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

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journal contribution
posted on 2005-01-06, 00:00 authored by Stephen P. Fletcher, Derrick L. J. Clive, Jianbiao Peng, David A. Wingert
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.