ORGN 480 |
| The development of a simple, cost-efficient, and environmentally friendly Lewis acid-induce reaction of structurally diverse compounds is under active investigation. The major improvement from our laboratory is to use bismuth derived reagents. We have been studying environmentally friendly reactions mediated by metals or their salts with the aim of developing several biologically active compounds, including several anticancer agents and â-lactams. This paper describes an efficient nitration of estrone using various metal salts-induced reactions. The nitration of estrone has been performed using different solid surfaces: montmorillonite clay, silica gel, florisil, molecular sieves, and egg shells. This reaction is more rapid and efficient, and utilized readily available reagents. These results indicate that the nitration reaction depends strongly on the nature of the solid support. Furthermore, according to our results, two solid adsorbents of identical structure with different surface area (particle size) can give different product distributions. Additionally, we believe that the binding of the metal nitrate to the free hydroxyl group of the multi-metallic montmorillonite and other solid surfaces is important and that this complex produces the nitronium ion. The superiority of this method over others includes an extremely rapid reaction (approximately 10 minutes) with readily available reagents. Also, our method requires no strong acid for the preparation of the surface, no acetic anhydride for the reaction, when applied to a sex hormone it results in a high overall yield. This project is supported through a HHMI grant. |
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New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |