γ-Al₂O₃-Supported 12-Tungstosilicic Acid as an Efficient Heterogeneous Catalyst for the Synthesis of α-Aminonitrile

REFERENCES

• (a) Holderich , W. F. In Comprehensive Supramolecular Chemistry ; J. L. Atwood , J. E. P. Davies , D. D. MacNicol , F. Vögtle , (Eds.); Pergamon Press : Oxford , 1996 . vol. 7 , p. 671 ; (b) Pope, M. T.; In Comprehensive Coordination Chemistry II; A. G. Wedd (Ed.); Elsevier: Oxford, U.K., 2004; vol. 4, p. 635; (c) HillC. L. In Comprehensive Coordination Chemistry II; A. G. Wedd (Ed.); Elsevier: Oxford, U.K., 2004; vol. 4, p. 679 .
   Google Scholar
• (a) Drago , R. S. ; Dias , J. A. ; Maier , T. O. An acidity scale for Br⊘nsted acids including H3PW12O40 . J. Am. Chem. Soc. 1997 , 119 , 7702 – 7710 ; (b) Dias, J. A.; Dias, S. C. L.; Kob, N. E. Dehydration of 1-propanol using H3PW12O40 as catalyst. J. Chem. Soc., Dalton Trans. 2001, 3, 228–231 .
   Web of Science ®Google Scholar
• (a) Kozhevnikov , I. V. ; Sinnema , A. ; Jansen , R. J. J. ; Pamin , K. ; Van Bekkum , H. New acid catalyst comprising heteropoly acid on a mesoporous molecular sieve MCM-41 . Catal. Lett. 1995 , 30 , 241 – 252 ; (b) Moffat, J. B. Metal–Oxygen Cluster—The Surface and Catalytic Properties of Heteropoly Oxometalates; Kluwer: New York, 2001; p. 25; (c) Kozhevnikov, I. V.; Kloetstra, K. R.; Sinnema, A.; Zandbergen, H. W.; van Bekkum, H. The study of catalysts comprising heteropoly acid H3PW12O40 supported on MCM-41 molecular sieve and amorphous silica. J. Mol. Catal. A: Chem. 1996, 114, 287–298 .
   Web of Science ®Google Scholar
• (a) Rafiee , E. ; Shahbazi , F. One-pot synthesis of dihydropyrimidones using silica-supported heteropoly acid as an efficient and reusable catalyst: Improved protocol conditions for the Biginelli reaction . J. Mol. Catal. A: Chem. 2006 , 250 , 57 – 61 ; (b) Rafiee, E.; Rashidzadeh, S.; Azad, A. Silica-supported heteropoly acids: Highly efficient catalysts for synthesis of α-aminonitriles, using trimethylsilyl cyanide or potassium cyanide. J. Mol. Catal. A: Chem. 2006, 261, 49–52; (c) Izumi, Y.; Hisano, K.; Hida, T. Acid catalysis of silica-included heteropolyacid in polar reaction media. Appl. Catal. A 1999, 181, 277–282 .
   Web of Science ®Google Scholar
• (a) Enders , D. ; Shilvock , J. P. Some recent application of α-aminonitrile chemistry . Chem. Soc. Rev. 2000 , 29 , 359 – 373 ; (b) Shafran, Y. M.; Bakulev, V. A.; Mokrushin, V. S. Synthesis and properties of α-aminonitriles. Russ. Chem. Rev. 1989, 58, 148–162; (c) March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1999; p. 965; (d) González-Vera, J. A.; García-López, M. T.; Herranz, R. Molecular diversity via amino acid derived α-aminonitriles: Synthesis of spirocyclic 2,6-dioxopiperazine derivatives. J. Org. Chem. 2005, 70, 3660–3666; (e) Dyker, G. Amino acid derivatives by multicomponent reactions. Angew. Chem., Int. Ed. 1997, 36, 1700–1702 .
   Web of Science ®Google Scholar
• (a) Weinstock , L. M. ; Davis , P. ; Handelsman , B. ; Tull , R. A. General synthetic system for 1,2,5-thiadiazoles . J. Org. Chem. 1967 , 32 , 2823 – 2829 ; (b) Matier, W. L.; Owens, D. A.; Comer, W. T.; Deitchman, D.; Ferguson, H. C.; Seidehamel, R. J.; Young, J. R. Antihypertensive Agents: Synthesis and biological properties of 2-amino-4-aryl-2-imidazolines. J. Med. Chem. 1973, 16, 901–908 .
