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Date of Award
2024
Document Type
Restricted Thesis: Campus only access
Degree Name
Bachelor of Science
Department
Chemistry
First Advisor
Dr. Raymond Dominey
Second Advisor
Dr. Emma Goldman
Abstract
Flow chemistry serves as an important synthetic alternative for the formation of organic pharmaceutical cores. This project explores the continuous flow synthesis of polysubstituted pyrroles, motifs essential to the derivatization of pharmaceuticals such as atorvastatin, a drug that treats cholesterol1. While current literature relies on batch techniques to access pyrroles, this project proposes a flow process by employing β-chloroenals as useful precursors. The β-chloroenal intermediate is derived from readily available aryl-ketone starting material using simple flow chemistry methods at 80oC with a 50-minute residence time. Additionally, it was found that for an optimal transformation of the β-chloroenal to the polysubstitued pyrrole, the reaction could be performed at 145oC with a 30-minute residence time using glycine methyl ester and diisopropylethylamine (DIEA) for high yield and rapid synthesis. Furthermore, this proposed flow process successfully generated a library of 12 different polysubstituted pyrroles from readily available starting material.
Recommended Citation
Ramirez, Evelyn, "Continuous Flow Synthesis of Polysubstituted Pyrroles" (2024). Honors Theses. 1759.
https://scholarship.richmond.edu/honors-theses/1759