SIOC English
有机化学
高级检索

有机化学 >

2013 , Vol. 33 >Issue 11: 2417 - 2422

DOI: https://doi.org/10.6023/cjoc201305012

研究简报

离子液体1-甲基咪唑硫酸氢盐催化合成取代吡咯衍生物

  • 吴长春 ,
  • 臧洪俊 ,
  • 李大庆 ,
  • 於年琴 ,
  • 程博闻 ,
  • 于楷
展开
  • a 天津工业大学环境与化学工程学院 天津改性与功能纤维重点实验室 天津 300387;
    b 铁岭港华燃气有限公司 铁岭 112002

收稿日期: 2013-05-13

  修回日期: 2013-07-06

  网络出版日期: 2013-07-19

基金资助

天津市自然科学基金（No. 11JCZDJC21300）资助项目.

收起

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).

Fold

摘要

以2，5-己二酮和胺为原料，1-甲基咪唑硫酸氢盐（[HMIM]HSO4）作为环境友好型催化剂，甲醇为溶剂，回流条件下，高效地合成了一系列取代吡咯类衍生物，其结构通过1H NMR，FT-IR，质谱和元素分析表征. 考察了催化剂种类和用量对反应的影响，确定了最佳反应条件，并提出了可能的反应机理. 此外，还研究了催化剂的循环使用性能，研究表明[HMIM]HSO4具有很好的催化性能和重复使用性. 该方法具有条件温和、时间短、产率高及催化剂可重复使用等优点.

关键词： 吡咯衍生物; 离子液体; 2,5-己二酮; 胺; 环境友好型催化剂

本文引用格式

吴长春 , 臧洪俊 , 李大庆 , 於年琴 , 程博闻 , 于楷 . 离子液体1-甲基咪唑硫酸氢盐催化合成取代吡咯衍生物[J]. 有机化学, 2013 , 33(11) : 2417 -2422 . DOI: 10.6023/cjoc201305012

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.

Key words： pyrroles; ionic liquid; 2,5-hexanedione; amine; eco-friendly catalyst

参考文献

[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.
Options
文章导航

/

〈 〉