Tieling 112002

Received date: 2013-05-13

  Revised date: 2013-07-06

  Online published: 2013-07-19

Supported by

Project supported by the Natural Science Foundation of Tianjin City (No. 11JCZDJC21300).

Abstract

Using ionic liquid [HMIM]HSO4 as a eco-friendly catalyst, a variety of N-substituted pyrroles were synthesized by the reaction of 2, 5-hexanedione and primary amines in methanol at reflux. The new compounds were characterized by 1H NMR, FT-IR, mass spectra and elemental analysis. The influence of different catalysts and catalyst loading were investigated, and the optimal reaction conditions were then obtained. A possible mechanism was also proposed. Furthermore, the recycling experiment of the catalyst was conducted and the green catalytic system can be recycled for several times with no decreases in yields and reaction rates. The present methodology offers several advantages such as mild conditions, short reaction time, excellent yields, and recyclable catalyst.

Cite this article

Wu Changchun , Zang Hongjun , Li Daqing , Yu Nianqin , Cheng Bowen , Yu Kai . 1-Methylimidazolium Hydrogen Sulfate: An Efficient Catalyst for the Synthesis of Substituted Pyrroles[J]. Chinese Journal of Organic Chemistry, 2013 , 33(11) : 2417 -2422 . DOI: 10.6023/cjoc201305012

References

[1] Rango,R.; Marshall,G.R.; Di Santo,R.; Costi,R.; Massa,S.; Rompei,R.; Artico,M.Bioorg.Med.Chem.2000,8,1423.
[2] FÜrstner,A.Angew.Chem.,Int.Ed.2003,42,3582.
[3] De Leo,C.Y.; Ganem,B.Tetrahedron 1997,53,7731.
[4] Weidner,M.F.; Sigurdsson,S.T.; Hopkins,P.B.Biochemistry 1990,29,9225.
[5] Trautwein,A.W.; Submuth,R.D.; Jung,G.Bioorg.Med.Chem.Lett.1998,8,2381.
[6] Alberola,A.; González Ortega,A.; Sádaba,M.L.; Sañudo,C.Tetrahedron 1999,55,6555.
[7] Katritzky,A.R.; Jiang,J.; Steel,P.J.J.Org.Chem.1994,59,4551.
[8] Raghavan,S.; Anuradha,K.Synlett 2003,711.
[9] Shaw,D.J.; Wood,W.F.J.Chem.Educ.1992,69,A313.
[10] Broadbent,H.S.; Burnham,W.S.; Olsen,R.K.; Sheeley,R.M.J.Heterocycl.Chem.1968,5,757.
[11] Banik,B.K.; Samajdar,S.; Banik,I.J.Org.Chem.2004,69,213.
[12] Abid,M.; Spaeth,A.; Török,B.Adv.Synth.Catal.2006,348,2191.
[13] Chen,J.; Wu,H.; Zheng,Z.; Jin,C.; Zhang,X.; Su,W.Tetrahedron Lett.2006,47,5383.
[14] Banik,B.K.; Banik,I.; Renteria,M.; Dasgupta,S.K.Tetrahedron Lett.2005,46,2643.
[15] Satyanarayana,V.S.V.; Sivakumar,A.Ultrason.Sonochem.2011,18,917.
[16] De,S.K.Catal.Lett.2008,124,174.
[17] Armugam,P.; Perumal,P.T.Chem.Lett.2006,35,632.
[18] Rahmatpour,A.Monatsh.Chem.2012,143,491.
[19] Curini,M.; Montanari,F.; Rosati,O.; Lioy,E.; Margarita,R.Tetrahedron Lett.2003,44,3923.
[20] Abbas,T.; Najafi,C.A.Chin.J.Chem.2012,30,372.
[21] Zhan,Z.H.; Li,J.J.; Li,T.S.Ultrason.Sonochem.2008,15,673.
[22] Danks,T.N.Tetrahedron Lett.1999,40,3957.
[23] Ullrich,T.; Ghobrial,M.; Weigand,K.; Marzinzik,A.L.Synth.Commun.2007,37,1109.
[24] Van Rantwijk,F.; Sheldon,R.A.Chem.Rev.2007,107,2757.
[25] Welton,T.Chem.Rev.1999,99,2071.
[26] Sheldon,R.Chem.Commun.2001,23,2399.
[27] Wilkes,J.S.Green Chem.2002,4,73-80.
[28] Zare,A.; Parhami,A.; Moosavi-Zare,A.R.; Hasaninejad,A.; Khalafi-Nezhad,A.Can.J.Chem.2009,87,416.
[29] Yue,C.B.; Fang,D.; Liu,L.; Yi,T.F.J.Mol.Liq.2011,163,99.
[30] Zang,H.J.; Su,Q.H.; Mo,Y.M.; Cheng,B.W.; Song,J.Ultrason.Sonochem.2010,17,749.
[31] Zang,H.J.; Su,Q.H.; Mo,Y.M.; Cheng,B.W.Ultrason.Sonochem.2011,18,68.
[32] Zang,H.J.; Su,Q.H.; Guo,S.; Mo,Y.M.; Cheng,B.W.Chin.J.Chem.2011,29,2202.
[33] Zang,H.J.; Wang,M.L.; Song,J.Ultrason.Sonochem.2009,16,301.
[34] Zang,H.J.; Zhang,Y.; Zang,Y.P.; Cheng,B.W.Ultrason.Sonochem.2010,17,495.
[35] Li,D.Q.; Zang,H.J.; Wu,C.C.; Lu,B.; Cheng,B.W.Chin.J.Org.Chem.2012,32,2193 (in Chinese).(李大庆,臧洪俊,吴长春,卢波,程博闻,有机化学,2012,32,2193.)
[36] Gui,J.Z.; Cong,X.H.; Liu,D.; Zhang,X.T.; Hu,Z.; Sun,Z.L.Catal.Commun.2004,5,473.
[37] Miao,C.X.; He,L.N.; Wang,J.Q.; Wang,J.L.Adv.Synth.Catal.2009,351,2209.
[38] Deng,Y.F.; Long,T.; Zhang,D.L.; Chen,J.; Gan,S.C.J.Chem.Eng.Data 2009,54,2470.
[39] Hasan,M.; Kozhevnikov,I.V.; Siddiqui,M.R.H.; Steiner,A.; Winterton,N.Inorg.Chem.1999,38,5637.
[40] Zhou,X.P.; Wang,Y.L.; Meng,F.W.; Fan,X.M.; Qin,S.B.Chin.J.Chem.2008,26,607.
[41] Kang,L.Q.; Zhou,Y.P.; Cai,Y.Q.Chin.J.Org.Chem.2010,30,1230 (in Chinese).(康丽琴,周燕萍,蔡月琴,有机化学,2010,30,1230.)
[42] Sun,A.J.; Nie,Y.; Li,C.X.; Wang,Z.G.Chin.J.Chem.Eng.2008,16,151.
[43] Yang,X.J.; Li,X.W.; Chen,B.; Wu,L.Z.; Zhang,L.P.; Zheng,L.Q.; Tung,C.H.Chin.J.Chem.2013,31,603.
Outlines

/