Facile Preparation of Indolyl-2/3-methylsulfoxides Using HF/H₂O₂

REFERENCES

• (a) Sato , K. ; Hyodo , M. ; Aoki , M. ; Zheng , X.-Q. ; Noyorip , R. Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions . Tetrahedron 2001 , 57 , 2469 – 2476 ; (b) Fraile , J. M. ; García , J. I. ; Lázaro , B. ; Mayoral , J. A. A mild, efficient, and selective oxidation of sulfides to sulfoxides . Chem. Commun. 1998 , 1807 – 1808 ; (c) Greenhalgh , R. P. Selective oxidation of phenyl sulphides to sulphoxides or sulphones using oxone and wet alumina . Synlett 1992 , 235 – 236 ; (d) Shukla , V. G. ; Salgaonkar , P. D. ; Akamanchi , K. G. A mild, chemoselective oxidation of sulfides to sulfoxides using o-iodoxybenzoic acid and tetraethylammonium bromide as a catalyst . J. Org. Chem. 2003 , 68 , 5422 – 5425 ; (e) Hajipour , A. R. ; Ruoho , A. E. Benzyltriphenylphosphoniumchlorochromate (BTPPCC): An efficient and novel reagent for oxidation of sulfide to the corresponding sulfoxides under non-aqueous conditions . Sulfur Lett. 2003 , 26 , 83 – 87 ; (f) Kowalski , P. ; Mitka , K. ; Ossowska , K. ; Kolarska , Z. Oxidation of sulfides to sulfoxides. Part 1: Oxidation using halogen derivatives . Tetrahedron 2005 , 61 , 1933 – 1953 .
   Web of Science ®Google Scholar
• (a) Hauser , F. M. ; Chakrapani , S. ; Ellenberger , W. P. Total synthesis of (±)-7-con-O-methylnogarol . J. Org. Chem. 1991 , 56 , 5248 – 5250 ; (b) Hauser , F. M. ; Gauuan , P. J. F. Total synthesis of (±)-biphyscion . Org. Lett. 1999 , 1 , 671 – 672 ; (c) Hauser , F. M. ; Yin , H. A new route to benzo[4,5]cyclohepta[1,2-b]naphthalenes: Synthesis of radermachol . Org. Lett. 2000 , 2 , 1045 – 1047 ; (d) Hauser , F. M. ; Dorsch , W. A. ; Mal , D. Total synthesis of (±)-O-methyl PD 116740 . Org. Lett. 2002 , 4 , 2237 – 2239 ; (e) Hauser , F. M. ; Liao , H. ; Sun , Y. Regiospecific synthesis of a benanomicinone/pradimicinone analogue . Org. Lett. 2002 , 4 , 2241 – 2243 ; (f) Hauser , F. M. ; Dorsch , W. A. A new regiospecific preparation of xanthones . Org. Lett. 2003 , 5 , 3753 – 3754 .
   Google Scholar
• (a) Williams , T. M. ; Ciccarone , T. M. ; MacTough , S. C. ; Rooney , C. S. ; Balani , S. K. ; Condra , J. H. ; Emini , E. A. ; Goldman , M. E. ; Greenlee , W. J. ; Kauffman , L. R. ; O'Brien , J. A. ; Sardana , V. ; Schleif , W. A. ; Theoharides , A. D. ; Anderson , P. S. 5-Chloro-3-(phenylsulfonyl)indole-2-carboxamide: A novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase . J. Med. Chem. 1993 , 36 , 1291 – 1294 ; (b) Silvestri , R. ; De Martino , G. ; La Regina , G. ; Artico , M. ; Massa , S. ; Vargiu , L. ; Mura , M. ; Loi , A. G. ; Marceddu , T. ; La Colla , P. Novel indolyl aryl sulfones active against HIV-1 carrying NNRTI resistance mutations: Synthesis and SAR studies . J. Med. Chem. 2003 , 46 , 2482 – 2493 .
   PubMed Web of Science ®Google Scholar
• (a) La Regina , G. ; Edler , M. C. ; Brancale , A. ; Kandil , S. ; Coluccia , A. ; Piscitelli , F. ; Hamel , E. ; De Martino , G. ; Matesanz , R. ; Díaz , J. F. ; Scovassi , A. I. ; Prosperi , E. ; Lavecchia , A. ; Novellino , E. ; Artico , M. ; Silvestri , R. Arylthioindole inhibitors of tubulin polymerization, 3: Biological evaluation, structure–activity relationships and molecular modeling studies . J. Med. Chem. 2007 , 50 , 2865 – 2874 ; (b) La Regina , G. ; Coluccia , A. ; Piscitelli , F. ; Bergamini , A. ; Sinistro , A. ; Cavazza , A. ; Maga , G. ; Samuele , A. ; Zanoli , S. ; Novellino , E. ; Artico , M. ; Silvestri , R. Indolyl aryl sulfones as HIV-1 non-nucleoside reverse transcriptase inhibitors: Role of two halogen atoms at the indole ring in developing new analogues with improved antiviral activity . J. Med. Chem. 2007 , 50 , 5034 – 5038 .
   PubMed Web of Science ®Google Scholar
• Romanelli , G. P. ; Vázquez , G. P. ; Tundo , P. New heteropolyacids as catalysts for the selective oxidation of sulfides to sulfoxides with hydrogen peroxide. Synlett 2005, 75–78.
   Google Scholar
• Bahrami , K. Selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide (H2O2) in the presence of zirconium tetrachloride . Tetrahedron Lett. 2006 , 47 , 2009 – 2012 .
   Web of Science ®Google Scholar
• Jeyakumar , K. ; Chand , D. K. Selective oxidation of sulfides to sulfoxides and sulfones at room temperature using H2O2 and a Mo(VI) salt as catalyst . Tetrahedron Lett. 2006 , 47 , 4573 – 4576 .
   Web of Science ®Google Scholar
• Mohanakrishnan , A. K. ; Ramesh , N. An efficient preparation of 1-phenylsulfonylindolyl methylsulfoxides using KF/m-CPBA . Tetrahedron Lett. 2005 , 46 , 4231 – 4233 .
   Web of Science ®Google Scholar
• Agnihotri , G. ; Misra , A. K. Fast and selective oxidation of thioglycosides to glycosyl sulfoxides using KF/m-CPBA . Tetrahedron Lett. 2005 , 46 , 8113 – 8116 .
   Web of Science ®Google Scholar
• Rozen , S. ; Bareket , Y. Oxidation of sulfur containing compounds with HOF·CH3CN . J. Org. Chem. 1997 , 62 , 1457 – 1462 .
   Web of Science ®Google Scholar
• (a) Mohanakrishnan , A. K. ; Srinivasan , P. C. A versatile construction of the 8H-quino[4,3-b]carbazole ring system as a potential DNA binder . J. Org. Chem. 1993 , 60 , 1939 – 1946 ; (b) Mohanakrishnan , A. K. ; Balamurugan , R. A novel synthesis of N-protected carbazoles involving electrocyclization of in situ generated enamines . Tetrahedron Lett. 2005 , 46 , 4045 – 4048 .
   Google Scholar
• Mohanakrishnan , A. K. ; Srinivasan , P. C. One pot synthesis of 4-hydroxy-3-substituted carbazoles via sulfoxide stabilised carbanion . Tetrahedron Lett. 1993 , 34 , 1343 – 1346 .
   Google Scholar