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Synlett 2010(4): 644-648  
DOI: 10.1055/s-0029-1219391
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Palladium-Catalyzed Cross-Coupling Reactions of 2,4,7-Trichloroquinazoline

Peter Wipf*, Kara M. George
University of Pittsburgh, Pittsburgh, PA 15260, USA
Fax: +1(412)6240787; e-Mail: pwipf@pitt.edu;
Further Information

Publication History

Received 17 December 2009
Publication Date:
10 February 2010 (online)

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Abstract

The regioselective palladium-catalyzed cross-coupling reactions of 2,4,7-trichloroquinazoline with various aryl- and heteroarylboronic acids are reported. An efficient, sequential strategy was developed that provides access to novel, functionalized heterocycles.

Key words

palladium catalysis - cross-coupling - heterocycles - regioselectivity - quinazoline

    References and Notes

  • 1 Kalinin VN. Synthesis  1992,  413 
    Article in Thieme ConnectGoogle Scholar
  • 2 Schröter S. Stock C. Bach T. Tetrahedron  2005,  61:  2245 
    CrossrefGoogle Scholar
  • 3a Fry DW. Kraker AJ. McMichael A. Ambroso LA. Nelson JM. Leopold WR. Connors RW. Bridges AJ. Science  1994,  265:  1093 
    Google Scholar
  • 3b Uckun FM. Sudbeck EA. Mao C. Ghosh S. Liu X.-P. Vassilev AO. Navara CS. Narla RK. Curr. Cancer Drug Targets  2001,  1:  59 
    Google Scholar
  • 3c Strawn LM. Shawver LK. Exp. Opin. Invest. Drugs  1998,  7:  553 
    Google Scholar
  • 4 Bedi PMS. Kumar V. Mahajan MP. Bioorg. Med. Chem. Lett.  2004,  14:  5211 
    CrossrefGoogle Scholar
  • 5 Foster BA. Coffey HA. Morin MJ. Rastinejad F. Science  1999,  286:  2507 
    CrossrefGoogle Scholar
  • 6 Bernotas RC, Ullrich JW, Travins JM, Wrobel JE, and Unwalla RJ. inventors; WO 2009020683  A2. 
  • 7 Gundla R. Kazemi R. Sanam R. Muttineni R. Sarma JARP. Dayam R. Neamati N. J. Med. Chem.  2008,  51:  3367 
    CrossrefGoogle Scholar
  • 8a Wakeling AE. Guy SP. Woodburn JR. Ashton SE. Curry BJ. Barker AJ. Gibson KH. Cancer Res.  2002,  62:  5749 
    Google Scholar
  • 8b Baselga J. Rischin D. Ranson M. Calvert H. Raymond E. Kieback DG. Kaye SB. Gianni L. Harris A. Bjork T. Averbuch SD. Feyereislova A. Swaisland H. Rojo F. Albanell J. J. Clin. Oncol.  2002,  20:  4292 
    Google Scholar
  • 8c Twombly R. J. Natl. Cancer Inst.  2002,  94:  1596 
    Google Scholar
  • 9 da Silva JFM. Walters M. Al-Damluji S. Ganellin CR. Bioorg. Med. Chem.  2008,  16:  7254 
    CrossrefGoogle Scholar
  • 10a Mangalagiu I. Benneche T. Undheim K. Tetrahedron Lett.  1996,  37:  1309 
    Google Scholar
  • 10b Qingbo L. Mangalagiu I. Benneche T. Undheim K. Acta Chem. Scand.  1997,  51:  302 
    Google Scholar
  • 11 Mangalagiu I. Benneche T. Undheim K. Acta Chem. Scand.  1996,  50:  914 
    CrossrefGoogle Scholar
  • 12 Charpiot B. Brun J. Donze I. Naef R. Stefani M. Mueller T. Bioorg. Med. Chem. Lett.  1998,  8:  2891 
    CrossrefGoogle Scholar
  • 13a Eicher T. Hauptmann S. The Chemistry of Heterocycles   Wiley-VCH; Weinheim: 2003. 
    Google Scholar
  • 13b Garcia Y. Schoenebeck F. Legault CY. Merlic CA. Houk KN. J. Am. Chem. Soc.  2009,  131:  6632 
    Google Scholar
  • 14 Curd HS. Landquist JK. Rose FL. J. Chem. Soc.  1948,  1759 
    CrossrefGoogle Scholar
  • 16a Barder TE. Walker SD. Martinelli JR. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  4685 
    Google Scholar
  • 16b Billingsley K. Buchwald SL. J. Am. Chem. Soc.  2007,  129:  3358 
    Google Scholar
  • 17 Liebeskind LS. Srogl J. Org. Lett.  2002,  4:  979 
    CrossrefPubMedGoogle Scholar
  • 18a Decornez H. Gulyás-Forró A. Papp Á. Szabó M. Sármay G. Hajdú I. Cseh S. Dormán G. Kitchen DB. ChemMedChem  2009,  4:  1273 
    Google Scholar
  • 18b Peng J. Lin W. Jiang D. Yuan S. Chen Y. J. Comb. Chem.  2007,  9:  431 
    Google Scholar
  • 18c Wipf P. Minion DJ. Halter RJ. Berggren MI. Ho CB. Chiang GG. Kirkpatrick L. Abraham R. Powis G. Org. Biomol. Chem.  2004,  2:  1911 
    Google Scholar
15

Exclusive coupling at the C-2 position was determined by 2D NMR experiments.