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Synthesis 2001(12): 1837-1845
DOI: 10.1055/s-2001-17510
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of Stable 2-(Trifluoromethyl)-2,3-dihydro-1H-pyrrol-2-ols and Derived Fluorinated Heterocycles

Orazio A. Attanasi, Paolino Filippone*, Barbara Guidi, Fabio Mantellini, Stefania Santeusanio*
Organic Chemistry Institute, University of Urbino, Piazza della Repubblica 13, 61029 Urbino, Italy
Fax: +39(0722)2907; e-Mail: attanasi@uniurb.it;
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Publikationsverlauf

Received 14 May 2001
Publikationsdatum:
11. August 2004 (online)

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Abstract

1,2-Diaza-1,3-butadienes react regioselectively with trifluoromethylated β-dicarbonyl compounds to give stable 2-(trifluoromethyl)-2,3-dihydro-1H-pyrrol-2-ol derivatives, which upon treatment with trifluoromethanesulphonic anhydride or with heterogeneous catalysts give rise to fluorinated 1-aminopyrrole derivatives in good to excellent yields. The reaction of 2-(trifluoromethyl)-2,3-dihydro-1H-pyrrol-2-ol derivative with 2-haloketone affords fluorinated furo[2,3-b]pyrroline derivative, while that of diethyl 1-[(anilinocarbonyl)amino]-2-methyl-5-(trifluoromethyl)-1H-pyrrole-3,4-dicarboxylate with hydrazine hydrate affords fluorinated pyrrolo[3,4-d]pyridazindione derivative.

Key words

1,2-diaza-1,3-butadienes - Michael additions - regioselectivity - 2-(trifluoromethyl)-2,3-dihydro-1H-pyrrol-2-ols - heterocycles

