Download PDF
Synthesis 2008(24): 4036-4040  
DOI: 10.1055/s-0028-1083236
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Indoles via Diethylzinc-Mediated Intramolecular Hydroamination Reactions of Alkynyl Sulfonamides

Yan Yin, Zhuo Chai, Wen-Ying Ma, Gang Zhao*
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: zhaog@mail.sioc.ac.cn;
Further Information

Publication History

Received 17 April 2008
Publication Date:
01 December 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

A series of indole derivatives were synthesized through the intramolecular hydroamination of alkynyl sulfonamides using 20 mol% of diethylzinc as the catalyst. A tandem cyclization-nucleophilic addition reaction was also possible to afford C2,C3-disubstituted indoles using 120 mol% of diethylzinc.

Key words

diethylzinc - intramolecular hydroamination - alkynyl sulfonamides - cyclizations - tandem reactions

    References

  • 1a Hibino S. Choshi T. Nat. Prod. Rep.  2002,  19:  148 
    Google Scholar
  • 1b Gupta RR. Heterocyclic Chemistry   Vol. 2:  Springer; New York: 1999.  p.193 
    Google Scholar
  • 1c Rahman A. Basha A. Indole Alkaloids   Harwood Academic; Amsterdam: 1998. 
    Google Scholar
  • 1d Dewick PM. Medicinal Natural Products   Wiley; Chichester: 1997. 
    Google Scholar
  • 2a Sundberg RJ. Indoles   Academic Press; London: 1996. 
    Google Scholar
  • 2b Humphery GR. Kuethe JT. Chem. Rev.  2006,  106:  2875 
    Google Scholar
  • 2c Patil S. Buolamwini JK. Curr. Org. Synth.  2006,  3:  477 
    Google Scholar
  • 2d Song JJ. Reeves JT. Gallow F. Tan Z. Yee NK. Chem. Soc. Rev.  2007,  36:  1120 
    Google Scholar
  • 3a Aillaud I. Collin J. Duhayon C. Guillot R. Lyubov D. Schulz E. Trifonov A. Chem. Eur. J.  2008,  14:  2189 
    Google Scholar
  • 3b Ackermann L. Sandmann R. Villar A. Kaspar LT. Tetrahedron  2007,  64:  769 
    Google Scholar
  • 3c Ebrahimi D. Kennedy DF. Messerle BA. Hibbert DB. Analyst  2008,  133:  817 
    Google Scholar
  • 4a Nakamura M. Ilies L. Otsubo S. Nakamura E. Angew. Chem. Int. Ed.  2006,  45:  944 
    Google Scholar
  • 4b Nakamura M. Ilies L. Otsubo S. Nakamura E. Org. Lett.  2006,  8:  2803 
    Google Scholar
  • 5a Yin Y. Ma W.-Y. Chai Z. Zhao G. J. Org. Chem.  2007,  72:  5731 
    Google Scholar
  • For related works in this field from our group, see:
  • 5b Yin Y. Zhao G. Heterocycles  2006,  68:  23 
    Google Scholar
  • 5c Yin Y. Zhao G. J. Fluorine Chem.  2007,  128:  40 
    Google Scholar
  • 6 Gregory YY. Stephenson GA. Mitchell S. Tetrahedron Lett.  2006,  47:  3811 
    CrossrefGoogle Scholar
  • 7a Baldwin JE. J. Chem. Soc., Chem. Commun.  1976,  734 
    Google Scholar
  • 7b Baldwin JE. Cutting J. Dupont W. Kruse L. Sillberman L. Thomas RC. J. Chem. Soc., Chem. Commun.  1976,  736 
    Google Scholar
  • 8a Yang CX. Patel HH. Ku YY. Synth. Commun.  1997,  27:  2125 
    Google Scholar
  • 8b Browder CC. Mitchell MO. Smith RL. el-Sulayman G. Tetrahedron Lett.  1993,  34:  6245 
    Google Scholar
  • 8c Knochel P. Singer RD. Chem. Rev.  1993,  93:  2117 ; and references cited therein
    Google Scholar
  • 8d Bergman J. Venemalm L. Tetrahedron  1990,  46:  6061 
    Google Scholar
  • 9a Kang Q. Zhao Z.-A. You S.-L. J. Am. Chem. Soc.  2007,  129:  1416 
    Google Scholar
  • 9b Terada M. Sorimach K. J. Am. Chem. Soc.  2007,  129:  292 
    Google Scholar
  • 9c Jia Y.-X. Zhong J. Zhu S.-F. Zhang C.-M. Zhou Q.-L. Angew. Chem. Int. Ed.  2007,  46:  5565 
    Google Scholar
  • 9d Wang YQ. Song J. Hong R. Li HM. Deng L. J. Am. Chem. Soc.  2006,  128:  8186 
    Google Scholar
  • 9e Trost BM. Quancard J. J. Am. Chem. Soc.  2006,  128:  6314 
    Google Scholar
  • 9f Li DP. Guo YC. Ding Y. Xiao WJ. Chem. Commun.  2006,  799 
    Google Scholar
  • 9g Bandini M. Melloni A. Tommasi S. Umani-Ronchi A. Synlett  2005,  1199 ; and references cited therein
    Google Scholar
  • 9h Herrera RP. Sgarzani V. Bernardi L. Ricci A. Angew. Chem. Int. Ed.  2005,  44:  6576 
    Google Scholar
  • 9i Yasuda M. Somyo T. Baba A. Angew. Chem. Int. Ed.  2005,  44:  1 
    Google Scholar