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Synthesis 2008(16): 2537-2542  
DOI: 10.1055/s-2008-1067181
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New and Efficient Palladium(0)-Mediated Microwave-Assisted Direct C3 Alkenylation of Imidazo[1,2-a]pyridines

Jamal Koubachia,b, Saïd El Kazzoulia,b, Sabine Berteina-Raboin*a, Abderrahim Mouaddibb, Gérald Guillaumeta
a Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d’Orléans, BP 6759, 45067 Orléans Cedex 2, France
e-Mail: sabine.berteina-raboin@univ-orleans.fr;
b Faculté des Sciences et Techniques de Beni-Mellal, Université Soultan Moulay Sliman, BP 523, 23000 Beni-Mellal, Morocco
Further Information

Publication History

Received 31 March 2008
Publication Date:
17 July 2008 (online)

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Abstract

In this paper, we present the synthesis of 3-alkenylimidazo[1,2-a]pyridines in high to moderate yields by microwave direct palladium-catalyzed C-H alkenylation between bromoalkenes and imidazo[1,2-a]pyridines. The scope and limitation of the palladium(0)-catalyzed alkenylation method were investigated. Optimized conditions were successfully applied to a wide variety of imidazo[1,2-a]pyridine derivatives and bromoalkenes. The compatibility of the synthesis with the presence of a chloro substituent in the 6-position was investigated. The 6-chloroimidazo[1,2-a]pyridines were functionalized using Suzuki cross-coupling conditions to give polyfunctional compounds.

Key words

palladium-catalyzed coupling - alkenylation - imidazo[1,2-a]pyridines - microwave irradiation

