Silica Sulphuric Acid Catalyzed Intra‐Molecular Alkyne Carbonyl Metathesis (ACM): A Rapid Access to 2H‐Chromenes

IF 2.8 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI:10.1002/ajoc.202400219
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Abstract

A highly efficient, convenient and ecofriendly approach to access highly functionalized 2H‐chromenes via intramolecular aldehyde alkyne metathesis reaction was established starting from readily accessible alkyne‐tethered 2‐((3‐phenylprop‐2‐yn‐1‐yl) oxy)benzaldehydes and catalyzed by silica sulfuric acid (SiO2‐OSO3H, SSA) coupled with microwave irradiation. This reaction was well tolerated for various substituents including different functional groups and furnished the desired highly functionalized 2H‐chromene derivatives in good to excellent yields in a very short time. A systematic study of the conventional heating approach and microwave irradiation was performed to demonstrate the advantages of the microwave‐assisted condition in terms of high yield and shorter reaction time.
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二氧化硅硫酸催化的分子内炔羰基复分解反应 (ACM):快速获得 2H- Chromenes
从容易获得的炔拴 2-((3-苯基丙-2-炔-1-基)氧基)苯甲醛开始,在二氧化硅硫酸(SiO2-OSO3H,SSA)和微波辐照的催化下,建立了一种通过分子内醛炔元合成反应获得高官能度 2H-铬烯的高效、便捷和生态友好的方法。这种反应对包括不同官能团在内的各种取代基都有很好的耐受性,并能在很短的时间内以良好到极好的收率获得所需的高官能度 2H-chromene 衍生物。对传统加热方法和微波辐照进行了系统研究,以证明微波辅助条件在高产率和缩短反应时间方面的优势。
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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