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EnglishA Deep Eutectic Solvent like choline chloride/glycerol (1:2 mol mol–1) proved to be an effective, sustainable reaction medium to easily synthesize both phenacyl azides and symmetrical 2,5-diarylpyrazines of interest in pharmacology and in coordination chemistry. Notable features of our report include: (i) nucleophilic substitution reactions of α-halo carbonyl compounds to the corresponding phenacyl azides compatible with the eutectic mixture, (ii) the reduction of phenacyl azides to α-amino carbonyl compounds, which undergo spontaneous dimerisation/cyclisation/aromatisation in the same eutectic mixture to provide valuable pyrazines. Telescoped, one-pot, two-steps stoichiometric/catalytic processes have also been successfully developed to furnish 2,5-diarylpyrazines in up to 95 % yield.
| Titolo: | Streamlined Routes to Phenacyl Azides and 2,5-Diarylpyrazines Enabled by Deep Eutectic Solvents | |
| Autori: | ||
| Data di pubblicazione: | 2019 | |
| Rivista: | ||
| Abstract: | A Deep Eutectic Solvent like choline chloride/glycerol (1:2 mol mol–1) proved to be an effective, sustainable reaction medium to easily synthesize both phenacyl azides and symmetrical 2,5-diarylpyrazines of interest in pharmacology and in coordination chemistry. Notable features of our report include: (i) nucleophilic substitution reactions of α-halo carbonyl compounds to the corresponding phenacyl azides compatible with the eutectic mixture, (ii) the reduction of phenacyl azides to α-amino carbonyl compounds, which undergo spontaneous dimerisation/cyclisation/aromatisation in the same eutectic mixture to provide valuable pyrazines. Telescoped, one-pot, two-steps stoichiometric/catalytic processes have also been successfully developed to furnish 2,5-diarylpyrazines in up to 95 % yield. | |
| Handle: | http://hdl.handle.net/11587/436396 | |
| Appare nelle tipologie: | Articolo pubblicato su Rivista |
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