CC BY-NC-ND 4.0 · SynOpen 2020; 04(02): 17-22
DOI: 10.1055/s-0040-1707517
paper
This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/) (2020) The Author(s)

Aerobic Iron(III)-Catalyzed Direct Thiolation of Imidazo[1,2-a]pyridine with Thiols

Ling Qin
a  Department of Pharmaceutics, Nanfang Hospital, Southern Medical University, Guangzhou 510515, P. R. of China
,
Hui-bin Wu
a  Department of Pharmaceutics, Nanfang Hospital, Southern Medical University, Guangzhou 510515, P. R. of China
,
Lidong Weng
b  School of Traditional Chinese Medicine, Southern Medical University, Shatainan road 1023th, Guangzhou 510515, P. R. of China   Email: sq@smu.edu.cn   Email: chenhuoji@smu.edu.cn
,
Qun Shen
b  School of Traditional Chinese Medicine, Southern Medical University, Shatainan road 1023th, Guangzhou 510515, P. R. of China   Email: sq@smu.edu.cn   Email: chenhuoji@smu.edu.cn
,
Huoji Chen
b  School of Traditional Chinese Medicine, Southern Medical University, Shatainan road 1023th, Guangzhou 510515, P. R. of China   Email: sq@smu.edu.cn   Email: chenhuoji@smu.edu.cn
› Author Affiliations
Funding was provided by the Natural Science Foundation of Guangdong Province (2017A030310021), the Science and Technology Program of Guangdong Province (2017A050506027, 2017B090912005) and the Science and Technology Program of Guangzhou (201807010053).
Further Information

Publication History

Received: 10 March 2020

Accepted after revision: 31 March 2020

Publication Date:
21 April 2020 (online)


§ These authors contributed equally to this work.

Abstract

A novel and efficient iron(III)-catalyzed regioselective C-3 sulfenylation of imidazo[1,2-a]pyridines with thiols under oxygen atmosphere has been developed. The reaction proceeds in moderate to good yields with a broad range of substrates, providing a novel, efficient and green route for accessing synthetically useful C3-sulfenated imidazo-[1,2-a]pyridines. Moreover, the fluoride-containing C3-sulfenated imidazo-[1,2-a]pyridine 3ai exhibited superior anticancer activity and good safety profiles.

