Simple and Highly Efficient Procedure for Conversion of Aldoximes to Nitriles Using N-(p-Toluenesulfonyl) Imidazole

REFERENCES

• (a) Rappoport , Z. In The Chemistry of the Cyano Group ; Wiley-Interscience : New York , 1970 ; (b) March , J. Advanced Organic Chemistry , , 4th ed. ; John Wiley & Sons (Asia) Ltd. : Singapore , 2005 ; (c) Larock , R. C. Comprehensive Organic Transformations , , 2nd ed. ; VCH : New York , 1999 ; (d) Mowry, D. T. The preparation of nitriles. Chem. Rev. 1947, 42, 189–283.
   Google Scholar
• (a) Brase , S. ; Gil , C. ; Knepper , K. ; Zimmermann , V. Organic azides: An exploding diversity of a unique class of compounds . Angew. Chem., Int. Ed. 2005 , 44 , 5188 – 5240 ; (b) Serrano , J. L. ; Sierra , T. ; Gonzalez , Y. ; Bolm , C. ; Weickhardt , K. ; Magnus , A. ; Moll , G. Improving FLC properties: Simplicity, planarity, and rigidity in new chiral oxazoline derivatives . J. Am. Chem. Soc. 1995 , 117 , 8312 – 8321 ; (c) Diana , G. D. ; Cutcliffe , D. ; Volkots , D. L. ; Mallamo , J. P. ; Bialey , T. R. ; Vescio , N. ; Oglesby , R. C. ; Nitz , T. J. ; Wetzel , J. ; Giranda , V. ; Pevear , D. C. ; Dutko , F. J. Antipicornavirus activity of tetrazole analogs related to disoxaril . J. Med. Chem. 1993 , 36 , 3240 – 3250 .
   PubMed Web of Science ®Google Scholar
• (a) Soli , E. D. ; Manoso , A. S. ; Patterson , M. C. ; Deshong , P. , Favor , D. A. ; Hirschmann , R. ; Smith , A. B. Azide and cyanide displacement via hypervalent silicate intermediates . J. Org. Chem. 1999 , 64 , 3171 – 3177 ; (b) Lian-Hua , L. ; Zhen-Liang , P. ; Xin-Hua , D. ; Yong-Min , L. An environmentally benign procedure for the synthesis of aryl and arylvinyl nitriles assisted by microwave in ionic liquid . Synlett 2006 , 2094 – 2098 ; (c) Harusawa , S. ; Yoneda , R. ; Omori , Y. ; Kurihara , T. Non-aqueous cyanation of halides using lithium cyanide . Tetrahedron Lett. 1987 , 28 , 4189 – 4190 .
   PubMed Web of Science ®Google Scholar
• (a) Movassagh , B. ; Shokri , S. An efficient and convenient KF/Al2O3-mediated synthesis of nitriles from aldehydes . Tetrahedron Lett. 2005 , 46 , 6923 – 6925 ; (b) Das , B. ; Ramesh , C. ; Madhusudhan , P. An improved one-pot conversion of aldehydes into nitriles under microwave irradiation using ammonium acetate . Synlett 2000 , 1599 – 1600 ; (c) Srinivas , K. V. N. S. ; Bolla Reddy , E. ; Das , B. Highly convenient and efficient one-pot conversions of aldehydes into nitriles and ketones into amides using HY-zeolite . Synlett 2002 , 625 – 627 ; (d) Khezri , S. H. ; Azimi , N. ; Mohammed-Vali , M. ; Eftekhari-Sis , B. ; Hashemi , M. M. ; Baniasadi , M. H. ; Teimouri , F. Red mud–catalyzed one-pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride under microwave irradiation . Arkivoc 2007 , 15 , 162 – 170 ; (e) Blatter , H. M. ; Lukaszewski , H. ; De Stevens , G. A new general synthesis of aromatic nitriles from aldehydes . J. Am. Chem. Soc. 1961 , 83 , 2203 ; (f) Talukdar , S. ; Hsu , J. L. ; Chou , T. C. ; Fang , J. M. Direct transformation of aldehydes to nitriles using iodine in ammonia water . Tetrahedron Lett. 2001 , 42 , 1103 – 1105 ; (g) Lai , G. ; Bhamare , N. K. ; Anderson , W. K. A one-pot method for the efficient preparation of aromatic nitriles from aldehydes using ammonia, magnesium sulfate, and manganese dioxide . Synlett 2001 , 230 – 231 ; (h) Das , B. ; Madhusudhan , P. ; Venkataiah , B. An efficient microwave-assisted one-pot conversion of aldehydes into nitriles using silica gel–supported NaHSO4 catalyst . Synlett 1999 , 1569 – 1570 ; (i) Miller , M. J. ; Loudon , G. M. A convenient, high-yield conversion of aldehydes to nitriles . J. Org. Chem. 1975 , 40 , 126 – 127 .
