Synthesis 2013; 45(10): 1387-1405
DOI: 10.1055/s-0032-1316906
paper
© Georg Thieme Verlag Stuttgart · New York

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

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Publication History

Received: 03 December 2012

Accepted after revision: 20 March 2013

Publication Date:
04 April 2013 (online)


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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.