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Synthesis 2007(4): 558-564  
DOI: 10.1055/s-2007-965898
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel Reaction of 4-(Arylmethylene)-2-phenyloxazol-5(4H)-ones with Pyridin-2-amine: Formation of 3-(Arylmethyl)-3-(benzoylamino)imidazo-[1,2-a]pyridin-2(3H)-ones

Shujiang Tu*, Junyong Zhang, Runhong Jia, Yan Zhang, Bo Jiang, Feng Shi
Department of Chemistry, Xuzhou Normal University, Key Laboratory of Biotechnology for Medicinal Plant, Xuzhou, Jiangsu, 221116, P. R. of China
Fax: +86(516)83403164; e-Mail: laotu@xznu.edu.cn;
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Publication History

Received 28 September 2006
Publication Date:
22 January 2007 (online)

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Abstract

A new series of imidazo[1,2-a]pyridin-2-one derivatives were synthesized by a novel reaction of 4-(arylmethylene)-2-phenyl­oxazol-5(4H)-one with pyridin-2-amine under microwave irradiation in ethylene glycol. The starting materials were easily obtained and the operation was convenient.

Key words

heterocycles - microwave irradiation - 4-(arylmethylene)-2-phenyloxazol-5(4H)-ones - 3-(arylmethyl)-3-(benzoylamino)imidazo[1,2-a]pyridin-2(3H)-ones - cascade reaction

