Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2004(6): 928-934
DOI: 10.1055/s-2004-822311
DOI: 10.1055/s-2004-822311
PAPER
© Georg Thieme Verlag Stuttgart · New YorkEfficient New Protocol to Synthesize Aromatic and Heteroaromatic Dithioesters
Further Information
Received
15 December 2003
Publication Date:
15 March 2004 (online)
Publication History
Publication Date:
15 March 2004 (online)
Abstract
A very efficient, high yielding procedure to synthesize substituted aromatic and heteroaromatic dithioesters is described. It involves the reaction between (phenylsulfonyl)methyl (hetero)aromatic derivatives and elemental sulfur in basic medium, followed by alkylation.
Key words
dithioester - sulfone - carbene insertion - arylsulfonyl elimination
- Reviews:
- 1a
Metzner P. In Top. Curr. Chem. 204, Organosulfur Chemistry IPage PCB. Springer-Verlag; Berlin: 1999. p.127 - 1b
Masson S. Heteroat. Chem. 1995, 12: 69 - 2a
Duus F. In Comprehensive Organic Chemistry, The synthesis and reactions of organic compounds Vol. 3:Jones N. Pergamon; Oxford: 1979. p.373 - 2b
Bulpin A.Le Roy-Gouvernnec S.Masson S. Phosphorus, Sulfur, Silicon Relat. Elem. 1994, 89: 119 - 2c
Pfund E.Lequeux T.Masson S.Vazeux M. Org. Lett. 2002, 4: 843 - 3a
Beslin P.Metzner P. Tetrahedron Lett. 1980, 21: 4657 - 3b
Vyas DM.Hay GW. Can. J. Chem. 1971, 49: 3755 - 3c
Vyas DM.Hay GW. J. Chem. Soc., Perkin Trans. 1 1975, 180 - 3d
Vedejs E.Arnost MJ.Dolphin JM.Eustache J. J. Org. Chem. 1980, 45: 2601 - 3e
Kirby GW.Lochead AW.Williamson S. J. Chem. Soc., Perkin Trans. 1 1996, 977 - 3f
Portella C.Shermolovich YG.Tschenn O. Bull. Soc. Chim. Fr. 1997, 134: 697 - 3g
Boerma JA.Nilsson NH.Senning A. Tetrahedron 1974, 30: 2735 - 3h
Heuzé B.Gasparova R.Heras M.Masson S. Tetrahedron Lett. 2000, 41: 7327 - 3i
Heras M.Gulea M.Masson S. Chem. Commun. 2001, 611 - 3j
Lequeux T.Pfund E.Masson S.Vazeux M. Tetrahedron Lett. 2002, 43: 2033 - 4a
Beiner JM.Lecadet D.Paquer D.Thuillier A. Bull. Soc. Chim. 1973, 1979 - 4b
Alcázar V.Tapia I.Morán JR. Tetrahedron 1990, 46: 1057 - 4c
Mloston G.Heimgartner H. Helv. Chim. Acta 1992, 75: 1825 - 4d
Urbaniak K.Mloston G.Gulea M.Masson S. Communication, 20th International Symposium on the Organic Chemistry of Sulfur July: Flagstaf; Az USA: 2002. p.14-19 - 5a
Levillain J.Masson S.Hudson A.Alberti A. J. Am. Chem. Soc. 1993, 115: 8444 - 5b
Alberti A.Benaglia M.Della Bona MA.Macciantelli D.Heuzé B.Masson S.Hudson A. J. Chem. Soc., Perkin Trans. 2 1996, 1057 - 5c
Alberti A.Benaglia M.Bonora M.Borzatta V.Hudson A.Macciantelli D.Masson S. Polym. Degrad. Stab. 1998, 62: 559 - 6a
Laus M.Papa R.Sparnacci K.Alberti A.Benaglia M.Macciantelli D. Macromolecules 2001, 34: 7269 - 6b
Mayadunne RTA.Moad G.Rizzardo E. Tetrahedron Lett. 2002, 43: 6811 - 6c
Hawthorne DG.Moad G.Rizzardo E.Thang SH. Macromolecules 1999, 32: 5457 - 6d
Stenzel-Rosenbaum M.Davis TP.Chen V.Fane AG. J. Pol. Sci.: Part A: Pol. Chem. 2001, 39: 2777 - 6e
