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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 13
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Original Articles

One-Pot Conversion of Aldehyde Sodium Bisulfites into Nitriles

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Pages 1934-1940 | Received 11 Sep 2009, Published online: 26 Mar 2012

REFERENCES

  • (a) Fatiadi , A. J. Preparation and Synthetic Applications of Cyano Compounds ; S. Patai , Z. Rappaport (Eds.); Wiley : New York , 1983 ; pp. 1057 – 1061 ; (b) Uehling , D. E. ; Nanthakumar , S. S. ; Croom , D. ; Emerson , D. L. ; Leitner , P. P. ; Luzzio , M. J. ; McIntyre , G. ; Morton , B. ; Profeta , S. Synthesis, topoisomerase I inhibitory activity, and in vivo evaluation of 11-azacamptothecin analogs. J. Med. Chem. 1995, 38, 1106–1118; (c) Nagamura , S. ; Kobayashi , E. ; Gomi , K. ; Saito , H. Synthesis and antitumor activity of duocarmycin derivatives: A-ring pyrrole analogues of duocarmycin B2. Bioorg. Med. Chem. 1996, 4, 1379–1391 .
  • Friedrich , K. ; Wallenfels , K. The Chemistry of the Cyano Groups ; Z. Rappoport (Ed.); Wiley-Interscience : New York , 1970 ; pp. 67 – 73 .
  • (a) Quada , J. C. ; Levy , M. J. ; Hecht , S. M. Highly efficient DNA strand scission by photoactivated chlorobithiazoles . J. Am. Chem. Soc. 1993 , 115 , 12171 – 12172 ; (b) Thomas , C. J. ; McCormick , M. M. ; Vialas , C. ; Tao , Z. F. ; Leitheiser , C. J. ; Reshel , M. J. ; Wu , X. ; Hecht , S. M. Alteration of the selectivity of DNA cleavage by a deglycobleomycin analogue containing a trithiazole moiety . J. Am. Chem. Soc. 2002 , 124 , 3875 – 3884 .
  • Fabiani , M. E. Angiotensin receptor subtypes: Novel targets for cardiovascular therapy. Drug News Perspect. 1999, 12, 207–216.
  • Campiani , G. ; De Angelis , M. ; Armaroli , S. ; Fattorusso , C. ; Catalanotti , B. ; Ramunno , A. ; Nacci , V. ; Novellino , E. ; Grewer , C. ; Ionescu , D. ; Rauen , T. ; Griffiths , R. ; Sinclair , C. ; Fumagalli , E. ; Mennini , T. A Rational approach to the design of selective substrates and potent nontransportable inhibitors of the excitatory amino acid transporter EAAC1 (EAAT3): New glutamate and aspartate analogues as potential neuroprotective agents . J. Med. Chem. 2001 , 44 , 2507 – 2510 .
  • (a) Judkins , B. D. ; Allen , D. G. ; Cook , T. A. ; Evans , B. ; Sardharwala , T. E. A Versatile synthesis of amidines from nitriles via amidoximes . Synth. Commun. 1996 , 26 , 4351 – 4367 ; (b) Medwid , J. B. ; Paul , R. ; Baker , J. S. ; Brockman , J. A. ; Du , M. T. ; Hallett , W. A. ; Hanifin , J. W. ; Hardy , R. A. ; Tarrant , M. E. ; Torley , I. W. ; Wrenn , S. Preparation of triazolo[1,5-c]pyrimidines as potential antiasthma agents . J. Med. Chem. 1990 , 33 , 1230 – 1241 ; (c) Khanna , I. K. ; Weier , R. M. ; Yu , Y. ; Xu , X. D. ; Koszyk , F. J. ; Callins , P. W. ; Kobaldt , C. M. ; Veenhuizen , A. W. ; Perkins , W. E. ; Casler , J. J. ; Masferrer , J. L. ; Zhung , Y. Y. ; Gregory , S. A. ; Seibert , K. ; Isakson , P. C. 1,2-diarylimidazoles as potent, cyclooxygenase-2 selective, and orally active anti-inflammatory agents . J. Med. Chem. 1997 , 40 , 1634 – 1647 .
  • (a) Cai , L. Z. ; Liu , X. ; Tao , X. C. ; Shen , D. Efficient microwave-assisted cyanation of aryl bromide . Synth. Commun. 2004 , 34 , 1215 – 1221 ; (b) Petrillo , G. ; Novi , M. ; Garbarino , G. ; Dellerba , C. A convenient Sm1 synthesis of aromatic nitriles from diazonium salts via diazosulfides . Tetrahedron 1987 , 43 , 4625 – 4634 ; (c) Kornblum , N. ; Smiley , R. A. ; Blackwood , R. K. ; Iffland , D. C. The mechanism of the reaction of silver nitrite with alkyl halides: The contrasting reactions of silver and alkali metal salts with alkyl halides: The alkylation of ambident anions . J. Am. Chem. Soc. 1955 , 77 , 6269 – 6280.
