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Lewis acidic (choline chloride.3ZnCl2) ionic liquid: A green and recyclable catalyst for the one-pot synthesis of 4-((3-indolyl)(aryl)methyl)-N,N-dimethylanilines under solvent-free conditions

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Abstract

A green and convenient procedure for the one-pot multicomponent synthesis of 4-((3-indolyl)(aryl)methyl)-N,N-dimethylanilines using (choline chloride.3ZnCl2) ionic liquid as catalyst, at 100°C and under solvent-free condition is described. Utilizing environmentally benign reagents, elimination of organic solvents, enhanced rates, reusability and moisture stability of the catalyst are the remarkable features observed in the reported reaction system. The catalyst was recycled up to four times with no noticeable drop in activity.

A green and convenient procedure for the one-pot multicomponent synthesis of 4-((3-indolyl)(aryl)methyl)-N,N-dimethylanilines using (choline chloride.3ZnCl2) ionic liquid as catalyst, at 100°C and under solvent-free conditions is described. Environmentally benign reagents, elimination of organic solvents, enhanced rates, reusability and moisture stability of the catalyst are the remarkable features in the reported reaction system.

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References

  1. Horvath I T and Rabai J 1994 Science 25 72

    Article  Google Scholar 

  2. Kitazume T, Ishizuka T, Takedu M and Itoh K 1999 Green Chem. 1 221

    Article  CAS  Google Scholar 

  3. Welton T 1999 Chem. Rev. 99 2071

    Article  CAS  Google Scholar 

  4. Wasserscheid P and Keim W 2000 Angew. Chem. Int. Ed. 39 3772

    Article  CAS  Google Scholar 

  5. Hu S, Zhang Z, Song J, Zhou Y and Han B 2009 Green Chem. 11 1746

    Article  CAS  Google Scholar 

  6. Peng J and Deng Y 2001 Tetrahedron Lett. 42 5917

    Article  CAS  Google Scholar 

  7. Li C and Zhao Z K 2007 Adv. Synth. Catal. 349 1847

    Article  CAS  Google Scholar 

  8. Itoh T, Nishimura Y, Ouchi N and Hayase S 2003 J. Mol. Catal. B: Enzym. 26 41

    Article  CAS  Google Scholar 

  9. Duan Z, Gu Y and Deng Y 2006 Catal. Commun. 7 651

    Article  CAS  Google Scholar 

  10. Abbott A P, Capper G, Davies D L, Munro H and Rasheed R K 2004 Inorg. Chem. 43 3447

    Article  CAS  Google Scholar 

  11. Abbott A P, Capper G, Davies D L, Rasheed R K and Tambyrajah V 2001 Trans. Inst. Met. Finish. 79 204

    CAS  Google Scholar 

  12. Abbott A P, Capper G, Davies D L, Munro H, Rasheed R K and Tambyrajah V 2003 Ionic liquids as green solvents: Progress and prospects, R D Rogers and K R Seddon (Eds), Washington D C: ACS Symposium Series, American Chemical Society, pp. 439–452

  13. Abbott A P, Capper G, Davies D L, Rasheed R K and Tambyrajah V 2002 Green Chem. 4 24

    Article  CAS  Google Scholar 

  14. Morales R C, Tambyrajah V, Jenkins P R, Davies D L and Abbott A P 2004 Chem. Commun. 158

  15. Abbott A P, Bell T J, Handa S and Stoddart B 2005 Green Chem. 7 705

    Article  CAS  Google Scholar 

  16. Muthyala R 1997 Chemistry and applications of leuco dyes, A R Katrizky and G J Sabongi (Eds), Plenum: New York

  17. Duxbury D F 1993 Chem. Rev. 93 381

    Article  CAS  Google Scholar 

  18. Aldag R 1990 Photochroism: molecules and systems, H Durr and H Bouaslaurent (Eds), Elsevier: London

  19. Oclarit J M, Ohta S, Kamimura K, Yamaoka Y, Shimizu T and Ikegami S 1994 Nat. Prod. Lett. 4 309

    Article  CAS  Google Scholar 

  20. Mibu N, Yokomizo Y, Uyeda M and Sumoto K 2003 Chem. Pharm. Bull. 51 1325

    Article  CAS  Google Scholar 

  21. Poupelin J P, Saint-Ruf G, Foussard-Blanpin O, Narcisse G, Uchida-Ernouf G and Lacroix R 1978 Eur. J. Med. Chem. 13 67

    CAS  Google Scholar 

  22. Gribble G W 1996 Comprehensive heterocyclic chemistry, 2nd edn Pergamon Press: New York vol. 2, pp 203–257

  23. Snieckus V 1968 The alkaloids, Academic Press: New York, vol. 11, pp 1–33

  24. Gul W and Hamann M T 2005 Life Sci. 78 442

    Article  CAS  Google Scholar 

  25. Katritzky A R and Lan X 1994 Dyes Pigments 25 303

    Article  Google Scholar 

  26. Deb M L and Bhuyan P J 2008 Synthesis 2891

  27. Esquivias J, Arrayas R G and Carretero J C 2006 Angew. Chem. 118 645

    Article  Google Scholar 

  28. Das S K and Shagufta 2005 Tetrahedron Lett. 46 3097

  29. Katrizky A R and Toader D 1997 J. Org. Chem. 62 4137

    Article  Google Scholar 

  30. Abbott A P, Capper G, Davies D L, Munro H, Rasheed R K and Tambyrajah V 2001 Chem. Commun. 2010

  31. Liu J, He T and Wang L 2011 Tetrahedron 67 3420

    Article  CAS  Google Scholar 

  32. Disale S T, Kale S R, Kahandal S S, Srinivasan T G and Jayaram R V 2012 Tetrahedron Lett. 53 2277

    Article  CAS  Google Scholar 

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Acknowledgement

The authors are thankful to Alzahra Research Council for partial financial support.

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Authors and Affiliations

  1. Department of Chemistry, School of Science, Alzahra University, Vanak, Tehran, Iran

    RAHIM HEKMATSHOAR, FARNOUSH MOUSAVIZADEH & REYHANEH RAHNAMAFAR

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  1. RAHIM HEKMATSHOAR
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  2. FARNOUSH MOUSAVIZADEH
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  3. REYHANEH RAHNAMAFAR
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Correspondence to RAHIM HEKMATSHOAR.

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HEKMATSHOAR, R., MOUSAVIZADEH, F. & RAHNAMAFAR, R. Lewis acidic (choline chloride.3ZnCl2) ionic liquid: A green and recyclable catalyst for the one-pot synthesis of 4-((3-indolyl)(aryl)methyl)-N,N-dimethylanilines under solvent-free conditions. J Chem Sci 125, 1009–1013 (2013). https://doi.org/10.1007/s12039-013-0474-y

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