   Web of Science ®Google Scholar
• (a) McAllister , G. D. ; Wilfred , C. D. ; Taylor , R. J. K. Tandem oxidation processes: The direct conversion of activated alcohols into nitriles . Synlett 2002 , 1291 – 1292 ; (b) Iida , S. ; Togo , H. Direct and facile oxidative conversion of primary, secondary, and tertiary amines to their corresponding nitriles . Synlett 2006 , 2633 – 2635 ; (c) Iida , S. ; Togo , H. Iron-catalyzed cross-coupling between alkenyl and dienyl sulfonates and functionalized aryl copper reagents . Synlett 2006 , 407 – 410 , and all references cited therein .
   Web of Science ®Google Scholar
• (a) Rosenmund , K. W. ; Struck , E. Das am ringkohlenstoff gebundene halogen und sein ersatz durch andere substituenten, I: Mitteilung: Ersatz des halogens durch die carboxylgruppe . Ber. 1919 , 52 , 1749 – 1756 ; (b) Braun , J. V. ; Manz , G. Fluoranthen und seine derivate, III: Mitteilung . Ann. 1931 , 488 , 111 – 126 .
   Google Scholar
• (a) Sandmeyer , T. Ueber die ersetzung der amidgruppe durch chlor in den aromatischen substanzen . Ber. 1884 , 17 , 1633 – 1635 ; (b) Sandmeyer , T. Zur richtigstellung . Ber. 1890 , 23 , 1880 – 1881 .
   Google Scholar
• (a) Anand , N. ; Owston , N. A. ; Parker , A. J. ; Slatford , P. A. ; Williams , J. M. J. Ruthenium-catalysed conversion of oxime ethers into nitriles . Tetrahedron Lett. 2007 , 48 , 7761 – 7763 ; (b) Hegarty , A. F. ; Tuohey , P. J. Nitrile-forming eliminations from oxime ethers . J. Chem. Soc., Perkin Trans. 2 1980 , 1313 – 1317 .
   Web of Science ®Google Scholar
• Yang , S. H. ; Chang , S. Highly efficient and catalytic conversion of aldoximes to nitriles . Org. Lett. 2001 , 3 , 4209 – 4211 .
   PubMed Web of Science ®Google Scholar
• Sosnovsky , G. ; Krogh , J. A. A versatile method for the conversion of aldoximes to nitriles using selenium dioxide . Synthesis 1978 , 703 – 705 .
   Web of Science ®Google Scholar
• Olah , G. A. ; Vankar , Y. D. Synthetic methods and reactions, 52: Preparation of nitriles from aldoximes via dehydration with trimethylamine/sulfur dioxide complex . Synthesis 1978 , 702 – 703 .
   Web of Science ®Google Scholar
• Kim , J. N. ; Chung , K. H. ; Ryu , E. K. Improved dehydration method of aldoximes to nitriles: Use of acetonitrile to triphenylphosphine/carbon tetrachloride system . Synth. Commun. 1990 , 20 , 2785 – 2788 .
   Web of Science ®Google Scholar
• Foley , H. G. ; Dalton , D. R. Neutral conversion of aldoximes into nitriles at low temperature . J. Chem. Soc., Chem. Commun. 1973 , 628 – 629 .
   Google Scholar
• Gabriel , S. ; Meyer , R. Ueber einige aus der dinitrophenylessigsäure darstellbare verbindungen. Ber. 1881, 14, 2332–2341.
   Google Scholar
• Dulcere , J.-P. Vilsmeier reagent for a high yield conversion of aldoximes to nitriles . Tetrahedron Lett. 1981 , 22 , 1599 – 1600 .
   Web of Science ®Google Scholar
• Miller , C. P. ; Kaufman , D. H. Mild and efficient dehydration of oximes to nitriles mediated by the Burgess reagent . Synlett 2000 , 1169 – 1171 .
   Web of Science ®Google Scholar
• Chakrabarti , J. K. ; Hotten , T. M. A new route to nitriles: Dehydration of aldoximes using 2,4,6-trichloro-s-triazine (cyanuric chloride) . J. Chem. Soc., Chem. Commun. 1972 , 1226 – 1227 .
   Google Scholar
• Sarvari , M. H. ZnO/CH3COCl: A new and highly efficient catalyst for dehydration of aldoximes into nitriles under solvent-free condition . Synthesis 2005 , 787 – 790 .
   Web of Science ®Google Scholar
• Hart-Davis , J. ; Battioni , P. ; Boucher , J.-L. ; Mansuy , D. New catalytic properties of iron porphyrins: Model systems for cytochrome P450-catalyzed dehydration of aldoximes . J. Am. Chem. Soc. 1998 , 120 , 12524 – 12530 .
   Web of Science ®Google Scholar
• Kim , S. ; Yi , K. Y. Di-2-pyridyl sulfite: A new useful reagent for the preparation of N-sulfinylamines, nitriles, isocyanides, and carbodiimides under mild conditions . Tetrahedron Lett. 1986 , 27 , 1925 – 1928 .
   Web of Science ®Google Scholar
• Lee , K. ; Han , S. B. ; Yoo , E. M. ; Chung , S. R. ; Oh , H. ; Hong , S. Efficient transformation of aldoximes to nitriles using 2-chloro-1-methylpyridinium iodide under mild conditions . Synth. Commun. 2004 , 34 , 1775 – 1782 .
