Simple and Efficient One-Pot Synthesis of Nitriles from Amides and Oximes Using in Situ–Generated Burgess-Type Reagent

REFERENCES

• (a) Atkins , G. M. ; Burgess , E. M. The reaction of an N-sulfonyl amine inner salt . J. Am. Chem. Soc. 1968 , 90 , 4744 – 4745 ; (b) Cabañas , B. ; Baeza , M. T. ; Salgado , S. ; Martín , P. ; Taccone , R. ; Martínez , E. Oxidation of heterocycles in the atmosphere: Kinetic study of their reaction with NO3 radical . J. Phys. Chem. A 2004 , 108 , 10818 – 10823 .
   Google Scholar
• (a) Schaffer , P. ; Morel , P. ; Britten , J. F. ; Valliant , J. F. Unexpected formation of an azetidine-carborane derivative by dehydration of N-(1,12-dicarba-closo-dodecaboran-1-yl)formamide: The first x-ray structure of a 2,3-bis(imino)-azetidine . Inorg. Chem. 2002 , 41 , 6493 – 6499 ; (b) Wipf , P. ; Venkatraman , S. From Aziridines to oxazolines and thiazolines: The heterocyclic route to thiangazole . Synlett 1997 , 1 – 10 ; (c) Christopher , T. B. ; Paul , J. M. ; Loong , Y. ; Oakley , P. J. Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave condition . Tetrahedron Lett. 1999 , 40 , 3275 – 3278 ; (d) Brain , C. T. ; Paul , J. M. Rapid synthesis of oxazoles under microwave conditions . Synlett 1999 , 1642 – 1644 ; (e) Burckhardt , S. Methyl N-(triethylammonium-sulf-onyl)carbamate: “Burgess reagent.” Synlett 2000 , 559 – 560 .
   Google Scholar
• Nicolaou , K. C. ; Huang , X. ; Snyder , S. A. ; Rao , P. B. ; Bella , M. ; Reddy , M. V. A novel regio- and stereoselective synthesis of sulfamidates from 1,2-diols using Burgess and related reagents: A facile entry into β-amino alcohols . Angew. Chem., Int. Ed. 2002 , 41 , 834 – 838 .
   PubMedGoogle Scholar
• Mamaghani , M. ; Abed , B. One-pot easy conversion of Baylis–Hillman adducts into carbamates of unsaturated β-amino acids . Tetrahedron Lett. 2004 , 45 , 1547 – 1550 .
   Google Scholar
• Rinner , U. ; Adams , D. R. ; dos Santos , M. L. ; Abboud , K. A. ; Hudlicky , T. New application of Burgess reagent in its reaction with epoxides . Synlett 2003 , 1247 – 1252 .
   Google Scholar
• Nicolaou , K. C. ; Snyder , S. A. ; Longbottom , D. A. ; Nalbandian , A. Z.; Huang, X. New use for the Burgess reagent in chemical synthesis: Methods for the facile and stereoselective formation of sulfamidates, glycosylamines, and sulfamides . Chem. Eur. J. 2004 , 10 , 5581 – 5606 .
   PubMed Web of Science ®Google Scholar
• Nicolaou , K. C. ; Snyder , S. A. ; Nalbandian , A. Z. ; Longbottom , D. A. A new method for the stereoselective synthesis of α- and β-glycosylamines using Burgess reagent . J. Am. Chem. Soc. 2004 , 126 , 6234 – 6235 .
   Google Scholar
• Avenoza , A. ; Busto , J. H. ; Corzana , F. ; Oses , G. J. ; Peregrina , J. M. SN2 vs. E2 on quaternary centers: An easy approach to chiral β 2,2-amino acids from cyclic sulfamidates . Phosphorus, Sulfur, Silicon Relat. Elem. 2005 , 180 , 1459 – 1460 .
   Web of Science ®Google Scholar
• Wood , M. R. ; Kim , J. Y. ; Books , K. M. Novel one-step method for the conversion of primary alcohols into carbamate-protected amines . Tetrahedron Lett. 2002 , 43 , 3887 – 3890 .
   Google Scholar
• (a) Burgess , E. M. ; Penton , Jr. , H. R. ; Taylor , E. A. Thermal reactions of alkyl N-carbomethoxy sulfamate ester. J. Org. Chem. 1973, 38, 26–31; (b) Maugein , N. ; Wagner , A. ; Mioskowski , C. New conditions for the generation of nitrile oxide from primary nitroalkanes. Tetrahedron Lett. 1997, 38, 1547–1550; (c) Box , J. M. ; Harwood , L. M. ; Humphreys , J. L. ; Morris , G. A. ; Redon , P. M. ; Whitehead , R. C. Dehydration of quinate derivatives: Synthesis of a difluoromethylene homologue of shikimic acid. Synlett 2002, 358–360; (d) Creedon , S. M. ; Crowley , H. K. ; McCarthy , D. G. Dehydration of formamides using the Burgess reagent: A new route to isocyanides. J. Chem. Soc., Perkin Trans. 1 1998, 1015–1017.
   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
• Jose , B. ; Vishnu Unni , M. V. ; Prathapan , S. ; Vadakkan , J. J. Oxidation of benzoin to benzil using Burgess reagent . Synth. Commun. 2002 , 32 , 2495 – 2498 .
   Web of Science ®Google Scholar
• (a) Wipf , P. ; Venkatraman , S. An improved protocol for azole synthesis with PEG-supported burgess reagent . Tetrahedron Lett. 1996 , 37 , 4659 – 4662 ; (b) 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
• Sharghi , H. ; Hosseini , M. Solvent-free and one-step Beckmann rearrangement of ketones and aldehydes by zinc oxide . Synthesis 2002 , 1057 – 1060 .
   Google Scholar
• Schmidt , K. F. The imine residue . Ber. 1924 , 57 , 704 – 706 .
   Google Scholar