Synthesis of novel variations of n-methyl-5H-benzocycloheptanaphthaleneimines

CHED 1324

Kyle Kalstabakken and John C. DiCesare, john-dicesare@utulsa.edu. Department of Chemistry and Biochemistry, The University of Tulsa, 600 S. College Ave., Keplinger Hall, Tulsa, OK 74104
N-methyl-5H-benzocycloheptanaphthaleneimines have been shown to have potential for pharmaceutical activity. The main feature of this class of compounds is a four ring (6-6-7-6) carbocyclic fused ring system with various substituents. This unique backbone causes difficulty when introducing changes to create novel structures. In the past, progress has been made on the synthesis of various precursors, as well as towards the understanding of rearrangements of the final product. These studies are taken into consideration to improve synthetic methods and present new compounds that will hopefully continue the trend of pharmaceutical activity. The addition of various substituents is studied primarily through the use of various quinones in the 3+2 cycloaddion reaction with N-methyl-4-hydroxyquinoline. In addition, reaction conditions will be studied and optimized for the most efficient synthetic process.