Download PDF
Synthesis 2003(8): 1191-1200
DOI: 10.1055/s-2003-39401
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Triflic Anhydride-Promoted Cyclization of Sulfides: A Convenient Synthesis of Fused Sulfur Heterocycles

Nikolay E. Shevchenko, Valentine G. Nenajdenko*, Elizabeth S. Balenkova
Department of Chemistry, Moscow State University, Moscow, 119992, Russia
Fax: +7(095)9328846; e-Mail: nen@acylium.chem.msu.ru;
Further Information

Publication History

Received 6 March 2003
Publication Date:
26 May 2003 (online)

    Permissions and Reprints All articles of this category

Abstract

A new approach to the synthesis of annulated sulfur heterocycles based on triflic anhydride-promoted cyclization of the hetaryl(aryl) containing alkyl sulfides was elaborated. Smooth de­methylation of initially formed cyclic sulfonium salts by treatment with triethylamine afforded a number of five-, six- and seven-membered fused sulfur heterocycles. Unexpected ring opening took place in the reaction of diethylamine with 5-membered sulfonium salts.

Key words

cyclizations - electrophilic aromatic substitutions - sulfur heterocycles - bicyclic compounds - sulfonylsulfonium salts

    References

  • 1 Baraznenok IL. Nenajdenko VG. Balenkova ES. Tetrahedron  2000,  56:  3077 
    CrossrefGoogle Scholar
  • 2 Nenajdenko VG. Vertelezkij PV. Koldobskij AB. Alabugin IV. Balenkova ES. J. Org. Chem.  1997,  62:  2483 
    CrossrefGoogle Scholar
  • 3a Nenajdenko VG. Shevchenko NE. Balenkova ES. Alabugin IV. Chem. Rev.  2003,  103:  229 
    Google Scholar
  • 3b Nenajdenko VG. Shevchenko NE. Balenkova ES. J. Org. Chem.  1998,  63:  2168 
    Google Scholar
  • 3c Shevchenko NE. Nenajdenko VG. Balenkova ES. Izv. Akad. Nauk., Ser. Khim.  2000,  1421 ; Russ. Chem. Bull. (Engl. Transl); 2000, 49, 1415
    Google Scholar
  • 4 Shevchenko NE. Karpov AS. Zakurdaev EP. Nenajdenko VG. Balenkova ES. Khim. Get. Soed.  2000,  171 ; Chem. Heterocycl. Compd. (Engl. Transl.); 2000, 36: 146
    Google Scholar
  • 5 Clementi S. Fringuelli F. Linda P. Marino G. Savelli G. Taticchi A. J. Chem. Soc., Perkin Trans.2  1973,  2097 
    Google Scholar
  • 6 Nenajdenko VG. Vertelezkij PV. Balenkova ES. Synthesis  1997,  351 
    Article in Thieme ConnectGoogle Scholar
  • 7a Glennon RA. J. Med. Chem.  1987,  30:  1 
    CrossrefGoogle Scholar
  • 7b Depreux P. Lesieur D. Mansour H. Morgan P. Howell HE. Renard P. Caignard D. Pfeiffer B. Delagrange P. Guardiola B. Yous S. Demarque A. Adam G. Andrieux J. J. Med. Chem.  1994,  37:  3231 
    CrossrefGoogle Scholar
  • 7c Parker MA. Marona-Lewicka D. Lucaites VL. Nelson DL. Nichols DE. J. Med. Chem.  1998,  41:  5148 
    CrossrefGoogle Scholar
  • 8 Meth-Cohn O. Gronowitz S. Acta Chem. Scand.  1966,  20:  1577 
    Google Scholar
  • 9 Brandsma L. Preparative Polar Organometallic Chemistry   Vol. 1:  Springer; Heidelberg: 1990. 
    Google Scholar
  • 10 Gilman H. Blatt AH. Org. Synth., Coll. Vol. 1   Wiley; New York: 1941.  p.186 
    Google Scholar
  • 11 Stang PJ. Hanack M. Subramanian LR. Synthesis  1982,  85 
    Article in Thieme ConnectGoogle Scholar
  • 12 Noyce DS. Castenson RL. J. Am. Chem. Soc.  1973,  95:  1247 
    CrossrefGoogle Scholar
  • 13 Bahadur GA. Bailey AS. Middeton NW. Peach JM. J. Chem. Soc., Perkin Trans. 1  1980,  1688 
    Google Scholar
  • 14 Crane CW. Rydon HN. J. Chem. Soc.  1947,  766 
    Google Scholar
  • 15 Heaney H. Ley V. J. Chem. Soc., Perkin Trans. 1  1973,  499 
    CrossrefGoogle Scholar