A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene

Zhibao Huo, Ilya D. Gridnev and Yoshinori Yamamoto*

*Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Email: yoshimail.tains.tohoku.ac.jp

Z. Huo, I. D. Gridnev, Y. Yamamoto, J. Org. Chem., 2010, 75, 1266-1270.

DOI: 10.1021/jo902603v

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Abstract

The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene proceeds smoothly in the presence of electrophilic reagents in CH₃NO₂ at room temperature or in the presence of catalytic amounts of AuCl₃/AgNTf₂ in THF at 100 °C to afford the corresponding quinolines 2 in good to high yields.

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Key Words

Quinolines, NIS

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ID: J42-Y2010-0510