PDF herunterladen
Synthesis 2012(6): 934-940  
DOI: 10.1055/s-0031-1289705
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(I) Iodide Catalyzed 3-Sulfenylation of Indoles with Unsymmetric Benzothiazolyl-Containing Disulfides at Room Temperature

Wenlei Ge, Yunyang Wei*
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China
Fax: +86(25)84317078; e-Mail: ywei@mail.njust.edu.cn;
Weitere Informationen

Publikationsverlauf

Received 5 December 2011
Publikationsdatum:
14. Februar 2012 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A highly efficient protocol for the synthesis of 3-sulfenylindoles in moderate to excellent yields via the reaction of indoles with unsymmetric benzothiazolyl-containing disulfides is described. Copper(I) iodide is used as the catalyst and the reactions take place at room temperature. The by-product, 2-mercaptobenzothiazole, can be easily recovered and reused.

Key words

indoles - 3-sulfenylindoles - sulfur - copper(I) iodide - unsymmetric disulfides

    References

  • 1a Sundberg RJ. In The Chemistry of Indoles   Academic Press; New York: 1996. 
  • 1b Casapullo A. Bifulco G. Bruno I. Riccio R. J. Nat. Prod.  2000,  63:  447 
    Suche in Google Scholar
  • 1c Garbe TR. Kobayashi M. Shimizu N. Takesue N. Ozawa M. Yukawa H. J. Nat. Prod.  2000,  63:  596 
    Suche in Google Scholar
  • 1d Bao B. Sun Q. Yao X. Hong J. Lee CO. Sim CJ. Im KS. Jung JH. J. Nat. Prod.  2005,  68:  711 
    Suche in Google Scholar
  • 2a Ragno R. Coluccia A. La Regina G. De Martino G. Piscitelli F. Lavecchia A. Novellino E. Bergamini A. Ciaprini C. Sinistro A. Maga G. Crespan E. Artico M. Silvestri R. J. Med. Chem.  2006,  49:  3172 
    Suche in Google Scholar
  • 2b De Martino G. La Regina G. Coluccia A. Edler MC. Barbera MC. Brancale A. Wilcox E. Hamel E. Artico M. Silvestri R. J. Med. Chem.  2004,  47:  6120 
    Suche in Google Scholar
  • 2c Berger JP, Doebber TW, Leibowitz M, Moller DE, Mosley RT, Tolman RL, Ventre J, Zhang BB, and Zhou G. inventors; PCT Int. Appl. WO  0130343.  ; Chem. Abstr. 2001, 134, 320871
  • 2d Ramakrishna VSN, Shirsath VS, Kambhampati RS, Vishwakarma S, Kandikere NV, Kota S, and Jasti V. inventors; PCT Int. Appl. WO  2007020653.  ; Chem. Abstr. 2007, 146, 274218
  • 2e La Regina G. Edler MC. Brancale A. Kandil S. Coluccia A. Piscitelli F. Hamel E. De Martino G. Matesanz R. Díaz JF. Scovassi AI. Prosperi E. Lavecchia A. Novellino E. Artico M. Silvestri R. J. Med. Chem.  2007,  50:  2865 
    Suche in Google Scholar
  • 2f Funk CD. Nat. Rev. Drug Discovery  2005,  4:  664 
    Suche in Google Scholar
  • 2g Unangst PC. Connor DT. Stabler SR. Weikert RJ. Carethers ME. Kennedy JA. Thueson DO. Chestnut JC. Adolphson RL. Conroy MC. J. Med. Chem.  1989,  32:  1360 
    Suche in Google Scholar
  • 2h Armer RE, and Wynne GM. inventors; PCT Int. Appl. WO  2008012511.  ; Chem. Abstr. 2008, 148, 183423
  • 3a Maeda Y. Koyabu M. Nishimura T. Uemura S.
    J. Org. Chem.  2004,  69:  7688 
    Suche in Google Scholar
  • 3b De Martino G. Edler MC. La Regina G. Coluccia A. Barbera MC. Barrow D. Nicholson RI. Chiosis G. Brancale A. Hamel E. Artico M. Silvestri R. J. Med. Chem.  2006,  49:  947 
