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Synthesis 2006(22): 3855-3858  
DOI: 10.1055/s-2006-950303
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Step Polyfunctionalization of (Methylthio)thiophenes

Claudia Fattuoni*, Michele Usai, Maria G. Cabiddu, Enzo Cadoni, Stefania De Montis, Salvatore Cabiddu
Dipartimento di Scienze Chimiche, Università di Cagliari, Cittadella Universitaria di Monserrato, SS. 554, Bivio per Sestu, 09042 Monserrato (CA), Italy
Fax: +39(070)6754388; e-Mail: cfattuon@unica.it;
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Publication History

Received 6 July 2006
Publication Date:
09 October 2006 (online)

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Abstract

The one-step polyfunctionalization of 2- and 3-(methylthio)thiophenes was investigated. Direct polymetalation with superbases followed by quenching with an appropriate electrophile led to 2,αS-disubstituted derivatives starting from 2-(methyl­thio)thiophene, and 2,5,αS-trisubstituted derivatives starting from 3-(methylthio)thiophene.

Key words

heterocycles - metalation - regioselectivity - superbases - thiophenes

    References

  • 1 Hrib NJ. Jurcak JG. Bregna DE. Dunn RW. Geyer HM. Hartman HB. Roehr JE. Rogers KL. Rush DK. Szczepanik AM. Szewerak MR. Wilmot CA. Conway PG. J. Med. Chem.  1992,  35:  2712 ; and references cited therein
    CrossrefGoogle Scholar
  • 2 Connor DT. Cetenko WA. Mullican MD. Sorenson RJ. Unangst P. Weikert RJ. Adolphson RL. Kennedy JA. Thueson DO. Wright C. Conroy MC. J. Med. Chem.  1992,  35:  958 ; and references cited therein
    CrossrefGoogle Scholar
  • 3 Ahlheim M. Barzoukas M. Bedworth PV. Blanchard-Desce M. Fort A. Hu ZY. Marder SR. Perry JW. Runser C. Staehelin M. Zysset B. Science (Washington DC)  1996,  271:  335 
    CrossrefGoogle Scholar
  • 4 Benincori T. Gladiali S. Rizzo S. Sannicolò F. J. Org. Chem.  2001,  66:  5940 
    CrossrefGoogle Scholar
  • 5 Mandal SS. Samanta SS. Deb C. De A. J. Chem. Soc., Perkin Trans. 1  1998,  2559 
    CrossrefGoogle Scholar
  • 6 Mukherjee C. Kamila S. De A. Tetrahedron  2003,  59:  4767 
    CrossrefGoogle Scholar
  • 7 Snieckus V. Chem. Rev.  1990,  90:  879 ; and references cited therein
    Google Scholar
  • 8 Cabiddu S. Floris C. Melis S. Tetrahedron Lett.  1986,  27:  4625 
    CrossrefGoogle Scholar
  • 9 Cabiddu S. Fattuoni C. Floris C. Gelli G. Melis S. J. Organomet. Chem.  1992,  441:  197 
    CrossrefGoogle Scholar
  • 10 Cabiddu S. Fattuoni C. Floris C. Gelli G. Melis S. Tetrahedron  1993,  49:  4965 
    CrossrefGoogle Scholar
  • 11 Brandsma L. Verkruijsse H. In Preparative Polar Organometallic Chemistry 1   Springer-Verlag; Berlin: 1987.  Chap. V.
    Google Scholar
  • 12 Schlosser M. In Modern Synthetic Methods   Vol. 6:  Scheffold R. Verlag HCA; Basel and VCH: Weinheim: 1992. 
    Google Scholar
  • 13 Clayden J. In Organolithium: Selectivity for Synthesis   Pergamon; Amsterdam: 2002.  p.207 
    Google Scholar
  • 14 Duhamel L. Plaquevent JC. J. Org. Chem.  1979,  44:  3404 
    CrossrefGoogle Scholar
  • 15 Gol’dfarb YaL. Pokhil GP. Belen’kii LI. J. Gen. Chem. USSR  1967,  37:  2541 
    Google Scholar