Chinese Journal of Organic Chemistry >
Water-Promoted Green Synthesis of Heteroaryl Thioether
Received date: 2022-11-02
Revised date: 2023-01-02
Online published: 2023-01-12
Supported by
National Natural Science Foundation of China(22101243); Nanhu Scholars Program for Young Scholars of Xinyang Normal University; Training Program of Innovation and Entrepreneurship Plan for College Students in Henan Province(202210477010); Research and Innovation Projects for College Students of Xinyang Normal University(2022-DXS-089)
Heteroaryl thioethers are a class of important bioactive molecules, which exhibit good antibacterial, anti- inflammatory and anticancer activities. In this paper, a new, base-free and green synthesis of heteroaryl thioether in water media is developed. The reaction using alkyl halides and heteroaryl thiols as the starting materials can proceed well at room temperature for 0.5 h, affording the target thioether products in high yields. Compared with the available literature reports, this new method has the advantages of simple operation, mild conditions, less by-product, greeness and high efficiency, broad range of substrates, and etc. Moreover, the reaction can easily be scaled up in gram scale, also showing the good practical value of this new method. Mechanism studies suggested that both the tautomerism of mercaptopyridine to thiopyridone and the hydrogen bond and hydrophobic interaction of water played crucial roles in the reaction.
Key words： heteroaryl thioether; water media; base-free; mild conditions
Xiantao Ma , Xiaoyu Yan , Yingying Zhu , Shuanglin Niu , Yuxuan Wang , Chao Yuan . Water-Promoted Green Synthesis of Heteroaryl Thioether[J]. Chinese Journal of Organic Chemistry, 2023 , 43(6) : 2136 -2142 . DOI: 10.6023/cjoc202211004
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