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InCl催化N-炔丙基酰胺与对醌二甲烷进行5-外向-双环化/1,6-共轭加成反应以构建恶唑衍生物。

InCl-catalyzed 5-exo-dig cyclization/1,6-conjugate addition of N-propargylamides with p-QMs to construct oxazole derivatives.

作者信息

Nan Guang-Ming, Li Xue, Yao Tian-Yu, Yan Ting-Xun, Wen Li-Rong, Li Ming

机构信息

University and College Key Lab of Natural Product Chemistry and Application in Xinjiang, Yili Normal University, Yining 835000, China.

State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science & Technology, Qingdao 266042, China.

出版信息

Org Biomol Chem. 2020 Mar 4;18(9):1780-1784. doi: 10.1039/c9ob02651g.

Abstract

An InCl3-catalyzed atom-economic intramolecular 5-exo-dig cyclization/1,6-conjugate addition/aromatization of N-propargylamides with p-QMs to produce oxazoles tethering diarylmethane has been successfully developed. InCl3 not only served as Lewis acid to catalyze the cyclization of propargylic amides but also activated the carbonyl of p-QMs to achieve the 1,6-addition process in a one-pot manner. The reaction has attractive features, including mild reaction conditions, broad scope of substrates, good yields, and scalability.

摘要

已成功开发出一种由三氯化铟催化的原子经济型分子内5-外向-双环环化/1,6-共轭加成/ N-炔丙基酰胺与对醌二甲烷芳构化反应,以制备连接二芳基甲烷的恶唑。三氯化铟不仅作为路易斯酸催化炔丙基酰胺的环化反应,还能活化对醌二甲烷的羰基,以一锅法实现1,6-加成过程。该反应具有反应条件温和、底物范围广、产率高和可扩展性强等吸引人的特点。

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