With this Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Don Coltart of the University of Houston to develop novel ways of constructing nitrogen- and oxygen-containing heterocycles. Heterocycles are cyclic or ring-shaped molecular structures found in many compounds, such as pharmaceutical drugs. The vast majority of nitrogen and oxygen-containing heterocycles that are found in existing pharmaceuticals have a flat or disk-like structure. Moving away from these relatively simple flat heterocycles to ones that have greater three dimensionality may be beneficial in improving efforts aimed at developing new medicines. As a means of addressing this, the Coltart research group is developing a variety of synthetic tools and strategies to enable such three-dimensional nitrogen- and oxygen-containing heterocycles to be made effectively and simply. The educational aspects of this project are directed at the training of both graduate and undergraduate students in hands-on laboratory research. Professor Coltart also increases the awareness of early career undergraduate science students with regard to nontraditional career pathways in the chemical sciences.
Professor Coltart and his students develop novel approaches to the synthesis of saturated and partially saturated (SPS) N- and O-heterocycles using 3-amino-1-azopropenes and 3-hydroxy-1-azopropenes (AAPs and HAPs, respectively). These are compounds can be applied to the synthesis of biologically important natural products, drugs, and other compounds. The Coltart research group established that AAPs and HAPs exhibit 1,3-dipolar reactivity and can be coupled with partner dipoles to provide SPS N- and O-heterocycles, respectively. Numerous partner dipoles are available to engage AAPs and HAPs and are being used to generate a wide range of such heterocyclic compounds in a stereocontrolled way, including gamma-lactones, gamma-lactams, tetrahydrofurans, and pyrrolidines. Broader impacts of this work include the recruitment of students from under-represented groups to the chemical sciences, as well as an outreach program to educate undergraduate science students about the very broad range of nontraditional career opportunities available to them with a chemistry education.
This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.
