Synthesis of 5-(trifluoroacetyl)imidazoles from Bromoenones and Benzimidamides Aza-Michael Initiated Ring Closure Reaction.
作者信息
Romanov Alexey R, Kondrashov Evgeniy V, Zinchenko Sergey V
机构信息
The Laboratory of Halogen Organic Compound, A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, 664033, Russia.
出版信息
Curr Org Synth. 2024;21(2):195-209. doi: 10.2174/1570179420666230420100643.
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 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.
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