Efficient New Protocol to Synthesize Aromatic and Heteroaromatic Dithioesters

Isabelle Abrunhosa; Mihaela Gulea; Serge Masson

doi:10.1055/s-2004-822311

PAPER

Efficient New Protocol to Synthesize Aromatic and Heteroaromatic Dithioesters

Isabelle Abrunhosa, Mihaela Gulea, Serge Masson*
Laboratoire de Chimie Moléculaire et Thioorganique (LCMT), UMR CNRS 6507, ENSICAEN-Université de Caen, 6 Bd. Maréchal Juin, 14050 Caen, France
Fax: +33(231)452877; e-Mail: masson@ismra.fr;

Abstract

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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

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Referenzen

References

Reviews:

<A NAME="RP10303SS-1A">1a</A> Metzner P. In Top. Curr. Chem. 204, Organosulfur Chemistry I Page PCB. Springer-Verlag; Berlin: 1999. p.127

<A NAME="RP10303SS-1B">1b</A> Masson S. Heteroat. Chem. 1995, 12: 69

<A NAME="RP10303SS-2A">2a</A> Duus F. In Comprehensive Organic Chemistry, The synthesis and reactions of organic compounds Vol. 3: Jones N. Pergamon; Oxford: 1979. p.373

<A NAME="RP10303SS-2B">2b</A> Bulpin A. Le Roy-Gouvernnec S. Masson S. Phosphorus, Sulfur, Silicon Relat. Elem. 1994, 89: 119

<A NAME="RP10303SS-2C">2c</A> Pfund E. Lequeux T. Masson S. Vazeux M. Org. Lett. 2002, 4: 843

<A NAME="RP10303SS-3A">3a</A> Beslin P. Metzner P. Tetrahedron Lett. 1980, 21: 4657

<A NAME="RP10303SS-3B">3b</A> Vyas DM. Hay GW. Can. J. Chem. 1971, 49: 3755

<A NAME="RP10303SS-3C">3c</A> Vyas DM. Hay GW. J. Chem. Soc., Perkin Trans. 1 1975, 180

<A NAME="RP10303SS-3D">3d</A> Vedejs E. Arnost MJ. Dolphin JM. Eustache J. J. Org. Chem. 1980, 45: 2601

<A NAME="RP10303SS-3E">3e</A> Kirby GW. Lochead AW. Williamson S. J. Chem. Soc., Perkin Trans. 1 1996, 977

<A NAME="RP10303SS-3F">3f</A> Portella C. Shermolovich YG. Tschenn O. Bull. Soc. Chim. Fr. 1997, 134: 697

<A NAME="RP10303SS-3G">3g</A> Boerma JA. Nilsson NH. Senning A. Tetrahedron 1974, 30: 2735

<A NAME="RP10303SS-3H">3h</A> Heuzé B. Gasparova R. Heras M. Masson S. Tetrahedron Lett. 2000, 41: 7327

<A NAME="RP10303SS-3I">3i</A> Heras M. Gulea M. Masson S. Chem. Commun. 2001, 611

<A NAME="RP10303SS-3J">3j</A> Lequeux T. Pfund E. Masson S. Vazeux M. Tetrahedron Lett. 2002, 43: 2033

<A NAME="RP10303SS-4A">4a</A> Beiner JM. Lecadet D. Paquer D. Thuillier A. Bull. Soc. Chim. 1973, 1979

<A NAME="RP10303SS-4B">4b</A> Alcázar V. Tapia I. Morán JR. Tetrahedron 1990, 46: 1057

<A NAME="RP10303SS-4C">4c</A> Mloston G. Heimgartner H. Helv. Chim. Acta 1992, 75: 1825

<A NAME="RP10303SS-4D">4d</A> 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

<A NAME="RP10303SS-5A">5a</A> Levillain J. Masson S. Hudson A. Alberti A. J. Am. Chem. Soc. 1993, 115: 8444

<A NAME="RP10303SS-5B">5b</A> Alberti A. Benaglia M. Della Bona MA. Macciantelli D. Heuzé B. Masson S. Hudson A. J. Chem. Soc., Perkin Trans. 2 1996, 1057

<A NAME="RP10303SS-5C">5c</A> Alberti A. Benaglia M. Bonora M. Borzatta V. Hudson A. Macciantelli D. Masson S. Polym. Degrad. Stab. 1998, 62: 559

<A NAME="RP10303SS-6A">6a</A> Laus M. Papa R. Sparnacci K. Alberti A. Benaglia M. Macciantelli D. Macromolecules 2001, 34: 7269

<A NAME="RP10303SS-6B">6b</A> Mayadunne RTA. Moad G. Rizzardo E. Tetrahedron Lett. 2002, 43: 6811

<A NAME="RP10303SS-6C">6c</A> Hawthorne DG. Moad G. Rizzardo E. Thang SH. Macromolecules 1999, 32: 5457

<A NAME="RP10303SS-6D">6d</A> Stenzel-Rosenbaum M. Davis TP. Chen V. Fane AG. J. Pol. Sci.: Part A: Pol. Chem. 2001, 39: 2777

<A NAME="RP10303SS-6E">6e</A> Quinn JF. Chaplin RPM. Davis TP. J. Pol. Sci.: Part A: Pol. Chem. 2002, 40: 2956

<A NAME="RP10303SS-6F">6f</A> Duréault A. Gnanou Y. Taton D. Destarac M. Leising F. Angew. Chem. Int. Ed. 2003, 42: 2869

