ORGN 426 |
| The indolizine and indole ring systems are featured in natural products and medicinal agents. Several methods for the preparation of these isomeric heterocycles are known. However, many classical syntheses require harsh reaction conditions, including elevated temperatures, extended reaction times, and/or highly basic or acidic environments. Traditional protocols, thus, may not be compatible with some highly functionalized substrates, and more mild approaches to the construction of these ubiquitous heterocycles are warranted. In this poster, we present a mild and convenient synthesis of substituted indolizines and indoles from simple aromatic precursors using (trimethylsilyl)diazomethane. Exposure of 2-(pyridin-2-yl)acetyl substrates to (trimethylsilyl)diazomethane at room temperature and open to air furnishes a variety of functionalized indolizines in moderate to good yields. 2-Aminobenzladehydes can be converted to substituted indoles under slightly modified conditions.
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Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster
Division of Organic Chemistry |
