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Synthesis 2005(20): 3581-3588  
DOI: 10.1055/s-2005-916028
PAPER
© Georg Thieme Verlag Stuttgart · New York

Versatile and Convenient Methods for the Synthesis of C-2 and C-3 Functionalised 5-Azaindoles

Myriam Lefoix, Jean-Philippe Daillant, Sylvain Routier, Jean-Yves Mérour*, Isabelle Gillaizeau, Gérard Coudert*
Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d’Orléans, Rue de Chartres, BP 6759, 45067 Orléans Cedex 2, France
Fax: +33(2)38417281; e-Mail: jean-yves.merour@univ-orleans.fr; e-Mail: gerard-coudert@univ-orleans.fr;
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Publikationsverlauf

Received 26 April 2005
Publikationsdatum:
16. September 2005 (online)

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Abstract

Functionalisation at C-2 and C-3 of N-protected-5-azaindole leads to a variety of very useful new substituted 5-azaindole derivatives in fair to good yields.

Keywords

5-azaindole - lithiation - stannylation - 2-substituted-5-azaindole - 3-substituted-5-azaindole

    References

  • 1a Alonso F. Beletskaya IP. Yus M. Chem. Rev.  2004,  104:  3079 
    CrossrefPubMedGoogle Scholar
  • 1b Knölker H.-J. Reddy KR. Chem. Rev.  2002,  102:  4303 
    CrossrefPubMedGoogle Scholar
  • 2a Le Hyaric M. Viera de Almeida M. Norade Souza MV. Quim. Nova  2002,  25:  1165 
    CrossrefGoogle Scholar
  • 2b Mérour J.-Y. Joseph B. Curr. Org. Chem.  2000,  5:  471 
    CrossrefGoogle Scholar
  • 2c L’Heureux A. Thibault C. Ruel R. Tetrahedron Lett.  2004,  45:  2317 
    CrossrefGoogle Scholar
  • 2d Lane BS. Sames D. Org. Lett.  2004,  6:  2897 
    CrossrefGoogle Scholar
  • 3a Mendiola J. Baeza A. Alvarez-Builla JJ. J. Org. Chem.  2004,  69:  4974 
    Google Scholar
  • 3b Molina P. Fresnada PM. Delgado S. J. Org. Chem.  2003,  68:  489 
    Google Scholar
  • 3c Ahaidar A. Fernández D. Danelón G. Cuevas C. Manzanares I. Albericio F. Joule JA. Álvarez M. J. Org. Chem.  2003,  68:  10020 
    Google Scholar
  • 3d Anderson RJ. Morris JC. Tetrahedron Lett.  2001,  42:  8697 
    Google Scholar
  • 3e Fernández D. Ahaidar A. Danelón G. Cironi P. Marfil M. Pérez O. Cuevas C. Albericio F. Joule JA. Álvarez M. Monatsh. Chem.  2004,  135:  614 
    Google Scholar
  • 4a Curtis NR. Kulagowski JJ. Leeson PD. Ridgill MP. Emms F. Freedman SB. Patel S. Patel S. Bioorg. Med. Chem. Lett.  1999,  9:  585 
    CrossrefGoogle Scholar
  • 4b Oh S.-J. Lee KC. Lee S.-Y. Ryu EK. Saji H. Choe YS. Chi DY. Kim SE. Lee J. Kim B.-T. Bioorg. Med. Chem.  2004,  12:  5505 
    CrossrefGoogle Scholar
  • 5 Desarbre E. Coudret S. Meheust C. Mérour J.-Y. Tetrahedron  1997,  53:  3637 
    CrossrefGoogle Scholar
  • 6 Joseph B. Da Costa H. Mérour J.-Y. Léonce S. Tetrahedron  2000,  56:  3189 
    Google Scholar
  • 7 Routier S. Ayerbe N. Mérour J.-Y. Coudert G. Bailly C. Pierré A. Pfeiffer B. Caignard D.-H. Renard P. Tetrahedron  2002,  58:  6621 
