PCC-Promoted Dehydration of Aldoximes: A Convenient Access to Aromatic, Heteroaromatic, and Aliphatic Nitriles

REFERENCES

• (a) Fatiadi , A. J. In Preparation and Synthetic Applications of Cyano Compounds ; S. Patai and Z. Rappaport (Eds.); Wiley : New York , 1983 ; (b) Miller , J. S. ; Manson , J. L. Designer magnets containing cyanides and nitriles. Acc. Chem. Res. 2001, 34, 563–570 ; (c) Magnus , P. ; Scott , D. A. ; Fielding , M. R. Direct conversion of α,β-unsaturated nitriles into cyanohydrins using Mn(dpm)3 catalyst, dioxygen, and phenylsilane. Tetrahedron Lett. 2001, 42, 4127–4129 .
   Google Scholar
• Romero , M. ; Renard , P. ; Caignard , D. H. ; Atassi , G. ; Solans , X. ; Constans , P. ; Bailly , C. ; Pujol , M. D. Synthesis and structure–activity relationships of new benzodioxinic lactones as potential anticancer drugs . J. Med. Chem. 2007 , 50 , 294 – 307 .
   PubMed Web of Science ®Google Scholar
• (a) Ellis , G. P. ; Romney-Alexander , T. M. Cyanation of aromatic halides . Chem. Rev. 1987 , 87 , 779 – 794 ; (b) Raja , R. ; Adams , R. D. ; Blom , D. A. ; Pearl , W. C. ; Gianotti Jr. , E. ; Thomas , J. M. A new catalytic liquid-phase ammoxidation approach towards the preparation of niacin (vitamin B3) . Langmuir 2009 , 25 , 7200 – 7204 .
   Web of Science ®Google Scholar
• Kim , H. S. ; Kim , S. H. ; Kim , J. N. Highly efficient Pd-catalyzed synthesis of nitriles from aldoximes . Tetrahedron Lett. 2009 , 50 , 1717 – 1719 .
   Web of Science ®Google Scholar
• Singh , M. K. ; Lakshman , M. K. A simple synthesis of nitriles from aldoximes . J. Org. Chem. 2009 , 74 , 3079 – 3084 .
   PubMed Web of Science ®Google Scholar
• Gucma , M. ; Golebiewski , W. M. Convenient conversion of aldoximes into nitriles with N-chlorosuccinimide and pyridin . Synthesis 2008 , 1997 – 1999 .
   Web of Science ®Google Scholar
• Supsana , P. ; Liaskopoulos , T. ; Tsoungas , P. G.; Varvounis, G. DMF-catalysed thermal dehydration of aldoximes: A convenient access to functionalized aliphatic and aromatic nitrile . Synlett. 2007 , 2671 – 2674 .
   Web of Science ®Google Scholar
• Yamaguchi , K. ; Fujiwara , H. ; Ogasawara , Y. ; Kotani , M. ; Mizuno , N. A tungsten–tin mixed hydroxide as an efficient heterogeneous catalyst for dehydration of aldoximes to nitriles. Angew. Chem., Int. Ed. 2007, 46, 3922–3925.
   PubMed Web of Science ®Google Scholar
• Sardarian , A. R. ; Shahsavari-Fard , Z. ; Shahsavari , H. R. ; Ebrahimi , Z. Efficient Beckmann rearrangement and dehydration of oximes via phosphonate intermediates . Tetrahedron Lett. 2007 , 48 , 2639 – 2643 .
   Web of Science ®Google Scholar
• Campbell , J. A. ; McDougald , G. ; McNab , H. ; Rees , L. V. C. ; Tyas , R. G. Laboratory-scale synthesis of nitriles by catalysed dehydration of amides and oximes under flash vacuum pyrolysis (FVP) conditions . Synthesis 2007 , 3179 – 3184 .
   Web of Science ®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
• 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 nitrile . Synlett. 2004 , 2019 – 2021 .
   Web of Science ®Google Scholar
• Jie , Z. ; Rammoorty , V. ; Fischer , B. Diethyl chlorophosphite: A versatile reagent . J. Org. Chem. 2002 , 67 , 711 – 719 .
   PubMed Web of Science ®Google Scholar
• Heqedues , A. ; Cwik , A. ; Hell , Z. ; Horvath , Z. ; Esek , A. ; Uzsoki , M. Microwave-assisted conversion of oximes into nitriles in the presence of a zeolite . Green Chem. 2002 , 4 , 618 – 620 .
   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
• Heravi , M. M. ; Sadjadi , S. ; Hekmatshoar , R. ; Oskooie , H. A. ; Bamoharram , F. F. Dehydration of oximes to nitriles catalyzed by a green heteropolyacid catalyst: Preyssler's anion, [NaP5W30O110]14− . Chin. J. Chem. 2009 , 27 , 607 – 609 .
   Web of Science ®Google Scholar
• Jose , B. ; Sulatha , M. S. ; Pillai , P. M. ; Prathapan , S. A new method for the generation of nitriles from aldoximes . Synth. Commun. 2000 , 30 , 1509 – 1514 .
   Web of Science ®Google Scholar
• Chaudhari , S. S. ; Akananchi , K. G. Thionyl chloride–benzotriazole: An efficient system for transformation of aldoximes to nitriles . Synth. Commun. 1999 , 29 , 1741 – 1756 .
   Web of Science ®Google Scholar
• Arumugam , S. ; Verkade , J. G. P(CH3NCH2CH2)3N: A nonionic superbase for efficient dehydrohalogenation . J. Org. Chem. 1997 , 62 , 4827 – 4828 .
   Web of Science ®Google Scholar
• Augustine , K. ; Rajendra , N. A. ; Balakrishna , K. R. ; Chandrakantha , B. Propylphosphonic anhydride (T3P®): A remarkably efficient reagent for the one-pot transformation of aromatic, heteroaromatic, and aliphatic aldehydes to nitriles . Synlett. 2009 , 20 , 3378 – 3382 .
   Web of Science ®Google Scholar
• Corey , E. J. ; Ensley , H. E. ; Suggs , W. J. Convenient synthesis of (S)−(-)-pulegone from (−)-citronellol . J. Org. Chem. 1976 , 41 ( 2 ), 380 – 381 .
   Web of Science ®Google Scholar
• Hollenberg , D. H. ; Klien , R. S. ; Fox , J. J. Pyridiniumchlorochromate for the oxidation of carbohydrates . Carbohydr. Res. 1978 , 67 , 491 – 494 .
   Web of Science ®Google Scholar
• (a) Piancatelli , G. ; Scettri , A. ; Auria , M. D. The oxidation of furan derivatives with pyridiniumchlorochromate: A novel synthesis of 6-hydroxy-2h-pyran-3(6H)-ones . Tetrahedron Lett. 1977 , 18 , 2199 – 2200 ; (b) Piancatelli , G. ; Scettri , A. ; Auria , M. D. Pyridiniumchlorochromate in the organic synthesis: A convenient oxidation of 5-bromo-2-furan-derivatives to γ-hydroxybutenolides . Tetrahedron Lett. 1979 , 20 , 1507 – 1508 .
   Google Scholar
• Corey , E. J. ; Suggs , W. J. Pyridiniumchlorochromate: An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds . Tetrahedron Lett. 1975 , 16 , 2647 – 2650 .
   Google Scholar