    References

  • 1a Elhakmaoui A. Gueiffier A. Milhavet J.-C. Blache Y. Chapat J.-P. Chavignon O. Teulade J.-C. Snoeck R. Andrei G. De Clercq E. Bioorg. Med. Chem. Lett.  1994,  4:  1937 
    Google Scholar
  • 1b Gueiffier A. Lhassani M. Elhakmaoui A. Snoeck R. Andrei G. Chavignon O. Teulade J.-C. Kerbal A. Essassi EM. Debouzy J.-C. Witvrouw M. Blache Y. Balzarini J. De Clercq E. Chapat J.-P. J. Med. Chem.  1996,  39:  2856 
    Google Scholar
  • 1c Townsend LB, and Drach JC. inventors; WO  09727205.  ; Chem. Abstr., 1997, 127, 190983
  • 1d Gueiffier A. Mavel S. Lhassani M. Elhakmaoui A. Snoeck R. Andrei G. Chavignon O. Teulade J.-C. Witvrouw M. Balzarini J. De Clercq E. Chapat J.-P. J. Med. Chem.  1998,  41:  5108 
    Google Scholar
  • 1e Mavel S. Renou JL. Galtier C. Snoeck R. Andrei G. Balzarini J. De Clercq E. Gueiffier A. Arzneim.-Forsch.  2001,  51:  304 ; Chem. Abstr., 2001, 135, 131730
    Google Scholar
  • 2 Teulade JC. Grassy G. Girard JP. Chapat JP. de Buochberg MMS. Eur. J. Med. Chem.  1978,  13:  271 
    Google Scholar
  • 3a Almirante L. Polo L. Mugnaini A. Provinciali E. Rugarli P. Biancotti A. Gamba A. Murmann W. J. Med. Chem.  1965,  8:  305 
    Google Scholar
  • 3b Abignente E. Arena F. Luraschi E. Saturnino C. Rossi F. Lampa E. Cazzola M. Brandinelli E. Marrazzo R. Marmo E. Rend. Atti. Accad. Sci. Med. Chir.  1985,  139:  313 ; Chem. Abstr., 1986, 105, 126822
    Google Scholar
  • 3c Abignente E. Actual. Chim. Ther.  1991,  18:  193 , Chem. Abstr., 1991, 115, 256028
    Google Scholar
  • 4 Bartholini G. In Imidazopyridines in Anxiety Disorders; L.E.R.S. Monograph Series   Vol. 8:  Raven Press; New York: 1993.  p.1-5  ; Chem. Abstr., 1996, 124, 164079
    Google Scholar
  • 5 Fuchs K, Romig M, Mendla K, Briem H, and Fechteler K. inventors; WO  0214313.  ; Chem. Abstr., 2002, 136, 183824
  • 6 Abe Y. Kayakiri H. Satoh S. Inoue T. Sawada Y. Imai K. Inamura N. Asano M. Hatori C. Katayama A. Oku T. Tanaka H. J. Med. Chem.  1998,  41:  564 
    CrossrefGoogle Scholar
  • 7 Moog C. Wick A. Le Ber P. Kirn A. Aubertin A.-M. Antiviral Res.  1994,  24:  275 
    CrossrefGoogle Scholar
  • 8 Langer SZ. Arbilla S. Benavides J. Scatton B. Adv. Biochem. Psychopharmacol.  1990,  46:  61 
    PubMedGoogle Scholar
  • 9a Hand ES. Paudler WW. J. Org. Chem.  1978,  43:  2900 
    CrossrefGoogle Scholar
  • 9b Rydzkowski R. Blondeau D. Sliwa H. Tetrahedron Lett.  1985,  26:  2571 
    CrossrefGoogle Scholar
  • 9c Löber S. Hübner H. Gmeiner P. Bioorg. Med. Chem. Lett.  1999,  9:  97 
    CrossrefGoogle Scholar
  • 9d Tomoda H. Hirano T. Saito S. Mutai T. Araki K. Bull. Chem. Soc. Jpn.  1999,  72:  1327 
    CrossrefGoogle Scholar
  • 9e Ikemoto T. Wakimasu M. Heterocycles  2001,  55:  99 
    CrossrefGoogle Scholar
  • 10 Hubert AJ. Reimlinger H. Chem. Ber.  1970,  103:  3811 
    CrossrefGoogle Scholar
  • 11 Galons H. Bergerat I. Combet Farnoux C. Miocque M. Synthesis  1982,  1103 
    Article in Thieme ConnectGoogle Scholar
  • 12 Knölker H.-J. Boese R. Hitzemann R. Chem. Ber.  1990,  123:  327 
    CrossrefGoogle Scholar
  • 13 Groziak MP. Wilson SR. Clauson GL. Leonard NJ. J. Am. Chem. Soc.  1986,  108:  8002 
    CrossrefGoogle Scholar
  • 14 Groebke K. Weber L. Mehlin F. Synlett  1998,  661 
    Article in Thieme ConnectGoogle Scholar
  • 15a Tu S. Fang F. Miao C. Jiang H. Feng Y. Shi D. Wang X. Tetrahedron Lett.  2003,  44:  6153 
    CrossrefGoogle Scholar
  • 15b Tu S. Fang F. Zhu S. Li T. Zhang X. Zhuang Q. Synlett  2004,  537 
    CrossrefGoogle Scholar
  • 15c Tu S. Li T. Shi F. Wang Q. Zhang J. Xu J. Zhu X. Zhang X. Zhu S. Shi D. Synthesis  2005,  3045 
    CrossrefGoogle Scholar
  • 15d Tu S. Zhang J. Zhu X. Xu J. Zhang Y. Wang Q. Jia R. Jiang B. Zhang J. Bioorg. Med. Chem. Lett.  2006,  16:  3578 
    CrossrefGoogle Scholar
  • 15e Tu S. Zhu X. Zhang J. Xu J. Zhang Y. Wang Q. Jia R. Jiang B. Zhang J. Yao C. Bioorg. Med. Chem. Lett.  2006,  16:  2925 
    CrossrefGoogle Scholar
  • 16 Tu SJ. Jiang H. Zhuang QY. Miao CB. Shi DQ. Wang XS. Gao Y. Chin. J. Org. Chem.  2003,  23:  491 
    Google Scholar
  • 17 Mustafa A. Asker W. Harhash AH. Khalifa MAE. Zayed EM. Justus Liebigs Ann. Chem.  1968,  713:  151 
    CrossrefGoogle Scholar
  • 18 Vanghelovici M. Stefanescu A. Soc. Chim. Romania, Sect. Soc. romane Stiinte, Bul. Chim. pura apl.  1942,  3A:  159 ; Chem. Abstr. 1944, 38, 36952
    Google Scholar