  • (a) Shinpei , I. ; Hideo , T. Oxidative conversion of primary alcohols, and primary, secondary, and tertiary amines into the corresponding nitriles with 1,3-diiodo-5,5-dimethylhydantoin in aqueous NH3 . Synlett 2007 , 123 , 407 – 410 ; (b) Yamaguchi , K. ; Mizuno , N. Efficient heterogeneous aerobic oxidation of amines by a supported ruthenium catalyst . Angew. Chem. Int. Ed. 2003 , 42 , 1480 – 1483 ; (c) Nicolaou , K. C. ; Mathison , C. J. N. Synthesis of imides, N-acyl vinylogous carbamates and ureas, and nitriles by oxidation of amides and amines with dess-martin periodinane . Angew. Chem. Int. Ed. 2005 , 44 , 5992 – 5997 .
  • Henis , N. B. H. ; Miller , L. L. Production of acrylonitrile and other unsaturated nitriles from alkenes and alkynes . J. Am. Chem. Soc. 1982 , 104 , 2526 – 2529 .
  • (a) Movassagh , B. ; Fazeli , A. Direct synthesis of aromatic nitriles from aldehydes using hydroxylamine and oxalyl chloride. Synth. Commun. 2007, 37, 623–628; (b) Bandgar , B. P. ; Makone , S. S. Organic reactions in water: Transformation of aldehydes to nitriles using NBS under mild conditions. Synth. Commun. 2006, 36, 1347–1352; (c) Subhas , B. D. ; Ravinder , G. P. Bis(trichloromethyl)carbonate, an efficient activator for the one-pot conversion of aldehydes into nitriles under mild conditions. Synth. Commun. 2002, 32, 3621–3624; (d) Elmorsy , S. S. ; El-Ahl , A. A. S. ; Soliman , H. ; Amer , F. A. Synthesis of triazidochlorosilane (TACS): A novel silicon-mediated one pot conversion of aldehydes to nitriles. Tetrahedron Lett. 1995, 36, 2639–2640; (e) Nishiyama , K. ; Oba , M. ; Watanabe , A. Reactions of trimethylsilyl azide with aldehydes: Facile and convenient syntheses of diazides, tetrazoles, and nitriles. Tetrahedron 1987, 43, 693–700; (f) Movassagh , B. ; Shokri , S. An efficient and convenient KF/Al2O3-mediated synthesis of nitriles from aldehydes. Tetrahedron Lett. 2005, 46, 6923–6925; (g) 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; (h) Juršić , B. Dehydration of aldoximes by dichlorocarbene in reverse micelle. Synth. Commun. 1989, 19, 689–693; (i) Liguori , A. ; Sindona , G. ; Romeo , G. ; Uccella , N. Direct conversion of hydroxamic acid into nitriles. Synthesis 1987, 168–169; (j) Orazio , A. ; Pierangela , P. ; Serra-Zanetti , F. Effect of metal ions in organic synthesis; X. Mild, easy, and high-yield conversion of aldoximes into nitriles under copper(I) acetate catalysis. Synthesis 1983, 741–742; (k) Molina , P. ; Alajarin , M. ; Vilaplana , M. J. 4,6-Diphenyl-2-methyl-pyrylium tetrafluoroborate: A new reagent for the dehydration of aldoximes. Synthesis 1982, 1016–1017.
  • Young , S. D. ; Buse , C. T. ; Heathcock , C. H. 2-Methyl-2-(trimethylsiloxy)pentan-3-one . Org. Synth. Collect. 1990 , 7 , 381 – 386.
  • Odyakov , V. F. ; Titova , T. F. ; Matveev , K. I. ; Krysin , A. P. Vitamin K3, synthesis, properties, and analysis . Pharm. Chem. J. 1992 , 26 , 622 – 635 .
  • Li , Z. B. ; He , X. Y. ; Zuo , H. Synthesis of novel analogues on the α -carbon of houttuyfonate and SAR analysis of antibacterial activity with MOPAC . Med. Chem. Res. 2009 , 18 , 362 – 372 .
  • Olah , G. A. ; Keumi , T. Synthetic methods and reactions, 60: Improved one-step conversion of aldehydes into nitriles with hydroxylamine in formic acid solution . Synthesis 1979 , 112 – 113 .
  • Coskun , N. Mild and efficient method for the synthesis of nitriles . Synth. Commun. 2004 , 34 , 1625 – 1630 .
  • Desai , D. G. ; Swami , S. S. ; Mahale , G. D. A new, mild, neutral and inexpensive method for conversion of aldoximes to nitriles anhydrous ferric sulphate . Synth. Commun. 2000 , 30 , 1623 – 1625 .
  • Rappoport , Z. ; Frankel , M. CRC Handbook of Tables for Organic Compound Identification, , 3rd ed. ; CRC Press : Cleveland , 1967 .
  • Lide , D. B. CRC Handbook of Chemistry and Physics, , 87th ed. ; Taylor and Francis : Boca Raton , FL , 2007 .

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