Download PDF
Synthesis 2017; 49(22): 5017-5024
DOI: 10.1055/s-0036-1589073
paper
© Georg Thieme Verlag Stuttgart · New York

K2S2O8-Activated Friedel–Crafts Type Alkylation of Indoles with α-Amido Sulfones

Xiaoyan Wu
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, No.55 Daxuecheng, South Rd., Shapingba, Chongqing 401331, P. R. of China   Email: wenling.qin@cqu.edu.cn
,
Lu Xue
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, No.55 Daxuecheng, South Rd., Shapingba, Chongqing 401331, P. R. of China   Email: wenling.qin@cqu.edu.cn
,
Shilong Luo
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, No.55 Daxuecheng, South Rd., Shapingba, Chongqing 401331, P. R. of China   Email: wenling.qin@cqu.edu.cn
,
Shiqi Jia
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, No.55 Daxuecheng, South Rd., Shapingba, Chongqing 401331, P. R. of China   Email: wenling.qin@cqu.edu.cn
,
Jun Ao
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, No.55 Daxuecheng, South Rd., Shapingba, Chongqing 401331, P. R. of China   Email: wenling.qin@cqu.edu.cn
,
Wenling Qin*
Innovative Drug Research Centre, School of Pharmaceutical Sciences, Chongqing University, No.55 Daxuecheng, South Rd., Shapingba, Chongqing 401331, P. R. of China   Email: wenling.qin@cqu.edu.cn
› Author AffiliationsThis work was supported by the Fundamental Research Funds for the Central Universities (Grant No. 0903005203479), NSFC (21402016).
Further Information

Publication History

Received: 20 April 2017

Accepted after revision: 14 June 2017

Publication Date:
25 July 2017 (online)

    Permissions and Reprints All articles of this category


Abstract

A K2S2O8-activated regioselective alkylation of α-amido sulfones at the C-3 position of indoles is reported. The protocol developed herein provides an alternative new strategy to the previous approach by using Lewis acid, clay, and resin as catalyst for this Friedel–Crafts type alkylation of indoles with α-amido sulfones. The formed product bears a versatile transformable sulfone group and an amino group. The reaction condition is tolerant to a wide range of substrates, including a series of indoles with electron-withdrawing and electron-donating groups at different positions. Moreover, a variety of α-substituted phenylamido sulfones and some α-aliphatic amido sulfones also give the desired products in modest yield. Furthermore, a preliminary mechanism study was performed and the plausible reaction mechanism is discussed.

