Diversity Oriented Synthesis of Macrocyclic Triazole Rings

Mentors: Ann Kelly & Jen Beaudoin

Jimmy’s project centered around synthesizing 16 new chemical compounds called macrocyclic triazole rings. Triazoles have been found useful in protecting against fungal infections and contain many possibilities for making a diverse library. Jimmy synthesized each triazole by joining an azido acid with a propargilic amine to form an amide, and then joining the functional groups of the amide in an intra-molecular coupling reaction to form a triazole. For each reaction, he used either copper or ruthenium to catalyze the final ring closure step.

Jimmy used these steps to create a library of 16 triazoles encompassing all stereo and regio-isomeric combinations. Because Jimmy worked with 4 starting acids, 2 starting amines, and 2 catalysts (copper and ruthenium), the library he generated contained a total of 4 x 2 x 2 = 16 compounds. In the future, the 16 compounds Jimmy synthesized will be used in high throughput screening to test for activity in a variety of therapeutic areas.




Jimmy, a senior at Mira Costa High School, synthesized a collection of macrocyclic triazole rings, in order to incorporate them into current chemical screening libraries.