有机化学 ›› 2021, Vol. 41 ›› Issue (9): 3682-3691.DOI: 10.6023/cjoc202104005 上一篇    下一篇

研究论文

三乙胺促进的邻亚甲基苯醌与β-羰基硫代酰胺的[4+2]环加成反应构建功能化4H-色烯衍生物

南光明a, 詹靖波a, 原春鸣a, 文丽荣b,*(), 李明a,b,*()   

  1. a 伊犁师范大学 新疆天然产物化学与应用高等学校重点实验室 新疆伊宁 835000
    b 青岛科技大学化学与分子工程学院 生态化工国家重点实验室培育基地 山东青岛 266042
  • 收稿日期:2021-04-02 修回日期:2021-05-26 发布日期:2021-06-17
  • 通讯作者: 文丽荣, 李明
  • 基金资助:
    国家自然科学基金(21572110); 及山东省自然科学基金(ZR2019MB010)

NEt3-Promoted Construction of Functionalized 4H-Chromenes via [4+2] Cycloaddition Reaction of ortho-Quinone Methides with β-Ketothioamides

Guangming Nana, Jingbo Zhana, Chunming Yuana, Lirong Wenb(), Ming Lia,b()   

  1. a University and College Key Lab of Natural Product Chemistry and Application in Xinjiang, Yili Normal University, Yining, Xinjiang 835000
    b State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Sahndong 266042
  • Received:2021-04-02 Revised:2021-05-26 Published:2021-06-17
  • Contact: Lirong Wen, Ming Li
  • Supported by:
    National Natural Science Foundation of China(21572110); Natural Science Foundation of Shandong Province(ZR2019MB010)

建立了一种通过NEt3促进的β-羰基硫代酰胺(KTAs)和邻亚甲基苯醌(o-QMs)环合来合成高度取代的4H-色烯衍生物的新方法. 该方法涉及一个串联序列, 该序列包括1,6-共轭加成/O-环化/开环/O-环化. 该过程表现出良好的官能团耐受性及可扩展性, 且操作简单.

关键词: 邻亚甲基苯醌, β-羰基硫代酰胺, 4H-色烯衍生物, [4+2]环加成

A novel and efficient method for the synthesis of highly substituted 4H-chromene derivatives by NEt3-promoted annulation of β-ketothioamides (KTAs) and ortho-quinone methides (o-QMs) has been developed. This protocol involves a tandem sequence including 1,6-conjugate addition/O-cyclization/ring-opening/O-cyclization. This process exhibits good functional group tolerance, operationally-simple conditions and scalability.

Key words: ortho-quinone methide (o-QMs), β-ketothioamide, 4H-chromene derivative, [4+2] cycloaddition