Journal
CHEMSUSCHEM
Volume 14, Issue 8, Pages 1853-1863Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.202100433
Keywords
computational analysis; fluorescence; green chemistry; hydrothermal synthesis; quinoxalines
Funding
- Vienna Science and Technology Fund (WWTF) [LS17-051]
- Austrian Science Fund (FWF) [START Y1037-N28]
Ask authors/readers for more resources
The hydrothermal synthesis of 2,3-diarylquinoxalines from 1,2-diketones and o-phenylendiamines is simple, fast, and high-yielding, without the need for organic solvents, strong acids, or toxic catalysts. The method is environmentally friendly and less toxic compared to existing methods, with potential for improved reaction yields. The synthesized compounds show promise for application as fluorescent dyes for cell staining.
Here, the hydrothermal synthesis (HTS) of 2,3-diarylquinoxalines from 1,2-diketones and o-phenylendiamines (o-PDAs) was achieved. The synthesis is simple, fast, and generates high yields, without requiring any organic solvents, strong acids or toxic catalysts. Reaction times down to <10 min without decrease in yield could be achieved through adding acetic acid as promoter, even for highly apolar biquinoxalines (yield >90 % in all cases). Moreover, it was shown that HTS has high compatibility: (i) hydrochlorides, a standard commercial form of amines, could be used directly as combined amine source and acidic catalyst, and (ii) Boc-diprotected o-PDA could be directly employed as substrate that underwent HT deprotection. A systematic large-scale computational comparison of all reported syntheses of the presented quinoxalines from the same starting compounds showed that this method is more environmentally friendly and less toxic than all existing methods and revealed generic synthetic routes for improving reaction yields. Finally, the application of the synthesized compounds as fluorescent dyes for cell staining was explored.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available