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碱促进下2,3-二取代苯并呋喃的高效合成OA

Base-Promoted Efficient Synthesis of 2,3-Disubstituted Benzofurans

中文摘要英文摘要

苯并呋喃作为一种重要的杂环结构单元,广泛存在于天然产物、药物分子、农药以及功能材料中.同时,其本身作为一种潜力的合成子,用于制备多种多样的生物活性分子.迄今为止,尽管苯并呋喃母核的合成方法已较为成熟,但针对2,3-二取代苯并呋喃的高效、通用的合成方法仍相对有限.现有的一些方法往往面临反应条件苛刻、步骤繁琐或底物普适性不佳等挑战.因此,开发一种条件温和、高效、操作简便的合成方法是非常有必要的.基于此,设计以易于制备的邻羟基查尔酮与商业可得的γ-溴代巴豆酸酯为原料,在温和的碱性条件下,经过一锅多步串联反应生成一系列2,3-二取代苯并呋喃类化合物.该策略避免了使用昂贵金属催化剂或苛刻反应条件,展现出良好的官能团兼容性与操作简便性.该合成策略不仅为2,3-二取代苯并呋喃类化合物的高效合成提供了一条新颖途径,也为后续深入研究这类化合物的生物活性及材料性能奠定了坚实的物质基础,在药物化学和有机合成领域具有潜在的应用价值.

Benzofuran is a heterocyclic structural unit that occurs widely in natural products,drugs,pesticides,and functional materials,and it is used as a potential synthetic building block in preparing various biologically active molecules.The synthesis of benzofuran cores is well-established,but efficient general methods of synthesizing 2,3-disubstituted benzofurans remain relatively limited.Several reported methods often suffer from challenges,such as harsh reaction conditions,cumbersome steps,and poor substrate generalities,and thus,developing a facile,mild,efficient,operationally simple synthetic method is necessary.This study designed a method of synthesizing 2,3-disubstituted benzofuran derivatives using easily prepared o-hydroxychalcones and commercially available γ-bromocrotonates as starting materials.The reaction proceeded via a one-pot multistep tandem process under mildly basic conditions.This strategy avoided the use of expensive metal catalysts and harsh reaction conditions,demonstrating a good functional-group compatibility and operational simplicity.This synthetic strategy provided a novel approach for use in efficiently synthesizing 2,3-disubstituted benzofuran derivatives.It also laid a solid foundation for further in-depth research into their biological activities and material properties,displaying potential for application in the fields of medicinal chemistry and organic synthesis.

张金坤;李芷乐;邱小权;黄年玉;王能中

三峡大学第一临床医学院,湖北宜昌 443002||宜昌市中心人民医院,湖北宜昌 443003三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室,湖北宜昌 443002三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室,湖北宜昌 443002三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室,湖北宜昌 443002三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室,湖北宜昌 443002

化学化工

苯并呋喃合成碱促进邻羟基查尔酮γ-溴代巴豆酸酯

benzofuransynthesisbase promotiono-hydroxychalconeγ-bromocrotonate

《化学试剂》 2026 (3)

12-18,7

湖北省中央引导地方科技发展资金项目(2024BSB016)湖北省自然科学基金宜昌创新发展联合基金重点项目(2025AFD262).

10.13822/j.cnki.hxsj.2025.0318

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