Quinn JF.Chaplin RPM.Davis TP. J. Pol. Sci.: Part A: Pol. Chem. 2002, 40: 2956 - 6f
Duréault A.Gnanou Y.Taton D.Destarac M.Leising F. Angew. Chem. Int. Ed. 2003, 42: 2869 - 7
Leflemme N.Marchand P.Gulea M.Masson S. Synthesis 2000, 1143 - 8
Abrunhosa I.Gulea M.Levillain J.Masson S. Tetrahedron: Asymmetry 2001, 2851 - 9
Thiel W.Mayer R. J. Prakt. Chem. 1989, 243 - 10
Lempereur C.Plé N.Turk A.Quéguiner G.Corbin F.Alayrac C.Metzner P. Heterocycles 1998, 48: 2019 - 11a
Masson S.Saquet M.Thuillier A. Tetrahedron Lett. 1976, 28: 4179 - 11b
Ramadas SR.Srinivasan PS.Ramachandran J.Sastry VVSK. Synthesis 1983, 605 - 11c
Metzner P.Thuillier A. Sulfur Reagents in Organic Synthesis Academic Press; London: 1994. - 12a
Pedersen BS.Scheibye S.Clausen K.Lawesson SO. Bull. Soc. Chim. Belg. 1978, 87: 293 - 12b
Yousif MN.Pedersen U.Yde B.Lawesson SO. Tetrahedron 1984, 14: 2663 - 12c
Voss J. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 43: 129 - 13
Davy H. J. Chem. Soc., Chem. Commun. 1982, 457 - 14
Gosselin P.Masson S.Thuillier A. Tetrahedron Lett. 1978, 30: 2715 - 15
Dieter KR.Lugade AG. Synthesis 1988, 303 - 16a
Morrison CF.Burnell DJ. Org. Lett. 2000, 3891 - 16b
Gonnella NC.Lakshmikantham MV.Gava MP. Synth. Commun. 1979, 9: 17 - 17a
Corbin F. PhD Thesis Université de Caen; France: 1998. - 17b This reference does not contain NMR data:
Budzikiewicz H.Lange E.Ockels W. Phosphorus Sulfur Relat. Elem. 1981, 11: 33 - 17c
Nakajima T.Kashiwabara T.Izawa T.Nakajima S. Bioorg. Med. Chem. Lett. 1994, 4: 2485 - 18 The 8-bromomethyl quinoline 1f, precursor of 2f, was prepared from 8-methylquinoline following the method described in:
Dalley NK.Xue G.Bradshaw JS.Zhang X.Harisson RG.Savage PB.Krakowiak KE.Izatt RM. J. Heterocycl. Chem. 2001, 38: 1 - 19
Léger L.Saquet M. Bull. Soc. Chim. 1975, 3-4: 657 - 20
Jolivet B.Uguen D. Tetrahedron Lett. 2002, 7907 - 21
Trost B.Braslau R. J. Org. Chem. 1988, 53: 532 - 22
Grierson D.Bettiol J.-L.Buck I.Husson H.-P.Rubiralta M.Diez A. J. Org. Chem. 1992, 57: 6414 - 23
Crispino G.Breslow R. J. Org. Chem. 1992, 57: 1849 - 24
Kaufmann T.Jousen R. Chem. Ber. 1977, 110: 3930 - 25
Shaabani A.Teimouri F.Lee D. Synth. Commun. 2003, 33: 1057 - 26
Orita A.Yoshioka N.Struwe P.Braier A.Beckmann A.Otera J. Chem.-Eur. J. 1999, 5: 1355 - 27
Sperandio D.Hansen H.-J. Helv. Chim. Acta 1995, 78: 765 - 28a
Wladislaw B.Marzorati L.Ebeling G. Phosphorus, Sulfur, Silicon Relat. Elem. 1990, 48: 1 - 28b
Wladislaw B.Marzorati L.Ebeling G. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 48: 163 - 29
Jarvis M. J. Org. Chem. 1977, 42: 2679 - 30
Jarvis M.Bruce A. J. Org. Chem. 1977, 42: 2676 - 31
Meijer J.Vermeer P.Brandsma L. Recl. Trav. Chim. Pays-Bas. 1973, 92: 601 - 32
Verkruijsse HD.Brandsma L. J. Organomet. Chem. 1987, 332: 95 - 33
Levesque G.Gressier JC.Proust M. Synthesis 1981, 12: 963 - 34
Blumenkopf TA. Synth. Commun 1986, 16: 139 - 35
Grisley DW. J. Org. Chem. 1961, 26: 2544Reference Ris Wihthout Link