水促进下杂芳基硫醚的绿色合成
收稿日期: 2022-11-02
修回日期: 2023-01-02
网络出版日期: 2023-01-12
基金资助
国家自然科学基金(22101243); 信阳师范学院南湖学者青年计划; 河南省大学生创新创业计划训练计划(202210477010); 信阳师范学院大学生科研基金(2022-DXS-089)
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)
马献涛 , 闫晓雨 , 朱影影 , 牛双林 , 王喻璇 , 袁超 . 水促进下杂芳基硫醚的绿色合成[J]. 有机化学, 2023 , 43(6) : 2136 -2142 . DOI: 10.6023/cjoc202211004
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
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