Efficient Procedure for Beckmann Rearrangement of Ketoximes Catalyzed by Sulfamic Acid/Zinc Chloride

REFERENCES

• Smith , M. B. ; March , J. Advanced Organic Chemistry, , 5th ed. ; John Wiley & Sons : New York , 2001 .
   Google Scholar
• (a) Narasaka , K. ; Kusama , H. ; Yamashita , Y. ; Sato , H. Beckmann rearrangement catalyzed by the combined use of tetrabutylammonium perrhenate(VII) and trilfluoromethanesulfonic acid . Chem. Lett. 1993 , 489 – 492 ; (b) Ikushima , Y. ; Sato , O. ; Sato , M. ; Hatakeda , K. A. ; Arai , M. Innovations in chemical reaction processes using supercritical water: An environmental application to the production of ε-caprolactam . Chem. Eng. Sci. 2003 , 58 , 935 – 941 ; (c) Srinvas , K. V. N. S. ; Reddy , E. B. ; Das , B. Highly convenient and efficient one-pot conversions of aldehydes into nitriles and ketones into amides using HY-zeolite . Synlett 2002 , 625 – 627 .
   Web of Science ®Google Scholar
• (a) Mao , D. ; Chen , Q. ; Lu , G. Vapor-phase Beckmann rearrangement of cyclohexanone oxime over B2O3/TiO2-ZrO2 . Appl. Catal. A 2003 , 244 , 273 – 282 ; (b) Dongare , M. K. ; Bhagwat , V. V. ; Ramana , C. V. ; Gurjar , M. K. Silica-supported MoO3: A mild heterogeneous catalyst for the Beckmann rearrangement and its application to some sugar derived ketoximes . Tetrahedron Lett. 2004 , 45 , 4759 – 4762 ; (c) Ko , Y. ; Kim , M. H. ; Kim , S. J. ; Seo , G. ; Kim , M. Y. ; Uh , Y. S. Vapor-phase Beckmann rearrangement of cyclohexanone oxime over a novel tantalum pillared-ilerite . Chem. Commun. 2000 , 829 – 830 ; (d) Izumi , Y. ; Sato , S. ; Urabe , K. Vapor-phase Beckmann rearrangement of cyclohexanone oxime over boria-hydroxyapatite catalyst . Chem. Lett. 1983 , 1649 – 1652 .
   Web of Science ®Google Scholar
• (a) Nguyen , M. T. ; Raspoet , G. ; Vanquickenborne , L. G. A new look at the classical Beckmann rearrangement: A strong case of active solvent effect . J. Am. Chem. Soc. 1997 , 119 , 2552 – 2562 ; (b) Furuya , Y. ; Ishihara , K. ; Yamamoto , H. Cyanuric chloride as a mild and active Beckmann rearrangement catalyst . J. Am. Chem. Soc. 2005 , 127 , 11240 – 11241 ; (c) Zhu , M. ; Cha , C. T. ; Deng , W.-P. ; Shi , X. X. A mild and efficient catalyst for the Beckmann rearrangement, BOP-Cl . Tetrahedron Lett. 2006 , 47 , 4861 – 4863 ; (d) 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
• Izumi , Y. Catalytic Beckmann rearrangement of oximes in homogeneous liquid phase . Chem. Lett. 1990 , 2171 – 2174 .
   Web of Science ®Google Scholar
• Sato , H. ; Yoshioka , H. ; Izumi , Y. Homogeneous liquid-phase Beckmann rearrangement of oxime catalyzed by phosphorous pentaoxide and accelerated by fluorine-containing strong acid . J. Mol. Catal. A. Chem. 1999 , 149 , 25 – 32 .
   Google Scholar
• (a) Peng , J. ; Deng , Y. Catalytic Beckmann rearrangement of ketoximes in ionic liquids . Tetrahedron Lett. 2001 , 42 , 403 – 405 ; (b) Ren , R. X. ; Zueva , L. D. ; Ou , W. Formation of ε-caprolactam via catalytic Beckmann rearrangement using P2O5 in ionic liquids . Tetrahedron Lett. 2001 , 42 , 8441 – 8443 ; (c) Gui , J. ; Deng , Y. ; Hu , Z. ; Sun , Z. A novel task-specific ionic liquid for Beckmann rearrangement: A simple and effective way for product separation . Tetrahedron Lett. 2004 , 45 , 2681 – 2683 .
   Web of Science ®Google Scholar
• Luca , L. D. ; Giacomelli , G. ; Porcheddu , A. Beckmann rearrangement of oximes under very mild conditions. J. Org. Chem. 2002, 67, 6272–6274.
   PubMed Web of Science ®Google Scholar
• Xiao , L. F. ; Xia , C. G. ; Chen , J. p-Toluenesulfonic acid mediated zinc chloride: Highly effective catalyst for the Beckmann rearrangement . Tetrahedron Lett. 2007 , 48 , 7218 – 7221 .
   Web of Science ®Google Scholar
• Anilkumar , R. ; Chandrasekhar , S. Improved procedures for the Beckmann rearrangement: The reaction of ketoxime carbonates with boron trifluoride etherate . Tetrahedron Lett. 2000 , 41 , 5427 – 5429 .
   Web of Science ®Google Scholar
• De , S. K. RuCl3-catalyzed facile conversion of arylalkyl ketoximes to amides . Synth. Commun. 2004 , 34 , 3431 – 3434 .
