2-芳基乙烯苯并咪唑串联反应合成多取代二氢吡啶并[1,2-a]苯并咪唑衍生物
收稿日期: 2021-03-21
修回日期: 2021-05-26
网络出版日期: 2021-06-17
基金资助
国家自然科学基金(21462034); 兵团优秀青年教师(2017CB001); 兵团优秀青年教师(CZ027203); 石河子大学国际合作(GJHZ201801)
Synthesis of Mutisubstituted Dihydropyridino[1,2-a]benzimidazole Derivatives via Tandem Reaction of 2-Arylbenzimidazoles
Received date: 2021-03-21
Revised date: 2021-05-26
Online published: 2021-06-17
Supported by
National Natural Science Foundation of China(21462034); Excellent Young Teachers Plan of Bingtuan(2017CB001); Excellent Young Teachers Plan of Bingtuan(CZ027203); International Cooperation Project of Shihezi University(GJHZ201801)
发展了一种“一锅法”合成二氢吡啶并[1,2-a]苯并咪唑衍生物的新方法. 在碱和氧化剂的共同作用下, 2-芳基乙烯苯并咪唑可以发生分子间Michael加成/分子内Michael加成/氧化脱氢串联反应, 以38%~85%的产率和4∶1~>25∶1的非对映选择性得到多取代二氢吡啶并[1,2-a]苯并咪唑衍生物. 产物的结构经1H NMR, 13C NMR, HRMS, IR以及单晶衍射进行了表征.
关键词： 串联反应; 一锅法; 二氢吡啶并[1,2-a]苯并咪唑; 加成反应
郭钰钰 , 陈祥杰 , 李师伍 , 蔡志华 , 何林 . 2-芳基乙烯苯并咪唑串联反应合成多取代二氢吡啶并[1,2-a]苯并咪唑衍生物[J]. 有机化学, 2021 , 41(9) : 3692 -3700 . DOI: 10.6023/cjoc202103036
A new one-pot method for the synthesis of dihydropyridino[1,2-a]benzimidazole derivatives has been developed. Under the mediation of base and oxidant, mutisubstituted dihydropyridino[1,2-a]benzimidazoles were obtained in 38%~85% yields and 4∶1 to >25∶1 d.r. through a tandem intermolecular Michael addition/intramolecular Michael addition/ oxidative dehydrogenation process of 2-arylbenzimidazoles. The structures of these products were characterized by 1H NMR, 13C NMR, HRMS, IR and single-crystal X-ray analysis.
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