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Synthesis 2010(17): 2926-2930  
DOI: 10.1055/s-0030-1258141
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Improved Method for the Synthesis of Carbazolones by Palladium/Copper-Catalyzed Intramolecular Annulation of N-Arylenaminones

Bojie Weng, Rui Liu, Jing-Hua Li*
College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
e-Mail: lijh@zjut.edu.cn;
Further Information

Publication History

Received 8 January 2010
Publication Date:
30 June 2010 (online)

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Abstract

An improved method for the synthesis of carbazolones via the condensation of arylamines with 1,3-cyclodiketones followed by intramolecular oxidative cyclization catalyzed by palladium acetate and copper acetate in ethanol under an oxygen atmosphere was established. The improved method has the advantage of easily available starting materials and affords good yields.

Key words

carbazolones - intramolecular oxidative cyclization - oxygen - palladium acetate - copper acetate

    References

  • 1a Knölker H.-J. Reddy KR. Chem. Rev.  2002,  102:  4303 
    Google Scholar
  • 1b Prakash SR. Cable KM. Correa ID. Fellows I. Montgomery S. Newman JJ. Waterhouse I. Wells GN. Sutherland DR. J. Labelled Compd. Radiopharm.  1995,  36:  993 
    Google Scholar
  • 1c Kilpatrick GJ. Butler A. Hagan RM. Jones BJ. Tyers MB. Naunyn-Schmiedeberg’s Arch. Pharmacol.  1990,  342:  22 
    Google Scholar
  • 1d Bouaziz Z. Nebois P. Poumaroux A. Fillion H. Heterocycles  2000,  52:  977 
    Google Scholar
  • 1e Toral J. Hu W. Critchett D. Solmon AJ. Barrett JE. Sokol PT. Ziai MR.
    J. Pharm. Pharmacol.  1995,  47:  618 
    Google Scholar
  • 1f Gao Y.-D, and Shen D.-M. inventors; Patent WO  2006044232. 
  • 2a Kukushkin SYu. Ivanov PYu. Alekseeva LM. Levina VI. Kobrakov KI. Grigor’ev NB. Granik VG. Russ. Chem. Bull.  2005,  54:  1887 
    Google Scholar
  • 2b Czeskis BA. Wheeler WJ. J. Labelled Compd. Radiopharm.  2005,  48:  407 
    Google Scholar
  • 2c Li X. Vince R. Bioorg. Med. Chem.  2006,  14:  2942 
    Google Scholar
  • 2d Romeo G. Materia L. Pittala V. Modica M. Salerno L. Siracusa M. Russo F. Minneman KP. Bioorg. Med. Chem.  2006,  14:  5211 
    Google Scholar
  • 3a Sorensen US. Pombo-Villar E. HeIv. Chim. Acta  2004,  87:  82 
    Google Scholar
  • 3b Ponsinet R. Chassaing G. Vaissermann J. Lavielle S. Eur. J. Med. Chem.  2000,  35:  83 
    Google Scholar
  • 3c Yan S. Wu H. Wu N. Jiang Y. Synlett  2007,  2699 
    Google Scholar
  • 3d Chen L.-C. Yang S.-C. Wang H.-M. Synthesis  1995,  385 
    Google Scholar
  • 3e Edmondson SD. Mastracchio A. Parmee ER. Org. Lett.  2000,  2:  1109 
    Google Scholar
  • 4 Osuka A. Mori Y. Suzuki H. Chem. Lett.  1982,  2031 
    CrossrefGoogle Scholar
  • 5a Bartlett MF. Dickel DF. Taylor WI. J. Am. Chem. Soc.  1958,  80:  126 
    Google Scholar
  • 5b Oikawa Y. Yonemitsu O. J. Org. Chem.  1977,  42:  1213 
    Google Scholar
  • 5c Sissouma D. Collet SC. Guingant AY. Synlett  2004,  2612 
    Google Scholar
  • 6a Scott TL. Soderberg BCG. Tetrahedron  2003,  59:  6323 
    Google Scholar
  • 6b Scott TL. Yu X. Gorugantula SP. Carrero-Martinez G. Soederberg BCG. Tetrahedron  2006,  62:  10835 
    Google Scholar
  • 7 Kawai H. Nagasu T. Takeda T. Fujiwara K. Tsuji T. Ohkita M. Nishida J. Suzuki T. Tetrahedron Lett.  1975,  45:  4533 
    CrossrefGoogle Scholar
  • 8 Tietcheu C. Garcia C. Gardette D. Dugat D. Gramain J. J. Heterocycl. Chem.  2002,  39:  965 
    CrossrefGoogle Scholar
  • 9 Iida H. Yuasa Y. Kibayashi C. J. Org. Chem.  1980,  45:  2938 
    CrossrefGoogle Scholar
  • For reviews, see:
  • 10a Li B.-J. Yang S.-D. Shi Z.-J. Synlett  2008,  949 
    Google Scholar
  • 10b Seregin IV. Gevorgyan V. Chem. Soc. Rev.  2007,  36:  1173 
    Google Scholar
  • 10c Alberico D. Scott ME. Lautens M. Chem. Rev.  2007,  107:  174 
    Google Scholar
