| A-functionalized aziridinyl alcohols, which come from nucleophilic addition of ?-acyl aziridines, are versatile synthetic building blocks for the preparation of natural compunds and nitrogen-containing biologically active molecules, as they can undergo facile ring opening and expansion reactions. However, ?-trifluoromethylated aziridinyl alcohols and its derivative are rarely reported. At that case, this paper had a research on the reaction and derivatization of N-alkyl-2-aroyl aziridines with CF3 TMS. The detail studies are as follows:(1) The nucleophilic reaction of N-alkyl-2-aroyl aziridines, which were prepared from Gabriel–Cromwell reaction, with CF3 TMS has been explored at the room temperature. The best reaction condition, conducting in THF with cesium carbonate giving a high yield of 85%, has been chosen after several experiments. Through this reaction, we obtained 22 ?-trifluoromethylate-?-aziridinyl alcohols above average yield.(2) The reaction of ?-trifluoromethylate-?-aziridinyl alcohols with acetyl chloride has been operated, the directly ring-opening products and aza-Payne rearrangement products have been obtained because of the different electronic property on benzene rings. In addition, the aza-Payne rearrangement of 1-allykl-2-(phenyl((trimethylsilyl)oxy)methyl)aziridine under base condition has been studied.(3) ?-trifluoromethylate-?-aziridinyl alcohols and nitrile conducted a [3+2] annulation process in the presence of Lewis acid BF3·Et2O and gave multisubstituted dihydrogen oxazole products. We selected the dosage of BF3·Et2O, temperature and solvent of this reaction, and obtained an average yield under the optimal reaction conditions.(4) Designed the molecular(1-benzylaziridin-2-yl)(2-bromophenyl) methanone, then through trifluoromethylated, ring-opening and intramolecular coupling reactions the compound 4-trifluoromethylate-3, 4-dihydroxy quinolone has been obtained in moderate yield. |
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