Ferric Perchlorate–Catalyzed One‐Pot Synthesis of α‐Aminonitriles using Trimethylsilylcyanide

References

• Shafran , Y. M. , Bakulev , V. A. and Mokrushin , V. S. 1989 . Synthesis and properties of α‐Aminonitriles . Russ. Chem. Rev. , 58 : 148
   Google Scholar
• Weinstock , L. M. , Davis , P. , Handelsman , B. and Tull , R. 1967 . A general synthetic system for 1,2,5‐thiadiazoles . J. Org. Chem. , 32 : 2823
   Web of Science ®Google Scholar
• Matier , W. L. , Owens , D. A. , Comer , W. T. , Deitchman , D. , Ferguson , H. C. , Seidehamel , R. J. and Young , J. 1973 . Antihypertensive agent: Synthesis and biological properties of 2‐amino‐4‐aryl‐2‐imidazolines . J. Med. Chem. , 16 : 901
   PubMed Web of Science ®Google Scholar
• Strecker , A. 1850 . General catalyst for the asymmetric Strecker reaction . Ann. Chem. Pharm , 75 : 27
   Google Scholar
• Mai , K. and Patil , G. 1984 . Facile synthesis of aminonitriles . Tetrahedron Lett. , 25 : 4583
   Web of Science ®Google Scholar
• Harusawa , S. , Hamada , Y. and Shioiri , T. 1979 . Diethyl phosphorocyanidated (DEPC): A novel reagent for the classical Strecker's α‐amino nitrile synthesis . Tetrahedron Lett. , 20 : 4663
   Google Scholar
• Mai , K. and Patil , G. 1984 . Facile synthesis of aminonitriles . Tetrahedron Lett. , 25 : 4583
   Web of Science ®Google Scholar
• Harusawa , S. , Hamada , Y. and Shioiri , T. 1979 . Diethyl phosphorocyanidated (DEPC): A novel reagent for the classical Strecker's a‐amino nitrile synthesis . Tetrahedron Lett. , 20 : 4663
   Google Scholar
• Chakraborty , T. K. , Reddy , G. V. and Hussain , K. A. 1991 . Diastereoselective Strecker synthesis using α‐phenylglycinol as chiral auxiliary . Tetrahedron Lett. , 32 : 7597
   Google Scholar
• Leblanc , J. and Gibson , H. W. 1992 . Synthesis of α‐aminonitriles by self‐catalyzed, stoichiometric reaction of primary amines, aldehydes, and trimethylsily cyanide . Tetrahedron Lett. , 33 : 6295
   Web of Science ®Google Scholar
• Heydari , A. , Fatemi , P. and Alizadeh , A. 1998 . Lithium perchlorate/diethylether–catalyzed aminocyanation of aldehydes . Tetrahedron Lett. , 39 : 3049
   Web of Science ®Google Scholar
• Kobayashi , S. , Ishitani , H. and Ueno , M. 1997 . Facile synthesis of α‐amino nitriles using lanthanide triflate as a Lewis acid catalyst . Synlett , : 115
   Google Scholar
• Kobayashi , S. , Busujima , T. and Nagayama , S. 1998 . 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 . J. Chem. Soc., Chem. Commun. , : 981
   Google Scholar
• Subba Reddy , B. V. , Eeshwaraiah , B. and Srinivas , M. 2004 . Montmorillonite KSF clay catalyzed one‐pot synthesis of α‐aminonitriles . Tetrahedron , 60 : 1767 – 1771 .
   Google Scholar
• De , S. K. and Gibbs , R. A. 2004 . Bismuth trichloride catalyzed synthesis of α‐aminonitriles . Tetrahedron Lett. , 45 : 7407 – 7408 .
   Web of Science ®Google Scholar
• De , S. K. 2005 . Nickel(II) chloride catalyzed one‐pot synthesis of α‐aminonitriles . J. Mol. Cata. A: Chem. , 225 : 169 – 171 .
   Web of Science ®Google Scholar
• Ranu , B. C. , Dey , S. S. and Hajra , A. 2002 . Indium trichloride catalyzed one‐step synthesis of α‐amino nitriles by a three‐component condensation of carbonyl compounds, amines and potassium cyanide . Tetrahedron , 58 : 2529 – 2532 .
   Web of Science ®Google Scholar
• Martínez , R. , Ramó , D. J. and Yus , M. 2005 . Catalyst‐free multicomponent Strecker reaction in acetonitrile . Tetrahedron Lett. , 46 : 8471 – 8474 .
   Web of Science ®Google Scholar
• Heravi , M. M. , Behbahani , F. K. , Oskooie , H. A. and Hekmatshoar , R. 2005 . Mild and efficient tetrahydropyranylation of alcohols and dehydropyranylation of THP ethers catalyzed by ferric perchlorate . Tetrahedron Lett. , 46 : 2543 – 2545 .
