Download PDF
Synthesis 2011(19): 3195-3203  
DOI: 10.1055/s-0030-1260162
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Route for the Synthesis of Isochromenocarbazolones through Palladium-Catalyzed Intramolecular ortho-Arylation

Devanga K. Sreenivas, Rajagopal Nagarajan*
School of Chemistry, University of Hyderabad, Hyderabad 500 046, India
e-Mail: rnsc@uohyd.ernet.in;
Further Information

Publication History

Received 13 May 2011
Publication Date:
08 August 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A new efficient protocol for the synthesis of iso­chro­meno[3,4-b]-, [4,3-a]-, -[4,3-b]-, and -[3,4-c]carbazolones has been successfully established via palladium-catalyzed intramolecular ortho-arylation of C-H bond under ligand-free conditions.

Key words

isochromenocarbazolones - intramolecular arylation - carbazolyl iodobenzoates

    References

  • 1a Goodwin S. Smith FA. Horning CE. J. Am. Chem. Soc.  1959,  81:  1903 
    Google Scholar
  • 1b Bergman J. Pelcman B. Pure Appl. Chem.  1990,  62:  1967 
    Google Scholar
  • 1c Knölker H.-J. Reddy KR. Chem. Rev.  2002,  102:  4303 
    Google Scholar
  • 1d Campbell N. Barclay BM. Chem. Rev.  1947,  40:  359 
    Google Scholar
  • 1e Knölker H.-J. Reddy KR. In The Alkaloids   Vol. 65:  Cordell GA. Academic Press; Amsterdam: 2008.  p.1 
    Google Scholar
  • 1f Ishikura M. Hino A. Yaginuma T. Agata I. Katagiri N. Tetrahedron  2000,  56:  193 
    Google Scholar
  • 1g Archer S. Ross BS. Pica-Mattoccia L. Cioli D. J. Med. Chem.  1987,  30:  1204 
    Google Scholar
  • 1h Monks NR. Blankey DC. East SJ. Dowell RI. Caluete JA. Curtin NJ. Arris CE. Newell DR. Eur. J. Cancer  2002,  11:  1543 
    Google Scholar
  • 1i Molina P. Fresneda PM. Almendros P. Tetrahedron  1993,  49:  1223 
    Google Scholar
  • 1j Gribble GW. Synlett  1991,  289 
    Google Scholar
  • 1k Marsais F. Pineau P. Nivolliers F. Mallat M. Turck A. Godard A. Queguiner G. J. Org. Chem.  1992,  57:  565 
    Google Scholar
  • 1l Akue-Gedu R. Rossignol E. Azzaro S. Knapp S. Filippakopoulos P. Bullock AN. Bain J. Cohen P. Prudhomme M. Anizon F. Moreau PJ.
    J. Med. Chem.  2009,  52:  6369 
    Google Scholar
  • 1m Ayats C. Soley R. Albericio F. Alvarez M. Org. Biomol. Chem.  2009,  5:  860 
    Google Scholar
  • 1n Laronze M. Boisbrun M. Léonce S. Pfeiffer B. Renard P. Lozach O. Meijer L. Lansiaux A. Bailly C. Sapi J. Laronze J.-Y. Bioorg. Med. Chem.  2005,  13:  2263 
    Google Scholar
  • 2a Kavitha C. Rajendra P. J. Chem. Res., Synop.  2003,  10:  606 
    Google Scholar
  • 2b Chakraborty DP. Islam A. J. Indian Chem. Soc.  1971,  48:  91 
    Google Scholar
  • 2c Chakraborty DP. Islam A. Bhattacharyya P. J. Org. Chem.  1973,  38:  2728 
    Google Scholar
  • 2d Knölker H.-J. Hofmann C. Tetrahedron Lett.  1996,  37:  7947 
    Google Scholar
  • 2e Gruner KK. Knölker H.-J. Org. Biomol. Chem.  2008,  6:  3902 
    Google Scholar
  • 3a Ito C. Katsuno S. Ruangrungsi N. Furukawa H. Chem. Pharm. Bull.  1998,  46:  344 
    Google Scholar
  • 3b Wu T.-S. Huang S.-C. Wu P.-L. Chem. Pharm. Bull.  1998,  46:  1459 
    Google Scholar
  • 3c Ito C. Itoigawa M. Aizawa K. Yoshida K. Ruangrungsi N. Furukawa H. J. Nat. Prod.  2009,  72:  1202 
    Google Scholar
  • 3d Lebold TP. Kerr MA. Org. Lett.  2008,  10:  997 
    Google Scholar
