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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 4
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Original Articles

Magnesium‐Catalyzed Proficient Reduction of Oximes to Amines Using Ammonium Formate

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Pages 599-605 | Received 14 Aug 2003, Published online: 16 Aug 2006

References

  • Carr , D. , Iddon , B. and Suschitzky , H. 1980 . Synthesis and some reactions of 3,4,5,6‐tetrahydro‐3,6‐diemthyl‐2,6‐methano‐3‐benzazocin‐1(2H‐one2,5‐dimethyl‐8‐oxo‐67‐benzomorphan) . J. Chem. Soc. Perkin Trans. 1 , : 2374 – 2379 .
  • Herscovici , J. , Egron , M. J. and Antonakis , K. 1988 . Preparation of 4′‐amino hexopyranose nucleosides an approach to amino nucleoside antibiotics . J. Chem. Soc. Perkin Trans. 1. , : 1219 – 1226 . [CROSSREF]
  • Hutchins , R. O. and Hutchins , M. K. 1991 . “ Reduction of C˭N to CHNH by metal hydrides ” . In Comprehensive Organic Synthesis Edited by: Trost , B. M. and Fleming , I. Vol. 8 , 60 – 70 . Oxford : Pergamon Press .
  • Demir , A. S. , Tanyeli , C. , Sesenoglu , O. and Demic , S. A. 1996 . Simple NaBH4 in presence of transition metal compounds . Tetrahedron Lett. , 37 : 407 – 410 . [CROSSREF]
  • Diab , Y. , Laurent , A. and Mison , P. 1974 . Synthesis d'aziridines secondaires cis disubstituees . Tetrahedron Lett. , 17 : 1605 – 1607 . [CROSSREF]
  • Rahman , M. A. and Fraser‐Reid , B. 1985 . Actinobolin via the anomeric effect . J. Am. Chem. Soc. , 107 : 5576 – 5578 .
  • Pitts , M. R. , Harrison , J. R. and Moody , C. J. 2001 . Indium metal as a reducing agent in organic synthesis . J. Chem. Soc. Perkin Trans. 1. , 9 : 955 – 977 . [CROSSREF]
  • Cipolla , L. , Lay , L. , Nicotra , F. , Panza , L. and Russo , G. 1995 . First synthesis of the phosphono analogue of N‐acetyl‐α‐D‐mannosamine 1‐phosphate . J. Chem. Soc. Chem. Commun. , : 1993 – 1994 . [CROSSREF]
  • Booker‐Milburn , K. I. , Dunkin , I. R. , Kelly , F. C. , Khalaf , A. I. , Learmonth , D. A. , Proctor , G. R. and Scopes , D. I.C. 1997 . Azabenzocycloheptanones. Part 20. Synthesis and utilization of 4‐amino‐1,2,3,4‐tetrahydro‐1(1H)‐benzazepines . J. Chem. Soc. Perkin Trans. 1. , : 3261 – 3273 . [CROSSREF]
  • Popp , F. D. and Schultz , H. P. 1962 . Electrolytic reduction of organic compounds . Chem. Rev. , 62 : 19 – 40 .
  • Ranu , B. C. , Majee , A. and Das , A. R. 1996 . A convenient synthesis of β,γ‐unsaturated ketones through zinc‐mediated allylation of acid chlorides . Tetrahedron Lett. , 37 ( 7 ) : 1109 – 1112 . [CROSSREF]
  • Ranu , B. C. , Dutta , P. and Sarkar , A. 1998 . Indium promoted reductive homocoupling of alkyl and aryl halides . Tetrahedron Lett. , 39 ( 57 ) : 9557 – 9558 . [CROSSREF]
  • Zhou , J. Y. , Chen , Z. G. and Wu , S. H. 1994 . Tin promoted stereocontrolled intramolecular allylation of carbonyl compounds: a facile and stereoselective method for ring construction . J. Chem. Soc. Chem. Commun. , 24 : 2783 – 2784 . [CROSSREF]
  • House , H. O. 1972 . “ Dissolving metal reductions and related reactions ” . In Modern Synthetic Reactions Edited by: Bartlett , P. D. , Curtin , D. , Johnson , W. S. , Roberts , J. D. and Woodward , R. B. 145 – 227 . USA : Benzamin, Inc. .
  • Salomon , R. G. 1974 . A fecile one‐step synthesis of 5‐silaspiro [4,4]nona‐2,7‐diene . J. Org. Chem. , 39 ( 24 ) : 3602
  • Prajapathi , D. , Borah , H. N. , Sandhu , J. S. and Ghosh , A. C. 1995 . Ammonium sulphate–magnesium promoted selective reduction of aromatic nitro compounds . Synth. Commun. , 25 ( 24 ) : 4025 – 4028 .
  • Blomberg , C. and Hartog , F. A. 1977 . The barbier reaction—a one‐step alternative for syntheses via organomagnesium compounds . Synthesis , 1 : 18 – 30 . [CROSSREF]
  • Merker , R. L. and Scott , M. J. 1964 . Grignard reactions of polyhalocarbons. In situ grignard reactions of carbon tetrahalides with organochlorosilanes . J. Org. Chem. , 29 ( 4 ) : 953 – 955 .
  • Johnstone , R. A.W. , Wilby , A. H. and Entwistle , I. D. 1985 . Heterogeneous catalytic transfer hydrogenation and its relation to other methods for reduction of organic compounds . Chem. Rev. , 85 : 129 – 170 .
  • Ram , S. and Ehrenkaufer , R. E. 1988 . Ammonium formate in organic synthesis: a versatile agent in catalytic transfer hydrogenation . Synthesis , 1 : 91 – 97 . [CROSSREF]
  • Gowda , S. and Gowda , D. C. 2002 . Application of hydrazinium monoformate as new hydrogen donor with raney nickel; a facile reduction of nitro and nitrile moieties . Tetrahedron , 58 ( 11 ) : 2211 – 2213 . [CROSSREF]
  • Gowda , D. C. , Gowda , A. S.P. , Baba , A. R. and Gowda , S. 2000 . Nickel‐catalyzed formic acid reductions, a selective method for the reduction of nitro compounds . Synth. Commun. , 30 ( 16 ) : 2885 – 2889 .
  • Jnaneshwara , G. K. , Sudalai , A. and Deshpande , V. H. 1998 . Palladium catalyzed transfer hydrogenation of azo compounds and oximes using ammonium formate . J. Chem. Res. (S). , 3 : 160 – 161 . [CROSSREF]
  • Brieger , G. and Nestrick , T. J. 1974 . Catalytic transfer hydrogenation . Chem. Rev. , 74 : 567 – 580 .
  • Gowda , D. C. 2002 . Magnesium/hydrazinium monoformate: a new hydrogenation method for the removal of some commonly used protecting groups in peptide synthesis . Tetrahedron Lett. , 43 : 311 – 313 . [CROSSREF]
  • Vogel , A. I. 1997 . Text Book of Practical Organic Chemistry , 5th Ed. Edited by: Furniss , B. S. , Hannaford , A. J. , Smith , P. W.G. and Tatchell , A. R. 1298 UK : Addison Wesley Longman Limited . Revised by
  • Budavari , S. 1989 . The Merck Index , 11th Ed. USA : Merck & Co. Inc. .

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