2007
DOI: 10.1080/00397910701462732
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Ferric Perchlorate–Catalyzed One‐Pot Synthesis of α‐Aminonitriles using Trimethylsilylcyanide

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2007
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Cited by 14 publications
(2 citation statements)
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“…The addition of cyanide anions to imines (the Strecker reaction) 2 provides one of the most important and straightforward methods for the synthesis of a-aminonitriles, which are useful intermediates for the synthesis of amino acids 3,4 and nitrogen containing heterocycles such as thiadiazoles and imidazoles 5,6 and other biologically useful molecules such as saframycin A, a natural product with anti-tumour activity, or phthalascidi, a synthetic analogue, which exhibits even greater potency. 7 Several modifications of Strecker reaction have been reported using a variety of cyanide reagents, such as alkaline cyanides 2,8,9 diethylphosphoro cyanidate 10 Bu 3 SnCN, 11 and Et 2 AlCN, 12 as well as catalysts such as InCl 3 , 13 BiCl 3 , 14 montmorillonite KSF clay, 15 silica-based scandium(III), 16 SO 4 2À /ZrO 2 , 17 ferric perchlorate, 18 Fe(Cp) 2 PF 6 , 19 InI 3 , 20 I 2 , 21 K 5 CoW 12 O 40 Á 3H 2 O, 22 vanadyl triflate, 23 Fe 3 O 4 , 24 guanidine hydrochloride, 25 xanthan sulfuric acid, 26 [bmim]BF 4 , 27 silica sulfuric acid, 28 hydrophobic sulfonic acid based nanoreactors 29 and silica-bonded S-sulfonic acid 30 under various reaction conditions. However, many of these methods involve the use of stoichiometric reagents, low yields of the products, the use of hazardous and often expensive catalysts, harsh reaction conditions, extended reaction times, tedious procedure for the preparation of catalysts, the use of volatile and hazardous organic solvents, no compliance with the green chemistry protocols and also require tedious workup leading to the generation of a large amount of toxic waste.…”
Section: Introductionmentioning
confidence: 99%
“…The addition of cyanide anions to imines (the Strecker reaction) 2 provides one of the most important and straightforward methods for the synthesis of a-aminonitriles, which are useful intermediates for the synthesis of amino acids 3,4 and nitrogen containing heterocycles such as thiadiazoles and imidazoles 5,6 and other biologically useful molecules such as saframycin A, a natural product with anti-tumour activity, or phthalascidi, a synthetic analogue, which exhibits even greater potency. 7 Several modifications of Strecker reaction have been reported using a variety of cyanide reagents, such as alkaline cyanides 2,8,9 diethylphosphoro cyanidate 10 Bu 3 SnCN, 11 and Et 2 AlCN, 12 as well as catalysts such as InCl 3 , 13 BiCl 3 , 14 montmorillonite KSF clay, 15 silica-based scandium(III), 16 SO 4 2À /ZrO 2 , 17 ferric perchlorate, 18 Fe(Cp) 2 PF 6 , 19 InI 3 , 20 I 2 , 21 K 5 CoW 12 O 40 Á 3H 2 O, 22 vanadyl triflate, 23 Fe 3 O 4 , 24 guanidine hydrochloride, 25 xanthan sulfuric acid, 26 [bmim]BF 4 , 27 silica sulfuric acid, 28 hydrophobic sulfonic acid based nanoreactors 29 and silica-bonded S-sulfonic acid 30 under various reaction conditions. However, many of these methods involve the use of stoichiometric reagents, low yields of the products, the use of hazardous and often expensive catalysts, harsh reaction conditions, extended reaction times, tedious procedure for the preparation of catalysts, the use of volatile and hazardous organic solvents, no compliance with the green chemistry protocols and also require tedious workup leading to the generation of a large amount of toxic waste.…”
Section: Introductionmentioning
confidence: 99%
“…In this letter, ascorbic acid -functionalized cellulose-coated Fe3O4 nanoparticles (Fe3O4/cellulose/ vitamin C) is introduced. Herein, in continuation of our previous works on one-pot multicomponent reaction in organic synthesis [18][19][20]. Fe3O4/cellulose/ vitamin C as a nontoxic and environmentally-friendly heterogeneous nanocatalyst was used in the synthesis of, (α-aminoalkyl) naphthol derivatives via an one-pot multicomponent reaction of 2-naphthol, alkylamines and aldehydes under solvent-free conditions at room temperature (Scheme 1).…”
Section: Introductionmentioning
confidence: 99%