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Catalytic Synthesis of -Aminonitriles Using Nano Copper Ferrite under Green Conditions

DOI: 10.1155/2014/169803

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Abstract:

Copper ferrite nanomaterial as reusable heterogeneous initiator in the synthesis of α-aminonitriles. The nanocatalyst is easily recovered and its reusability is recorded. Synthesis of α-aminonitriles derivatives by one-pot reaction of different aldehydes with amines and trimethylsilyl cyanides has been developed using nano copper ferrite catalyst under room temperature and green solvent (water as solvent) conditions. α-aminonitriles are important in preparing a wide variety of amino acids, amides, diamines, and nitrogen containing heterocycles. 1. Introduction α-aminonitriles are significantly important intermediates for the synthesis of a wide variety of amino acids, amides, diamines, and nitrogen-containing heterocycles [1]. Among the methods reported for the synthesis of α-aminonitriles, nucleophilic addition of cyanide ion to imines (Strecker reaction) is of great importance to modern organic chemistry as it offers one of the most direct and viable methods for the synthesis of α-aminonitriles [2]. Strecker reaction [3], the oldest known synthesis of α-aminonitriles, is one of the most general methods potentially useful for syntheses of amino acids and other bioactive compounds including natural products. In addition, the Strecker reaction represents one of the simplest and most economical methods for the preparation of α-amino acids for both laboratory and industrial scales [2]. Since 1850, a number of publications have appeared on this reaction. Still this reaction is under active investigation. Recently, synthesis of hepatitis C virus NS3 serine protease inhibitors [4], (±)-phthalascidin 622 [5], and novel boron-containing retinoids [6] has been reported following this strategy. A number of new catalysts have also been reported for this reaction which includes lanthanum(III)-binaphthyl disulfonate [7], nanocrystalline magnesium oxide [8], BINOL-phosphoric acid [9, 10], Fe(Cp)2PF6 [11], Jacobsen’s thiourea catalyst [12], N-heterocyclic carbene (NHC)-amidate palladium (II) complex [13], Yb(OTf)3-pybox [14], K2PdCl4[15], gallium (III) triflate [16], bisformamides [17], IBX/TBAB [18], Lewis base, for example, N,N-dimethylcyclohexylamine [19], superparamagnetic iron oxide [20], and ionic liquid [21]. To prepare α-aminonitriles (precursor to -amino acids) generally an imine is reacted with a cyanide source. Notable among them are HCN [22], KCN [23], (EtO)2P(O)CN [24, 25], Et2AlCN [26, 27], Bu3SnCN [28, 29], and TMSCN [6, 7, 9–29]. Among these cyanide sources, trimethylsilyl cyanide (TMSCN) is relatively easy to handle and highly soluble in organic

