Synthesis 2011(4): 626-634  
DOI: 10.1055/s-0030-1258411
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Assembly of 11H-Indolo[3,2-c]quinoline by a Two-Step Protocol Involving a Regioselective 6-endo-Cyclization Promoted by the Hendrickson Reagent

Min Xua, Qiwen Houa, Shaozhong Wang*a, Huaqin Wangb, Zhu-Jun Yaoa
a School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P. R. of China
Fax: +86(25)83317761; e-Mail: [email protected];
b Modern Analytical Center of Nanjing University, Nanjing 210093, P. R. of China
Further Information

Publication History

Received 1 November 2010
Publication Date:
14 January 2011 (online)

Abstract

An expedient approach was developed to construct the 11H-indolo[3,2-c]quinoline scaffold starting from acyclic alkyne substrates. The five- and six-membered nitrogen-containing rings in the tetracyclic skeleton were elaborated efficiently by gold(III)-catalyzed 5-endo-dig cyclization and Hendrickson reagent promoted regioselective 6-endo cyclization.

    Reference

  • 1 For a review, see: Lavrado J. Moreira R. Paulo A. Curr. Med. Chem.  2010,  17:  2348 
  • 2a Pousset J.-L. Martin M.-T. Jossang A. Bodo B. Phytochemistry  1995,  39:  735 
  • 2b Van Miert S. Hostyn S. Maes BUW. Cimanga K. Brun R. Kaiser M. Matyus P. Dommisse R. Lemiere G. Vlietinck A. Pieters L. J. Nat. Prod.  2005,  68:  674 
  • 3a Lu C.-M. Chen Y.-L. Chen H.-L. Chen C.-A. Lu P.-J. Yang C.-N. Tzeng C.-C. Bioorg. Med. Chem.  2010,  18:  1948 
  • 3b He L. Chang H.-X. Chou T.-C. Savaraj N. Cheng C.-C. Eur. J. Med. Chem.  2003,  38:  101 
  • 3c Chen Y.-L. Chung C.-H. Chen I.-L. Chen PH. Jeng H.-Y. Bioorg. Med. Chem.  2002,  10:  2705 
  • 4a Dhanabal T. Sangeetha R. Mohan PS. Tetrahedron  2006,  62:  6258 
  • 4b Nandha Kumar R. Suresh T. Mohan PS. Tetrahedron Lett.  2002,  43:  3327 
  • 5a Kraus GA. Guo H. Tetrahedron Lett.  2010,  51:  4137 
  • 5b Beres M. Timari G. Hajos G. Tetrahedron Lett.  2002,  43:  6035 
  • 5c Fresneda PM. Molina P. Delgado S. Tetrahedron  2001,  57:  6197 
  • 5d Fresneda PM. Molina P. Delgado S. Tetrahedron Lett.  1999,  40:  7275 
  • 6a Meyers C. Rombouts G. Loones KTJ. Coelho A. Maes BUW. Adv. Synth. Catal.  2008,  350:  465 
  • 6b Jonckers THM. Maes BUW. Lemiere GLF. Rombouts G. Pieters L. Haemers A. Dommisse RA. Synlett  2003,  615 
  • 7 Agarwal PK. Sawant D. Sharma S. Kundu B. Eur. J. Org. Chem.  2009,  292 
  • 8 Miki Y. Kuromatsu M. Miyatake H. Hamamoto H. Tetrahedron Lett.  2007,  48:  9093 
  • 9 Cacchi S. Fabrizi G. Pace P. Marinelli F. Synlett  1999,  620 
  • 10 Sakai N. Annaka K. Konakahara T. J. Org. Chem.  2006,  71:  3653 
  • 11 Sakai N. Annaka K. Fujita A. Sato A. Konakahara T. J. Org. Chem.  2008,  73:  4160 
  • 12a Alfonsi M. Acradi A. Aschi M. Bianchi G. Marinelli F. J. Org. Chem.  2005,  70:  2265 
  • 12b Arcadi A. Bianchi G. Marinelli F. Synthesis  2004,  610 
  • 13 Hendrickson JB. Schwartzman SM. Tetrahedron Lett.  1975,  16:  277 
  • 14a Wu M. Wang S. Synthesis  2010,  587 
  • 14b Liu G.-S. Yao Y.-S. Xu P. Wang S. Yao Z.-J. Chem. Asian J.  2010,  5:  1382 
  • 14c Zhou H.-B. Liu G.-S. Yao Z.-J. J. Org. Chem.  2007,  72:  6270 
  • 14d Zhou H.-B. Liu G.-S. Yao Z.-J. Org. Lett.  2007,  9:  2003 
  • 14e You S.-L. Kelly JW. Org. Lett.  2004,  6:  1681 
  • 14f You S.-L. Kelly JW. J. Org. Chem.  2003,  68:  9506 
  • 14g You S.-L. Razavi H. Kelly JW. Angew. Chem. Int. Ed.  2003,  42:  83 
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CCDC 780631 and 793932 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.