Synthesis 2009(21): 3689-3693  
DOI: 10.1055/s-0029-1217018
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Reactions of 4-(Trifluoromethylsulfonyloxy)coumarins with Amides and NH-Heterocycles

Olga G. Ganinaa, Alexey Yu. Fedorovb, Irina P. Beletskaya*a
a Department of Chemistry, Moscow State Lomonosov University, Vorobyevy Gory, 119991 Moscow, Russian Federation
Fax: +7(495)9393618.; e-Mail: beletska@org.chem.msu.ru;
b Department of Organic Chemistry, Nizhny Novgorod State University, 23 Gagarin Avenue, 603950 Nizhny Novgorod, Russian Federation
e-Mail: afnn@rambler.ru;
Further Information

Publication History

Received 18 June 2009
Publication Date:
23 September 2009 (online)

Abstract

Palladium-catalyzed reactions of 4-(trifluoromethylsulfonyloxy)coumarins with amides and NH-heterocycles afforded 4-amido- and 4-(N-hetaryl)coumarins in 60-96% yield.

    References

  • 1a Soenen DR. Hwang I. Hedrick MP. Boger DL. Bioorg. Med. Chem. Lett.  2003,  13:  1777 
  • 1b Borges F. Roleira F. Milhazes N. Santana L. Uriarte E. Curr. Med. Chem.  2005,  12:  887 
  • 2a Schio L. Chatreaux F. Klich M. Tetrahedron Lett.  2000,  41:  1543 
  • 2b Kominek LA. Antimicrob. Agents Chemother.  1972,  1:  123 
  • 2c Pojer F. Wemakor E. Kammerer B. Chen H. Walsh CT. Li SM. Heide L. Proc. Natl. Acad. Sci. U.S.A.  2003,  100:  2316 
  • 3 Chartreaux F, Klich M, and Schio L. inventors; EP Patent  894805.  ; Chem. Abstr. 1999, 130, 125344
  • 4 Avendano C. Menendez JC. Curr. Med. Chem.  2002,  9:  159 
  • 5 Reddy MVR. Rao MR. Rhodes D. Hansen MST. Rubins K. Bushman FD. Venkateswarlu Y. Faulkner DJ. J. Med. Chem.  1999,  42:  1901 
  • 6a Azim SA. Al-Hazmy SM. Ebeid EM. El-Daly SA. Opt. Laser Tech.  2005,  37:  245 
  • 6b Dahiya P. Kumbhakar M. Mukherjee T. Pal H. Chem. Phys. Lett.  2005,  414:  148 
  • 6c Sivakumar K. Xie F. Cash BM. Long S. Barnhill HN. Wang Q. Org. Lett.  2004,  6:  4603 
  • 6d Trenor SR. Shultz AR. Love BJ. Long TE. Chem. Rev.  2004,  104:  3059 
  • 7a Traven VF. Bochkov AY. Krayushkin MM. Yarovenko VN. Nabatov BV. Dolotov SM. Barachevsky VA. Beletskaya IP. Org. Lett.  2008,  10:  1319 
  • 7b Lee M.-T. Yen C.-K. Yang W.-P. Chen H.-H. Liao C.-H. Tsai C.-H. Chen CH. Org. Lett.  2004,  6:  1241 
  • 8a Bennett FA. Barlow DJ. Dodoo NO. Hider RC. Lansley AB. Lawrence MJ. Marriott C. Bansal SS. Anal. Biochem.  1999,  270:  15 
  • 8b Lo L.-C. Liao Y.-C. Kuo C.-H. Chen C.-T. Org. Lett.  2000,  2:  683 
  • 8c Murata C. Masuda T. Kamochi Y. Todoroki K. Yoshida H. Nohta H. Yamaguchi M. Takadate A. Chem. Pharm. Bull.  2005,  53:  750 
  • 8d Coleman RS. Berg MA. Murphy CJ. Tetrahedron  2007,  63:  3450 
  • 9 Nakata E. Koshi Y. Koga E. Katayama Y. Hamachi I. J. Am. Chem. Soc.  2005,  127:  13253 
  • 10 Ganina OG. Daras E. Bourgarel-Rey V. Peyrot V. Andresyuk AN. Finet J.-P. Fedorov AYu. Beletskaya IP. Combes S. Bioorg. Med. Chem.  2008,  16:  8806 
  • 11a Ganina OG. Veselov IS. Grishina GV. Fedorov AYu. Beletskaya IP. Russ. Chem. Bull.  2006,  9:  1642 
  • 11b Griffin RJ. Fontana G. Golding BT. Guiard S. Hardcastle IR. Leahy JJJ. Martin N. Richardson C. Rigoreau L. Stockley M. Smith GCM. J. Med. Chem.  2005,  48:  569 
  • 11c Stoyanov EV. Ivanov IC. Molecules  2004,  9:  627 
  • 11d Hishmat OH. Gohar AM. Wassef ME. Shalash MR. Ismail I. Pharm. Acta Helv.  1977,  52:  252 
  • 11e Zagorevsky VA. Savel’ev VL. Mesheryakova LM. Chem. Heterocycl. Compd.  1970,  947 
  • 12 Audisio D. Messaoudi S. Peyrat J.-F. Brion J.-D. Alami M. Tetrahedron Lett.  2007,  48:  6928 
  • 13 Beletskaya IP. Ganina OG. Tsvetkov AV. Fedorov AYu. Finet J.-P. Synlett  2004,  2797 
  • 14 Willis MC. Brace GN. Holmes IP. Synthesis  2005,  3229 
  • 15 Klapars A. Campos KR. Chen C. Volante RP. Org. Lett.  2005,  7:  1185 
  • 16 Wallace DJ. Klauber DJ. Chen C. Volante RP. Org. Lett.  2003,  5:  4749 
  • 17 Sergeev AG. Artamkina GA. Khrustalev VN. Antipin MYu. Beletskaya IP. Mendeleev Commun.  2007,  17:  142 
  • 18 Yang BH. Buchwald SL. J. Organomet. Chem.  1999,  576:  125 
  • 19 Old DW. Harris MC. Buchwald SL. Org. Lett.  2000,  2:  1403 
  • 20a Barton DHR. Donnelly DMX. Finet J.-P. Guiry PJ. J. Chem. Soc., Perkin Trans. 1  1992,  1365 
  • 20b Boland GM. Donnelly DMX. Finet J.-P. Rea MD. J. Chem. Soc., Perkin Trans. 1  1996,  2591 
  • 20c Combes S. Finet J.-P. Siri D. J. Chem. Soc., Perkin Trans. 1  2002,  38