(Bromodimethyl)sulfonium Bromide–Mediated Thiolysis of Epoxides: An Easy Access to β-Hydroxy Sulfides and Benzoxathiepinones in Solvent-Free Conditions

REFERENCES

• Tanaka , K. ; Toda , F. Foreword. In Solvent-Free Organic Synthesis ; Wiley-VCH : Weinheim , Germany , 2003 .
   Google Scholar
• Olah , G. A. ; Vankar , Y. D. ; Arvanghi , M. Synthetic methods and reactions. Conversion of epoxides and enamines into α–haloketones with halodimethyl sulfonium halides . Tetrahedron Lett. 1979 , 38 , 3653 – 3656 .
   Google Scholar
• Das , B. ; Holla , H. ; Srinivas , Y. Efficient (bromodimethyl)sulfonium bromide mediated synthesis of benzimidazoles. Tetrahedron Lett. 2007, 48, 61–64.
   Web of Science ®Google Scholar
• Vittal Rao , B. ; Sucheta , K. (Bromodimethyl)sulfonium bromide: An inexpensive reagent for the solvent–free, one pot synthesis of α-amino phophonates . Tetrahedron Lett. 2005 , 46 , 1209 – 1210 .
   Web of Science ®Google Scholar
• Shailaja , M. ; Manjula , A. ; Vittal Rao , B. (Bromodimethyl) sulfonium bromide mediated Michael addition of thiols to α,β-unsaturated ketones . J. Sulfur Chem. 2007 , 28 , 31 – 38 .
   Google Scholar
• Shailaja , M. ; Manjula , A. ; Vittal Rao , B. (Bromodimethyl) sulfonium bromide mediated rapid and facile protection of amines . Org. Chem. Ind. J. 2006 , 2 , 5 .
   Google Scholar
• Shailaja , M. ; Manjula , A. ; Vittal Rao , B. Three component one pot synthesis of β-Amino ketones mediated by (Bromodimethyl) sulfonium Bromide postet presented at RRTSONPC-08, S. V. University, Thirupathi, India, February 25–26, 2008.
   Google Scholar
• Lidy , W. ; Sundermeyer , W. Spattungsreaktionen des trimethylsilylcyanids Durch Epoxide Carbonsaurechloride, chorokohlensaureester und Sulfenylchloride . Tetrahedron Lett. 1973 , 14 , 1449 – 1450 .
   Google Scholar
• Mullis , J. C. ; Weber , W. P. Regiospecificity of reactions of epoxides and oxetanes with trimethyl silylcyanide . J. Org. Chem. 1983 , 47 , 2873 – 2875 .
   Web of Science ®Google Scholar
• Blandy , C. ; Choukroun , T. L. ; Gervias , D. Gold(III) chloride promoted addition of electron-rich heteroaromatic compounds to the C˭C and C˭O bonds of enals . Tetrahedron Lett. 1983 , 47 , 2871 – 2873 .
   Google Scholar
• Sinou , D. ; Emziane , M. Overture regioselective depoxydes par Me3SiN3 catalysee par Ti [oiPr]4. . Tetrahedron Lett. 1986 , 27 , 6423 – 6432 .
   Web of Science ®Google Scholar
• Kesavan , V. ; Daniele , B. D. ; Begue , J. P. Highly Diastereoselective dihydroxylation of Cis – Substituted sulfonyl vinyl oxiranes . Tetrahedron Lett. 2000 , 41 , 2871 – 2874 .
   Web of Science ®Google Scholar
• Devan , N. ; Sridhar , P. R. ; Prabhu , R. K. ; Chandrasekaran , S. Tetrathiomolybdate assisted epoxide ring opening with masked thiolates and selenoates: Multistep reactionsin one pot . J. Org. Chem. 2002 , 67 , 9417 – 9420 .
   PubMed Web of Science ®Google Scholar
• Posner , G. H. ; Rogers , D. Z. Organic reactions at alumina surfaces mild and selective opening of epoxides by alcohols, thiols, benzeneselenol, amines and acetic acid . J. Am. Chem. Soc. 1977 , 99 , 8208 – 8214 .
