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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

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