SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

0 0

DOI: https://doi.org/10.6023/cjoc202510021

ARTICLE

DBDMH-Mediated Regioselective C3-Methylthiolation of Imidazo[1,2-a]pyridines in Dimethylsulfoxide

  • Yang Kai ,
  • Fu Xinlei ,
  • Wu Longhui ,
  • Yu Shuqin ,
  • Zhu Xue ,
  • Liu Zhaowen ,
  • Huang Zhiqin
Expand
  • a College of pharmacy, Gannan Medical University, Ganzhou 341000, China;
    b Department, Institution, City, Postal code

Received date: 2026-01-01

  Revised date: 2026-02-09

  Online published: 2026-06-04

Supported by

Natural Science Foundation of Jiangxi Province (20224BAB203010) and the Science and Technology Projects of Ganzhou (2023CYZ17866).

Fold

Abstract

An efficient DBDMH mediated regioselective C3-methylation of imidazo[1,2-a]pyridines was developed using DMSO as SMe source and solvent. This method exhibits excellent functional group tolerance and offers a metal-free, simple, and efficient approach for the C3-methylthiolation of variously substituted imidazo[1,2-a]pyridines. Diethyl sulfoxide and dibenzyl sulfoxide can also be used as alkyl sulfur sources for this conversion. Under optimized conditions, the scope of this method was successfully extended to 26 target compounds, achieving a maximum yield of 88%.

Key words： imidazo[1,2-a]pyridines; methylthiolation; 1,3-dibromo-5,5-dimethylhydantoin; dimethylsulfoxide

Cite this article

Yang Kai , Fu Xinlei , Wu Longhui , Yu Shuqin , Zhu Xue , Liu Zhaowen , Huang Zhiqin . DBDMH-Mediated Regioselective C3-Methylthiolation of Imidazo[1,2-a]pyridines in Dimethylsulfoxide[J]. Chinese Journal of Organic Chemistry, 0 : 0 . DOI: 10.6023/cjoc202510021

