2,3-二氯-5,6-二氰基-1,4-苯醌促进的3,4-二氢嘧啶硫酮的氧化偶联反应合成1,2-二嘧啶基二硫醚
收稿日期: 2015-12-25
修回日期: 2016-01-21
网络出版日期: 2016-02-18
基金资助
国家自然科学基金(Nos.21362032,21362031)资助项目.
Synthesis of 1,2-Di(pyrimidin-2-yl)disulfides from the Oxidative Coupling and Aromatization of 3,4-Dihydropyrimidin-2-thiones by Using 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone as Oxidant
Received date: 2015-12-25
Revised date: 2016-01-21
Online published: 2016-02-18
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21362032, 21362031).
在室温、空气气氛下, 以2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)为氧化剂, 快速实现了3,4-二氢嘧啶-2-硫酮的氧化偶联芳构化反应, 以较高产率合成了系列1,2-二嘧啶基二硫醚. 该法与已知的合成1,2-二嘧啶基二硫醚的方法相比, 具有反应温度低、反应时间短及产率高的优点. 通过1H NMR, 13C NMR, HRMS及X射线单晶衍射对其结构进行了表征, 并简要探讨了其结构特性和反应机理.
关键词： 3, 4-二氢嘧啶-2-硫酮; 1,2-二嘧啶基二硫醚; DDQ; 氧化偶联
王刚, 郭燕, 吕颖, 王喜存, 权正军 . 2,3-二氯-5,6-二氰基-1,4-苯醌促进的3,4-二氢嘧啶硫酮的氧化偶联反应合成1,2-二嘧啶基二硫醚[J]. 有机化学, 2016 , 36(6) : 1375 -1381 . DOI: 10.6023/cjoc201512038
The oxidative coupling and aromatization of 3,4-dihydropyrimidin-2-thiones to produce 1,2-di(pyrimidin-2-yl)- disulfides by using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant at room temperature under an air atmosphere are reported. Compared with the reported procedures, this method has obvious advantages at mild reaction conditions including lower reaction temperature and shorter reaction time with higher yields of products.
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