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Zn(OTf)2-Catalyzed Cyclization of Proparyl Alcohols with Anilines, Phenols, and Amides for Synthesis of Indoles, Benzofurans, and Oxazoles through Different Annulation Mechanisms

Manyam Praveen Kumar and Rai-Shung Liu*

*Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan 30043, Email: rsliumx.nthu.edu.tw

M. P. Kumar, R.-S. Liu, J. Org. Chem., 2006, 71, 4951-4955.

DOI: 10.1021/jo0606711 (free Supporting Information)


Abstract

Zn(OTf)2 catalyzed the cyclization of propargyl alcohols with anilines and phenols in toluene at 100C without additive and gave various indole and benzofuran products with different structures. The cyclization of propargyl alcohols and amides gave oxazoles. Mechanisms for the different substituation patterns are discussed.

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Key Words

Indoles, Benzofurans, Oxazoles


ID: J42-Y2006-1700