New synthetic approach to highly functionalized 2-aminophenyl naphthohydroquinones

ORGN 544

Kimberly D. Fisher, kfisher2@mix.wvu.edu and Björn C. G. Söderberg, bjorn.soderberg@mail.wvu.edu. Department of Chemistry, West Virginia University, P.O. Box 6045, Morgantown, WV 26506
Herein we wish to present a short synthetic methodology to 2-aminophenyl naphthohydroquinones and 2-aminophenylnaphthoquinones. Our approach begins with ortholithiation of protected anilines followed by addition to diisopropyl squarate. These addition products readily rearrange to cyclobutenediones in the presence of acid. Addition of aromatic lithium reagents to the cyclobutenediones followed by protection then thermolysis affords protected hydroquinones. Synthesis of a variety of these highly functionalized compounds and further reaction will be presented.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006