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Synthesis 2009(18): 3039-3046  
DOI: 10.1055/s-0029-1216893
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Synthetic Method for Fluorine-Containing 1,7-Phenanthrolines: Pyridine-Ring Formation Reaction of N-Propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine with Various Nucleophiles

Dai Shibataa, Etsuji Okada*b, Mamoru Hinoshitab, Maurice Médebiellec
a Graduate School of Science and Technology, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan
b Department of Chemical Science and Engineering, Graduate School of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan
Fax: +81(78)8036194; e-Mail: okaetsu@kobe-u.ac.jp;
c Université de Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Laboratoire de Synthèse de Biomolécules (LSB), UMR 5246 CNRS-UCBL-INSA Lyon-CPE Lyon, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne, France
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Publikationsverlauf

Received 25 March 2009
Publikationsdatum:
10. Juli 2009 (online)

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Abstract

Novel fluorine-containing 1,7-phenanthrolines with a variety of substituents at the 3-position were easily synthesized in moderate to high yields by the pyridine-ring formation reaction of N-propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine with various amines, thiols, alcohols, and phenols.

Key words

1,7-phenanthrolines - fluorine - pyridine-ring formation - propargylamines - 5-quinolines

    References

  • 1 Prado S. Michel S. Tillequin F. Koch M. Pfeiffer B. Pierré A. Léonce S. Colson P. Baldeyrou B. Lansiauxe A. Bailly C. Bioorg. Med. Chem.  2004,  12:  3943 
    CrossrefGoogle Scholar
  • 2a Yapi AD. Mustofa M. Valentin A. Chavignon O. Teulade J.-C. Mallie M. Chapat J.-P. Blache Y. Chem. Pharm. Bull.  2000,  48:  1886 
    Google Scholar
  • 2b Scheibel LW. Adler A. Mol. Pharmacol.  1982,  22:  140 
    Google Scholar
  • 3a Cuesta J. Read MA. Neidle S. Mini Rev. Med. Chem.  2003,  3:  11 
    Google Scholar
  • 3b Mergny J.-L. Lacroix L. Teulade-Fichou M.-P. Hounsou C. Guittat L. Hoarau M. Arimondo PB. Vigneron J.-P. Lehn J.-M. Riou J.-F. Garestier T. Hélène C. Proc. Natl. Acad. Sci. U.S.A.  2001,  98:  3062 
    Google Scholar
  • 4 Pedireddi VR. Cryst. Growth Des.  2001,  1:  383 
    CrossrefGoogle Scholar
  • 5a Zhang Q. Chen Y. Zheng YQ. Xia P. Xia Y. Yang ZY. Bastow KF. Morris-Natschke SL. Lee K.-H. Bioorg. Med. Chem.  2003,  11:  1031 
    Google Scholar
  • 5b Mahata PK. Venkatesh C. Kumar UKS. Ila H. Junjappa H. J. Org. Chem.  2003,  68:  3966 
    Google Scholar
  • 5c Graf GI. Hastreiter D. Everson a Silva L. Rebelo RA. Montalban AG. McKillop A. Tetrahedron  2002,  58:  9095 
    Google Scholar
  • 5d Bethke J. Margaretha P. Helv. Chim. Acta  2002,  85:  544 
    Google Scholar
  • 5e Molock FF. Boykin DW. J. Heterocycl. Chem.  1983,  20:  681 
    Google Scholar
  • 6a Kouznetsov VV. Mendez LYV. Tibaduiza B. Ochoa C. Pereira DM. Ruiz JJN. Portillo CF. Serrano SM. Barrio AG. Bahsas A. Amaro-Luis J. Arch. Pharm. (Weinheim, Ger.)  2004,  337:  127 
    Google Scholar
  • 6b Jordis U. Sauter F. Rudolf M. Cai G. Monatsh. Chem.  1988,  119:  761 
    Google Scholar
  • 7a Tatibouet A. Hancock R. Demeunynck M. Lhomme J. Angew. Chem., Int. Ed. Engl.  1997,  36:  1190 
    Google Scholar
  • 7b Nutaitis CF. Smith K. Org. Prep. Proced. Int.  2007,  39:  611 
    Google Scholar
  • 7c Jastrzebska-Glapa M. Mlochowski J. Rocz. Chem.  1976,  50:  987 
    Google Scholar
  • 8a Filler R. Kobayashi Y. Biomedicinal Aspects of Fluorine Chemistry   Kodansha & Elsevier Biomedical; Tokyo: 1982.  p.1-240  
    Google Scholar
  • 8b Welch JT. Tetrahedron  1987,  43:  3123 
    Google Scholar
  • 8c Filler R. Kobayashi Y. Yagupolskii LM. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications   Elsevier; Amsterdam: 1993.  p.1-380  
    Google Scholar
  • 8d Burger K. Wucherpfennig U. Brunner E. Adv. Heterocycl. Chem.  1994,  60:  1 
    Google Scholar
  • 9a Hojo M. Masuda R. Okada E. Tetrahedron Lett.  1987,  28:  6199 
    Google Scholar
  • 9b Hojo M. Masuda R. Okada E. Miya H. Synthesis  1989,  870 
    Google Scholar
  • 10a Okada E. Tsukushi N. Synlett  1999,  210 
    Google Scholar
  • 10b Okada E. Tsukushi N. Shimomura N. Synthesis  2000,  237 
    Google Scholar
  • 11 Okada E. Tsukushi N. Otsuki Y. Nishiyama S. Fukuda T. Synlett  1999,  126 ; and references cited therein
    Artikel in Thieme ConnectGoogle Scholar
  • 12 Okada E. Tsukushi N. Shimomura N. Synthesis  2000,  1822 ; and references cited therein
    Artikel in Thieme ConnectGoogle Scholar
  • 13 Okada E. Tone H. Tsukushi N. Otsuki Y. Takeuchi H. Hojo M. Heterocycles  1997,  45:  339 
    CrossrefGoogle Scholar
  • 14 Shibata D. Okada E. Molette J. Médebielle M. Tetrahedron Lett.  2008,  49:  7161 
    CrossrefGoogle Scholar
  • 15 Mellor JO. Merriman GD. Steroids  1995,  60:  693 
    CrossrefGoogle Scholar
  • 16 Feller C. Renault J. Bull. Soc. Chim. Fr.  1973,  3:  1112 
    Google Scholar