Organic letters

Oxidation of p-Aminophenols and Formal Radical Cyclization onto Benzene Rings: Formation of Benzo-Fused Nitrogen Heterocycles

SP Fletcher, DLJ Clive, J Peng, DA Wingert

Index: Fletcher, Stephen P.; Clive, Derrick L. J.; Peng, Jianbiao; Wingert, David A. Organic Letters, 2005 , vol. 7, # 1 p. 23 - 26

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Citation Number: 11

Abstract

p-Iodophenol and its O-MOM-protected ether can be converted into iodoamines 2. These give cross-conjugated ketones 3 on oxidation with hypervalent iodides in the presence of methanol, and the ketones undergo radical cyclization. Exposure of the products to acid or sequential treatment with a Grignard reagent and acid effects rearomatization to produce benzo-fused nitrogen heterocycles 4.