Journal of Organic Chemistry 2012-12-21

Synthesis of o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles by the reaction of hydrazones and arynes.

Anton V Dubrovskiy, Richard C Larock

Index: J. Org. Chem. 77(24) , 11232-56, (2012)

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Abstract

A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.