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2024 , Vol. 44 >Issue 1: 195 - 203

DOI: https://doi.org/10.6023/cjoc202307019

研究论文

邻亚甲醌与硫叶立德反应合成2,3-二取代苯并二氢呋喃化合物

  • 李梦竹 ,
  • 孟博莹 ,
  • 兰文捷 ,
  • 傅滨
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  • 中国农业大学理学院 北京 100193

收稿日期: 2023-07-19

  修回日期: 2023-08-28

  网络出版日期: 2023-09-21

基金资助

国家重点研发计划(2017YFD0200301)

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Synthesis of 2,3-Disubstituted Dihydrobenzofurans from o-Quinone Methides and Sulfur Ylides

  • Mengzhu Li ,
  • Boying Meng ,
  • Wenjie Lan ,
  • Bin Fu
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  • College of Science, China Agricultural University, Beijing 100193
*E-mail:

Received date: 2023-07-19

  Revised date: 2023-08-28

  Online published: 2023-09-21

Supported by

National Key Research and Development Program of China(2017YFD0200301)

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摘要

发展了一种简便有效的通过邻甲亚醌与硫叶立德反应合成苯并二氢呋喃化合物的方法. 在二氯甲烷中和二异丙基乙基胺存在下, 反应能够在室温下1 h内完成, 以良好至优秀的收率得到反式-2,3-二取代二氢苯并呋喃产物. 反应能够扩大到克级规模, 产物能够转化为潜在生物活性的苯并呋喃衍生物, 并推测了可能的反应机理,

关键词： 苯并二氢呋喃; 邻亚甲醌; 硫叶立德; [4＋1]环加成; 碱催化

本文引用格式

李梦竹 , 孟博莹 , 兰文捷 , 傅滨 . 邻亚甲醌与硫叶立德反应合成2,3-二取代苯并二氢呋喃化合物[J]. 有机化学, 2024 , 44(1) : 195 -203 . DOI: 10.6023/cjoc202307019

Abstract

A facile and efficient approach to dihydrobenzofurans from sulfur ylides and o-quinone methides (o-QMs) was developed. In most cases, the reaction could be completed in the presence of N,N-diisopropylethylamine (DIPEA) in CH2Cl2 at room temperature within 1 h, providing trans-2,3-disubstitiuted dihydrobenzofurans in good to excellent yields. The reaction could expand to a scale of grams, and the products could be converted into the potentially bioactive benzofuran derivatives. The plausible mechanism is proposed.

Key words： dihydrobenzofuran; o-quinone methides; sulfur ylide; [4＋1] cycloaddition; base-catalysis

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