    Suche in Google Scholar
  • 4 Tomita K. Terada A. Tachikawa R. Heterocycles  1976,  4:  729 
    Suche in Google Scholar
  • 5 Jain S. Shukla K. Mukhopadhyay A. Suryawashi SN. Bhakuni DS. Synth. Commun.  1990,  20:  1315 
    Suche in Google Scholar
  • 6a Raban M. Chern L. J. Org. Chem.  1980,  45:  1688 
    Suche in Google Scholar
  • 6b Ranken PF. McKinnie BG. J. Org. Chem.  1989,  54:  2985 
    Suche in Google Scholar
  • 6c Browder CC. Mitchell MO. Smith RL. el-Sulayman G. Tetrahedron Lett.  1993,  34:  6245 
    Suche in Google Scholar
  • 6d Hamel P. Préville P. J. Org. Chem.  1996,  61:  1573 
    Suche in Google Scholar
  • 6e Hamel P. Tetrahedron Lett.  1997,  38:  8473 
    Suche in Google Scholar
  • 6f Hamel P. J. Org. Chem.  2002,  67:  2854 
    Suche in Google Scholar
  • 7a Matsugi M. Murata K. Gotanda K. Nambu H. Anilkumar G. Matsumoto K. Kita Y. J. Org. Chem.  2001,  66:  2434 
    Suche in Google Scholar
  • 7b Matsugi M. Murata K. Nambu H. Kita Y. Tetrahedron Lett.  2001,  42:  1077 
    Suche in Google Scholar
  • 8a Schlosser KM. Krasutsky AP. Hamilton HW. Reed JE. Sexton K. Org. Lett.  2004,  6:  819 
    Suche in Google Scholar
  • 8b Tudge M. Tamiya M. Savarin C. Humphrey GR. Org. Lett.  2006,  8:  565 
    Suche in Google Scholar
  • 8c Silveira CC. Mendes SR. Wolf L. Martins GM. Tetrahedron Lett.  2010,  51:  2014 
    Suche in Google Scholar
  • 9 Kisaki S. Tominaga Y. Matsuda Y. Kobayashi G. Chem. Pharm. Bull.  1974,  22:  2246 
    Suche in Google Scholar
  • 10 Woodbridge RG. Dougherty G. J. Am. Chem. Soc.  1950,  72:  4320 
    Suche in Google Scholar
  • 11 Campbell JA. Broka CA. Gong L. Walker KAM. Wang J.-H. Tetrahedron Lett.  2004,  45:  4073 
    Suche in Google Scholar
  • 12 Yadav JS. Reddy BVS. Reddy YJ. Tetrahedron Lett.  2007,  48:  7034 
    Suche in Google Scholar
  • 13a Ranken PF. McKinnie BG. J. Org. Chem.  1989,  54:  2985 
    Suche in Google Scholar
  • 13b Maeda Y. Koyabu M. Nishimura T. Uemura S. J. Org. Chem.  2004,  69:  7688 
    Suche in Google Scholar
  • 13c Yadav JS. Reddy BVS. Reddy YJ. Praneeth K. Synthesis  2009,  1520 
  • 13d Fang X.-L. Tang R.-Y. Zhong P. Li J.-H. Synthesis  2009,  4183 
  • 13e Li Z. Hong JQ. Zhou XJ. Tetrahedron  2011,  67:  3690 
    Suche in Google Scholar
  • 14a Brzezinska E. Ternay AL. J. Org. Chem.  1994,  59:  8239 
    Suche in Google Scholar
  • 14b Giuseppe L. Antonio T. Ann. Chim. (Rome)  1955,  45:  842 
    Suche in Google Scholar
  • 15a Stein A. Alves D. da Rocha J. Nogueira C. Zeni G. Org. Lett.  2008,  10:  4983 
    Suche in Google Scholar
  • 15b Taniguchi N. J. Org. Chem.  2006,  71:  7874 
    Suche in Google Scholar
  • 15c Taniguchi N. Tetrahedron  2009,  65:  2782 
    Suche in Google Scholar
  • 15d Takeuchi H. Hiyama T. Kamai N. Oya H.
    J. Chem. Soc., Perkin Trans. 2  1997,  2301 
  • 15e Taniguchi N. Synlett  2006,  1351 
  • 16 Wu GL. Wu J. Wu JL. Wu LM. Synth. Commun.  2008,  38:  1036 
    Suche in Google Scholar
  • 17 Beveridge S. Harris RLN. Aust. J. Chem.  1971,  24:  1229 
    Suche in Google Scholar
  • 18 Plate R. Ottenheijm HCJ. Nivard RJF. J. Org. Chem.  1984,  49:  540 
    Suche in Google Scholar