CHED 421 |
| Pyrrole amides have shown possibilities for a myriad of uses, including use as hosts in anion binding and molecular recognition due to the multiple hydrogen bonding sites. There are many methods for producing pyrrole amides; however most require tedious purification or expensive reagents. We sought an inexpensive method for producing a diverse array of pyrrole amides on large scale and good yields. Dioxinone (1), a diketene adduct, in the presence of an amine nucleophile provided a great method for acetoactylation. The acetoacetamides (2) were converted to the corresponding oximes using standard methods. The Knorr pyrrole synthesis was then used to prepare the pyrrole amides (3) from the oxime and a diketone. Conditions have been found for the preparation of a number of acetoacetamides and pyrrole amides in excellent to moderate yields in three overall steps.
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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 |
