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

Lisa-Maria Recnik; Mohammed Abd El Hameid; Maximilian Haider; Michael Schnürch; Marko D. Mihovilovic

doi:10.1055/s-0032-1316906

Synthesis, Table of Contents

Synthesis 2013; 45(10): 1387-1405
DOI: 10.1055/s-0032-1316906

paper

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

Lisa-Maria Recnik

^aInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria Fax: +43(1)58801163616 Email: michael.schnuerch@tuwien.ac.at Email: marko.mihovilovic@tuwien.ac.at

,

Mohammed Abd El Hameid

^bFaculty of Pharmacy, Cairo University, 33 Kasr El-Aini Street, P.O. Box 11562, Cairo, Egypt

,

Maximilian Haider

^aInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria Fax: +43(1)58801163616 Email: michael.schnuerch@tuwien.ac.at Email: marko.mihovilovic@tuwien.ac.at

,

Michael Schnürch*

^aInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria Fax: +43(1)58801163616 Email: michael.schnuerch@tuwien.ac.at Email: marko.mihovilovic@tuwien.ac.at

,

Marko D. Mihovilovic*

^aInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria Fax: +43(1)58801163616 Email: michael.schnuerch@tuwien.ac.at Email: marko.mihovilovic@tuwien.ac.at

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Abstract

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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.

Key words

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

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References

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