Area of Expertise: Organic Chemistry and Organic Synthesis
Below is a contracted list of research interest. Both undergrad and graduate student will be fully engaged in a very interactive research group, which focuses on two main things: (a) continuous update of new and current research; and (b) utilizing current research as a template or inspiration to do new and creative things.
In general, I am interested in the application of heterocyclic chemistry and its’ biological and pharmacological significance. As a result, my research group is focused on:
- Synthesis of benz-fused five-membered heterocyclic ring.
Benz-fused-azoles, which include Benzothiazoles, benzoxazoles, and benzimidazoles as well as their analogous benzofuran, benzothiophene, and indole have shown significant application as pharmaceuticals, hence have generated significant interest among synthetic chemist. A number of natural products have been isolated from marine sources and microorganism possessing these subunits, and have shown a myriad of biological properties. As a result, I am interested in the synthesis of polycyclic marine alkaloids with a benz-fused-azole subunit and their analogs in on ongoing effort towards drug development.
- Synthesis of benz-fused six-membered heterocyclic ring.
Also, Chromenes, isochromenes, benzothiazines, quinolines, and isoquinonlines are all examples of benz-fused six-membered heterocyclic systems which have huge application in medicine and agriculture. Many of these systems are not extensively studied, though possessing important biological activity; hence, I am interested in the development new methodologies and new reactions towards the synthesis of various benz-fused six-membered heterocyclic systems, which will give us many entries, and thereby allow for structure activity relationship (SAR) studies.
Selected Publication in Refereed Journals:
> Barrett, O. V., Downer-Riley, N. K., Jackson, Y. A., Thermally-Induced Cyclization of Electron-rich Thiobenzanilides to Benzothiazoles, Synthesis, 2012, 44, 2579.
o Developed a new reaction for cyclization of thiobenzanilides and 2-halogenothiobenzanilides to benzothiazoles and benzobisthiazoles.
> Barrett, O. V., Downer-Riley, N. K., Jackson, Y. A., Synthesis of Some Novel Benzobisthiazoles, Heterocycles, 2010, 81 (7), 1641.
o Developed new methods for the synthesis of benzobisthiazoles
Selected Working Papers:
> Barrett, O. V., Downer-Riley, N. K., Jackson, Y. A., Further Investigation into the Cyclization of o-Methoxythiobenzanilides. Not yet submitted
o Developed a better understanding of oxidative and thermally induced cyclization of thiobenzanilides using both reactions and DFT calculations
o As a result we were better able to predict the outcome of some unexpected cyclization reactions leading to Benzo-bis-azoles.
> Barrett, O. V., Downer-Riley, N. K., Jackson, Y. A., Approaches to the Synthesis of Benz-fused 5-Membered Heterocycles from Thiocarbonyl Precursors. Not yet submitted
o Developed new methods to prepare Benz-fused azoles, benzofuran, and benzothiophenes
o Developed new reactions to make benzothiophenes directly from carbonyl precursor
o Synthesis of Benzimidazoles from the cyclization of thiobenzanilides
Selected Conferences/Research Presentations:
> Barrett, O. V., Downer-Riley, N. K., Jackson, Y. A., The Versatility of Thiocarbonyl Compounds as Precursors to 5-Membered Heterocycles, 2014 Annual Florida Heterocyclic and Synthetic Conference, University of Florida, Gainesville, Florida, (July 2014).
> Barrett, O. V., Downer-Riley, N. K., Jackson, Y. A., New Methodology toward Synthesis of Benz-Fused-Azoles and their Analogs, Mona Symposium of Natural Product and Medicinal Chemistry (January 2012).
> Barrett, O. V., Downer-Riley, N. K., Jackson, Y. A., Novel Approaches Towards the Synthesis of Benzothiazoles and their analogs, American Chemical Society (ACS) (March 2010).
> Barrett, O. V., Downer-Riley, N. K., Jackson, Y. A., Novel Approaches To the Synthesis of Benzobisthiazoles and their derivatives, Mona Symposium of Natural Product and Medicinal Chemistry (January 2010).
Selected Public Lecture:
> Barrett, O. V., Understanding the Minute: Key to Solving the Complex, Homehood-Flossmore Science Pub, Country Club Hills, IL (February 2016)