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A Convenient Approach to meso-Uracil–4,4-Difluoro-4-bora-3a, 4a-diaza-s-indacene Derivatives
Synlett ( IF 2 ) Pub Date : 2021-07-07 , DOI: 10.1055/a-1545-7086
M. Cordaro 1 , M. Trapani 2 , M. A. Castriciano 2 , J. A. A. W. Elemans 3 , A. Nicosia 4 , P. Mineo 4, 5
Affiliation  

An effective and convenient protocol for the synthesis of 1-substituted uracil-6-carbaldehyde derivatives has been developed. A three-step sequence permits the preparation of uracil-6-carbaldehydes with various substituents at the N-1 in large quantities by using low-cost precursors. The aldehyde-functionalized uracils served as useful precursors for the preparation of meso-(1-substituted 6-uracil)-derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY). In this way, regioselectively functionalized BODIPYs with a direct connection to a nucleobase were prepared in yields of 30–45%. MALDI-TOF mass spectrometry, NMR, UV/vis absorption, and steady-state and time-­resolved fluorescence spectroscopies were used to characterize the structures and the spectroscopic/photophysical properties of the resultant dyes.

中文翻译:

制备 meso-Uracil–4,4-Difluoro-4-bora-3a, 4a-diaza-s-indacene 衍生物的便捷方法

已开发出一种有效且方便的合成 1-取代尿嘧啶-6-甲醛衍生物的方案。三步序列允许使用低成本前体大量制备在 N-1 处具有各种取代基的尿嘧啶-6-甲醛。醛官能化尿嘧啶用作制备 4,4-二氟-4-bora-3a,4a-二氮杂-s-茚(BODIPY) 的内消旋-(1-取代的6-尿嘧啶)-衍生物的有用前体。通过这种方式,以 30-45% 的产率制备了与核碱基直接连接的区域选择性功能化 BODIPY。MALDI-TOF 质谱、核磁共振、紫外/可见吸收以及稳态和时间分辨荧光光谱用于表征所得染料的结构和光谱/光物理特性。
更新日期:2021-08-21
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