Synthesis of 4(5)-Acyl-2-aminoimidazoles and Vinylogues

Christoph Pöverlein; Nicolas Jacobi; Peter Mayer; Thomas Lindel

doi:10.1055/s-2007-990870

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Synthesis 2007(23): 3620-3626
DOI: 10.1055/s-2007-990870

PAPER

Synthesis of 4(5)-Acyl-2-aminoimidazoles and Vinylogues

Christoph Pöverlein^a, Nicolas Jacobi^b, Peter Mayer^a, Thomas Lindel*^b
^a Department of Chemistry and Biochemistry, Faculty of Chemistry and Pharmacy, Ludwig Maximilian University, Butenandtstr. 5-13, 81377 Munich, Germany
^b Institute of Organic Chemistry, Faculty of Life Sciences, TU Braunschweig, Hagenring 30, 38106 Brunswick, Germany
Fax: +49(531)3917744; e-Mail: th.lindel@tu-bs.de;

Further Information

Publication History

Received 1 June 2007
Publication Date:
31 October 2007 (online)

Abstract
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Abstract

A convenient protocol for the preparation of 4(5)-acyl-2-aminoimidazoles and vinylogues is disclosed employing a crystalline imidazole-derived iminophosphorane as the coupling partner in Heck and Sonogashira reactions. For the first time, derivatives of urocanic acid bearing a free amino group in the 2′-position are described.

Key words

aminoimidazole - iminophosphorane - cross coupling - pyrrole-imidazole-alkaloids - alkyne hydration

References

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CCDC numbers: 644864 (2), 644865 (18).