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Hβ Catalyzed Condensation Reaction Between Aromatic Ketones and Anilines: To Access Ketimines (Imines)

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Abstract

A simple approach for the formation of imines by condensation of ketones and anilines over heterogeneous catalyst (Hβ zeolite) has been successfully developed. The present catalytic system scope was explored for various aromatic ketones and anilines. Furthermore, Hβ zeolite can be easily separable and recycled several times (five times) without considerable loss of its catalytic activity.

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References

  1. Ricci A (2000) Modern amination reactions. Wiley, Weinheim

    Book  Google Scholar 

  2. Hartwig JF (2002) In: Negishi E, Meijere A (eds) Handbook of organopalladium chemistry for organic synthesis, vol 1. Wiley, New York

    Google Scholar 

  3. Lawrence SA (2004) Amines synthesis properties and application. Cambridge University Press, Cambridge

    Google Scholar 

  4. Rappoport ZJ, Liebman F (2009) The chemistry of hydroxylamines oximes and hydroxamic acids. Wiley, New York, p 609

    Google Scholar 

  5. Hadjipavlou-Litina DJ, Geronikaki AA (1998) Drug Des Discov 15:199–206

    CAS  Google Scholar 

  6. Kuznetsov VV, Palma AR, Aliev AE, Varlamov AV, Prostakov NS, Zh (1991) Org Khim l27:1579–1581

    Google Scholar 

  7. Tsuge O, Kanemasa R (1989) Adv Heterocycl Chem 45:231–349

    Article  CAS  Google Scholar 

  8. Aly MF, Younes MI, Matwally SAO (1994) Tetrahedron 50:3159–3168

    Article  CAS  Google Scholar 

  9. Hadjipavlou-litina DJ, Geronikaki AA (1996) Drug Des Discov 15:199–206

    Google Scholar 

  10. Cushman M, Nagarathnam D, Gopal D, Chakraborti AK, Lin CM, Hamel EJ (1991) Med Chem 34:2579–2588

    Article  CAS  Google Scholar 

  11. Cushman M, He HM, Lin CM, Hamel E (1993) J Med Chem 36:2817–2821

    Article  CAS  Google Scholar 

  12. Vicini P, Geronikaki A, Incerti M, Busonera B, Poni G, Cabras CA, Colla PL (2003) Bioorg Med Chem 11:4785–4789

    Article  CAS  Google Scholar 

  13. Patil RD, Adimurthy S (2013) Asian J Org Chem 2:726–744

    Article  CAS  Google Scholar 

  14. Angelici RJ (2013) Catal Sci Technol 3:279–296

    Article  CAS  Google Scholar 

  15. Qin W, Long S, Panunzio M, Biondi S (2013) Molecules 18:12264–12289

    Article  CAS  Google Scholar 

  16. Ryland BL, Stahl SS (2014) Angew Chem Int Ed 53:8824–8838

    Article  CAS  Google Scholar 

  17. Su F, Mathew SC, Mohlmann L, Antonietti M, Wang X, Blechert S (2011) Angew Chem Int Ed 50:657–660

    Article  CAS  Google Scholar 

  18. Chen B, Wang L, Dai W, Shang S, Lv Y, Gao S (2015) ACS Catal 5:2788–2794

    Article  CAS  Google Scholar 

  19. Chen B, Wang L, Gao S (2015) ACS Catal 5:5851–5876

    Article  CAS  Google Scholar 

  20. Blackburn L, Taylor RJK (2001) Org Lett 3:1637–1639

    Article  CAS  Google Scholar 

  21. Tamura M, Tomishige K (2015) Angew Chem Int Ed 54:864–867

    Article  CAS  Google Scholar 

  22. Pohlki F, Doye S (2001) Angew Chem Int Ed 40:2305–2308

    Article  CAS  Google Scholar 

  23. Johnson JS, Bergman RG (2001) J Am Chem Soc 123:2923–2924

    Article  CAS  Google Scholar 

  24. Li Y, Shi Y, Odom AL (2004) J Am Chem Soc 126:1794–1803

    Article  CAS  Google Scholar 

  25. Ryken SA, Schafer LL (2015) Acc Chem Res 48:2576–2586

    Article  CAS  Google Scholar 

  26. Srimani D, Feller M, Ben-David Y, Milstein D (2012) Chem Commun 48:11853–11855

    Article  CAS  Google Scholar 

  27. Chakraborty S, Berke H (2014) ACS Catal 4:2191–2194

    Article  CAS  Google Scholar 

  28. Sheldon RA, Dakka J (1994) Catal Today 19:215–246

    Article  CAS  Google Scholar 

  29. Clark JH (1995) Chemistry of waste minimisation. Chapman and Hall, London

    Book  Google Scholar 

  30. Hoelderich WF, Heitmann G (1997) Catal Today 8:227–233

    Article  Google Scholar 

  31. Anastas PT, Bartlett LB, Kirchhoff MM, Williamson TC (2000) Catal Today 55:11–22

    Article  CAS  Google Scholar 

  32. Cejka J, Centi G, Perez-Pariente J, Roth WJ (2012) Catal Today 179:2–15

    Article  CAS  Google Scholar 

  33. Martinez C, Corma A (2011) Coord Chem Rev 255:1558–1580

    Article  CAS  Google Scholar 

  34. Gupta P, Paul S (2014) Catal Today 236:153–170

    Article  CAS  Google Scholar 

  35. Clark JH (2002) Acc Chem Res 35:791–797

    Article  CAS  Google Scholar 

  36. Lok BM, Marcus BK, Angell CL (1986) Zeolites 6:185–194

    Article  CAS  Google Scholar 

  37. Scherzer J (1990) Octane-enhancing zeolitic FCC catalysts. Marcel Dekker, New York

  38. Mohan KVVK, Reddy KSK, Narender N, Kulkarni SJ (2009) J Mol Catal A 298:99–102

    Article  CAS  Google Scholar 

  39. Mohan KVVK, Narender N, Kulkarni SJ (2007) Micropor Mesopor Mater 106:229–235

    Article  Google Scholar 

  40. Mohan KVVK, Narender N, Kulkarni SJ (2006) Green Chem 8:368–372

    Article  CAS  Google Scholar 

  41. Naresh M, Swamy P, Reddy MM, Srujana K, Durgaiah C, Narender N (2015) Appl Catal A 505:213–216

    Article  Google Scholar 

  42. Narender N, Srinivasu P, Kulkarni SJ, Raghavan KV (2000) Green Chem 2:104–105

    Article  CAS  Google Scholar 

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Acknowledgements

We thank the DST, New Delhi for financial support under Indo-Russia (DST-RSF) (No. INT/RUS/RSF/P-7) programme. M. N, Ch. D and G. K. acknowledge the CSIR, India and K. S. and B. R. acknowledge the UGC, India for financial support in the form of fellowship.

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Correspondence to Narender Nama.

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Amrutham, V., Mameda, N., Kodumuri, S. et al. Hβ Catalyzed Condensation Reaction Between Aromatic Ketones and Anilines: To Access Ketimines (Imines). Catal Lett 147, 2982–2986 (2017). https://doi.org/10.1007/s10562-017-2196-0

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  • DOI: https://doi.org/10.1007/s10562-017-2196-0

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