Research Symposium

BIO

My name is Thomas, I am a second year undergraduate studying Biochemistry. I am from Ormond Beach Florida. After college I plan on applying to medical school. In Dr. Lei Zhu's research group we explore nuances in Organic Chemistry Synthesis and Photochemistry.

Photoconversion of 1,2,3-triazoles to indoles ​

Abstract

Photoconversion of 1,2,3-triazoles to indoles

The azide-alkyne cycloaddition to afford triazoles, also known as the click reaction, has gained lots of traction in organic chemistry research. It has opened many new routes for drug discovery and advances in materials science. This reaction entails an azide and an alkyne forming an aromatic five-membered “triazole” ring that has interesting chemical properties. This ring formation can be the key to many synthetic obstacles that organic chemists face. My research in Dr. Lei Zhu’s group is focused on finding a convenient route to form alkynyl-substituted triazoles which are a form of triazoles that are reactive when irradiated with light. As one adds substituents to either the azide or the alkyne, the click reaction requires different conditions to be successful. Synthesizing azides and alkynes that have interesting reactivities is important for forming a triazole. Aromatics azides and alkynes can be conjugated to afford alkynylated triazoles under copper catalyzed conditions. The products of this reaction are expected to undergo photoconversion to alkynylated indoles, which are valuable core structures for pharmaceutical candidates. The conversion from a triazole to an indole produces diatomic nitrogen gas as a byproduct. Going forward, I plan to develop the scope of my alkynyl triazole formation along with the indoles that are formed after photochemical conversion.

Keywords: Organic Chemistry, Chemistry, Photochemistry, Synthesis