<A NAME="RP10303SS-7">7</A> Leflemme N. Marchand P. Gulea M. Masson S. Synthesis 2000, 1143

<A NAME="RP10303SS-8">8</A> Abrunhosa I. Gulea M. Levillain J. Masson S. Tetrahedron: Asymmetry 2001, 2851

<A NAME="RP10303SS-9">9</A> Thiel W. Mayer R. J. Prakt. Chem. 1989, 243

<A NAME="RP10303SS-10">10</A> Lempereur C. Plé N. Turk A. Quéguiner G. Corbin F. Alayrac C. Metzner P. Heterocycles 1998, 48: 2019

<A NAME="RP10303SS-11A">11a</A> Masson S. Saquet M. Thuillier A. Tetrahedron Lett. 1976, 28: 4179

<A NAME="RP10303SS-11B">11b</A> Ramadas SR. Srinivasan PS. Ramachandran J. Sastry VVSK. Synthesis 1983, 605

<A NAME="RP10303SS-11C">11c</A> Metzner P. Thuillier A. Sulfur Reagents in Organic Synthesis Academic Press; London: 1994.

<A NAME="RP10303SS-12A">12a</A> Pedersen BS. Scheibye S. Clausen K. Lawesson SO. Bull. Soc. Chim. Belg. 1978, 87: 293

<A NAME="RP10303SS-12B">12b</A> Yousif MN. Pedersen U. Yde B. Lawesson SO. Tetrahedron 1984, 14: 2663

<A NAME="RP10303SS-12C">12c</A> Voss J. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 43: 129

<A NAME="RP10303SS-13">13</A> Davy H. J. Chem. Soc., Chem. Commun. 1982, 457

<A NAME="RP10303SS-14">14</A> Gosselin P. Masson S. Thuillier A. Tetrahedron Lett. 1978, 30: 2715

<A NAME="RP10303SS-15">15</A> Dieter KR. Lugade AG. Synthesis 1988, 303

<A NAME="RP10303SS-16A">16a</A> Morrison CF. Burnell DJ. Org. Lett. 2000, 3891

<A NAME="RP10303SS-16B">16b</A> Gonnella NC. Lakshmikantham MV. Gava MP. Synth. Commun. 1979, 9: 17

<A NAME="RP10303SS-17A">17a</A> Corbin F. PhD Thesis Université de Caen; France: 1998.

<A NAME="RP10303SS-17B">17b</A> This reference does not contain NMR data: Budzikiewicz H. Lange E. Ockels W. Phosphorus Sulfur Relat. Elem. 1981, 11: 33

<A NAME="RP10303SS-17C">17c</A> Nakajima T. Kashiwabara T. Izawa T. Nakajima S. Bioorg. Med. Chem. Lett. 1994, 4: 2485

<A NAME="RP10303SS-18">18</A> 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

<A NAME="RP10303SS-19">19</A> Léger L. Saquet M. Bull. Soc. Chim. 1975, 3-4: 657

<A NAME="RP10303SS-20">20</A> Jolivet B. Uguen D. Tetrahedron Lett. 2002, 7907

<A NAME="RP10303SS-21">21</A> Trost B. Braslau R. J. Org. Chem. 1988, 53: 532

<A NAME="RP10303SS-22">22</A> Grierson D. Bettiol J.-L. Buck I. Husson H.-P. Rubiralta M. Diez A. J. Org. Chem. 1992, 57: 6414

<A NAME="RP10303SS-23">23</A> Crispino G. Breslow R. J. Org. Chem. 1992, 57: 1849

<A NAME="RP10303SS-24">24</A> Kaufmann T. Jousen R. Chem. Ber. 1977, 110: 3930

<A NAME="RP10303SS-25">25</A> Shaabani A. Teimouri F. Lee D. Synth. Commun. 2003, 33: 1057

<A NAME="RP10303SS-26">26</A> Orita A. Yoshioka N. Struwe P. Braier A. Beckmann A. Otera J. Chem.-Eur. J. 1999, 5: 1355

<A NAME="RP10303SS-27">27</A> Sperandio D. Hansen H.-J. Helv. Chim. Acta 1995, 78: 765

<A NAME="RP10303SS-28A">28a</A> Wladislaw B. Marzorati L. Ebeling G. Phosphorus, Sulfur, Silicon Relat. Elem. 1990, 48: 1

<A NAME="RP10303SS-28B">28b</A> Wladislaw B. Marzorati L. Ebeling G. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 48: 163

<A NAME="RP10303SS-29">29</A> Jarvis M. J. Org. Chem. 1977, 42: 2679

<A NAME="RP10303SS-30">30</A> Jarvis M. Bruce A. J. Org. Chem. 1977, 42: 2676

<A NAME="RP10303SS-31">31</A> Meijer J. Vermeer P. Brandsma L. Recl. Trav. Chim. Pays-Bas. 1973, 92: 601

<A NAME="RP10303SS-32">32</A> Verkruijsse HD. Brandsma L. J. Organomet. Chem. 1987, 332: 95

<A NAME="RP10303SS-33">33</A> Levesque G. Gressier JC. Proust M. Synthesis 1981, 12: 963

<A NAME="RP10303SS-34">34</A> Blumenkopf TA. Synth. Commun 1986, 16: 139

<A NAME="RP10303SS-35">35</A> Grisley DW. J. Org. Chem. 1961, 26: 2544