Our laboratory is interested in the synthesis of heterocyclic compounds as well as general synthetic methods. We have been very active in the area of cyclopropane synthesis. We have developed a method for preparing highly substituted cyclopropanes via a non-carbene approach. This allows the preparation of a variety of cyclopropanes with control of the substituents around the ring. From this work, we are looking at ways to utilize these cyclopropanes in expansion reactions and in alkene trapping reactions as a method for obtaining larger ring systems with varied substitution patterns.
We make our highly substituted cyclopropanes by thermolysis of substituted pyrazolines. Therefore, we have developed some novel approaches to preparing pyrazolines which should not be ignored. We are also exploring ways to directly utilize these pyrazolines as a synthetic intermediate for the preparation of larger ring systems and other useful heterocycles.
In addition to our synthetic methods work, we are actively involved in the synthesis of novel heterocyclic compounds. The main focus of our work in this area is to prepare compounds as potential anti-HIV agents. Our strategy has been to start with known nucleic acid binding agents and modify them in ways we feel will make them more active as antiviral agents. We have prepared a variety of heterocyclic systems that have been screened as anti-HIV agents. This approach has lead to the development of some compounds we hope will be useful antiviral agents.
- Vasquez,P.C., Bennett,D.C., Towns,K.K., Kennedy,G.D., and Baumstark,A.L. (2000). Thermolysis of hexasubstituted-4,5-dihydro-3H-pyrazoles: Kinetics and activation parameters. Heteroatom Chemistry, 11, 299-302.
- Hearn, J., Rigl, C.T., Kumar, A., Kennedy, G.D., Boykin, D.W., and Wilson, W.D. (1996). Design and Evaluation of Organic Dications and Tetracations that Inhibit HIV-1 TAR/Tat Interaction: Thermal Melting and Gel Shift Studies. Abstracts Of Papers Of The American Chemical Society 212, 142.
- Kennedy, G. D., Krishnan, G., Karim, M., and Harden, D. (1996). Preparation and Nucleic-Acid Binding of Ellipticine Derivatives. Heterocyclic Communications, 2, 125-128.
- Wang, X.H., Donovalova, J., Hollis, A., Johnson, D., Rodriguez, A., Kennedy, G.D., Krishnan, G., and Banks, H. (1994). Diels-Alder Reactivity of Vinylsulfoxyallenes. Journal Of Heterocyclic Chemistry, 31, 871-876. Padwa, A. and Kennedy, G.D. (1988). Dimerization and Cycloaddition Reactions of a Carbomethoxy Substituted Cyclopropene, J. Am. Chem. Soc., 105, 137.
- Kennedy, G.D., Baumstark, A.L., Dotrong, M., Thomas, T., and Narayanan N. (1991). Thermolysis of Hexasubstituted-4,5-dihydro-3H-pyrazoles: Synthesis of 1-Alkoxy- and 1-Acetoxy-1,2,2,3,3-pentasubstituted cyclopropanes. J. Heterocyclic Chem., 28, 1773.
- Padwa, A., and Kennedy, G.D. (1988). Dimerization and Cycloaddition Reactions of a Carbomethoxy Substituted Cyclopropene, J. Am. Chem. Soc., 105, 137.