Efficient synthesis and preliminary biological evaluations of trifluoromethylated imidazo[1,2-a]pyrimidines and benzimidazo[1,2-a]pyrimidines

Abstract

Fluoromethylated imidazo[1,2-a]pyrimidines and benzimidazo[1,2-a]pyrimidines were synthesized through Michael addition/intramolecular cyclization reaction by condensation of 2-amino imidazole derivatives with ethyl 4,4,4-trifluorobut-2-ynoate and using C–O bond activation. The synthons thus obtained can be functionalized by forming new chemical bonds, including C–C, C–N and C–S, to provide easy access to a wide range of novel trifluoromethylated imidazo[1,2-a]pyrimidines and benzimidazo[1,2-a]pyrimidines in good to excellent yields. Preliminary biological evaluation revealed a number of derivatives displaying micromolar IC₅₀ values against monoamine oxidase B and butyrylcholinesterase, two important targets in the field of neurodegenerative disorders.