A method for the synthesis of substituted quinolines via electrophilic cyclization of 1-azido-2-(2-propynyl) benzene

Z Huo, ID Gridnev, Y Yamamoto

Index: Huo, Zhibao; Gridnev, Ilya D.; Yamamoto, Yoshinori Journal of Organic Chemistry, 2010 , vol. 75, # 4 p. 1266 - 1270

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Citation Number: 95

Abstract

A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl) benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br2, ICl, NBS, NIS, and HNTf2) 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 ...