THE SYNTHESIS OF NITROGENOUS HETEROCYCLES FROM CYCLOPROPANOL FRAGMENTATION

Our group has extended a cyclopropanol fragmentation strategy from the preparation of oxygenated ring systems to nitrogenous systems. Azepine formation was previously developed, albeit in low and inconsistent yields. The approach begins with N,N-dibenzyl-protected ß-amino acid ethyl esters which were transformed to cyclopropanols via the Kulinkovich reaction and mono-deprotected. Resulting ß-benzylamino cyclopropanols were then reacted with various aldehydes to form aminals. Subsequently, various Lewis acids were used to promote the rearrangement of the aminal into the azepine. Dimethylaluminum chloride (Me2AlCl) proved to be the Lewis acid of choice for the formation of the azepine. Currently, a variety of solvents, substituents, temperatures, Lewis acids, and purification strategies are tested to increase the yield and reliability of azepine formation.

Additional Abstract Information

Student(s): Georgia Stoyanov

Department: Chemistry and Biochemistry

Faculty Advisor: Dr. Kevin P.C. Minbiole

Type: Oral

Year: 2011