   Web of Science ®Google Scholar
• Chini , M. ; Crotti , E. ; Giovani , E. ; Macchia , F. ; Pineschi , M. Ytterbium triflate and high pressure mediated ring opening of epoxides . Synlett. 1992 , 303 – 308 .
   Google Scholar
• Meguro , M. ; Asao , N. ; Yamamoto. Ytterbium triflate and high pressure-mediated ring opening of epoxides with amines . J. Chem. Soc. Perkin Trans.1 1994 , 2597 – 2601 .
   Google Scholar
• Cote , V. ; Di Furia , F. ; Licini , G. ; Modena , G. ; Valle , G. Enantioselective oxidation of β-hydroxyl thioethers. Synthesis of optically active alcohols and epoxides . Tetrahedron Assymmetry 1991 , 2 , 257 – 276 .
   Google Scholar
• Su , W. ; Chen , J. ; Wu , H. ; Jin , C. A general and efficient method for the selective synthesis of β-hydroxy sulfides and β-hydroxy sulfoxides catalyzed by gallium(III) triflate . J. Org. Chem. 2007 , 72 , 4524 – 4527 .
   PubMed Web of Science ®Google Scholar
• Gabbi , C. ; Ghelfi , F. ; Grandi , R. The preparation of β-hydroxyl sulfoxides . Synth. Commun. 1997 , 27 , 2857 – 2863 .
   Web of Science ®Google Scholar
• Luly , J. R. ; Soderquist , N. Yi. H. ; Stein , J. ; Perun , T. J. ; Plattner , J. J. New inhibitors of human rennin that contain novel Leu-Val replacements . J. Med. Chem. 1987 , 30 , 1609 – 1616 .
   PubMed Web of Science ®Google Scholar
• Corey , E. J. ; Clark , D. A. ; Goto , G. ; Marfat , C. ; Mioskowski , B. ; Hammarstro , S. S. Stereospecific total synthesis of a slow reacting substance of anaphylaxis, Leukotriene C-1 . J. Am. Chem. Soc. 1980 , 102 , 3663 – 3670 .
   Web of Science ®Google Scholar
• Corey , E. J. ; Clark , D. A. ; Goto , G. Total synthesis of slow reacting substances (SRS) Leukotriene C-2(11-trans-leukotreiene c) (3) and Leukotriene D (4) . Tetrahedron Lett. 1980 , 21 , 3143 – 3146 .
   Web of Science ®Google Scholar
• Piper , G. M. ; Siebeneich , W. Temocapril, an angiotensin converting enzyme inhibitor, protects against diabetes-induced endothelial dysfunction. Eur. J. Phamacol. 2000, 403, 129–132.
   PubMed Web of Science ®Google Scholar
• Lesuisse , D. ; Deprez , P. ; Albert , E. ; Duc , T. T. ; Sortais , B. ; Gofflo , D. ; Jean-Baptiste , V. ; Marquette , J. P. ; Schoot , B. ; Sarubbi , E. ; Lange , G. ; Broto , P. ; Mandine , E. Discovery of thiazepinone Lignds for Src SH2; From non-specific to specific binding . Bioorg. Med. Chem. Lett. 2001 , 11 , 2127 – 2131 .
   PubMed Web of Science ®Google Scholar
• Ambliard , M. ; Daffix , I. ; Bedos , P. ; Berge , G. ; Pruneau , D. ; Paquetr , J. L. ; Luccarini , J. M. ; Belichard , P. ; Dodey , P. ; Martinez , J. Design and synthesis of potent Bradykinin agonists containing a benzothiazepine moiety . J. Med. Chem. 1999 , 42 , 4185 – 4192 .
   PubMed Web of Science ®Google Scholar
• Fringuelli , F. ; Pizzo , F. ; Tortoioli , S. ; Vacaro , L. One pot synthesis benzo [e] 1,4-oxathiepin-5-one under solvent free condition via self – promoted thiolysis of 1,2–epoxides . J. Org. Chem. 2004 , 69 , 8780 – 8785 (references cited therein) .
