Selective Sequential Cross-Coupling Reactions on Imidazole towards Neurodazine and Analogues

Abstract

Polysubstituted imidazoles represent a common structural motif in bioactive molecules. A modular and flexible strategy towards 2,4,5-triarylated imidazoles is reported applying a Suzuki–Miyaura cross-coupling protocol. Employing 1-protected 2,4,5-tribromoimidazole as starting material, both stepwise and one-pot protocols towards the title compounds are disclosed. The utility of the approach was demonstrated by synthesizing neurodazine, a biologically active molecule affecting neuronal cell differentiation.

Key words

heterocycles - cross-coupling - palladium - regioselectivity - homogeneous catalysis

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