   Web of Science ®Google Scholar
• Strecker , A. Ueber die Künstliche Bildung der Milchsäure und einen neuen, dem Glycocoll homologen Körper . Ann. Chem. Pharm. 1850 , 75 , 27 – 45 .
   Google Scholar
• (a) Duthaler , R. O. Recent developments in the stereoselective synthesis of α-aminoacids . Tetrahedron 1994 , 50 , 1539 – 1650 ; (b) Martinez, E. J.; Corey, E. J. Enantioselective synthesis of saframycin A and evaluation of antitumor activity relative to ecteinascidin/saframycin hybrids. Org. Lett. 1999, 1, 75–78 .
   Web of Science ®Google Scholar
• (a) Ranu , B. C. ; Dey , S. S. ; Hajra , A. Indium trichloride catalyzed one-pot synthesis of α-aminonitriles by a three-component condensation of carbonyl compounds, amines, and potassium cyanide . Tetrahedron 2002 , 58 , 2529 – 2532 ; (b) Harusawa, S.; Hamada, Y.; Shioiri, T. Diethyl phosphorocyanidate (DEPC), a novel reagent for the classical Strecker's α-aminonitriles synthesis. Tetrahedron Lett. 1979, 48, 4663–4666; (c) Royer, L.; De, S. K.; Gibbs, R. A. Iodine as a novel efficient reagent for the synthesis of α-aminonitriles by a three-component condensation of carbonyl compounds, amines, and trimethylsilyl cyanide. Tetrahedron Lett. 2005, 46, 4595–4597; (d) Suginome, M.; Yamamoto, A.; Ito, Y. Bis(dialkylamino)cyanoboranse: Highly efficient reagents for the Strecker–type aminative cyanation of aldehydes and ketones. Chem. Commun. 2002, 1392–1393; (e) Kobayashi, S.; Busujima, T.; Nagayama, S. Scandium triflate–catalyzed Strecker-type reactions of aldehydes, amines, and tributyltin cyanide in both organic and aqueous solutions: Achievement of complete recovery of the tin compounds toward environmentally friendly chemical processes. Chem. Commun. 1998, 981–982 .
   Web of Science ®Google Scholar
• (a) Yadav , J. S. ; Reddy , B. V. S. ; Eeshwaraiah , B. ; Srinivas , M. Montmorillonite KSF clay catalyzed one-pot synthesis of α-aminonitriles . Tetrahedron 2004 , 60 , 1767 – 1771 ; (b) Fetterly, B. M.; Jana, N. K.; Verkade, J. G. [HP(HNCH2)3N]NO3: An efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions. Tetrahedron 2005, 61, 1–18; (c) Kobayashi, S.; Nagayama, S.; Busujima, T. Polymer scandium-catalyzed three-component reactions leading to diverse amino ketone, amino ester, and amino nitrile derivatives. Tetrahedron Lett. 1996, 37, 9221; (d) Yadav, J. S.; Reddy, B. V. S.; Eshwaraiah, B.; Srinivas, M.; Vishnumurthy, P. Three-component coupling reactions in ionic liquids: A facile synthesis of α-aminonitriles. New J. Chem. 2003, 27, 462–465; (e) De, S. K.; Gibbs, R. A. Bismuth trichloride–catalyzed synthesis of α-aminonitriles. Tetrahedron Lett. 2004, 45, 7407–7408; (f) Heydari, A.; Fatemi, P.; Alizadeh, A. Lithium perchlorate/diethylether–catalyzed aminocyanation of aldehydes. Tetrahedron Lett. 1998, 39, 3049–3050; (g) De, S. K. Nickel(II) chloride–catalyzed one-pot synthesis of α-aminonitriles. J. Mol. Catal. A: Chem. 2005, 225, 169–171 .
   Web of Science ®Google Scholar
• (a) De , S. K. RuCl3-catalyzed one-pot synthesis of α-aminonitriles . Synth. Commun. 2005 , 35 , 653 – 656 ; (b) De, S. K.; Gibbs, R. A. Praseodynium trifluromethylsulfonate as an efficient and recyclable catalyst for the synthesis of α-aminonitriles. Synth. Commun. 2005, 35, 961–966; (c) Kobayashi, S.; Ishitani, H.; Ueno, M. Facile synthesis of α-aminonitriles using lanthanide triflate as a Lewis acid catalyst. Synlett 1997, 115–116 .
   Web of Science ®Google Scholar
• Kozhevnikov , I. V. Catalysis for Fine Chemical Syntheses—Catalysis by Polyoxometalates ; John Wiley & Sons : Chichester , 2002 ; p. 50 .
   Google Scholar