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Sequentially Catalyzed Three-Component Masuda–Suzuki–Sonogashira Synthesis of Fluorescent 2-Alkynyl-4-(7-azaindol-3-yl)pyrimidines: Three Palladium-Catalyzed Processes in a One-Pot Fashion
Synlett ( IF 1.7 ) Pub Date : 2020-05-29 , DOI: 10.1055/s-0040-1707818
Thomas J. J. Müller , Daniel Drießen , Lukas Biesen

The Masuda–Suzuki–Sonogashira sequence efficiently unites, in a one-pot fashion, a borylation, an arylation, and an alkynylation in the sense of a sequentially Pd-catalyzed three-component reaction to give fluorescent 2-alkynyl-4-(7-azaindol-3-yl) pyrimidines in yields of 24–83% (14 examples). Time-dependent density-functional theory calculations supported the electronic structure of the longest wavelength absorption bands, revealing that this novel consecutive three-component synthesis opens an efficient access to alkynyl meriolins, a novel class of potential inducers of apoptosis.

中文翻译:

荧光 2-Alkynyl-4-(7-azaindol-3-yl) 嘧啶的顺序催化三组分 Masuda-Suzuki-Sonogashira 合成:三种钯催化的一锅法工艺

Masuda-Suzuki-Sonogashira 序列以一锅法有效地结合了硼酸化、芳基化和炔基化,在顺序 Pd 催化的三组分反应的意义上,得到荧光 2-炔基-4-(7 -azaindol-3-yl) 嘧啶的产率为 24-83%(14 个实例)。时间相关的密度泛函理论计算支持最长波长吸收带的电子结构,表明这种新型连续三组分合成开辟了有效途径获得炔基 meriolins,一种新型的潜在凋亡诱导剂。
更新日期:2020-05-29
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