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
Ricci A (2000) Modern amination reactions. Wiley, Weinheim
Hartwig JF (2002) In: Negishi E, Meijere A (eds) Handbook of organopalladium chemistry for organic synthesis, vol 1. Wiley, New York
Lawrence SA (2004) Amines synthesis properties and application. Cambridge University Press, Cambridge
Rappoport ZJ, Liebman F (2009) The chemistry of hydroxylamines oximes and hydroxamic acids. Wiley, New York, p 609
Hadjipavlou-Litina DJ, Geronikaki AA (1998) Drug Des Discov 15:199–206
Kuznetsov VV, Palma AR, Aliev AE, Varlamov AV, Prostakov NS, Zh (1991) Org Khim l27:1579–1581
Tsuge O, Kanemasa R (1989) Adv Heterocycl Chem 45:231–349
Aly MF, Younes MI, Matwally SAO (1994) Tetrahedron 50:3159–3168
Hadjipavlou-litina DJ, Geronikaki AA (1996) Drug Des Discov 15:199–206
Cushman M, Nagarathnam D, Gopal D, Chakraborti AK, Lin CM, Hamel EJ (1991) Med Chem 34:2579–2588
Cushman M, He HM, Lin CM, Hamel E (1993) J Med Chem 36:2817–2821
Vicini P, Geronikaki A, Incerti M, Busonera B, Poni G, Cabras CA, Colla PL (2003) Bioorg Med Chem 11:4785–4789
Patil RD, Adimurthy S (2013) Asian J Org Chem 2:726–744
Angelici RJ (2013) Catal Sci Technol 3:279–296
Qin W, Long S, Panunzio M, Biondi S (2013) Molecules 18:12264–12289
Ryland BL, Stahl SS (2014) Angew Chem Int Ed 53:8824–8838
Su F, Mathew SC, Mohlmann L, Antonietti M, Wang X, Blechert S (2011) Angew Chem Int Ed 50:657–660
Chen B, Wang L, Dai W, Shang S, Lv Y, Gao S (2015) ACS Catal 5:2788–2794
Chen B, Wang L, Gao S (2015) ACS Catal 5:5851–5876
Blackburn L, Taylor RJK (2001) Org Lett 3:1637–1639
Tamura M, Tomishige K (2015) Angew Chem Int Ed 54:864–867
Pohlki F, Doye S (2001) Angew Chem Int Ed 40:2305–2308
Johnson JS, Bergman RG (2001) J Am Chem Soc 123:2923–2924
Li Y, Shi Y, Odom AL (2004) J Am Chem Soc 126:1794–1803
Ryken SA, Schafer LL (2015) Acc Chem Res 48:2576–2586
Srimani D, Feller M, Ben-David Y, Milstein D (2012) Chem Commun 48:11853–11855
Chakraborty S, Berke H (2014) ACS Catal 4:2191–2194
Sheldon RA, Dakka J (1994) Catal Today 19:215–246
Clark JH (1995) Chemistry of waste minimisation. Chapman and Hall, London
Hoelderich WF, Heitmann G (1997) Catal Today 8:227–233
Anastas PT, Bartlett LB, Kirchhoff MM, Williamson TC (2000) Catal Today 55:11–22
Cejka J, Centi G, Perez-Pariente J, Roth WJ (2012) Catal Today 179:2–15
Martinez C, Corma A (2011) Coord Chem Rev 255:1558–1580
Gupta P, Paul S (2014) Catal Today 236:153–170
Clark JH (2002) Acc Chem Res 35:791–797
Lok BM, Marcus BK, Angell CL (1986) Zeolites 6:185–194
Scherzer J (1990) Octane-enhancing zeolitic FCC catalysts. Marcel Dekker, New York
Mohan KVVK, Reddy KSK, Narender N, Kulkarni SJ (2009) J Mol Catal A 298:99–102
Mohan KVVK, Narender N, Kulkarni SJ (2007) Micropor Mesopor Mater 106:229–235
Mohan KVVK, Narender N, Kulkarni SJ (2006) Green Chem 8:368–372
Naresh M, Swamy P, Reddy MM, Srujana K, Durgaiah C, Narender N (2015) Appl Catal A 505:213–216
Narender N, Srinivasu P, Kulkarni SJ, Raghavan KV (2000) Green Chem 2:104–105
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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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