    CrossrefGoogle Scholar
  • 8a Praly-Deprez I. Rivalle C. Belehradek J. Huel C. Bisagni E. J. Chem. Soc., Perkin Trans. 1  1991,  3173 
    CrossrefGoogle Scholar
  • 8b Bisagni E. Chi Hung N. Lhoste JM. Tetrahedron  1983,  39:  1777 
    CrossrefGoogle Scholar
  • 9 Dormoy J.-R. Heymes A. Tetrahedron  1993,  49:  2885 
    CrossrefGoogle Scholar
  • 10a Eldrup AB. Prhavc M. Brooks J. Bhat B. Prakash TP. Song Q. Bera S. Bhat N. Dande P. Cook PD. Bennett CF. Carroll SS. Ball RG. Bosserman M. Burlein C. Colwell LF. Fay JF. Flores OA. Getty K. LaFemina RL. Leone J. MacCoss M. McMasters DR. Tomassini JE. Von Langen D. Wolanski B. Olsen DB. J. Med. Chem.  2004,  47:  5284 
    CrossrefGoogle Scholar
  • 10b McCort G. Hoornaert C. Aletru M. Denys C. Duclos O. Cadilhac C. Guilpain E. Dellac G. Janiak P. Galzin A.-M. Delahaye M. Guilbert F. O’Connor S. Bioorg. Med. Chem.  2001,  9:  2129 
    CrossrefGoogle Scholar
  • 10c Cooper LC. Chicchi GG. Dinnell K. Elliott JM. Hollingworth GJ. Kurtz MM. Locker KL. Morrison D. Shaw DE. Tsao K.-L. Watt AP. Williams AR. Swain CJ. Bioorg. Med. Chem. Lett.  2001,  11:  1233 
    CrossrefGoogle Scholar
  • 10d Gong Y. Becker M. Choi-Sledeski YM. Davis RS. Salvino JM. Chu V. Brown KDH. Pauls W. Bioorg. Med. Chem. Lett.  2000,  10:  1033 
    CrossrefGoogle Scholar
  • 10e Beck B. Hess S. Dömling A. Bioorg. Med. Chem. Lett.  2000,  10:  1701 
    CrossrefGoogle Scholar
  • 10f Takeuchi K. Bastian JA. Gifford-Moore DS. Harper RW. Miller SC. Mullaney JTD. Sall J. Smith GF. Zhang M. Fisher MJ. Bioorg. Med. Chem. Lett.  2000,  10:  2347 
    CrossrefGoogle Scholar
  • 10g Mazéas D. Guillaumet G. Viaud M.-C. Heterocycles  1999,  50:  1065 
    CrossrefGoogle Scholar
  • 11 Choi-Sledeski YM. Kearney R. Poli G. Pauls H. Gardner C. Gong Y. Becker M. Davis R. Spada A. Liang G. Chu V. Brown K. Collussi D. Leadley R. Rebello S. Moxey P. Morgan S. Bentley R. Kasiewski C. Maignan S. Guilloteau J.-P. Mikol V. J. Med. Chem.  2003,  46:  681 
    CrossrefGoogle Scholar
  • 12a Choi-Sledeski YM, Pauls HW, Barton JN, Ewing WR, Green DM, Becker MR, Gong Y, and Levell J. inventors; US  6281227. 
  • 12b Scherlock MH, and Tom WC. inventors; US  5023265. 
  • 12c Mantovanini M, Melillo G, and Daffonchio L. inventors; WO  95/04742. 
  • 12d Bradley ST, Krulle TM, Murray PJ, Procter MJ, Rowley RJ, Sambrook SCP, and Thomas GH. inventors; WO  2004104001. 
  • 12e Zhang H.-C, Maryanoff BE, and Ye H. inventors; US  20040192718. 
  • 13 Xu L. Lewis IR. Davidsen SK. Summers JB. Tetrahedron Lett.  1998,  39:  5159 
    CrossrefGoogle Scholar
  • 14 Zhang Z. Yang Z. Wong H. Zhu J. Meanwell NA. Kadow JF. Wang T. J. Org. Chem.  2002,  67:  6226 
    CrossrefPubMedGoogle Scholar
  • 15 Kelly TA. McNeil DW. Rose JM. Davi E. Shih C.-K. Grob PM. J. Med. Chem.  1997,  40:  2430 
    CrossrefGoogle Scholar