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Synfacts 2006(11): 1110-1110  
DOI: 10.1055/s-2006-949422
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Highly Substituted Imidazoles from Lithiated Methoxyallene

Contributor(s): Victor Snieckus, Yigang Zhao
M. Gwiazda, H.-U. Reissig*
Freie Universität Berlin, Germany
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

A three-step sequence beginning with lithiated methoxyallene 1, proceeding via imine addition (2) and iodonium-mediated cyclization (3), provides access to functionalized imidazoles 4 in reasonable yields. Mild-base-induced elimination leads to alkynyl-substituted imidazole derivatives 5. Both products 4 and 5 are versatile intermediates for further cross-coupling reactions, such as the Sonogashira reaction.