AI Article Synopsis
- A series of novel compounds called 4-(aryl)-benzo[4,5]imidazo[1,2-]pyrimidine-3-carbonitriles were synthesized using Povarov reactions and oxidation techniques starting from specific benzimidazole derivatives.
- During the synthesis process, it was found that certain structural rearrangements, termed [1,3] sigmatropic rearrangement, occurred, leading to the formation of dihydrobenzimidazo[1,2-]pyrimidines.
- The newly formed compounds were characterized using various analytical techniques and exhibited interesting photophysical properties, including solvatochromism and changes in emission upon mechanical stimulation.
Article Abstract
A series of novel 4-(aryl)-benzo[4,5]imidazo[1,2-]pyrimidine-3-carbonitriles were obtained through the Povarov (aza-Diels-Alder) and oxidation reactions, starting from benzimidazole-2-arylimines. Based on the literature data and X-ray diffraction analysis, it was discovered that during the Povarov reaction, [1,3] sigmatropic rearrangement leading to dihydrobenzimidazo[1,2-]pyrimidines took place. The structures of all the obtained compounds were confirmed based on the data from H- and C-NMR spectroscopy, IR spectroscopy, and elemental analysis. For all the obtained compounds, their photophysical properties were studied. In all the cases, a positive emission solvatochromism with Stokes shifts from 120 to 180 nm was recorded. Aggregation-Induced Emission (AIE) has been illustrated for compound using different water fractions (fw) in THF. The compounds and demonstrated changes in emission maxima or/and intensities after mechanical stimulation.
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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9698514 | PMC |
| http://dx.doi.org/10.3390/molecules27228029 | DOI Listing |
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