Synthesis 2001(6): 0871-0876
DOI: 10.1055/s-2001-13409
PAPER
© Georg Thieme Verlag Stuttgart · New York

Pyridazines Part XXIII: [1] Efficient Arylation at Position 5 of the 6-Phenyl-(2H)-pyridazin-3-one System Using a Suzuki Cross-Coupling Reaction

Alberto Coelho, Eddy Sotelo, Isabel Estévez, Enrique Raviña*
Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15706 Santiago de Compostela, Spain.
Further Information

Publication History

Received 29 December 2000
Publication Date:
24 September 2004 (online)

Abstract

A highly efficient procedure for introducing aryl or heteroaryl rings at position 5 of the 6-phenyl-(2H)-pyridazin-3-one system using a Suzuki cross-coupling reaction has been developed in the search for new platelet aggregation inhibitors.

    References

  • 1a

    Part of this work was presented at the 7 th International Symposium on the Chemistry and Pharmacology of Pyridazines, Santiago de Compostela, Spain, September 2000.

  • 1b For the previous paper in this series, see: Sotelo E. Pita B. Raviña E. Tetrahedron Lett.  2000,  41:  2863 
  • 2 Frank H. Heinisch G. Pharmacologically Active Pyridazines. Part 1  In Progress in Medicinal Chemistry   Vol. 27:  Ellis GP. West GB. Elsevier; Amsterdam: 1990.  p.1 
  • 3 Frank H. Heinisch G. Pharmacologically Active Pyridazines. Part 2  In Progress in Medicinal Chemistry   Vol. 29:  Ellis GP. Luscombe DK. Elsevier; Amsterdam: 1992.  p.141 
  • 4a Raviña E. García-Mera G. Santana L. Orallo F. Calleja JM. Eur. J. Med. Chem.  1985,  20:  475 
  • 4b García Domínguez N. Raviña E. Santana L. Terán C. García Mera G. Orallo F. Crespo M. Fontenla J. Arch. Pharm. (Weinheim, Ger.)  1988,  321:  735 
  • 4c Terán C. Raviña E. Santana L. García Domínguez N. García Mera G. Fontenla J. Orallo F. Calleja JM. Arch. Pharm. (Weinheim, Ger.)  1989,  322:  331 
  • 5a Raviña E. Terán C. Santana L. García Domínguez N. Estévez I. Heterocycles  1990,  31:  1967 
  • 5b Gil Longo J. Laguna R. Verde I. Castro M. Orallo F. Fontenla J. Calleja JM. Raviña E. Terán C. J. Pharm. Sci.  1993,  82:  286 
  • 6 Estévez I. Raviña E. Sotelo E. J. Heterocycl. Chem.  1998,  35:  1421 
  • 7 Sotelo E. Raviña E. Estévez I. J. Heterocycl. Chem.  1999,  36:  985 
  • 8 Laguna R. Rodriguez-Liñares B. Cano E. Estévez I. Raviña E. Sotelo E. Chem. Pharm. Bull.  1997,  45:  151 
  • 9 Montero-Lastres A. Fraiz N. Cano E. Laguna R. Estévez I. Raviña E. Biol. Pharm. Bull.  1999,  22:  1376 
  • 10 Sotelo E. PhD Thesis   University of Santiago de Compostela; Spain: 2000. 
  • 11a Brown DJ. The Pyridazines I  In Chemistry of Heterocyclic Compounds   Vol. 56:  Taylor EC. Wipf P. Wiley; New York: 2000.  p.23 
  • 11b Coates WJ. Pyridazines and their Benzo Derivatives  In Comprehensive Heterocyclic Chemistry   Vol. 6:  Katritzky AR. Rees CW. Pergamon Press; New York: 1996.  p.63 
  • 12a Miyara N. Yanagi T. Suzuki A. Synth. Commun.  1981,  11:  513 
  • 12b Kalinin VN. Synthesis  1992,  413 
  • 13 Tsuji J. Palladium Reagents and Catalysts   Wiley; Chichester: 1995. 
  • 14a Malleron JL. Fiaud JC. Legros JY. Handbook of Palladium-Catalysed Organic Reactions   Academic Press; San Diego: 1997. 
  • 14b Diederich F. Stang PJ. Metal-Catalysed Cross-Coupling Reactions   Wiley-VCH; Weinheim: 1998. 
  • 15a Konno S. Sagi M. Siga F. Yamanaka H. Heterocycles  1992,  34:  225 
  • 15b Oshawa A. Abe Y. Igeta H. Chem. Pharm. Bull.  1980,  28:  3488 
  • 15c Toussaint D. Suffert J. Wermuth CG. Heterocycles  1994,  38:  1273 
  • 15d Rohr M. Toussaint D. Chayer S. Mann A. Suffert J. Wermuth CG. Heterocycles  1996,  43:  1459 
  • 16 Estévez I. Coelho A. Raviña E. Synthesis  1999,  9:  1666 
  • 17 Maes B. Lemiére GLF. Dommisse R. Augustyns K. Haemers A. Tetrahedron  2000,  56:  1777 
  • 18 Novoa H. Blaton NM. Peeters OM. DeRanter CJ. Pita B. Sotelo E. Raviña E. Suárez M. Acta Crystallogr., Sect. C  2000,  56:  345 
  • 19 Suzuky A. Recent Advances in the Cross-Coupling Reactions of Organoboron Derivatives with Organic Electrophiles,  In Perspectives in Organopalladium Chemistry for the XXI Century   Tsuji J. Elsevier; Amsterdam: 1999.  p.145 
  • 20a Gronowitz S. Lawitz K. Chem. Scr.  1983,  22:  265 
  • 20b Gronowitz S. Stevens MFG. J. Chem. Soc., Perkin Trans. 1  1994,  3311