Donor-acceptor cyclopropanes are generally used to produce five and six membered
cyclic rings. This project investigated the possibility of forming novel seven-membered
benzoxepines. This scaffold can be found in antibacterial, antioxidant, anticancer, anti-diabetic,
and a host of other medicinal compounds and natural products. One example is the antimalarial
drug Artemisinin. Nitrocyclopropane was reacted with salicylaldehyde under microwave
irradiation to yield a product following nucleophilic attack and ring opening of the cyclopropane
ring. The base, solvent, and equivalents of each reagent were optimized to promote full
conversion of the nitrocyclopropane. Proton and carbon nuclear magnetic resonance (NMR)
analysis provided insight into the formation of a dihydrobenzoxepine, a derivative of the desired
7-membered ring. Current efforts focus on identifying the proper purification method to isolate
the novel product from excess salicylaldehyde, obtaining a yield for this transformation, and
exploring the scope of the reaction with other salicylaldehyde derivatives. If the reaction can be
generally applied to other salicylaldehyde analogues, a new family of benzoxepines can be
prepared and analyzed for any biological activity.