  • 10d Yu J.-Q. Giri R. Chen X. Org. Biomol. Chem.  2006,  4:  4041 
    Google Scholar
  • 10e Campeau L.-C. Fagnou K. Chem. Commun.  2006,  1253 
    Google Scholar
  • 10f Dick AR. Sanford MS. Tetrahedron  2006,  62:  2439 
    Google Scholar
  • 10g Daugulis O. Zaitsev VG. Shabashov D. Pham Q.-N. Lazareva A. Synlett  2006,  3382 
    Google Scholar
  • 11a Xia J.-B. Wang X.-Q. You S.-L. J. Org. Chem.  2009,  74:  456 
    Google Scholar
  • 11b Takahashi M. Masui K. Sekiguchi H. Kobayashi N. Mori A. Funahashi M. Tamaoki N. J. Am. Chem. Soc.  2006,  128:  10930 
    Google Scholar
  • 11c Hull KL. Lanni EL. Sanford MS. J. Am. Chem. Soc.  2006,  128:  14047 
    Google Scholar
  • 12a Xu Y.-H. Lu J. Loh T.-P. J. Am. Chem. Soc.  2009,  131:  1372 
    Google Scholar
  • 12b Li B.-J. Tian S.-L. Fang Z. Shi Z.-J. Angew. Chem. Int. Ed.  2008,  47:  1115 
    Google Scholar
  • 12c Brasche G. Garca-Fortanet J. Buchwald SL. Org. Lett.  2008,  10:  2207 
    Google Scholar
  • 12d Li R. Jiang L. Lu W. Organometallics  2006,  25:  5973 
    Google Scholar
  • 12e Stuart DR. Fagnou K. Science  2007,  316:  1172 
    Google Scholar
  • 12f Dwight TA. Rue NR. Charyk D. Josselyn R. DeBoef B. Org. Lett.  2007,  9:  3137 
    Google Scholar
  • 12g Xia J.-B. You S.-L. Organometallics  2007,  26:  4869 
    Google Scholar
  • 12h Hull KL. Sanford MS. J. Am. Chem. Soc.  2007,  129:  11904 
    Google Scholar
  • 12i Stuart DR. Villemure E. Fagnou K. J. Am. Chem. Soc.  2007,  129:  12072 
    Google Scholar
  • 13a Liégault B. Lee D. Huestis MP. Stuart DR. Fagnou K. J. Org. Chem.  2008,  73:  5022 
    Google Scholar
  • 13b Wada Y. Nagasaki H. Tokuda M. Orito K. J. Org. Chem.  2007,  72:  2008 
    Google Scholar
  • 13c Wang J. Rosingana M. Watson DJ. Dowdy ED. Discordia RP. Soundarajan N. Li W.-S. Tetrahedron Lett.  2001,  42:  8935 
    Google Scholar
  • 13d Åkermark B. Oslob JD. Heuschert U. Tetrahedron Lett.  1995,  36:  1325 
    Google Scholar
  • 13e Knölker H.-J. Fröhner W. Synthesis  2002,  557 
    Google Scholar
  • 13f Matsubara S. Asano K. Kajita Y. Yamamoto M. Synthesis  2007,  2055 
    Google Scholar
  • 13g Watanabe T. Ueda S. Inuki S. Oishi S. Fujii N. Ohno H. Chem. Commun.  2007,  4516 
    Google Scholar
  • 13h Shi Z. Zhang C. Li S. Pan D. Ding S. Cui Y. Jiao N. Angew. Chem. Int. Ed.  2009,  48:  4572 
    Google Scholar
  • 14 Würtz S. Rakshit S. Neumann JJ. Dröge T. Glorius F. Angew. Chem. Int. Ed.  2008,  47:  7230 
    CrossrefGoogle Scholar
  • 15 Xu S.-L. Li C.-P. Li J.-H. Synlett  2009,  818 
    Article in Thieme ConnectGoogle Scholar
  • 16a Sakamoto T. Nagano T. Kondo Y. Yamanaka H. Synthesis  1990,  215 
    Google Scholar
  • 16b Baraladi PG. Simoni D. Manfredini S. Synthesis  1983,  902 
    Google Scholar
  • 16c Martin DF. Janusonis GA. Martin BB. J. Am. Chem. Soc.  1961,  83:  73 
    Google Scholar
  • 16d Ferraz HMC. Oliceira EO. Payret-Arrua ME. Brandt CA. J. Org. Chem.  1995,  60:  7357 
    Google Scholar
  • 16e Kloek JA. Leschinsky KL. J. Org. Chem.  1978,  43:  1460 
    Google Scholar
  • 16f Soloshonok VA. Kukhar V. Tetrahedron  1996,  52:  6953 
    Google Scholar
  • 16g Lflemme N. Dallemange P. Rault S. Synthesis  2002,  1740 
    Google Scholar
  • 17a Braibante MEF. Braibante HTS. Costa CC. Martins DB. Tetrahedron Lett.  2002,  43:  8079 
    Google Scholar
  • 17b Braibante MEF. Braibante HS. Missio L. Andricopulo A. Synthesis  1994,  898 
    Google Scholar
  • 17c Ge H. Niphakis MJ. Georg GI. J. Am. Chem. Soc.  2008,  130:  3708 
    Google Scholar
  • 18 Caubere C. Caubere P. Ianelli S. Nardelli M. Jamart-Gregoire B. Tetrahedron  1994,  50:  11903 
    CrossrefGoogle Scholar
  • 19 Baldwin JE. Tzodikov NR. J. Org. Chem.  1977,  42:  1878 
    CrossrefGoogle Scholar
  • 20 Link JT. Org. React.  2002,  60:  157 
    Google Scholar
  • 21 Wang H.-M. Chou H.-L. Chen L.-C. J. Chin. Chem. Soc-Taip.  1995,  42:  593 
    Google Scholar