Event Title

Cycloaddition of an Isomuchnone Compound and Stilbene

Presenter Information

Patrick Hovda, Minnesota State University, Mankato

Location

CSU 253/4/5

Start Date

4-4-2011 11:00 AM

End Date

4-4-2011 12:30 PM

Student's Major

Chemistry and Geology

Student's College

Science, Engineering and Technology

Mentor's Name

Michael J. Lusch

Mentor's Department

Chemistry and Geology

Mentor's College

Science, Engineering and Technology

Description

The focus of this experiment was the exploration of an inter-ring cycloaddition of an isomuchnone compound (which is derived from a Biginelli compound) and stilbene. The purpose of this reaction was to produce a new class of compounds to be studied in the future for their pharmaceutical potential or other uses. To develop the isomunchnone compound, a procedure developed by Oliver Kappe was used. A Biginelli compound was first produced using a cyclic aldehyde, β-dicarbonyl, and urea. From the Biginelli compound, a diazo intermediate was produced and isolated. In order to get the reaction to proceed as desired and avoid an unwanted rearrangement of the isomuchnone, a protecting group was placed onto the diazo compound.

The diazo compound with protecting group was isolated and characterized to ensure that the compound was synthesized correctly. Once complete, the protected diazo compound was introduced to a catalytic amount of Rhodium acetate. This process produces the isomuchnone intermediate. After 30min, stilbene was introduced in to the reaction vessel. The compound was isolated and characterized by using proton and carbon NMR, mass spectroscopy, IR spectroscopy, and thin layer chromatography.