无过渡金属存在下从缺电子烯烃出发合成3位未取代的中氮茚
收稿日期: 2015-09-30
修回日期: 2015-10-26
网络出版日期: 2015-11-03
基金资助
国家自然科学基金(No. 21202058)、江苏省高校重大(No. 13KJA150001)、中国博士后基金(Nos. 2012M511645, 2013T60483)资助项目
Synthesis of 3-Unsubstituted Indolizines from Electron Deficient Alkenes under Transition Metal Free Conditions
Received date: 2015-09-30
Revised date: 2015-10-26
Online published: 2015-11-03
Supported by
Project supported by the National Natural Science Foundation of China (No. 21202058), the Department of Education of Jiangsu Province (No. 13KJA150001), the China Postdoctoral Science Foundation (Nos. 2012M511645, 2013T60483).
3位未取代的中氮茚不仅具有多种重要的生物活性, 且是重要的有机合成中间体. 报道了一种从吡啶衍生物、氯乙酸和缺电子烯烃出发, 在无过渡金属存在下合成3位未取代的中氮茚的新方法. 该反应的关键步骤为四氢中氮茚中间体在2,2,6,6-四甲基哌啶氮氧自由基(TEMPO)存在下的氧化脱氢芳构化和脱羧反应. 该反应操作简便, 原料易得, 且在反应中无需使用任何过渡金属试剂, 具有一定的实用价值.
关键词： 中氮茚; 2,2,6,6-四甲基哌啶氮氧自由基; 1,3-偶极环加成; 无过渡金属反应; 脱氢芳构化
胡华友 , 李国栋 , 顾宁 , 吉民 . 无过渡金属存在下从缺电子烯烃出发合成3位未取代的中氮茚[J]. 有机化学, 2016 , 36(2) : 330 -335 . DOI: 10.6023/cjoc201509044
3-Unsubstituted indolizine not only exhibits a variety of important biological activities, but also is a kind of important intermediate in organic synthesis. A transition metal free method for synthesizing 3-unsubstituted indolizines from pyridines, 2-chloroacetic acid and electron deficient alkenes has been invented in this paper. The designed products were obtained via oxidative dehydrogenation and decarboxylation reactions, and 2,2,6,6-tetramthyl-1-piperidinyloxy (TEMPO) was used as an oxidant. This method featured simple procedure, easy available starting materials and transition metal free conditions.
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