   PubMed Web of Science ®Google Scholar
• Corbelli , F. ; Monetti , F. ; Tafi , A. ; Nacci , V. ; Botta , M. Diitiazem-like calcium entry blockers: A Hypothesis of the receptors-binding site based on a comparative molecular field analysis model . J. Med. Chem. 1997 , 40 , 125 – 131 .
   PubMed Web of Science ®Google Scholar
• Peach , M. E. In The Chemistry of the Thiol Group ; S. Patai (Ed.); John Wiley & Sons : New York , 1974 ; Part 3 , p. 771 .
   Google Scholar
• Chini , M. ; Crotti , E. ; Giovani , E. ; Macchia , F. ; Pineschi , M. Stereo and regioselective metl salt-promoted Ring Opening of 1,2-epoxides with thiols in acetonitrile . Synlett. 1992 , 303 – 305 (and references cited therein) .
   Web of Science ®Google Scholar
• Vougioukas , A. E. ; Kagan , H. B. Oxirane ring opening Reactions with thiols Catalyzed by lanthanide complexes . Tetrahedron Lett. 1987 , 28 , 6065 – 6068 .
   Web of Science ®Google Scholar
• Iqbal , J. ; Padey , A. ; Shukla , A. ; Srivastava , R. R. ; Tripathi , S. Cobalt mediated regioselective ring opening of oxiranes with benzenethiol: A mechanistic study . Tetrahedron 1990 , 28 , 6423 – 6432 .
   Google Scholar
• Matti , A. K. ; Battacharyya , P. Polyethylene glycol (PEG)4000 catalysed regioselective nucleophilic ring opening of oxiranes-Anew and convenient synthesis of β-hydroxyl sulfone and β-hydroxyl sulfide . Tetrahedron 1994 , 50 , 10483 – 10490 .
   Web of Science ®Google Scholar
• Lida , T. ; Yamamoto , N. ; Sasai , H. ; Shibasaki , M. New asymmetric reactions using a gallium complex: A highly enantioselective ring opening of epoxides with thiols catalyzed by a gallium · lithium · bis(binaphthoxide) complex . J. Am. Chem. Soc. 1997 , 119 , 4783 – 4784 .
   Web of Science ®Google Scholar
• Mukherjee , C. ; Gour Hari , M. ; Anup Kumar , M. Regioselective ring opening of epoxides with thiols in water . ARKIVOC 2008 , 11 , 46 – 55 .
   Google Scholar
• Guindon , Y. ; Young , R. N. ; Frenette , R. Synthesis of β-trimethylsilyloxythioethers and β-hydroxy thioethers . Synth. Commun. 1981 , 11 , 391 – 398 .
   Web of Science ®Google Scholar
• De Pomar , J. C. J. ; Soderquist , J. A. Regio and stereospecific synthesis of (o-TIPS) –protected 2-hydroxyl alky lmercaptans from epoxides and trisopropylsilanethiol . Tetrahedron Lett. 1998 , 39 , 4409 – 4412 .
   Google Scholar
• Buchanan , J. B. ; Sable , H. Z. ; Thyagarajan , B. S. (Ed.), In Selective Organic Transformations ; Wiley-Interscience : New York , Vol. 2 , 1972 .
   Google Scholar
• Vivek , P. ; Kaushik , M. P. CSF-Celite catalyzed region- and chemoselective SN2 type ring opening of epoxide with thiol . Catal. Commun. 2004 , 5 , 515 – 518 .
   Web of Science ®Google Scholar
• Aziz , N. ; Saidi , M. R. LiClO4 · 3H2O promoted highly regioselective ring-opening of epoxide with thiols under neutral conditions . Catal. Commun. 2006 , 7 , 224 – 227 .
   Web of Science ®Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Gakul , B. Incl3-catalyzed highly regioselective ring opening of epoxides with thiols . Chem. Lett. 2002 , 906 – 907 .
   Web of Science ®Google Scholar
• Presented at the Asian Symposium on Medicinal Plants, Spices and Other Natural Products (ASOMPS-XIII), Indian Institute of Chemical Technology, Hyderabad, India, November 3–6, 2008.
   Google Scholar