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Synthesis 2010(23): 4075-4081  
DOI: 10.1055/s-0030-1258289
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 3-Heteroaryloxindoles through t-BuOCl-Mediated Oxidation of 3-Heteroarylindoles

Marco Baronia, Giordano Lesmab, Letizia Puleioa, Alessandro Sacchettic, Alessandra Silvani*b, Marco Zancheta
a Sanofi-Aventis, Centro Ricerche Sanofi-Midy, Via G. Sbodio 2, 20134 Milano, Italy
b Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via G. Venezian 21, 20133 Milano, Italy
Fax: +39(02)50314078; e-Mail: alessandra.silvani@unimi.it;
c Politecnico di Milano, Dipartimento di Chimica, Materiali ed Ingegneria Chimica ‘Giulio Natta’, Via Mancinelli 7, 20131 Milano, Italy
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Publication History

Received 23 July 2010
Publication Date:
07 October 2010 (online)

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Synthesis of 3-Heteroaryloxindoles through t-BuOCl-Mediated Oxidation of 3-HeteroarylindolesSynthesis 2011; 2011(02): 352-352
DOI: 10.1055/s-0030-1258360

Abstract

The oxidation of 3-heteroarylindoles to the corresponding oxindoles with t-butyl hypochlorite has been investigated. Under carefully adjusted conditions, preparative scale of desired products can be achieved. Two competing pathways seem to contribute to the reaction mechanism, affording 3-heteroaryloxindoles bearing hydrogen or chlorine at C3, depending on stereoelectronic factors. The present methodology appears also generally applicable for the preparation of simple 3-aryloxindoles.

