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Robust Organocatalytic Three-Component Approach to 1,3-Diarylallylidene Pyrazolones via Consecutive Double Condensation Reactions
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-11-16 , DOI: 10.1021/acs.joc.4c02273
Ashvani K. Patel, Sampak Samanta

A robust pyrrolidine-BzOH salt-catalyzed one-pot three-component reaction involving 4-unsubstituted pyrazolones, aryl/heteroarylaldehydes, and aryl methyl ketones is reported for the first time. This catalytic process fortifies an efficient method, allowing for the practical synthesis of a wide array of synthetically useful 1,3-diarylallylidene pyrazolones in good to high yields exclusively in their single geometrical isomer forms. Furthermore, this catalyst facilitates a sequential double condensation reaction under thermal conditions, thereby enabling two consecutive C═C bonds through displacement of aryl groups. Moreover, this organocatalytic technique achieves a 100% carbon atom economy, marking a significant step forward toward efficient and sustainable synthesis.

中文翻译:


通过连续双缩合反应制备 1,3-二芳烯丙基吡唑酮的稳健有机催化三组分方法



首次报道了一种稳定的吡咯烷-BzOH 盐催化的一锅三组分反应,涉及 4-未取代的吡唑啉酮、芳基/杂芳醛和芳基甲基酮。这种催化过程强化了一种有效的方法,允许仅以单一几何异构体形式以高产率实际合成各种合成有用的 1,3-二芳烯丙烯丙烯基吡唑啉酮。此外,该催化剂在热条件下促进了连续的双缩合反应,从而通过芳基的置换实现两个连续的 C═C 键。此外,这种有机催化技术实现了 100% 的碳原子经济性,标志着朝着高效和可持续合成迈出了重要一步。
更新日期:2024-11-16
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