Supporting Information

 
  • References

  • 1 Gueiffier A, Viols H, Galtier C, Blache Y, Chavignon O, Teulade JC, Chapat JP. Heterocycl. Commun. 1994; 1: 83
  • 2 Salgado-Zamora H, Taylor EC. Heterocycl. Commun. 2006; 12: 307
  • 3 Du B, Shan A, Zhang Y, Zhong X, Chen D, Cai K. Am. J. Med. Sci. 2014; 347: 178
  • 4 Frett B, McConnell N, Smith CC, Wang Y, Shah NP, Li HY. Eur. J. Med. Chem. 2015; 94: 123
  • 5 Gueiffier E, Gueiffier CA. Mini-Rev. Med. Chem. 2007; 7: 888
  • 6 Alonso JM, Oehlrich D, Ahnaou A, Drinkenburg W, Mackie C, Andres JI, Lavreysen H, Cid JM. J. Med. Chem. 2012; 55: 2688
  • 7 Puerstinger G, Paeshuyse J, De Clercq E, Neyts J. Bioorg. Med. Chem. Lett. 2007; 17: 390
  • 8 Gudmundsson KS, Johns BA. Bioorg. Med. Chem. Lett. 2007; 17: 2735
  • 9 Heidari A. J. Data Min. Genomics Proteomics 2016; 7: 125
  • 10 Enguehard-Gueiffier C, Fauvelle F, Debouzy JC, Peinnequin A, Thery I, Dabouis V, Gueiffier A. Eur. J. Pharm. Sci. 2005; 24: 219
  • 11 Mutai T, Tomoda H, Ohkawa T, Yabe Y, Araki K. Angew. Chem. Int. Ed. 2008; 47: 9522
  • 12 Li Q, Zhou M, Han L, Cao Q, Wang X, Zhao L, Zhou J, Zhang H. Chem. Biol. Drug Des. 2015; 86: 849
  • 13 Cao H, Lei S, Li N, Chen L, Liu J, Cai H, Tan J. Chem. Commun. 2015; 51: 1823
  • 14 Lei S, Mai Y, Yan C, Mao J, Cao H. Org. Lett. 2016; 18: 3582
  • 15 Chezal JM, Moreau E, Delmas G, Gueiffier A, Blache Y, Grassy G, Teulade JC. J. Org. Chem. 2001; 66: 6576
  • 16 Mitra S, Ghosh M, Mishra S, Hajra A. J. Org. Chem. 2015; 80: 8275
  • 17 Kim H, Byeon M, Jeong E, Baek Y, Jeong SJ, Um K, Son JY. Adv. Synth. Catal. 2019; 361: 2094
  • 18 Wu Q, Zhao D, Qin X, Lan J, You J. Chem. Commun. 2011; 47: 9188
    • 19a Mohan DC, Rao SN, Ravi C, Adimurthy S. Asian J. Org. Chem. 2014; 3: 609
    • 19b Liu W, Wang S, Jiang Y, He P, Zhang Q, Cao H. Asian J. Org. Chem. 2015; 4: 312
    • 19c Li Z, Hong J, Zhou X. Tetrahedron 2011; 67: 3690
    • 19d Hamdouchi C, de Blas J, Ezquerra J. Tetrahedron 1999; 55: 541
    • 19e Cao H, Chen L, Liu J, Cai H, Deng H, Chen G, Yan C, Chen Y. RSC Adv. 2015; 5: 22356
    • 19f Ravi C, Chandra MohanD, Adimurthy S. Org. Biomol. Chem. 2016; 14: 2282
    • 19g Zheng Z, Qi D, Shi L. Catal. Commun. 2015; 66: 83
    • 19h Li J, Li C, Yang S, An Y, Wu W, Jiang H. J. Org. Chem. 2016; 81: 7771
    • 20a Hiebel M.-A, Berteina-Raboin S. Green Chem. 2015; 17: 937
    • 20b Bagdi AK, Mitra S, Ghosh M, Hajra A. Org. Biomol. Chem. 2015; 13: 3314
    • 20c Huang X, Wang S, Li B, Wang X, Ge Z, Li R. RSC Adv. 2015; 5: 22654
    • 20d Ding Y, Wu W, Zhao W, Li Y, Xie P, Huang Y, Liu Y, Zhou A. Org. Biomol. Chem. 2016; 14: 1428
    • 20e Wang D, Guo S, Zhang R, Lin S, Yan Z. RSC Adv. 2016; 6: 54377
    • 20f Ji X.-M, Zhou S.-J, Chen F, Zhang X.-G, Tang R.-Y. Synthesis 2015; 659
    • 20g Yan K, Yang D, Sun P, Wei W, Liu Y, Li G, Lu S, Wang H. Tetrahedron Lett. 2015; 56: 4792
    • 20h Zhu W, Ding Y, Bian Z, Xie P, Xu B, Tang Q, Wu W, Zhou A. Adv. Synth. Catal. 2016; 358: 2215
  • 21 Hamdouchi C, Sanchez C, Ezquerra J. Synthesis 1998; 867
  • 22 Patil SM, Kulkarni S, Mascarenhas M, Sharma R, Roopan SM, Roychowdhury A. Tetrahedron 2013; 69: 8255
  • 23 Gao Z, Zhu X, Zhang R. RSC Adv. 2014; 4: 19891
  • 24 Ravi C, Mohan CD, Adimurthy S. Org. Lett. 2014; 16: 2978
  • 25 Maddi RR, Shirsat PK, Kumar S, Meshram HM. ChemistrySelect 2017; 2: 1544
  • 26 Bochis RJ, Olen LE, Fisher MH, Reamer RA, Wilks G, Taylor JE, Olson G. J. Med. Chem. 1981; 24: 1483
  • 27 Ravi C, Joshi A, Adimurthy S. Eur. J. Org. Chem. 2017; 3646
  • 28 Rahaman R, Das S, Barman P. Green Chem. 2015; 20: 141
    • 29a Jia F, Li Z. Org. Chem. Front. 2014; 1: 194
    • 29b Yang X.-H, Song R.-J, Xie Y.-X, Li J.-H. ChemCatChem 2016; 8: 2429
    • 29c Piontek A, Bisz E, Szostak M. Angew. Chem. Int. Ed. 2018; 57: 11116
    • 29d Sreedevi R, Saranya S, Rohit KR, Anilkumar G. Adv. Synth. Catal. 2019; 361: 2236
    • 29e Shen C, Zhang P, Sun Q, Bai S, Hor TA, Liu X. Chem. Soc. Rev. 2015; 44: 291
  • 30 Bauer I, Knölker H.-J. Chem. Rev. 2015; 115: 3170
  • 31 Xiang S, Chen H, Liu Q. Tetrahedron Lett. 2016; 57: 3870
  • 32 Wu W, Wang Z, Shen Q, Liu Q, Chen H. Org. Biomol. Chem. 2019; 17: 6753
  • 33 Zeng L, Deng Y, Weng L, Yang Z, Chen H, Liu Q. Natural Sci. 2017; 9: 312
  • 34 Yi S, Li M, Mo W, Hu X, Hu B, Sun N, Jin L, Shen Z. Tetrahedron Lett. 2016; 57: 1912