Key words

indole - oxindole - t-BuOCl - oxidation - heterocycles

    References

  • 1a Galliford CV. Scheidt KA. Angew. Chem. Int. Ed.  2007,  46:  8748 
    Google Scholar
  • 1b Marti C. Carreira EM. Eur. J. Org. Chem.  2003,  2209 
    Google Scholar
  • 2a Kumar RR. Perumal S. Senthilkumar P. Yogeeswari P. Dharmarajan S. J. Med. Chem.  2008,  51:  5731 
    Google Scholar
  • 2b Mendel DB. Laird AD. Xin XH. Louie SG. Christensen JG. Li GM. Schreck RE. Abrams TJ. Ngai TJ. Lee LB. Murray LJ. Carver J. Chan E. Moss KG. Haznedar JO. Sukbuntherng J. Blake RA. Sun L. Tang C. Miller T. Shirazian S. McMahon G. Cherrington JM. Clin. Cancer Res.  2003,  9:  327 
    Google Scholar
  • 2c Sun L. Liang C. Shirazian S. Zhou Y. Miller T. Cui J. Fukuda JY. Chu JY. Nematalla A. Wang XY. Chen H. Sistla A. Luu TC. Tang F. Wei J. Tang C. J. Med. Chem.  2003,  46:  1116 
    Google Scholar
  • 3a Ding K. Lu Y. Nikolovska-Coleska Z. Wang G. Qiu S. Shangary S. Gao W. Qin D. Stuckey J. Krajewski K. Roller PP. Wang S. J. Med. Chem.  2006,  49:  3432 
    Google Scholar
  • 3b Luk KC, So SS, Zhang J, and Zhang Z. inventors; WO Patent  2006136606.  ; Chem. Abstr. 2006, 146, 100555
  • 4a Jiang T. Kuhen KL. Wolff K. Yin H. Bieza K. Caldwell J. Bursulaya B. Wu TY.-H. He Y. Bioorg. Med. Chem. Lett.  2006,  16:  2105 
    Google Scholar
  • 4b Jiang T. Kuhen KL. Wolff K. Yin H. Bieza K. Caldwell J. Bursulaya B. Tuntland T. Zhang K. Karanewsky D. He Y. Bioorg. Med. Chem. Lett.  2006,  16:  2109 
    Google Scholar
  • 5 Ding K. Lu Y. Nikolovska-Coleska Z. Qiu S. Ding Y. Gao W. Stuckey J. Krajewski K. Roller PP. Tomita Y. Parrish DA. Deschamps JR. Wang S. J. Am. Chem. Soc.  2005,  127:  10130 
    CrossrefPubMedGoogle Scholar
  • 6 Blakeney JS. Reid RC. Le GT. Fairlie DP. Chem. Rev.  2007,  107:  2960 
    CrossrefGoogle Scholar
  • 7a Decaux G. Soupart A. Vassart G. Lancet  2008,  371:  1624 
    Google Scholar
  • 7b Shimazaki T. Iijima M. Chaki S. Eur. J. Pharmacol.  2006,  543:  63 
    Google Scholar
  • 7c Bernard K. Bogliolo S. Ehrenfeld J. Br. J. Pharmacol.  2005,  144:  1037 
    Google Scholar
  • 8a Holst B. Frimurer TM. Mokrosinski J. Halkjaer T. Cullberg KB. Underwood CR. Schwartz TW. Mol. Pharm.  2009,  75:  44 
    Google Scholar
  • 8b Tokunaga T. Hume WE. Umezome T. Okazaki K. Ueki Y. Kumagai K. Hourai S. Nagamine J. Seki H. Taiji M. Noguchi H. Nagata R. J. Med. Chem.  2001,  44:  4641 
    Google Scholar
  • 9 Sato S. Shibuya M. Kanoh N. Iwabuchi Y. J. Org. Chem.  2009,  74:  7522 
    CrossrefGoogle Scholar
  • 10 Altman RA. Hyde AM. Huang X. Buchwald SL.
    J. Am. Chem. Soc.  2008,  130:  9613 ; and references cited therein
    CrossrefGoogle Scholar
  • 11 Lesma G. Landoni N. Pilati T. Sacchetti A. Silvani A. J. Org. Chem.  2009,  74:  4537 
    CrossrefPubMedGoogle Scholar
  • 12 Ghosha AK. Schiltz G. Perali RS. Leshchenko S. Kay S. Walters DE. Koh Y. Maedad K. Mitsuyad H. Bioorg. Med. Chem. Lett.  2006,  16:  1869 
    CrossrefGoogle Scholar
  • 13 Ben-Ishai D. Peled N. Sataty I. Tetrahedron Lett.  1980,  21:  569 
    CrossrefGoogle Scholar
  • 14 Buchwald SL. Hennessy EJ. J. Am. Chem. Soc.  2003,  125:  12084 ; and references cited therein
    CrossrefGoogle Scholar
  • 15 Baroni M, and Puleo L. inventors; WO Patent  2009056707.  ; Chem. Abstr. 2009, 150, 515023
  • 16 Vazquez E. Payack JF. Tetrahedron Lett.  2004,  45:  6549 
    CrossrefGoogle Scholar
  • 17 Burm BEA. Gremmen C. Wanner MJ. Koomen G.-J. Tetrahedron  2001,  57:  2039 
    CrossrefGoogle Scholar
  • 18a Ling K.-Q. Sayre LM. Bioorg. Med. Chem.  2005,  13:  3543 
    Google Scholar
  • 18b Alvarez RG. Hunter IS. Suckling CJ. Thomas M. Vitinius U. Tetrahedron  2001,  57:  8581 
    Google Scholar
  • 18c Van Deurzen MPJ. van Rantwijk F. Sheldon RA. J. Mol. Catal. B: Enzym.  1996,  2:  33 
    Google Scholar
  • 19a Movassaghi M. Schmidt MA. Ashenhurst JA. Org. Lett.  2008,  10:  4009 
    Google Scholar
  • 19b Walser A. Blount JF. Fryer RI. J. Org. Chem.  1973,  38:  3077 
    Google Scholar
  • 20a Ito M. Clark CW. Mortimore M. Goh JB. Martin SF. J. Am. Chem. Soc.  2001,  123:  8003 
    Google Scholar
  • 20b Poriel C. Lachia M. Wilson C. Davies JR. Moody CJ. J. Org. Chem.  2007,  72:  2978 
    Google Scholar
  • 22 Amat M. Hadida S. Sathyanarayana S. Bosch J. J. Org. Chem.  1994,  59:  10 
    CrossrefGoogle Scholar
  • 23 Yang C.-G. Liu G. Jiang B. J. Org. Chem.  2002,   67:   9392 
    Google Scholar
  • 24 Kotha S. Lahiri K. Kashinath D. Tetrahedron  2002,  58:  9633 ; and references cited therein
    CrossrefGoogle Scholar
  • 25 Lachia M. Poriel C. M Z. Slawin A. Moody CJ. Chem. Commun.  2007,  286 
    CrossrefGoogle Scholar
21

We also included the preparation of compound 3c, which, strictly speaking, is not a heteroaryl derivative, but could serve to test the generality of the proposed methodology.