Key words

K2S2O8 - indole alkylation - α-amido sulfone - Friedel–Crafts reaction
 

  • References

    • 1a Shaveta Singh A. Kaur M. Sharma S. Bhatti R. Singh P. Eur. J. Med. Chem. 2014; 77: 185
      CrossrefPubMed
    • 1b Faulkner DJ. Nat. Prod. Rep. 2002; 19: 1
    • 1c Bosch J. Bennasar M.-L. Synlett 1995; 587
      Article in Thieme Connect
    • 1d Chen F.-E. Huang J. Chem. Rev. 2005; 105: 4671
      CrossrefPubMed
    • 2a Wu L. Xie C. Mei H. Soloshonok VA. Han J. Pan Y. J. Org. Chem. 2014; 79: 7677
      CrossrefPubMed
    • 2b Lin J.-H. Xiao J.-C. Eur. J. Org. Chem. 2011; 4536
    • 2c Terrasson V. de Figueiredo RM. Campagne JM. Eur. J. Org. Chem. 2010; 2635
    • 2d Peng J. Du D.-M. Eur. J. Org. Chem. 2012; 4042
    • 2e Shi Z.-H. Sheng H. Yang K.-F. Jiang J.-X. Lai G.-Q. Lu Y. Xu L.-W. Eur. J. Org. Chem. 2011; 66
    • 2f Tang H.-Y. Lu A.-D. Zhou Z.-H. Zhao G.-F. He L.-N. Tang C.-C. Eur. J. Org. Chem. 2008; 1406
    • 2g Yu X. Lu A. Wang Y. Wu G. Song H. Zhou Z. Tang C. Eur. J. Org. Chem. 2011; 892
    • 2h Jia Y.-X. Xie J.-H. Duan H.-F. Wang L.-X. Zhou Q.-L. Org. Lett. 2006; 8: 1621
      Crossref
    • 2i McKeon SC. Müller-Bunz H. Guiry PJ. Eur. J. Org. Chem. 2009; 4833
    • 2j Chen L.-Y. He H. Chan W.-H. Lee AW. M. J. Org. Chem. 2011; 76: 7141
      CrossrefPubMed
    • 2k Bartoli G. Bosco M. Carlone A. Pesciaioli F. Sambri L. Melchiorre P. Org. Lett. 2007; 9: 1403
      CrossrefPubMed
    • 2l Fleming EM. McCabe T. Connon SJ. Tetrahedron Lett. 2006; 47: 7037
      Crossref
    • 2m Zheng C. Sheng Y.-F. Li Y.-X. You S.-L. Tetrahedron 2010; 66: 2875
      Crossref
    • 3a Somei M. Yamada F. Nat. Prod. Rep. 2004; 21: 278
      Crossref
    • 3b O’Connor SE. Maresh JJ. Nat. Prod. Rep. 2006; 23: 532
      CrossrefPubMed
    • 4a Zuo Z. Zhang S. Wang R. He W. Wu S. Xie X. Qin D. Jing L. Synthesis 2013; 45: 2832
      Article in Thieme Connect
    • 4b Wang R. Jing L. Qin D. Tetrahedron Lett. 2015; 56: 2867
      Crossref
    • 4c Cao L.-L. Li X.-N. Meng F.-Y. Jiang G.-F. Tetrahedron Lett. 2012; 53: 3873
      Crossref
    • 4d Jing L. Wei J. Zhou L. Huang Z. Li Z. Wu D. Xiang H. Zhou X. Chem. Eur. J. 2010; 16: 10955
      Crossref
    • 4e Chen P. Lu S.-m. Guo W. Liu Y. Li C. Chem. Commun. 2016; 52: 96
      CrossrefPubMed
    • 4f Ballini R. Palmieri A. Petrini M. Torregiani E. Org. Lett. 2006; 8: 4093
      Crossref
    • 4g Li Y. Shi F.-Q. He Q.-L. You S.-L. Org. Lett. 2009; 11: 3182
      CrossrefPubMed
    • 4h Shaikh RR. Mazzanti A. Petrini M. Bartoli G. Melchiorre P. Angew. Chem. Int. Ed. 2008; 47: 8707
      Crossref
    • 4i Huang W. Yang J. Li X. Yuan L. Ma Y. Zhou Q. Liang D. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191: 772
      Crossref
  • 5 Thirupathi P. Kim SS. J. Org. Chem. 2009; 74: 7755
    CrossrefPubMed
  • 6 Thirupathi P. Neupane LN. Lee K.-H. Tetrahedron 2011; 67: 7301
    Crossref
  • 7 Kuhakarn C. Tangdenpaisal K. Kongsaeree P. Prabpai S. Tuchinda P. Pohmakotr M. Reutrakul V. Tetrahedron Lett. 2007; 48: 2467
    Crossref
  • 8 Thirupathi P. Kim SS. Eur. J. Org. Chem. 2010; 1798
  • 9 Ballini R. Palmieri A. Petrini M. Torregiani E. Org. Lett. 2006; 8: 4093
    Crossref
  • 10 Kadam ST. Thirupathi P. Kim SS. Tetrahedron 2009; 65: 10383
    Crossref
  • 11 Blay G. Girón RM. Montesinos-Magraner M. Pedro JR. Eur. J. Org. Chem. 2013; 3885
    • 12a Zhang H. Bao X. Song Y. Qu J. Wang B. Tetrahedron 2015; 71: 8885
      Crossref
    • 12b Chawla R. Singh AK. Yadav LD. S. Eur. J. Org. Chem. 2014; 2032
    • 12c Rao H. Wang P. Wang J. Li Z. Sun X. Cao S. RSC Adv. 2014; 4: 49165
      Crossref
    • 12d Maeda Y. Koyabu M. Nishimura T. Uemura S. J. Org. Chem. 2004; 69: 7688
      Crossref
    • 12e Prasad CD. Kumar S. Sattar M. Adhikary A. Kumar S. Org. Biomol. Chem. 2013; 11: 8036
      CrossrefPubMed
    • 12f Ge W. Wei Y. Green Chem. 2012; 14: 2066
      Crossref
    • 12g Yang F.-L. Tian S.-K. Angew. Chem. Int. Ed. 2013; 52: 4929
      Crossref
    • 13a Kianmehr E. Pakbaznia A. Faghih N. Foroumadi A. Tetrahedron 2017; 73: 1407
      Crossref
    • 13b Yi F. Su J. Zhang S. Yi W. Zhang L. Eur. J. Org. Chem. 2015; 7360
    • 13c He X. Hu S. Liu K. Guo Y. Xu J. Shao S. Org. Lett. 2006; 8: 333
      CrossrefPubMed