   Web of Science ®Google Scholar
• Arisawa , M. ; Yamaguchi , M. Rhodium-catalyzed Beckmann rearrangement . Org. Lett. 2001 , 3 , 311 – 312 .
   PubMed Web of Science ®Google Scholar
• Sharghi , H. ; Sarvari , M. H. One-step Beckmann rearrangement from carbonyl compounds and hydroxylamine hydrochloride in Al2O3/CH3SO3H (AMA) as a new reagent . J. Chem. Res. 2001 , 446 – 449 .
   Web of Science ®Google Scholar
• (a) Chandrasekhar , S. ; Gopalaiah , K. Beckmann reaction of oximes catalysed by chloral: Mild and neutral procedures . Tetrahedron Lett. 2003 , 44 , 755 – 756 ; (b) Chandrasekhar , S. ; Gopalaiah , K. Beckmann rearrangement of ketoximes on solid metaboric acid: A simple and effective procedure . Tetrahedron Lett. 2002 , 43 , 2455 – 2457 .
   Web of Science ®Google Scholar
• (a) Ikushima , Y. ; Hatakeda , K. ; Sato , O. ; Yokoyama , T. ; Arai , M. Acceleration of synthetic organic reactions using supercritical water: Noncatalytic Beckmann and pinacol rearrangements . J. Am. Chem. Soc. 2000 , 122 , 1908 – 1918 ; (b) Sato , O. ; Ikushima , Y. ; Yokoyama , T. Noncatalytic Beckmann rearrangement of cyclohexanone–oxime in supercritical water . J. Org. Chem. 1998 , 63 , 9100 – 9102 ; (c) Boero , M. ; Ikeshoji , T. ; Liew , C. C. ; Terakura , K. ; Parrinello , M. Hydrogen bond–driven chemical reactions: Beckmann rearrangement of cyclohexanone oxime into ε-caprolactam in supercritical water . J. Am. Chem. Soc. 2004 , 126 , 6280 – 6286 .
   Web of Science ®Google Scholar
• (a) Wang , B. ; Yang , L. M. ; Suo , J. S. Ionic liquid–regulated sulfamic acid: Chemoselective catalyst for the transesterification of β-ketoesters . Tetrahedron Lett. 2003 , 44 , 5037 – 5039 ; (b) Wang , B. ; Yang , L. M. ; Suo , J. S. Solvent-free tetrahydropyranylation of alcohols with sulfamic acid as reusable catalyst . Synth. Commun. 2003 , 33 , 3929 – 3934 .
   Web of Science ®Google Scholar
• Wang , B. ; Gu , Y. ; Luo , C. ; Yang , T. ; Yang , L. ; Suo , J. Sulfamic acid as a cost-effective and recyclable catalyst for liquid Beckmann rearrangement, a green process to produce amides from ketoximes without waste . Tetrahedron Lett. 2004 , 45 , 3369 – 3372 .
   Web of Science ®Google Scholar
• (a) Du , G. ; Zhang , Q. The Beckmann rearrangement of acetophenonoxime under ultrasonic irradiation . J. Hebei Univ. (Nat. Sci. Ed.) 1997 , 38 – 40 ; (b) Zhou , H. ; Huang , W. Beckmann rearrangement of benzophenoneoxime under ultrasonic irradiation . J. Anqing Teach. Coll. (Nat. Sci.) 2002 , 8 , 42 – 45 .
   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
• Moghaddam , F. M. ; Rad , A. A. R. ; Hassan , Z. B. Solid-supported microwave-assisted Beckmann rearrangement of ketoximes in dry media . Synth. Commun. 2004 , 34 , 2071 – 2075 .
   Web of Science ®Google Scholar
• Küllertz , G. ; Fischer , G. ; Barth , A. Sekuedare D-isotopieeffekte bei der hydrolyse von p-nitroacetanilid . Tetrahedron , 1976 , 32 , 759 – 761 .
   Web of Science ®Google Scholar
• Newman , M. S. ; Hung , W. M. An improved aromatization of α-tetralone oximes to N-(1-naphthyl)acetamides . J. Org. Chem. 1973 , 38 , 4073 – 4704 .
   Web of Science ®Google Scholar
• (a) Banfield , J. E. Heterocyclic derivatives of guanidine, part II: Some derived products . J. Chem. Soc. 1961 , 2098 – 2106 ; (b) Nicanor , G. ; Marcial , M. M. ; Sebastian , R. M. ; Adelina , V. Dimethoxyethane as an alternative solvent for schmidt reactions: Preparation of homochiral N-(5-oxazolyl)oxazolidinones from N-acetoacetyl derivatives of oxazolidinones . Tetrahedron 1996 , 52 , 1609 – 1616 .
   Web of Science ®Google Scholar
• Thakur , A. J. ; Boruah , A. ; Prajapati , D. ; Sandhu , J. S. Microwave-induced bismuth trichloride–catalysed Beckmann rearrangement of oximes. Synth. Commun. 2000, 30, 2105–2111.
   Web of Science ®Google Scholar
• (a) Li , J. T. ; Li , X. L. ; Li , T. S. Synthesis of oximes under ultrasound irradiation . Ultrason. Sonochem. 2006 , 13 , 200 – 202 ; (b) Pan , Z. W. ; Li , Y. X. ; Xia , L. Synthesis of ethoxyamine hydrochloride via acetoxime . Fine Chem. Intermediates 2007 , 37 , 17 – 21 .
   PubMed Web of Science ®Google Scholar