References

[1]  R. O. Duthaler, “Recent developments in the stereoselective synthesis of α-aminoacids,” Tetrahedron, vol. 50, no. 6, pp. 1539–1650, 1994.
[2]  H. Gr?ger, “Catalytic enantioselective strecker reactions and analogous syntheses,” Chemical Reviews, vol. 103, no. 8, pp. 2795–2828, 2003.
[3]  A. Strecker, “Ueber die künstliche Bildung der Milchs?ure und einen neuen, dem Glycocoll homologen K?rper,” Justus Liebigs Annalen der Chemie, vol. 75, no. 1, pp. 27–45, 1850.
[4]  A. Arasappan, S. Venkatraman, A. I. Padilla et al., “Practical and efficient method for amino acid derivatives containing β-quaternary center: application toward synthesis of hepatitis C virus NS3 serine protease inhibitors,” Tetrahedron Letters, vol. 48, no. 36, pp. 6343–6347, 2007.
[5]  C. R. Razafindrabe, S. Aubry, B. Bourdon, M. Andriantsiferana, S. Pellet-Rostaing, and M. Lemaire, “Synthesis of (±)-phthalascidin 650 analogue: new synthetic route to (±)-phthalascidin 622,” Tetrahedron, vol. 66, no. 46, pp. 9061–9066, 2010.
[6]  B. C. Das, J. Anguiano, and S. M. Mahalingam, “Design and synthesis of α-aminonitrile-functionalized novel retinoids,” Tetrahedron Letters, vol. 50, no. 40, pp. 5670–5672, 2009.
[7]  M. Hatano, Y. Hattori, Y. Furuya, and K. Ishihara, “Chiral lanthanum(III)-binaphthyldisulfonate complexes for catalytic enantioselective strecker reaction,” Organic Letters, vol. 11, no. 11, pp. 2321–2324, 2009.
[8]  M. L. Kantam, K. Mahendar, B. Sreedhar, and B. M. Choudary, “Synthesis of α-amino nitriles through Strecker reaction of aldimines and ketoimines by using nanocrystalline magnesium oxide,” Tetrahedron, vol. 64, no. 15, pp. 3351–3360, 2008.
[9]  L. Simón and J. M. Goodman, “Mechanism of BINOL-phosphoric acid-catalyzed strecker reaction of benzyl imines,” Journal of the American Chemical Society, vol. 131, no. 11, pp. 4070–4077, 2009.
[10]  G.-W. Zhang, D.-H. Zheng, J. Nie, T. Wang, and J. Ma, “Br?nsted acid-catalyzed efficient Strecker reaction of ketones, amines and trimethylsilyl cyanide,” Organic and Biomolecular Chemistry, vol. 8, no. 6, pp. 1399–1405, 2010.
[11]  N. H. Khan, S. Agrawal, R. I. Kureshy et al., “Fe(Cp)2PF6 catalyzed efficient Strecker reactions of ketones and aldehydes under solvent-free conditions,” Tetrahedron Letters, vol. 49, no. 4, pp. 640–644, 2008.
[12]  S. C. Pan and B. List, “Catalytic asymmetric three-component acyl-strecker reaction,” Organic Letters, vol. 9, no. 6, pp. 1149–1151, 2007.
[13]  J. Jarusiewiez, Y. Choe, K. S. Yoo, C. P. Park, and K. W. Jung, “Efficient three-component strecker reaction of aldehydes/ketones via NHC-amidate palladium(II) complex catalysis,” Journal of Organic Chemistry, vol. 74, no. 7, pp. 2873–2876, 2009.
[14]  B. Karimi, A. Maleki, D. Elhamifar, J. H. Clark, and A. J. Hunt, “Self-assembled organic-inorganic hybrid silica with ionic liquid framework: a novel support for the catalytic enantioselective Strecker reaction of imines using Yb(OTf)3-pybox catalyst,” Chemical Communications, vol. 46, no. 37, pp. 6947–6949, 2010.
[15]  B. Karmakar and J. Banerji, “K2PdCl4 catalyzed efficient multicomponent synthesis of α-aminonitriles in aqueous media,” Tetrahedron Letters, vol. 51, no. 20, pp. 2748–2750, 2010.
[16]  G. K. S. Prakash, T. Mathew, C. Panja et al., “Gallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs,” Proceedings of the National Academy of Sciences of the United States of America, vol. 104, no. 10, pp. 3703–3706, 2007.
[17]  Y. Wen, Y. Xiong, L. Chang, J. Huang, X. Liu, and X. Feng, “Chiral bisformamides as effective organocatalysts for the asymmetric one-pot, three-component strecker reaction,” Journal of Organic Chemistry, vol. 72, no. 20, pp. 7715–7719, 2007.
[18]  P. Fontaine, A. Chiaroni, G. Masson, and J. Zhu, “One-pot three-component sysnthesis of α-iminonitriles by IBX/TBAB-mediated oxidative strecker reaction,” Organic Letters, vol. 10, no. 8, pp. 1509–1512, 2008.
