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Date of Award
5-2025
Document Type
Restricted Thesis: Campus only access
Degree Name
Bachelor of Science
Department
Biochemistry & Molecular Biol.
First Advisor
Dr. William O’Neal
Second Advisor
Dr. Miles Johnson
Abstract
Pyrroles are valuable nitrogen-containing heterocycles with widespread applications in medicinal and synthetic chemistry. Though well-known and studied, there are gaps in synthetic methodology for deriving specific substitution patterns that are found as naturally occurring pyrroles in various organisms. In this paper, we propose a novel and efficient synthetic route to 3,4-diaryl N-unsubstituted pyrroles using chalcone-derived intermediates. Building on previous methods involving enaminone intermediates, this work uses an oxidative rearrangement of chalcones to generate -ketoaldehydes and related structures that would be expected to cyclize to pyrroles in a similar fashion. We identify diethyl aminomalonate (DEAM), as a superior nucleophile for successful cyclization, and demonstrate that optimal performance was observed under aprotic conditions with Bi(OTf)₃ catalysis. Additional solvent screenings confirmed high product convergence and minimal side-product formation in toluene. The results showcase a mild, scalable, and selective method for synthesizing N-unsubstituted pyrroles with broad potential for derivatization and application in heterocyclic chemistry.
Recommended Citation
Shklyarevsky, Anna M., "Novel and Efficient Synthesis of 3,4-Diaryl N-Unsubstituted Pyrroles from Chalcones: Optimizing Cyclization Using DEAM Reagent" (2025). Honors Theses. 1860.
https://scholarship.richmond.edu/honors-theses/1860
