Fluorescent Azasteroids through Ultrasound Assisted Cycloaddition Reactions

Molecules

Gheorghita Zbancioc¹  Ionel Mangalagiu¹  Costel Moldoveanu¹ 

[1] Chemistry Department, Alexandru Ioan Cuza University of Iasi, 11 Carol 1st Bvd, 700506 Iasi, Romania;

关键词: azasteroid;    benzo[f]quinoline;    cycloaddition;    ultrasound irradiation;    fluorescent;   

DOI  :  10.3390/molecules26165098

来源: DOAJ

【 摘 要 】

We report here the synthesis and optical spectral properties of several new azasteroid derivatives. The formation of these compounds was explained based on the most probable mechanism. The luminescent heterocycles were synthesized by 1,3-dipolar cycloaddition reactions between benzo[f]quinoline and methylpropiolate or dimethyl acetylenedicarboxylate (DMAD). A selective and efficient way for [3+2]-dipolar cycloaddition of benzo[f]quinolinium ylides under ultrasound (US) irradiation (20 kHz processing frequency) is presented. We report substantially higher yields under US irradiation, whereas the solvent amounts required are at least three-fold less compared to classical heating. The azasteroid derivatives are blue emitters with λ_max of fluorescence around 430–450 nm. A certain influence of the azasteroid substituents concerning absorption and fluorescent properties was observed. Compounds anchored with a bulky pivaloyl group or without a C=O carbonyl group have shown increased fluorescence intensity.

【 授权许可】

Unknown