References

[1] (a) Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.(b) Conroy, S.; Kindon, N.; Kellam, B.; Stocks, M. J. J. Med. Chem. 2016, 59, 9981. (c) Park, S. Y.; Hwang, I.-S.; Lee, H.-J.; Song, C. E. Nat. Commun. 2017, 8, 14877. (d) Zhang, Y.; Ren, Y.; Zhang, J.; Liu, S.; Li, H. Chin. J. Chem. 2023, 41, 3045. (e) Yang, L.; Li, B.; Shu, C. Acta Chim. Sinica 2024, 82, 171 (in Chinese). (杨铃悦, 李赟婷, 舒超. 化学学报, 2024, 82, 171.) (f) Zhou, Q.; Jiang, J.; Luo, N.; Huang, J. Acta Chim. Sinica 2025, 83, 274 (in Chinese). (周泉, 蒋佳怡, 罗年华, 黄家翩. 化学学报, 2025, 83, 274.) (g) Du, Y.; Li, S.; Cheng, S.; Jia, H.; Wang, Z.; Han, L.; Zhu, N. Acta Chim. Sinica 2025, 83, DOI: 10.6023/A25060234 (in Chinese). (杜云哲, 李曙懿, 程思柳, 贾慧劼, 王政, 韩利民, 竺宁. 化学学报, 2025, 83, DOI10.6023/A25060234)
[2] (a) Chen, Y.; Zhou, J.; Wang, H.; Xia, Y.; Yang, Z. Y.; Xia, P. Chin. Chem. Lett. 2008, 19, 925.(b) Giannetti, A. M.; Wong, H.; Dijkgraaf, G. J. P.; Dueber, E. C.; Ortwine, D. F.; Bravo, B. J.; Gould, S. E.; Plise, E. G.; Lum, B. L.; Malhi, V.; Graham, R. A. J. Med. Chem. 2011, 54, 2592. (c) Dunbar, K.L.; Scharf, D.H.; Litomska, A.; Hertweck, C. Chem. Rev. 2017, 117, 5521-5577. (d) Wang, R.; Lu, L.; Shen, Q. Chin. J. Chem. 2023, 41, 2317. (e) Zheng, J.; Lin, J.; Xiao, J. Acta Chim. Sinica 2024, 82, 115-118 (in Chinese). (郑剑, 林锦鸿, 肖吉昌. 化学学报, 2024, 82, 115-118.)
[3] (a) Tashrifi, Z.; Khanaposhtani, M. M.; Larijani, B.; Mahdavi, M.Adv. Synth. Catal. 2020, 362, 65.(b) Wu X.-F.; Natte, K. Adv. Synth. Catal.2016, 358, 336.
[4] (a) Natarajan P.; Basaka A.; Metin O. Green Chem.,2023, 25, 3187.(b) Tian Y.; Zhang J.; Gao W.; Chang, H. Chin. J. Org. Chem.2023, 43, 2391. (c) Chen, X.-H.; Lhazom, T.; Cui, H.-L. J. Org. Chem. 2023, 88, 13598., 566.
[5] (a) Chang M.-Y.; Chen H.-Y.; Tsai Y.-L. Org. Lett.2019, 21, 1832.(b) Huang M.-H.; Zhu C.-F.; He C.-L.; Zhu Y.-L.; Hao W.-J.; Wang D.-C.; Tu S.-J.; Jiang, B. Org. Chem. Front.2018, 5, 1643. (c) Zhao, P.; Wu, X.; Geng, X.; Wang, C.; Zhou, Y.; Wu, Y.-D.; Wu, A.-X. J. Org. Chem. 2019, 84, 8322., 6688.
[6] (a) Toyoda, S.; Iizumi, K.; Yamaguchi, J. Chem. Sci. 2025, 16, 11559.(b) Li, X.; Sun, F.; He, J.; Shi, H.; Zhang, S.; Du, Y. J. Org. Chem. 2025, 90, 9928. (c) Zhou, Y.-J.; Fang, Y.-G.; Yang, K.; Lin, J.-Y.; Li, H.-Q.; Chen, Z.-J.; Wang, Z.-Y. Molecules 2023, 28, 5635. 2024, 44, 1576 (in Chinese). (张娟, 王奕森, 田钰, 徐晶, 高文超, 常宏宏, 孟凡会, 杨朋. 有机化学, 2024, 44, 1576.)
[7] (a) Devi N.; Singh D.;Rawal R. K.; Bariwal J.; Singh, V. Curr. Top. Med. Chem.2016, 16, 2963.(b) Samanta S.; Kumar S.; Aratikatla E. K.; Ghorpade S. R.; Singh, V. RSC Med. Chem.2023, 14, 644.
[8] (a) Abe Y.; Kayakiri H.; Satoh S.; Inoue T.; Sawada Y.; Inamura N.; Asano M.; Aramori I.; Hatori C.; Sawai H.; Oku T.; Tanaka, H. J. Med. Chem.1998, 41, 4587.(b) Okubo T.; Yoshikawa R.; Chaki S.; Okuyama S.; Nakazato, A. Bioorg. Med. Chem.2004, 12, 423. (c) Ismail, M. A.; Arafa, R. K.; Wenzler, T.; Brun, R.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. Biorg. Med. Chem., 2008, 16, 683., 359.
[9] (a) Bagdi, A. K.; Santra, S.; Monir, K.; Hajra, A. Chem. Commun. 2015, 51, 1555.(b) Patel, O. P. S.; Nandwana, N. K.; Legoabe, L. J.; Das, B. C.; Kumar, A. Adv. Synth. Catal. 2020, 362, 4226. (c) Liu, X.; Li, W.; Liu, H.; Cao, H. Chin. J. Org. Chem. 2021, 41, 1759 (in Chinese). (刘想, 李文, 刘环宇, 曹华. 有机化学, 2021, 41, 1759.) (d) Tali, J. A.; Kumar, G.; Sharma, B. K.; Rasool, Y.; Sharma, Y.; Shankar, R. Org. Biomol. Chem. 2023, 21, 7267. (e) Zhang, Z, Guo, Y.; Yang, J.; Wang, D.; Wang, j.; Hong, X.; Cai, P.; Rong, L. Chin. J. Org. Chem. 2023, 43, 2104 (in Chinese). (张周, 郭钰, 羊静, 吴丹, 王佳昕, 洪欣玥, 蔡佩君, 荣良策. 有机化学, 2023, 43, 2104.) (f) Gao, J.; Fu, X.; Yang, K.; Liu, Z.-W. Molecules 2025, 30, 607.
[10] (a) Yuan Y.; Cao Y.; Qiao J.; Lin Y.; Jiang X.; Weng Y.; Tang S.; Lei, A. Chin. J. Chem.2019, 37, 49.(b) Wen J.; Niu C.; Yan K.; Cheng X.; Gong R.; Li M.; Guo Y.; Yang J.; Wang H. Green Chem.2020, 22, 1129.
[11] Patil S. M.; Kulkarni S.; Mascarenhas M.; Sharma R.; Roopan S. M.; Roychowdhury A. Tetrahedron2013, 69, 8255.
[12] (a) Ravi C.; Mohan D. C.; Adimurthy, S. Org. Biomol. Chem.2016, 14, 2282.(b) Zhang, L.-Y.; Wu, Y.-H.; Wang, N.-X.; Gao, X.-W.; Yan, Z.; Xu, B.-C.; Liu, N.; Wang, B.-Z.; Xing, Y.Eur. J. Org. Chem. 2021, 1446.
[13] Feng Z.; Fan Y.; Qiang C.; Liu P.; Sun P. Green Chem.2024, 26, 3517.
[14] (a) Yang K.; Luo S.; Chen S.; Cao X.; Zhou Y.; Lin J.; Huo Y.; Wang, Z.-Y. Org. Biomol. Chem.2021, 19, 8133.(b) Yang K.; Chen Z.; Zhou Y.; Chen Q.; Yu S.; Luo S.; Wang, Z.-Y. Org. Chem. Front.2022, 9, 1127. (c) Gao, J.; Liu, Z.; Guo, X.; Wu, L.; Chen, Z.; Yang, K. Molecules 2023, 28, 7522., 1756.
[15] (a) Fu D.; Dong J.; Wang J.; Wang J.; Xu, J. Asian J. Org. Chem.2021, 10, 1756.(b) Ma C.-H.; Chen M.; Feng Z.-W.; Zhang Y.; Wang J.; Jiang Y.-Q.; Yu, B. New J. Chem.2021, 45, 9302.
[16] Lu R.; Tao Q.; Qian Q.; Li B.; Zhang Y.; Gao, Y. Adv. Synth. Catal.2024, 366, 4084.
[17] Chen Z.; Cao G.; Zhang F.; Li H.; Xu J.; Miao M.; Ren H. Synlett2017, 28, 1795.
Options
Outlines

/

〈 〉