    References

  • 1 Attanasi OA. Caglioti L. Org. Prep. Proced. Int.  1986,  18:  299 ; and references cited therein
    CrossrefSuche in Google Scholar
  • 2 Banert K. In Targets in Heterocycles Systems-Chemistry and Properties   Vol. 3:  Attanasi OA. Spinelli D. Società Chimica Italiana; Rome: 2000.  Chap. 1. p.1 
    Suche in Google Scholar
  • 3 Polanc S. In Targets in Heterocycles Systems-Chemistry and Properties   Vol. 3:  Attanasi OA. Spinelli D. Società Chimica Italiana; Rome: 2000.  Chap. 2. p.33 ; and references cited therein
    Suche in Google Scholar
  • 4 Gilchrist TL. Sanchez Romero OA. Wasson RC. J. Chem. Soc., Perkin Trans. 1  1989,  353 
    Crossref
  • 5 Vors J. J. Heterocycl. Chem.  1990,  27:  579 
    Suche in Google Scholar
  • 6 Ferguson G. Lough AJ. Mackay D. Weeratunga G. J. Chem. Soc., Perkin Trans. 1  1991,  3361 
    Crossref
  • 7 Clarke SJ. Gilchrist TL. Lemos A. Roberts TG. Tetrahedron  1991,  47:  5615 
    CrossrefSuche in Google Scholar
  • 8 Gilchrist TL. Lemos A. J. Chem. Soc., Perkin Trans. 1  1993,  1391 
    Crossref
  • 9 Baccolini G. Orsolan G. Mezzina E. Tetrahedron Lett.  1995,  36:  447 
    CrossrefSuche in Google Scholar
  • 10 South MS. Jakuboski TL. Westmeyer MD. Dukesherer DR. J. Org. Chem.  1996,  61:  8921 
    CrossrefSuche in Google Scholar
  • 11 Caposcialli N. Dell’Erba C. Novi M. Petrillo G. Tavani C. Tetrahedron  1998,  54:  5315 
    CrossrefSuche in Google Scholar
  • 12 Palacios F. Aparicio D. de los Santos JM. Tetrahedron  1999,  55:  13767 ; and references cited therein
    CrossrefSuche in Google Scholar
  • 13 Attanasi OA. Filippone P. Synlett  1997,  1128 ; and references cited therein
    Thieme Connect
  • 14 Attanasi OA. DeCrescentini L. Filippone P. Perrulli FR. Santeusanio S. Synlett  1999,  339 
    Thieme Connect
  • 15 Attanasi OA. Filippone P. Fiorucci C. Foresti E. Mantellini F. J. Org. Chem.  1998,  63:  9880 
    CrossrefSuche in Google Scholar
  • 16 Attanasi OA. DeCrescentini L. Filippone P. Guidi B. Perrulli FR. Santeusanio S. Synlett  1999,  1367 
    Thieme Connect
  • 17 Arcadi A. Attanasi OA. Guidi B. Rossi E. Santeusanio S. Eur. J. Org. Chem.  1999,  3117 
    Crossref
  • 18 Attanasi OA. Filippone P. Foresti E. Guidi B. Santeusanio S. Tetrahedron  1999,  55:  13423 
    CrossrefSuche in Google Scholar
  • 19 Attanasi OA. Ballini R. DeCrescentini L. Filippone P. Mantellini F. J. Org. Chem.  1999,  64:  9653 
    CrossrefSuche in Google Scholar
  • 20 Attanasi OA. DeCrescentini L. Filippone P. Foresti E. Mantellini F. J. Org. Chem.  2000,  65:  2820 
    CrossrefSuche in Google Scholar
  • 21 Attanasi OA. DeCrescentini L. Filippone P. Mantellini F. Synlett  2001,  557 
  • 22 Attanasi OA. Filippone P. Guidi B. Perrulli FR. Santeusanio S. Synlett  2001,  144 
  • 23 Attanasi OA. Filippone P. Perrulli FR. Santeusanio S. Tetrahedron  2001,  57:  1387 
    CrossrefSuche in Google Scholar
  • 24 Cirrincione G. Almerico AM. Aiello E. Dattolo G. Pyrroles Part Two: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Aminopyrroles, The Chemistry of Heterocyclic Compounds   Jones RA. John Wiley & Sons; New York: 1992.  Chap. 3. p.299 
  • 25 Gribble GW. Pyrroles and Benzo Derivatives: Applications   Bird, C., Ed., In Comprehensive Heterocyclic Chemistry II Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Pergamon-Elsevier Science; Amsterdam: 1996.  Chap. 4.
    Suche in Google Scholar
  • 26 Sundberg RJ. Pyrroles and Benzo Derivatives: Synthesis   Bird, C., Ed., In Comprehensive Heterocyclic Chemistry II Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Pergamon-Elsevier Science; Amsterdam: 1996.  Chap. 3.
    Suche in Google Scholar
  • 27 Attanasi OA. Grossi M. Serra-Zanetti F. Foresti E. Tetrahedron  1987,  43:  4249 
    CrossrefSuche in Google Scholar
  • 28 Attanasi OA. Santeusanio S. Serra-Zanetti F. Gazz. Chim. Ital.  1989,  119:  631 
    Suche in Google Scholar
  • 29 Attanasi OA. DeCrescentini L. McKillop A. Santeusanio S. Serra-Zanetti F. J. Chem. Soc., Perkin Trans. 1  1992,  3099 
    Crossref
  • 30 Attanasi OA. Ballini R. Liao Z. Santeusanio S. Serra-Zanetti F. Tetrahedron  1993,  49:  7027 
    CrossrefSuche in Google Scholar
  • 31a Welch JT. Selective Fluorination in Organic and Bioorganic Chemistry   ACS Symposium Series 456; Washington D. C.: 1991. 
  • 31b Welch JT. Eswarakrishnan S. Fluorine in Bioorganic Chemistry   Wiley; New York: 1991. 
  • 32 Tipping AE. Jimenez P. Ballesteros E. Abboud J.-LM. Yànez M. Essefar M. Elguero J. J. Org. Chem.  1994,  59:  1039 
    Suche in Google Scholar
  • 33 Jones BG. Branch SK. Thompson AS. Threadgill MD. J. Chem. Soc., Perkin Trans. 1  1996,  2685 
    Crossref
  • 34 Alvernhe G. Langlois B. Laurent A. Le Drean I. Selmi A. Weissenfels M. Tetrahedron Lett.  1991,  32:  643 
    CrossrefSuche in Google Scholar
  • 35 Katsuyama I. Funabiki K. Matsui M. Muramatsu H. Shibata K. Tetrahedron Lett.  1996,  37:  4177 
    CrossrefSuche in Google Scholar
  • 36a Filler R. Kobayashi Y. Yagupolskii LM. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications   Elsevier; Amsterdam: 1993. 
  • 36b Filler R. Kobayashi Y. Biomedicinal Aspects of Fluorine Chemistry   Kodansha/Elsevier; New York: 1982. 
  • 37a Uneyama K. Sugimoto K. J. Org. Chem.  1992,  57:  6014 
    CrossrefSuche in Google Scholar
  • 37b Yoshioka H. Nakayama C. Matsuo N. J. Synth. Org. Chem. Jpn.  1984,  42:  809 
    CrossrefSuche in Google Scholar
  • 38 Meshram HM. Synthesis  1992,  943 
    Thieme Connect
  • 39 Baxter AJG. Fuher J. Teague SJ. Synthesis  1994,  207 
    Thieme Connect
  • 40 Threadgill MD. Heer AK. Jones BG. J. Fluorine Chem.  1993,  65:  21 
    Suche in Google Scholar
  • 41 Jones BG. Branch SK. Threadgill MD. Wilman DEV. J. Fluorine Chem.  1995,  74:  221 
    Suche in Google Scholar
  • 42 Sommer S. Tetrahedron Lett.  1977,  18:  117 
    CrossrefSuche in Google Scholar
  • 43 Attanasi OA. Filippone P. Mei A. Santeusanio S. Synthesis  1984,  671 
    Thieme Connect
  • 44 Attanasi OA. Filippone P. Mei A. Santeusanio S. Synthesis  1984,  873 
    Thieme Connect