Synthesis and Reactivity Study of Two New Dihydroisoquinoline-Derived Oxaziridines

REFERENCES

• Emmons , W. D. The synthesis of oxaziranes . J. Am. Chem. Soc. 1956 , 78 , 6208 – 6209 .
   Web of Science ®Google Scholar
• Andreae , S. ; Schmitz , E. Electrophilic aminations with oxaziridines . Synthesis 1991 , 5 , 327 – 346 .
   Google Scholar
• Hata , Y. ; Watanabe , M. Fragmentation reaction of ylide, 7: Reaction of oxaziridines with nucleophilic reagents . J. Am. Chem. Soc. 1979 , 101 , 6671 – 6679 .
   Web of Science ®Google Scholar
• Vidal , J. ; Damestoy , S. ; Guy , L. ; Hammachi , J.-C. ; Aubry , A. ; Collet , A. N-Alkyloxycarbonyl-3-aryl-oxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents . Eur. J. Chem. 1997 , 3 , 1691 – 1709 .
   Web of Science ®Google Scholar
• Armstrong , A. ; Atkin , M. A. ; Swallow , S. Electrophilic amination of carbanions by N-carboxamids oxaziridines . Tetrahedron Lett. 2000 , 41 , 2247 – 2251 .
   Web of Science ®Google Scholar
• Hata , Y. ; Watanabe , M. Is oxygen abstraction by nucleophilic reagents a characteristic reaction of oxaziridines? J. Org. Chem. 1981 , 46 , 610 – 614 .
   Web of Science ®Google Scholar
• Davis , F. A. ; Sheppard , A. C. Applications of oxaziridines in organic synthesis . Tetrahedron 1989 , 45 , 5703 – 5742 .
   Web of Science ®Google Scholar
• Boyd , D. R. ; Malone , J. F. ; McGuckin , M. R. ; Jennings , W. B. ; Rutherford , M. ; Saket , B. M. Synthesis and structural characterisation by nuclear magnetic resonance spectroscopy and a crystal structure of 3-(4-chlorophenyl)-2-(diphenylphosphinoyl)oxaziridine. J. Chem. Soc. Perkin Trans. 2 1988, 2, 1145–1150.
   Google Scholar
• DesMarteau , D. D. ; Petrov , V. A. ; Montanari , V. ; Pregnolato , M. ; Resnati , G. Mild and selective oxygenation of sulfides to sulfoxides and sulfones by perfluoro-cis-2,3-dialkyloxaziridines . J. Org. Chem. 1994 , 59 , 2762 – 2765 .
   Web of Science ®Google Scholar
• Hanquet , G. ; Lusinchi , X. ; Milliet , P. Acid catalysed oxygen transfer from an oxaziridine to a thioether . Tetrahedron Lett. 1988 , 28 , 2817 – 2818 .
   Web of Science ®Google Scholar
• Bohé , L. ; Lusinchi , M. ; Lusinchi , X. Oxygen atom transfert from a chiral N-alkyl oxaziridine promoted by acid: The asymmetric oxidation of sulfides to sulfoxides . Tetrahedron 1999 , 55 , 155 – 166 .
   Web of Science ®Google Scholar
• Akhatou , A. ; Rahimi , M. ; Cheboub , K. ; Ghosez , L. ; Hanquet , G. Acid-promoted enantioselective oxygen-atom transfer from N-alkyl binaphthyl-derived oxaziridines onto sulfides . Tetrahedron 2007 , 63 , 6232 – 6240 .
   Web of Science ®Google Scholar
• Schoumacker , S. ; Hamelin , O. ; Téti , S. ; Pécaut , J. ; Fontecave , M. Activation of oxaziridines by Lewis acids: Application in enantioselective sulfoxidation . J. Org. Chem. 2005 , 70 , 301 – 308 .
   PubMed Web of Science ®Google Scholar
• Ritter , J. J. ; Kalish , J. α,α-Dimethyl-β-phenetylamine . Org. Synth. 1964 , 44 , 44 – 47 .
   Google Scholar
• Seeger , E. ; Engel , W. ; Teufel , H. ; Machleidt , H. Isochinoline, 1: Synthese 3.3-dialkylsubstituierter 3.4-Dihydro- und 1.2.3.4-Tetrahydro-isochinoline . H. Chem. Ber. 1970 , 103 , 1674 – 1691 .
   Google Scholar
• Bohé , L. ; Kammoun , M. Catalytic oxaziridinium–mediated epoxidation of olefins by oxone: A convenient catalyst excluding common side reactions . Tetrahedron Lett. 2002 , 43 , 803 – 805 .
   Web of Science ®Google Scholar
• Larsen , R. D. ; Reamer , R. A. ; Corley , E. G. ; Davis , P. ; Grabowski , E. J. J. ; Reider , P. J. ; Shinkai , I. A modified Bischler–Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines . J. Org. Chem. 1991 , 56 , 6034 – 6038 .
   Web of Science ®Google Scholar
• McCoubey , A. ; Mathieson , D. W. Iso-quinolines, part III: The nitration of 3,4-dihydro- and 1,2,3,4-tetrahydro-isoquinolines . J. Chem. Soc. 1951 , 51 , 2851 – 2853 .
   Web of Science ®Google Scholar
• Bohé , L. ; Kammoun , M. Design of a highly efficient catalyst for the oxaziridinium-mediated epoxidation of olefins by oxone . Tetrahedron Lett. 2004 , 45 , 747 – 751 .
   Web of Science ®Google Scholar
• Bernotas , R. C. ; Adams , G. ; Carr , A. A. Synthesis of benzazepine-based nitrones as radical traps . Tetrahedron 1996 , 52 , 6519 – 6526 .
   Web of Science ®Google Scholar
• Ben Salah , H. ; Kammoun , M. ; Hamdi , B. ; Bohé , L. ; Damak , M. 2-Hydroxy-3,3-dimethyl-7-nitro-3,4-dihydroisoquinoline-1(2H)-one. Acta Cryst. 2008 , E64 , 1050 .
   Google Scholar
• Dadoun , H. ; Alazard , J. P. ; Lusinchi , X. Action de l'eau oxygénée et de l'acide p-nitroperbenzoïque sur des imines, des oxazirannes et des nitrones cycliques stereoidiques dérivés de la conanine . Tetrahedron 1981 , 37 , 1525 – 1540 .
   Web of Science ®Google Scholar
• Vanjari , H. ; Pande , R. J. Hydroxamic acids: Proton donor and acceptor strength for use in drug design . Pharm. Biomed. Anal. 2003 , 33 , 783 – 788 .
   PubMed Web of Science ®Google Scholar
• Porcheddu , A. ; Giacomelli , G. Angeli–Rimini's reaction on solid support: A new approach to hydroxamic acids . J. Org. Chem. 2006 , 71 , 7057 – 7059 .
   PubMed Web of Science ®Google Scholar
• Fink , K. ; Fink , R. M. Application of filter paper partition chromatography to qualitative analysis of volatile and nonvolatile organic acids . Proc. Soc. Exptl. Biol. Med. 1949 , 70 , 654 – 656 .
   PubMed Web of Science ®Google Scholar