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Abstract The trifluoroacetic anhydride promoted cyclization of enaminones derived from proline or pipecolic acid and β-ethoxyvinyl trifluoromethyl ketone was reinvestigated. An operationally simple procedure for the selective synthesis of bicyclic… Click to show full abstract
Abstract The trifluoroacetic anhydride promoted cyclization of enaminones derived from proline or pipecolic acid and β-ethoxyvinyl trifluoromethyl ketone was reinvestigated. An operationally simple procedure for the selective synthesis of bicyclic trifluoromethylated pyrroles and bicyclic pyrroles bearing trifluoromethyl and trifluoroacetyl groups on the pyrrole ring was developed. The mechanism of cyclization explaining the formation of bicyclic trifluoromethylpyrroles was discussed and previously described structures of the cyclization products were corrected.
Journal Title: Tetrahedron Letters
Year Published: 2020
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