CHED 389 |
| A new one-step reaction was developed for the synthesis of polysubstituted benzenes from C5-substituted indoles. Using NaY zeolites as nanoscopic reaction vessels, indoles containing electron withdrawing groups at C5 are photooxidized. The reaction occurs via the addition of oxygen to the double bond of the pyrrole ring and subsequent thermal cleavage to form the polysubstituted benzenes. At optimal ratios of indole to zeolite (1 substrate per 4 supercages), this reaction results in few or no by-products and occurs at 100% conversion. This reaction can be carried out on a larger scale to yield hundreds of milligrams of product without the loss of selectivity or a decrease in conversion. The feasibility of photooxidizing 5-nitroindole presents the potential for generating new photocleavable linkers for biological targets.
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Chemical Education |
