Current organic synthesis · 2024
Synthesis of 5-(trifluoroacetyl)imidazoles from Bromoenones and Benzimidamides via Aza-Michael Initiated Ring Closure Reaction.
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Romanov Alexey R, Kondrashov Evgeniy V, Zinchenko Sergey V
Аннотация
INTRODUCTION: A simple method for the preparation of 5-(trifluoroacetyl)imidazoles was elaborated.
METHODS: The reaction of trifluoromethyl(α-bromoalkenyl)ketones with benzimidamides was employed to afford the target heterocycles in good yields.
RESULTS: The assembly of imidazole core proceeds via aza-Michael adduct formation followed by intramolecular nucleophilic substitution and spontaneous aromatization as an oxidation sequence.
CONCLUSION: The yields of target imidazoles can be improved by the use of soft oxidizing agents.
METHODS: The reaction of trifluoromethyl(α-bromoalkenyl)ketones with benzimidamides was employed to afford the target heterocycles in good yields.
RESULTS: The assembly of imidazole core proceeds via aza-Michael adduct formation followed by intramolecular nucleophilic substitution and spontaneous aromatization as an oxidation sequence.
CONCLUSION: The yields of target imidazoles can be improved by the use of soft oxidizing agents.