Keywords
zeoliteP
powder diffraction
Povarov reaction
How to Cite
Abstract
A Na-P zeolite was synthesized and subjected to ion exchange with Ca2+, Cu2+, Al3+, and In3+, and supported with H+/NH4Cl (NH4-P) by in situ reaction of EtOH and NH4Cl. All the exchanged zeolites showed catalytic activity in the ABB’ Povarov reaction. However, zeolite NH4-P promoted a better yield. In all reactions two products were obtained, 2,6-dimethyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline and 1-(1-(4-methylphenylamino)ethyl)pyrrolidin 2-one. Synthesis using zeolite P as catalyst proves to be a simple method with high yields, short reaction times and easy preparation. The catalyst can be recovered by filtration and reused up to three times in good yields.
Krishna VV, Narender N. Synthesis of N-heterocyclic compounds over zeolite molecular sieve catalysts: an approach towards green chemistry, Catalysis Science and Technology, 2: 471-487, 2012.
doi: 10.1039/c2cy00162d
Candeias NR, Afonso CAM. Preparation of non-fused heterocycles in zeolites and mesoporous materials, Journal of Molecular Catalysis A: Chemical, 242(1): 195-217, 2005.
doi: 10.1016/j.molcata.2005.07.042
Corma A. State of the Art and Future Challenges of Zeolites as Catalysts, Journal of Catalysis, 216: 298-312, 2003.
doi: 10.1016/S0021-9517(02)00132-X
Corma A, Garcia H. Lewis acids: from conventional homogeneous to green homogeneous and heterogeneous catalysis, Chemical Review, 103(11): 4307-4365, 2003.
doi: 10.1021/cr030680z
Gomez MV, Cantin A, Corma A, de la Hoz A. Use of different microporous and mesoporous materials as catalyst in the Diels- Alder and retro-Diels-Alder reaction between cyclopentadiene and p-benzoquinone, Journal of Molecular Catalysis A: Chemical, 240(1): 16-21, 2005.
doi: 10.1016/j.molcata.2005.06.030
Olmos A, Rigolet S, Louis B, Pale P. Design of Scandium-Doped USY Zeolite: An Efficient and Green Catalyst for Aza Diels- Alder Reaction, The Journal of Physical Chemistry C, 116:13661-13670, 2012.
doi: 10.1021/jp303169h
Joshi SS, A. Bhatnagar, V.V. Ranade. Industrial Catalytic Processes for Fine and Specialty Chemicals. Chapter 8: Catalysis
for Fine and Specialty Chemicals. 2016 Elsevier Inc. 317-392.
Chassaing S, Bénéteau V, Pale P. Green catalysts based on zeolites for heterocycle synthesis, Current Opinion in Green and Sustainable Chemistry, 10: 35-39, 2018.
doi: 10.1016/j.cogsc.2018.02.007
Chassaing S, Bénéteau V, Louis B, Pale P. Zeolites as Green Catalysts for Organic Synthesis: the Cases of H-, Cu- &
Sc-Zeolites, Current Opinion in Green and Sustainable Chemistry, 21: 779-793, 2017.
doi: 10.2174/1385272820666160525130204
Keller M, Sido A, Pale P, Sommer J. Copper(I) Zeolites as Heterogeneous and Ligand-Free Catalysts: [3+2] Cycloaddition
of Azomethine Imines, Chemistry a European Journal, 15: 2810- 2817, 2009.
doi: 10.1002/chem.200802191
Nasrollahzadeh M, Habibi D, Shahkarami Z, Bayat Y. A general synthetic method for the formation of arylaminotetrazoles using natural natrolite zeolite as a new and reusable heterogeneous catalyst, Tetrahedron, 65: 10715-10719, 2009.
doi: 10.1016/j.tet.2009.10.029
Bénéteau V, Olmos A, Boningari T, Sommer J, Pale P. Zeoclick synthesis: CuI-zeolite-catalyzed one-pot two-step synthesis of triazoles from halides and related compounds, Tetrahedron Letters, 51: 3673-3677, 2010.
doi: 10.1016/j.tetlet.2010.05.036
Bakavoli M, Sabzevari O, Rahimizadeh M. H-Y-zeolites induced heterocyclization: Highly efficient synthesis of substitutedquinazolin- 4(3H)ones under microwave irradiation, Chinese Chemical Letters, 18: 533-535, 2007.
doi: 10.1016/j.cclet.2007.03.029
Nagendrappa G. Organic synthesis using clay and claysupported catalysts, Applied Clay Science, 53: 106-138, 2011.
doi: 10.1016/j.clay.2010.09.016
Forero JSB, Junior JJ, da Silva FM. The Povarov Reaction as a Versatile Strategy for the Preparation of 1,2,3,4-Tetrahydroquinoline Derivatives: An Overview, Current Organic Synthesis, 13: 157-175, 2016.
doi: 10.2174/1570179412666150706183906
Varma PP, Srinivasa A, Mahadevan KM. Efficient InCl3/ H2O-catalyzed one-pot stereoselective synthesis of cis-2- methyl4-amido-1,2,3,4-tetrahydroquinoline derivatives, Synthetic Communications, 41: 2186-2194, 2011.
doi: 10.1080/00397911003650453
Gates-Rector S, Blanton T. The Powder Diffraction File: a quality materials characterization database, Powder Diffraction, 34(4):352-360, 2020.
doi: 10.1017/S0885715619000812
Lyi N, Yamada H. Efficient decarbonation of carbonate-type layered double hydroxide (CO32−LDH) by ammonium salts in alcohol medium, Applied Clay Science, 65-66: 121-127, 2012.
doi: 10.1016/j.clay.2012.05.001
Brosius RG. Vapour-phase synthesis of 2-methyl- and 4-methylquinoline over BEA zeolite, Journal of Catalysis, 239(2):362-368, 2006.
doi: 10.1016/j.jcat.2006.02.015
Jiang R, Xu HY, Xu XP, Chu XQ, Ji SJ. Direct alkylation of indoles and amines by tert-enamides: facile access to pharmaceutically active 2-oxo-1-pyrrolidine analogues, Organic and Biomolecular Chemistry, 9:5659-5669, 2011.
doi: 10.1039/c1ob05546a
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