[19]  F. Cruz-Acosta, A. Santos-Expósito, P. de Armas, and F. García-Tellado, “Lewis base-catalyzed three-component Strecker reaction on water. An efficient manifold for the direct α-cyanoamination of ketones and aldehydes,” Chemical Communications, no. 44, pp. 6839–6841, 2009.
[20]  M. M. Mojtahedi, M. S. Abaee, and T. Alishiri, “Superparamagnetic iron oxide as an efficient catalyst for the one-pot, solvent-free synthesis of α-aminonitriles,” Tetrahedron Letters, vol. 50, no. 20, pp. 2322–2325, 2009.
[21]  M. M. Mojtahedi, M. S. Abaee, and H. Abbasi, “Environmentally friendly room temperature strecker reaction: one-pot synthesis of α-aminonitriles in ionic liquid,” Journal of the Iranian Chemical Society, vol. 3, no. 1, pp. 93–97, 2006.
[22]  N. Kato, M. Suzuki, M. Kanai, and M. Shibasaki, “Catalytic enantioselective Strecker reaction of ketoimines using catalytic amount of TMSCN and stoichiometric amount of HCN,” Tetrahedron Letters, vol. 45, no. 15, pp. 3153–3155, 2004.
[23]  E. Gruszecka, M. Soroka, and P. Mastalerz, “Preparation of D, L-phosphinothricin by Strecker reaction,” Polish Journal of Chemistry, vol. 53, pp. 937–941, 1979.
[24]  E. Reimann and W. Dammertz, “Bicyclic α-amino acids, IV: synthesis of 3-(1,2,3,4-tetrahydro-1-naphthalenyl)- and 3-(5,6,7,8-tetrahydro-5-quinolinyl)alanine,” Archiv der Pharmazie, vol. 316, no. 4, pp. 297–302, 1983.
[25]  S. Harusawa, Y. Hamada, and T. Shioiri, “Diethyl phosphorocyanidated (DEPC). A novel reagent for the classical Strecker's α-amino nitrile synthesis,” Tetrahedron Letters, vol. 20, no. 48, pp. 4663–4666, 1979.
[26]  F. A. Davis, K. R. Prasad, and P. J. Carroll, “Asymmetric synthesis of polyhydroxy α-amino acids with the sulfinimine-mediated asymmetric Strecker reaction: 2-amino 2-deoxy l-xylono-1,5-lactone (polyoxamic acid lactone),” Journal of Organic Chemistry, vol. 67, no. 22, pp. 7802–7806, 2002.
[27]  P. Kaur, S. Pindi, W. Wever, T. Rajale, and G. Li, “Asymmetric catalytic Strecker reaction of N-phosphonyl imines with Et 2AlCN using amino alcohols and BINOLs as catalysts,” Chemical Communications, vol. 46, no. 24, pp. 4330–4332, 2010.
[28]  Z. Xie, G. Li, G. Zhao, and J. Wang, “Strecker-type reaction catalyzed by carboxylic acids in aqueous media,” Synthesis, no. 12, pp. 2035–2039, 2009.
[29]  H. Ishitani, S. Komiyama, Y. Hasegawa, and S. Kobayashi, “Catalytic asymmetric Strecker synthesis. Preparation of enantiomerically pure α-amino acid derivatives from aldimines and tributyltin cyanide or achiral aldehydes, amines, and hydrogen cyanide using a chiral zirconium catalyst,” Journal of the American Chemical Society, vol. 122, no. 5, pp. 762–766, 2000.
[30]  J. March, Advanced Organic Chemistry, John Wiley & Sons, New York, NY, USA, 4th edition, 1995.
[31]  L. M. Weinstock, P. Davis, B. Handelsman, and R. Tull, “A general synthetic system for 1,2,5-thiadiazoles,” Journal of Organic Chemistry, vol. 32, no. 9, pp. 2823–2829, 1967.
[32]  W. L. Matier, D. A. Owens, W. T. Comer et al., “Antihypertensive agents. Synthesis and biological properties of 2-amino-4-aryl-2-imidazolines,” Journal of Medicinal Chemistry, vol. 16, no. 8, pp. 901–908, 1973.
[33]  S. Kobayashi and H. Ishitani, “Catalytic enantioselective addition to imines,” Chemical Reviews, vol. 99, no. 5, pp. 1069–1094, 1999.
[34]  A. T. Bell, “The impact of nanoscience on heterogeneous catalysis,” Science, vol. 299, no. 5613, pp. 1688–1691, 2003.
[35]  M. L. Kantam, J. Yadav, S. Laha, P. Srinivas, B. Sreedhar, and F. Figueras, “Asymmetric hydrosilylation of ketones catalyzed by magnetically recoverable and reusable copper ferrite nanoparticles,” Journal of Organic Chemistry, vol. 74, no. 12, pp. 4608–4611, 2009.
[36]  Y. L. N. Murhy, I. V. Kasi Viswanath, and T. K. Rao, “Nano crystalline powders of NiCu ferrite and NiCuZn ferrite prepared from citrate gel method: synthesis and characterization,” Journal of Chemistry and Chemical Engineering, vol. 3, no. 6, pp. 22–26, 2009.

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