   Web of Science ®Google Scholar
• Konwar , D. ; Boruah , R. C. ; Sandhu , J. S. A facile dehydration and Beckmann rearrangement of oximes with aluminium iodide . Tetrahedron Lett. 1990 , 31 , 1063 – 1064 .
   Web of Science ®Google Scholar
• Iranpoor , N. ; Zeynizadeh , B. Efficient dehydration of aldoximes to nitriles with TiCl3(OTf) . Synth. Commun. 1999 , 29 , 2747 – 2752 .
   Web of Science ®Google Scholar
• Arrieta , A. ; Palomo , C. Reagents and synthetic methods, 22: 1-Chlorosulfinyl-4-dimethylaminopyridinium chloride as a new reagent for the dehydration of aldoximes to nitriles . Synthesis 1983 , 472 – 474 .
   Web of Science ®Google Scholar
• Olah , G. A. ; Vankar , Y. D. ; Garcia-Luna , A. Synthetic methods and reactions, 64: Preparation of nitriles from amides and aldoximes with chlorosulfonyl isocyanate, an effective and mild dehydrating agent . Synthesis 1979 , 227 – 228 .
   Web of Science ®Google Scholar
• Boruah , M. ; Konwar , D. AlCl3·6H2O/KI/H2O/CH3CN: A new alternate system for dehydration of oximes and amides in hydrated media . J. Org. Chem. 2002 , 67 , 7138 – 7139 .
   PubMed Web of Science ®Google Scholar
• Li , D. ; Shi , F. ; Guo , S. ; Deng , Y. Highly efficient Beckmann rearrangement and dehydration of oximes . Tetrahedron Lett. 2005 , 46 , 671 – 674 .
   Web of Science ®Google Scholar
• Khan , T. A. ; Peruncheralathan , S. ; Ila , H. ; Junjappa , H. S,S-Dimethyl dithiocarbonate: A useful reagent for efficient conversion of aldoximes to nitriles . Synlett 2004 , 2019 – 2021 .
   Web of Science ®Google Scholar
• (a) Forster , M. O. ; Judd , H. M. XXVII—The triazo-group, part XII: Derivatives of para-triazobenzaldehyde . J. Chem. Soc. 1910 , 254 – 264 ; (b) Bentley , T. J. ; Mc Ghié , J. F. ; Barton , D. H. R. The synthesis of 32-oxygenated lanostane derivatives . Tetrahedron Lett. 1965 , 2497 – 2498 .
   Google Scholar
• (a) Soltani Rad , M. N. ; Behrouz , S. ; Khalafi-Nezhad , A. A simple one-pot procedure for the direct conversion of alcohols into azides using TsIm . Tetrahedron Lett. 2007 , 48 , 3445 – 3449 ; (b) Soltani Rad , M. N. ; Khalafi-Nezhad , A. ; Behrouz , S. ; Faghihi , M. A. A simple one-pot procedure for the direct conversion of alcohols into alkyl nitriles using TsIm . Tetrahedron Lett. 2007 , 48 , 6779 – 6784 ; (c) Soltani Rad , M. N. ; Behrouz , S. ; Faghihi , M. A. ; Khalafi-Nezhad , A. A simple procedure for the esterification of alcohols with sodium carboxylate salts using 1-tosylimidazole (TsIm) . Tetrahedron Lett. 2008 , 49 , 1115 – 1120 ; (d) Soltani Rad , M. N. ; Khalafi-Nezhad , A. ; Behrouz , S. ; Faghihi , M. A. ; Zare , A. ; Parhami , A. One-pot synthesis of N-alkyl purine and pyrimidine derivatives from alcohols using TsIm: A rapid entry into carboacyclic nucleoside synthesis . Tetrahedron 2008 , 64 , 1778 – 1785 .
   Web of Science ®Google Scholar
• Some of aldoximes used in this research were not commercially available. These aldoximes were synthesized from their corresponding aldehyde using methods described in literature. Buck , J. S. ; Ide , W. S. Veratronitrile. Org. Syn. Coll. Vol. II 1943, 622–624.
   Google Scholar
• Kokel , B. ; Menichi , G. ; Hubert-Habart , M. A convenient one-pot conversion of arene- and heteroarene-carboxaldehyde phenylhydrazones into nitriles via reaction with N,N-dimethyldichloromethaniminium chloride . Synthesis 1985 , 201 – 202 .
   Web of Science ®Google Scholar
• Karmarkar , S. N. ; Kelkar , S. L. ; Wadia , M. S. A simple unusual one-step conversion of aromatic aldehydes into nitriles . Synthesis 1985 , 510 – 512 .
   Web of Science ®Google Scholar
• Saednya , A. A mild, high-yield conversion of aldoximes into nitriles using trichloroacetyl chloride/triethylamine . Synthesis 1983 , 748 – 749 .
   Web of Science ®Google Scholar
• Vogel , A. I. Practical Organic Chemistry ; Longmans, Green and Co. : London , 1954 ; chap. 2 , pp. 161 – 176 .
   Google Scholar