   Web of Science ®Google Scholar
• Heravi , M. M. , Behbahani , F. K. , Oskooie , H. A. and Hekmatshoar , R. 2005 . Catalytic aromatization of Hantzsch 1,4‐dihydropyridines by ferric perchlorate in acetic acid . Tetrahedron Lett. , 46 : 2775 – 2777 .
   Web of Science ®Google Scholar
• Heravi , M. M. , Behbahani , F. K. , Oskooie , H. A. and Hekmatshoar , R. 2006 . Ferric perchlorate: A novel and highly efficient catalyst for direct acetylation of THP ethers with acetic acid . J. Mol. Cat. A: Chem. , 244 : 8 – 10 .
   Google Scholar
• Heravi , M. M. , Behbahani , F. K. , HekmatShoar , R. and Oskooie , H. A. 2006 . Catalytic acetylation of alcohols and phenols with ferric perchlorate in acetic acid . Catal. Commun. , 7 : 136 – 139 .
   Web of Science ®Google Scholar
• Heravi , M. M. , Behbahani , F. K. , Oskooie , H. A. and Hekmatshoar , R. Ferric perchlorate catalyzed one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐Ones and thiones: An expedient protocol for the Biginelli reaction . Mendeleev Commun. , Submitted
   Google Scholar
• Bamoharram , F. F. , Heravi , M. M. , Roshani , M. , Gharib , A. and Jahangir , M. 2006 . Preyssler catalyst [NaP5W30O110]14−: A green, efficient and reusable catalyst for esterification of salicylic acid with aliphatic and benzylic alcohols . Appl. Cata. , 302 : 42
   Google Scholar
• Heravi , M. M. , Hekmatshoar , R. and Pedram , L. 2005 . Synthesis of N‐arylphthalimides catalyzed by 1,4‐diazabicyclo[2,2,2]octane [DABCO] in solventless system . J. Mol. Catal. A: Chem. , 231 : 89
   Google Scholar
• Asadolah , K. and Heravi , M. M. 2004 . Bismuth (III) nitrate supported onto silica gel, a new catalyst for acetylation of alcohols and phenols under microwave irradiation . Phosphorus, Sulfur Silicon Relat. Elem. , 179 : 2335 – 2339 .
   Web of Science ®Google Scholar
• Bigdeli , M. M. , Nahid , M. A. and Ajami , D. 1999 . Sulphuric acid adsorbed on silica gel: An efficient catalyst for the protection and deprotection of alcohols with dihydropyran . Indian. J. Chem. Sect. , 38 : 1285 – 1286 .
   Google Scholar
• Heravi , M. M. , Bakhtiari , K. and Bamoharram , F. F. 2006 . 12‐Molybdophosphoric acid: A recyclable catalyst for the synthesis of Biginelli‐type 3,4‐dihydropyrimidine‐2(1H)‐ones . Catal. Commun. , 7 : 373
   Web of Science ®Google Scholar
• Bamoharram , F. F. , Heravi , M. M. , Roshani , M. , Gharib , A. and Jahangir , M. 2006 . A catalytic method for synthesis of γ‐butyrolactone, ϵ‐caprolactone and 2‐cumaranone in the presence of Preyssler's anion, [NaP5W30O110]14−, as a green and reusable catalyst . J. Mol. Catal. A: Chem. , 252 : 90
   Web of Science ®Google Scholar
• Bamoharram , F. F. , Heravi , M. M. , Roshani , M. and Tavakoli , N. 2006 . N‐oxidation of pyridine carboxylic acids using hydrogen peroxide catalyzed by a green heteropolyacid catalyst: Preyssler's anion, [NaP5W30O110]14 . J. Mol. Catal. A: Chem. , 252 : 219
   Web of Science ®Google Scholar
• Tajbakhsh , M. , Heravi , M. M. , Mohajerani , B. and Ahmadi , A. N. 2005 . Natural HEU type zeolite catalyzed Biginelli reaction for the synthesis of 3,4‐dihydropyrimidin‐2(1H) one derivatives . J. Mol. Catal. A: Chem. , 236 : 213
   Google Scholar
• Heravi , M. M. , Motamedi , R. , Siefi , N. and Bamoharram , F. F. 2006 . Catalytic synthesis of 6‐aryl‐1H‐pyrazolo[3,4‐d]pyrimidin‐4[5H]‐ones by heteropolyacid: H14[NaP5W30O110] and H3PW12O40 . J. Mol. Catal. , 249 : 1
   Web of Science ®Google Scholar
• Oskooie , H. A. , Heravi , M. M. , Bakhtiari , K. , Zadsirjan , V. and Bamoharram , F. F. 2006 . H14[NaP5W30O110] as an efficient catalyst for the one‐pot synthesis of α‐amino nitriles . Synlett , : 1768 – 1770 .
   Google Scholar
• Yadav , J. S. , Subba Reddy , B. V. , Eeshwaraiah , B. and Srinivas , M. 2004 . Montmorillonite KSF clay catalyzed one‐pot synthesis of α‐aminonitriles . Tetrahedron , 60 : 1767 – 1771 .
   Web of Science ®Google Scholar