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

Xiaoyan Wu; Lu Xue; Shilong Luo; Shiqi Jia; Jun Ao; Wenling Qin

doi:10.1055/s-0036-1589073

Synthesis, Table of Contents

Synthesis 2017; 49(22): 5017-5024
DOI: 10.1055/s-0036-1589073

paper

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 Affiliations

Abstract

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

Full Text

References

References

1a Shaveta Singh A. Kaur M. Sharma S. Bhatti R. Singh P. Eur. J. Med. Chem. 2014; 77: 185
1b Faulkner DJ. Nat. Prod. Rep. 2002; 19: 1
1c Bosch J. Bennasar M.-L. Synlett 1995; 587
1d Chen F.-E. Huang J. Chem. Rev. 2005; 105: 4671

2a Wu L. Xie C. Mei H. Soloshonok VA. Han J. Pan Y. J. Org. Chem. 2014; 79: 7677
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
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
2k Bartoli G. Bosco M. Carlone A. Pesciaioli F. Sambri L. Melchiorre P. Org. Lett. 2007; 9: 1403
2l Fleming EM. McCabe T. Connon SJ. Tetrahedron Lett. 2006; 47: 7037
2m Zheng C. Sheng Y.-F. Li Y.-X. You S.-L. Tetrahedron 2010; 66: 2875

3a Somei M. Yamada F. Nat. Prod. Rep. 2004; 21: 278
3b O’Connor SE. Maresh JJ. Nat. Prod. Rep. 2006; 23: 532

4a Zuo Z. Zhang S. Wang R. He W. Wu S. Xie X. Qin D. Jing L. Synthesis 2013; 45: 2832
4b Wang R. Jing L. Qin D. Tetrahedron Lett. 2015; 56: 2867
4c Cao L.-L. Li X.-N. Meng F.-Y. Jiang G.-F. Tetrahedron Lett. 2012; 53: 3873
4d Jing L. Wei J. Zhou L. Huang Z. Li Z. Wu D. Xiang H. Zhou X. Chem. Eur. J. 2010; 16: 10955
4e Chen P. Lu S.-m. Guo W. Liu Y. Li C. Chem. Commun. 2016; 52: 96
4f Ballini R. Palmieri A. Petrini M. Torregiani E. Org. Lett. 2006; 8: 4093
4g Li Y. Shi F.-Q. He Q.-L. You S.-L. Org. Lett. 2009; 11: 3182
4h Shaikh RR. Mazzanti A. Petrini M. Bartoli G. Melchiorre P. Angew. Chem. Int. Ed. 2008; 47: 8707
4i Huang W. Yang J. Li X. Yuan L. Ma Y. Zhou Q. Liang D. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191: 772

5 Thirupathi P. Kim SS. J. Org. Chem. 2009; 74: 7755
6 Thirupathi P. Neupane LN. Lee K.-H. Tetrahedron 2011; 67: 7301
7 Kuhakarn C. Tangdenpaisal K. Kongsaeree P. Prabpai S. Tuchinda P. Pohmakotr M. Reutrakul V. Tetrahedron Lett. 2007; 48: 2467
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
10 Kadam ST. Thirupathi P. Kim SS. Tetrahedron 2009; 65: 10383
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
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
12d Maeda Y. Koyabu M. Nishimura T. Uemura S. J. Org. Chem. 2004; 69: 7688
12e Prasad CD. Kumar S. Sattar M. Adhikary A. Kumar S. Org. Biomol. Chem. 2013; 11: 8036
12f Ge W. Wei Y. Green Chem. 2012; 14: 2066
12g Yang F.-L. Tian S.-K. Angew. Chem. Int. Ed. 2013; 52: 4929

13a Kianmehr E. Pakbaznia A. Faghih N. Foroumadi A. Tetrahedron 2017; 73: 1407
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