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Deep eutectic solvent catalyzed eco-friendly synthesis of imines and hydrobenzamides

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Abstract

The urea–choline chloride-based deep eutectic solvent was found to be an efficient catalyst and reaction media for the additive-free synthesis of imines (Schiff bases) and hydrobenzamides by the reaction of aldehydes with amines and ammonia in good to high yields. Outstanding features of this protocol were the general and atom-economical reaction, absence of external catalysts and additives, simple workup, and availability and recycling of urea–choline chloride as a green solvent.

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References

  1. Abbott AP, Davies DL, Rasheed RK, Tambyrajah V (2003) Chem Commun 70

  2. Smith EL, Abbott AP, Ryder KS (2014) Chem Rev 114:11060

    Article  CAS  Google Scholar 

  3. Tang B, Ho Row K (2013) Monatsh Chem 144:1427

  4. Zhang Q, Vigier KDO, Royer S, Jérôme F (2012) Chem Soc Rev 41:7108

    Article  CAS  Google Scholar 

  5. Singh B, Lobo H, Shankarling G (2011) Catal Lett 141:178

    Article  CAS  Google Scholar 

  6. Wang P, Ma F-P, Zhang Z-H (2014) J Mol Liq 198:259

    Article  CAS  Google Scholar 

  7. Hayyan A, Ali Hashim A, Hayyan M, Mjalli FS, Al Nashef IM (2014) J Clean Prod 65:246

    Article  CAS  Google Scholar 

  8. Kailas Sanap A, Shankarling GS (2014) Catal Commun 49:58

  9. Kumar D, Kommi DN, Bollineni N, Patela AR, Chakraborti AK (2012) Green Chem 14:2038

    Article  CAS  Google Scholar 

  10. Kumar D, Sonawane M, Pujala B, Jain VK, Bhagat S, Chakraborti AK (2013) Green Chem 15:2872

    Article  CAS  Google Scholar 

  11. Layer RW (1963) Chem Rev 63:489

    Article  CAS  Google Scholar 

  12. Roy SR, Jadhavar PS, Seth K, Sharma KK, Chakraborti AK (2011) Synthesis 2261

  13. Thomas G (2000) Medicinal chemistry. Wiley, New York

    Google Scholar 

  14. Ajamian A, Gleason JL (2004) Angew Chem Int Ed 43:3754

    Article  CAS  Google Scholar 

  15. Hart DJ, Ha DC (1989) Chem Rev 89:1447

    Article  CAS  Google Scholar 

  16. Choudhury LH, Parvin T (2011) Tetrahedron 67:8213

    Article  CAS  Google Scholar 

  17. Cushman M, He HM, Lin CM, Hamel E (1993) J Med Chem 36:2817

    Article  CAS  Google Scholar 

  18. Kommi DN, Kumar D, Seth K, Chakraborti AK (2013) Org Lett 15:1158

    Article  CAS  Google Scholar 

  19. Huang J-M, Zhang J-F, Dong Y, Gong W (2011) J Org Chem 76:3511

    Article  CAS  Google Scholar 

  20. Williams OF, Bailar JC (1959) J Am Chem Soc 81:4464

    Article  CAS  Google Scholar 

  21. Naka H, Koseki D, Kondo Y (2008) Adv Syn Catal 350:1901

    Article  CAS  Google Scholar 

  22. Li T, Cui X, Sun L, Li C (2014) RSC Adv 4:33599

    Article  CAS  Google Scholar 

  23. Fujii H, Nagamatsu K, Gunji T, Murafuji T, Abe N (2010) Heterocycles 81:2625

    Article  CAS  Google Scholar 

  24. Greger JG, Yoon-Miller SJP, Bechtold NR, Flewelling SA, MacDonald JP, Downey CR, Cohen EA, Pelkey ET (2011) J Org Chem 76:8203

    Article  CAS  Google Scholar 

  25. Seomoon D, Jaemyung A, Lee PH (2009) Org Lett 11:2401

    Article  CAS  Google Scholar 

  26. Chakraborti AK, Bhagat S, Rudrawar S (2004) Tetrahedron Lett 45:7641

    Article  CAS  Google Scholar 

  27. Azizi N, Rajabi F, Saidi MR (2004) Tetrahedron Lett 45:9233

    Article  CAS  Google Scholar 

  28. Abbiati G, Contini A, Nava D, Rossi E (2009) Tetrahedron 65:4664

    Article  CAS  Google Scholar 

  29. Karupaiyan S, Deshmukh B (1998) Tetrahedron 54:4375

    Article  CAS  Google Scholar 

  30. Chou CH, Chu LT, Chiu S, Lee CF, She YT (2004) Tetrahedron 60:6581

    Article  CAS  Google Scholar 

  31. Risse J, Scopelliti R, Severin K (2011) Organomet 30:3412

    Article  CAS  Google Scholar 

  32. Uchida H, Tanikoshi H, Nakamura S, Reddy PY, Toru T (2003) Synlett 1117

  33. Lozinskaya T, Proskurnina Z (2003) Russ Chem Bull 52:674

    Article  CAS  Google Scholar 

  34. Grigorev V, Mirskov R (2001) Russ J Gen Chem 71:149

    Article  CAS  Google Scholar 

  35. Pudovik S, Khairullin V, Chernova G (1996) Russ Chem Bull 45:1242

    Article  Google Scholar 

  36. Azizi N, Amiri AK, Ghafuri H, Bolourtchian M (2011) Mol Divers 15:157

    Article  CAS  Google Scholar 

  37. Azizi N, Batebi E (2012) Catal Sci Technol 2:2445

    Article  CAS  Google Scholar 

  38. Azizi N, Batebi E, Bagherpour S, Ghafuri H (2012) RSC Adv 2:2289

    Article  CAS  Google Scholar 

  39. Azizi N, Gholibeglo E (2012) RSC Adv 2:7413

    Article  CAS  Google Scholar 

  40. Azizi N, Manocheri Z (2012) Res Chem Intermed 38:1495

    Article  CAS  Google Scholar 

  41. Azizi N, Khajeh-Amiri A, Ghafuri H, Bolourtchian M, Saidi MR (2009) Synlett 2245

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Acknowledgments

Financial support of this work by Chemistry and Chemical Engineering Research Center of Iran is gratefully appreciated.

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Correspondence to Najmedin Azizi.

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Azizi, N., Edrisi, M. Deep eutectic solvent catalyzed eco-friendly synthesis of imines and hydrobenzamides. Monatsh Chem 146, 1695–1698 (2015). https://doi.org/10.1007/s00706-015-1447-2

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  • DOI: https://doi.org/10.1007/s00706-015-1447-2

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