Mechanosynthesis of polysubstituted pyridines via FeBr3-catalyzed cascade reaction of arylidene isoxazolones with β‑carbonyl esters

IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2025-05-15 Epub Date: 2025-03-28 DOI:10.1016/j.tetlet.2025.155569
Lei Wang, Ming-Jun Li, Qing-Hai Li, Peng Xu, Si-Qi Chen, Hui Xu, Ze Zhang
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Abstract

Under ball-milling and heating conditions, the cascade cyclization of arylidene isoxazolones with β‑carbonyl esters proceeded smoothly in the presence of catalytic amount of FeBr3, affording polysubstituted pyridines in moderate to excellent (68ᅳ93%) yields. A plausible reaction mechanism involving Michael addition, isoxazolone ring-opening, decarboxylation, and dehydration-driven aromatization was proposed. This mechanochemical protocol offers advantages such as high atom economy, solvent-free conditions and scalability making it a sustainable alternative for pyridine synthesis.
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通过 FeBr3 催化芳基异噁唑酮与β-羰基酯的级联反应合成多取代吡啶的机理研究
在球磨和加热条件下,在催化量为fe3的条件下,芳基异恶唑酮与β -羰基酯的级联环化反应顺利进行,得到了中至优异的多取代吡啶(68 ~ 93%)收率。提出了Michael加成、异恶唑酮开环、脱羧和脱水驱动芳构化的反应机理。这种机械化学方案具有高原子经济性,无溶剂条件和可扩展性等优点,使其成为吡啶合成的可持续替代方案。
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来源期刊
Tetrahedron Letters
Tetrahedron Letters 化学-有机化学
CiteScore
3.50
自引率
5.60%
发文量
521
审稿时长
28 days
期刊介绍: Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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