  • 3e Lebold TP. Kerr MA. Org. Lett.  2007,  9:  1883 
    Google Scholar
  • 3f Jana AK. Mal D. Chem. Commun.  2010,  46:  4411 
    Google Scholar
  • 4 Ito C. Itoigawa M. Furukawa H. Ichiishi E. Mukainaka T. Okuda M. Ogata M. Tokuda H. Nishino H. Cancer Lett.  1999,  142:  49 
    CrossrefGoogle Scholar
  • 5 Ramsewak RS. Nair MG. Strasburg GM. DeWitt DL. Nitiss JL. J. Agric. Food Chem.  1999,  47:  445 
    Google Scholar
  • 6a Itoigawa M. Kashiwada Y. Ito C. Furukawa H. Tachibana Y. Bastow KF. Lee K.-H. J. Nat. Prod.  2000,  63:  893 
    Google Scholar
  • 6b Wu T.-S. Wang M.-L. Wu P.-L. Phytochemistry  1996,  43:  785 
    Google Scholar
  • 7a Ito C. Katsuno S. Itoigawa M. Ruangrungsi N. Mukainaka T. Okuda M. Kitagawa Y. Tokuda H. Nishino H. Furukawa H. J. Nat. Prod.  2000,  63:  125 
    Google Scholar
  • 7b Ito C. Itoigawa M. Katsuno S. Omura M. Tokuda H. Nishino H. Furukawa H. J. Nat. Prod.  2000,  63:  1218 
    Google Scholar
  • 8a Forke R. Krahl MP. Krause T. Schlechtingen G. Knölker H.-J. Synlett  2007,  268 
    Google Scholar
  • 8b Gruner KK. Hopfmann T. Mastumoto K. Jäger A. Katsuli T. Knölker H.-J. Org. Biomol. Chem.  2011,  9:  2057 
    Google Scholar
  • 8c Konstanze KG. Knölker H.-J. Org. Biomol. Chem.  2008,  6:  3902 
    Google Scholar
  • 9a Correa A. Mancheno OG. Bolm C. Chem. Soc. Rev.  2008,  37:  1108 
    Google Scholar
  • 9b Guru MM. Ali MdA. Punniyamurthy T. Org. Lett.  2011,  13:  1194 
    Google Scholar
  • 9c Wang W. Luo F. Zhang S. Cheng J. J. Org. Chem.  2010,  75:  2415 
    Google Scholar
  • 9d Rao H. Fu H. Synlett  2011,  745 
    Google Scholar
  • 9e Liu C. Zhang H. Shi W. Lei A. Chem. Rev.  2011,  111:  1780 
    Google Scholar
  • 9f Nakamura I. Yamamoto Y. Chem. Rev.  2004,  104:  2127 
    Google Scholar
  • 9g Majumdar KC. Sinha B. Maji PK. Chattopadhyay SK. Tetrahedron  2009,  65:  2751 
    Google Scholar
  • 9h He C.-Y. Fan S. Zhang X. J. Am. Chem. Soc.  2010,  132:  12850 
    Google Scholar
  • 9i Sasaki Y. Horita Y. Zhong C. Sawamura M. Ito H. Angew. Chem. Int. Ed.  2011,  50:  2778 
    Google Scholar
  • 10a Campeau L.-C. Parisien M. Leblanc M. Fagnou K. J. Am. Chem. Soc.  2004,  126:  9186 
    Google Scholar
  • 10b Zhou G. Liu F. Zhang J. Chem. Eur. J.  2011,  17:  3101 
    Google Scholar
  • 10c Zaitsev VG. Daugulis O. J. Am. Chem. Soc.  2005,  127:  4156 
    Google Scholar
  • 10d Seregin IV. Gevorgyan V. Chem. Soc. Rev.  2007,  36:  1173 
    Google Scholar
  • 10e Koubachi J. Berteina-Raboin S. Mouaddib A. Guillaumet G. Tetrahedron  2010,  66:  1937 
    Google Scholar
11

The CCDC deposition number for compound 4b is 823151; formula: C26H15NO2; unit cell parameters: a = 8.2147(7), b = 9.9766(7), c = 12.2199(11), α = 88.285(6), β = 87.066(7), γ = 67.350(7); space group P 1. The CCDC deposition number for compound 4d is 824502; formula: C22H17NO2; unit cell parameters: a = 7.5580(5), b = 19.9905(8), c = 10.6520(6); space group Pna21. The CCDC deposition number for compound 5d is 823152; formula: C22H17NO2; unit cell parameters: a = 8.5988(6), b = 15.5481(14), c = 14.6529(12), β = 122.242(6); space group P21/c. The CCDC deposition number for compound 5f is 824503; formula: C23H19NO2; unit cell parameters: a = 7.5027(6), b = 9.1436(12), c = 12.7349(13), α = 100.156(0), β = 101.632(8), γ = 92.456(9); space group P 1.