    References

  • 1 Guillaumet G, Berteina-Raboin S, El Kazzouli S, Delagrange P, and Caignard D.-H. inventors; WO  2006,027,474.  ; Chem. Abstr. 2006, 144, 254132
  • 2a Elhakmaoui A. Gueiffier A. Milhavet JC. Blache Y. Chapat JP. Chavignon O. Teulade JC. Snoeck R. Andrei G. De Clercq E. Bioorg. Med. Chem. Lett.  1994,  4:  1937 
    Search in Google Scholar
  • 2b Gueiffier A. Lhassani M. Elhakmoui A. Snoeck R. Andrei G. Chavignion O. Teulade JC. Kerbal A. Essassi M. Debouzy JC. Witurowo JP. Blache Y. Balzarini J. De Clercq E. Chapat JP. J. Med. Chem.  1996,  39:  2856 
    Search in Google Scholar
  • 2c Lhassani M. Chavignon O. Chezal JM. Teulade JC. Chapat JP. Snoeck R. Andrei G. Balzarini J. De Clercq E. Gueiffier A. Eur. J. Med. Chem.  1999,  34:  2856 
    Search in Google Scholar
  • 2d Gudmundsson KS. Drach JC. Townsend LB. J. Org. Chem.  1997,  62:  3453 
    Search in Google Scholar
  • 2e Pan S. Wang G. Shinazi RF. Zhao K. Tetrahedron Lett.  1998,  39:  8191 
    Search in Google Scholar
  • 2f Hamdouchi C. de Blas J. del Prado M. Gruber J. Heinz BA. Vance L. J. Med. Chem.  1999,  42:  50 
    Search in Google Scholar
  • 2g Gudmundsson KS. Williams JD. Drach JC. Townsend LB. J. Med. Chem.  2003,  46:  1449 
    Search in Google Scholar
  • 3a Kaminsky JJ. Doweyko AM. J. Med. Chem.  1997,  40:  427 
    Search in Google Scholar
  • 3b Kaminsky JJ. Puchalski C. Solomon DM. Rizvi RK. Conn DJ. Elliot AJ. Lovey RG. Guzik H. Chui PJS. Long JF. McPhail AT. J. Med. Chem.  1989,  32:  1686 
    Search in Google Scholar
  • 4a Rival Y. Grassy G. Michael G. Chem. Pharm. Bull.  1992,  40:  1170 
    Search in Google Scholar
  • 4b Rewankar GR. Matthews JR. Robins RK. J. Med. Chem.  1975,  18:  1253 
    Search in Google Scholar
  • 5a Beswick PJ, Campbell IB, and Naylor A. inventors; WO  9,631,509.  ; Chem. Abstr. 1997, 126, 8117j
  • 5b Abiegnente E. Actual. Chim. Ther.  1991,  18:  1253 
    Search in Google Scholar
  • 6a Tully WR. Guardner CR. Gillespie RJ. Westwood R. J. Med. Chem.  1991,  34:  2060 
    Search in Google Scholar
  • 6b Trapani G. Franco M. Latrofa A. Ricciardi L. Carotti A. Serra M. Sanna E. Biggio G. Liso G. J. Med. Chem.  1999,  42:  3934 
    Search in Google Scholar
  • 6c Trapani G. Franco M. Ricciardi L. Latrofa A. Genchi G. Sanna E. Tuveri F. Gagetti E. Biggio G. Liso G. J. Med. Chem.  1997,  40:  3109 
    Search in Google Scholar
  • 7 Sanfilippo PJ. Urbanski M. Press JB. Dubinsky B. Moore JB. J. Med. Chem.  1988,  31:  2221 
    CrossrefSearch in Google Scholar
  • 8 Fuchs K, Romig M, Mendla K, Briem H, and Fechteler K. inventors; WO  0,214,131.  ; Chem. Abstr. 2002, 136, 183824r
  • 9 Zhuang ZP. Kung MP. Wilson A. Lee CW. Plössl K. Hou C. Holtzman DM. Kung HF. J. Med. Chem.  2003,  46:  237 
    CrossrefPubMedSearch in Google Scholar
  • 10 Franke H, Geisler J, Hartfiel U, Franke W, Dorfmeister G, Ganzer M, Johahann G, and Rees R. inventors; DE  4,120,108.  ; Chem. Abstr. 1992, 18, 213075v
  • 11 Byth KF. Culshaw JD. Green S. Oakes S. Thomas AP. Bioorg. Med. Chem. Lett.  2004,  14:  2245 
    CrossrefPubMedSearch in Google Scholar
  • 12 Humphries AC. Gancia E. Gilligan MT. Goodacre S. Hallett D. Merchant KJ. Thomas SR. Bioorg. Med. Chem. Lett.  2006,  16:  1518 
    CrossrefSearch in Google Scholar
  • 13 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 
    CrossrefSearch in Google Scholar
  • 14 Holm KJ. Goa KL. Drugs  2000,  59:  865 
    CrossrefSearch in Google Scholar
  • 15 Ueda T. Mizusgige K. Yukiiri K. Takahashi T. Kohno M. CerebroVasc. Dis.  2003,  16:  396 
    Search in Google Scholar
  • 16 Colletti SL. Frie JL. Dixon EC. Singh SB. Choi BK. Scapin G. Fitzgerald CE. Kumar S. Nichols EA. O’Keefe SJ. O’Neill EA. Porter G. Samual K. Schmatz DM. Schwartz CD. Shoop WL. Thompson CM. Thompson JE. Wang R. Woods A. Zaller DM. Doherty JB. J. Med. Chem.  2003,  46:  349 
    CrossrefSearch in Google Scholar
  • 17a Paolini JP. Robins RK. J. Org. Chem.  1965,  30:  4085 
    Search in Google Scholar
  • 17b Fischer MH. Lusi A. J. Med. Chem.  1972,  15:  982 
    Search in Google Scholar
  • 17c Hand ES. Paudler WW. J. Org. Chem.  1978,  43:  2900 
    Search in Google Scholar
  • 18 Gudmundsson KS. Drach JC. Townsend LB. Tetrahedron Lett.  1996,  37:  6275 
    CrossrefSearch in Google Scholar
  • 19a Kawai Y, Satoh S, Yamasaki H, Kayakiri N, Yoshihara K, and Oku T. inventors; WO  96.  ; 1996; Chem. Abstr. 1996, 126, 74840
  • 19b Badger A, Bender P, Esser K, Griswold D, Nabil H, Lee J, Votta B, and Simon P. inventors; WO  9,100,092.  ; Chem. Abstr. 1991, 115, 64756
  • 20 Enguehard C. Renou JL. Collot V. Hervet M. Rault S. Gueiffier A. J. Org. Chem.  2000,  65:  6572 
    CrossrefPubMedSearch in Google Scholar
  • 21a Bellina F. Cauteruccio S. Mannina L. Rossi R. Viel S. J. Org. Chem.  2005,  70:  3997 
    Search in Google Scholar
  • 21b Li W. Nelson DP. Jenson MS. Hoerrner RS. Javadi GJ. Cai D. Larsen RD. Org. Lett.  2003,  5:  4835 
    Search in Google Scholar
  • 21c Park C.-H. Ryabova V. Seregin IV. Sromek AW. Gevorgyan V. Org. Lett.  2004,  6:  1159 
    Search in Google Scholar
  • 21d Zhuravlev FA. Tetrahedron Lett.  2006,  47:  2929 
    Search in Google Scholar
  • 22a Zaitsev VG. Daugulis O. J. Am. Chem. Soc.  2005,  127:  4156 
    Search in Google Scholar
  • 22b Zaitsev VG. Daugulis O. Shabahov D. Pham Q.-N. Lazareva A. Synlett  2006,  3382 
  • 23a Oi S. Aizawa E. Ogino Y. Inoue Y. J. Org. Chem.  2005,  70:  3113 
    Search in Google Scholar
  • 23b Oi S. Ogino Y. Fukita S. Inoue Y. Org. Lett.  2002,  4:  1783 
    Search in Google Scholar
  • 23c Oi S. Fukita S. Hirata N. Watanuki N. Miyano S. Inoue Y. Org. Lett.  2001,  3:  2579 
    Search in Google Scholar
  • 24a El Kazzouli S. Berteina-Raboin S. Mouaddib A. Guillaumet G. Tetrahedron Lett.  2003,  44:  6265 
    Search in Google Scholar
  • 24b El Kazzouli S. Berthault A. Berteina-Raboin S. Mouaddib A. Guillaumet G. Lett. Org. Chem.  2005,  2:  184 
    Search in Google Scholar
  • 25a Koubachi J. El Kazzouli S. Berteina-Raboin S. Mouaddib A. Guillaumet G. Synlett  2006,  3237 
  • 25b Koubachi J. El Kazzouli S. Berteina-Raboin S. Mouaddib A. Guillaumet G. J. Org. Chem.  2007,  72:  7650 
    Search in Google Scholar
  • 26 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 JP. J. Med. Chem.  1998,  41:  5108 
    CrossrefSearch in Google Scholar