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Synthesis 2008(13): 2039-2044  
DOI: 10.1055/s-2008-1067108
PAPER
© Georg Thieme Verlag Stuttgart · New York

First Synthesis of 3,6′- and 3,7′-Biquinoline Derivatives

Sidonie Broch, Fabrice Anizon, Pascale Moreau*
Laboratoire de Synthèse Et Etude de Systèmes d’Intérêt Biologique-UMR CNRS 6504, Université Blaise Pascal, 24 Avenue des Landais, 63177 Aubière Cedex, France
Fax: +33(4)73407717; e-Mail: Pascale.MOREAU@univ-bpclermont.fr;
Further Information

Publication History

Received 12 February 2008
Publication Date:
21 May 2008 (online)

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Abstract

The preparation of new 3,6′- and 3,7′-biquinoline derivatives was achieved by microwave-assisted Suzuki cross-coupling between N-protected 6- or 7-bromoquinolin-2(1H)-ones and quinolin-3-ylboronic acid. Moreover, a new synthesis of 7-bromoquinolin-2(1H)-one leading solely to the 7-substituted isomer was carried out.

Keywords

quinoline - quinolinone - 6-bromoquinolin-2(1H)-one - 7-bromoquinolin-2(1H)-one - Suzuki cross-coupling

    References

  • 1 Li Q. Woods KW. Wang W. Lin N.-H. Claiborne A. Gu W.-Z. Cohen J. Stoll VS. Hutchins C. Frost D. Rosenberg SH. Sham HL. Bioorg. Med. Chem. Lett.  2005,  15:  2033 
    CrossrefGoogle Scholar
  • 2 Kelly TR. Bilodeau MT. Bridger GJ. Zhao C. Tetrahedron Lett.  1989,  30:  2485 
    CrossrefGoogle Scholar
  • 3 Araki K. Tada K.-I. Abe M. Mutai T. J. Chem. Soc., Perkin Trans. 2  1998,  1391 
    CrossrefGoogle Scholar
  • 4 Walsh TF. Toupence RB. Young JR. Huang SX. Ujjainwalla F. Devita RJ. Goulet MT. Wyvratt MJ. Fisher MH. Lo J.-L. Ren N. Yudkovitz JB. Yang YT. Cheng K. Smith RG. Bioorg. Med. Chem. Lett.  2000,  10:  443 
    CrossrefGoogle Scholar
  • 5 Young JR. Huang SX. Chen I. Walsh TF. Devita RJ. Wyvratt MJ. Goulet MT. Ren N. Lo J. Yang YT. Yudkovitz JB. Cheng K. Smith RG. Bioorg. Med. Chem. Lett.  2000,  10:  1723 
    CrossrefGoogle Scholar
  • 6 Zimmerman SC. Duerr BF. J. Org. Chem.  1992,  57:  2215 
    CrossrefGoogle Scholar
  • 7 Zaragoza F. Stephensen H. Peschke B. Rimvall K. J. Med. Chem.  2005,  48:  306 
    CrossrefGoogle Scholar
  • 8 Tedesco R. Shaw AN. Bambal R. Chai D. Concha NO. Darcy MG. Dhanak D. Fitch DM. Gates A. Gerhardt WG. Halegoua DL. Han C. Hofmann GA. Johnston VK. Kaura AC. Liu N. Keenan RM. Lin-Goerke J. Sarisky RT. Wiggall KJ. Zimmerman MN. Duffy KJ. J. Med. Chem.  2006,  49:  971 
    CrossrefGoogle Scholar
  • 9 Huang S. Garbaccio RM. Fraley ME. Steen J. Kreatsoulas C. Hartman G. Stirdivant S. Drakas B. Rickert K. Walsh E. Hamilton K. Buser CA. Hardwick J. Mao X. Abrams M. Beck S. Tao W. Lobell R. Sepp-Lorenzino L. Yan Y. Ikuta M. Murphy JZ. Sardana V. Munshi S. Kuo L. Reilly M. Mahan E. Bioorg. Med. Chem. Lett.  2006,  16:  5907 
    CrossrefGoogle Scholar
  • 10 Kajigaeshi S. Kakinami T. Yamasaki H. Fujisaki S. Okamoto T. Bull. Chem. Soc. Jpn.  1988,  61:  600 
    CrossrefGoogle Scholar
  • 11 Plevyak JE. Dickerson JE. Heck RF. J. Org. Chem.  1979,  44:  4078 
    CrossrefGoogle Scholar
  • 12 Breault G, Eyermann CJ, Geng B, Morningstar M, and Reck F. inventors; WO  2006,134,378.  ; Chem. Abstr. 2007, 146, 81779
  • 13 Horwitz JP, Corbett TH, Palomino E, Polin L, and Hazeldine ST. inventors; WO  2004,004,651.  ; Chem. Abstr. 2004, 140, 99632
  • 14 Roberts DA, and Campbell SF. inventors; CN  85100796.  ; Chem. Abstr. 1989, 110, 114694
  • 15 Alabaster CT. Bell AS. Campbell SF. Ellis P. Henderson CG. Roberts DA. Ruddock KS. Samuels GMR. Stefaniak MH. J. Med. Chem.  1988,  31:  2048 
    CrossrefGoogle Scholar
  • 16 Roberts DAM, and Campbell SF. inventors; EP  0,148,623.  ; Chem. Abstr. 1986, 104, 19525
  • 17 Becker MR. Ewing WR. Davis RS. Pauls HW. Ly C. Li A. Mason HJ. Choi-Sledeski YM. Spada AP. Chu V. Brown KD. Colussi DJ. Leadley RJ. Bentley R. Bostwick J. Kasiewski C. Morgan S. Bioorg. Med. Chem. Lett.  1999,  9:  2753 
    CrossrefGoogle Scholar
  • 18 Flatt AK. Yao Y. Maya F. Tour JM. J. Org. Chem.  2004,  69:  1752 
    CrossrefGoogle Scholar
  • 19 Sakamoto T. Kondo Y. Iwashita S. Yamanaka H. Chem. Pharm. Bull.  1987,  35:  1823 
    CrossrefGoogle Scholar
  • 20 Li W. Nelson DP. Jensen MS. Hoerrner RS. Cai D. Larsen RD. Reider PJ. J. Org. Chem.  2002,  67:  5394 
    CrossrefGoogle Scholar