Download PDF
Synthesis 2011(17): 2754-2760  
DOI: 10.1055/s-0030-1260133
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile and Convenient Syntheses of Fluorine-Containing Pyrido[2,3-h]-quinazolines and 1,7-Phenanthrolines by Condensation Reactions of 6,8-Bis(trifluoroacetyl)quinolin-5-amine with Carbonyl Compounds

Mamoru Hinoshitaa, Dai Shibatab, Mizuki Hatakenakaa, Etsuji Okada*a
a 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;
b Graduate School of Science and Technology, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan
Further Information

Publication History

Received 21 April 2011
Publication Date:
21 July 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

6,8-Bis(trifluoroacetyl)quinolin-5-amine reacted easily with various aldehydes in the presence of aqueous ammonia to afford trifluoromethylated pyrido[2,3-h]quinazoline derivatives and 1,7-phenanthroline derivatives in good to excellent yields. Under almost the same conditions, the use of ketones instead of aldehydes gave 1,7-phenanthroline derivatives selectively, except in the case of cyclohexanone.

Key words

pyrido[2,3-h]quinazolines - 1,7-phenanthrolines - fluorine - condensation reaction - quinolin-5-amines

    References

  • 1a Dey AS. Joullié MM. J. Heterocycl. Chem.  1965,  2:  120 
    Google Scholar
  • 1b Nyquist EB. Joullié MM. J. Heterocycl. Chem.  1967,  4:  539 
    Google Scholar
  • 1c Loy M. Joullié MM. J. Med. Chem.  1973,  16:  549 
    Google Scholar
  • 1d Filler R. Organofluorine Chemicals and Their Industrial Applications   Ellis Horwood; London: 1979. 
    Google Scholar
  • 1e Filler R. Kobayashi Y. Biomedicinal Aspects of Fluorine Chemistry   Kodansha & Elsevier Biomedical; Tokyo: 1982. 
    Google Scholar
  • 1f Welch JT. Tetrahedron  1987,  43:  3123 
    Google Scholar
  • 1g Filler R. Kobayashi Y. Yagupolskii LM. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications   Elsevier; Amsterdam: 1993. 
    Google Scholar
  • 1h Burger K. Wucherpfennig U. Brunner E. Adv. Heterocycl. Chem.  1994,  60:  1 
    Google Scholar
  • 2a Newkome GR. Paudler WW. Contemporary Heterocyclic Chemistry   Wiley; New York: 1982. 
    Google Scholar
  • 2b Gilchrist TL. Heterocyclic Chemistry   Pitman Publishing; London: 1985. 
    Google Scholar
  • 3a Czuba W. Rocz. Chem.  1967,  41:  289 ; Chem. Abstr. 1967, 67, 54056
    Google Scholar
  • 3b Tomioka Y. Ohkubo K. Yamazaki M. Chem. Pharm. Bul.  1985,  33:  1360 
    Google Scholar
  • 3c Ostrowski S. Heterocycles  1996,  43:  389 
    Google Scholar
  • 3d Murashima T. Fujita K. Ono K. Ogawa T. Uno H. Ono N. J. Chem. Soc., Perkin Trans. 1  1996,  1403 
    Google Scholar
  • 3e Kumari TA. Reddy MS. Rao PJ. Synth. Commun.  2002,  32:  235 
    Google Scholar
  • 3f Kumari TA. Rao PJ. Synth. Commun.  2002,  32:  2261 
    Google Scholar
  • 4 Prado S. Michel S. Tillequin F. Koch M. Pfeiffer B. Pierré A. Léonce S. Colson P. Baldeyrou B. Lansiaux A. Bailly C. Bioorg. Med. Chem.  2004,  12:  3943 
    CrossrefGoogle Scholar
  • 5a 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
  • 5b Scheibel LW. Adler A. Mol. Pharmacol.  1982,  22:  140 
    Google Scholar
  • 6a Cuesta J. Read MA. Neidle S. Mini-Rev. Med. Chem.  2003,  3:  11 
    Google Scholar
  • 6b 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
  • 7 Pedireddi VR. Cryst. Growth Des.  2001,  1:  383 
    CrossrefGoogle Scholar
  • Representative examples:
  • 8a Hojo M. Masuda R. Okada E. Synthesis  1990,  481 
    Google Scholar
  • 8b Okada E. Tone H. Tsukushi N. Otsuki Y. Takeuchi H. Hojo M. Heterocycles  1997,  45:  339 
    Google Scholar
  • 8c Okada E. Tsukushi N. Heterocycles  2000,  53:  127 
    Google Scholar
  • 8d Shibata D. Okada E. Miyaoku T. Molette J. Médebielle M. Tetrahedron  2009,  65:  6189 
    Google Scholar
  • 9a Okada E. Masuda R. Hojo M. Tone H. Gotoh N. Huang T.-K. Heterocycles  1995,  40:  905 
    Google Scholar
  • 9b Okada E. Tsukushi N. Huang T.-K. Tone H. Gotoh N. Takeuchi H. Hojo M. Heterocycles  1998,  48:  95 
    Google Scholar
  • 9c Okada E. Tsukushi N. Heterocycles  1999,  51:  2471 
    Google Scholar
  • 9d Okada E. Tsukushi N. Synthesis  2000,  499 
    Google Scholar
  • 10 Shibata D. Okada E. Hinoshita M. Médebielle M. Synthesis  2009,  3039 
    Article in Thieme ConnectGoogle Scholar
  • 11 Reduction of 5-nitroquinoline with Fe/AcOH: Mellor JM. Merriman GD. Steroids  1995,  60:  693 
    CrossrefGoogle Scholar
  • 12 N,N-Dimethylation of 5-aminoquinoline with MeI/LiNH2: Feller C. Renault J. Bull. Soc. Chim. Fr.  1973,  1112 
    Google Scholar
  • 13 Review: Marco-Contelles J. Pérez-Mayoral E. Samadi A. Carreiras MD. Soriano E. Chem. Rev.  2009,  109:  2652 
    CrossrefPubMedGoogle Scholar