Cyclizations of aniline N-oxides to give tetrahydroquinoline and related polycyclic scaffolds
| Author(s) | Swanson, Tyler L. | |
| Date Accessioned | 2025-05-27T18:23:07Z | |
| Date Available | 2025-05-27T18:23:07Z | |
| Publication Date | 2025 | |
| SWORD Update | 2025-05-19T01:01:58Z | |
| Abstract | Chapter 1 outlines the properties of tetrahydroquinolines, their utility in various biologically-relevant contexts as well as other non-therapeutic contexts, and the synthetic strategies towards tetrahydroquinolines. Several natural products containing tetrahydroquinoline cores are examined as well as various reported syntheses. Many other non-natural pharmaceutical molecules are similarly explored as well as the synthetic approaches towards them. This chapter does include syntheses from prior to 2019; however, this chapter aims to highlight the synthetic progress towards tetrahydroquinolines since 2019. Chapter 2, the first project herein, describes the synthesis of 4-amino- and 4-sulfanyltetrahydroquinolines from aniline N-oxides and nitrogen- or sulfur-containing alkenes. This chapter also addresses the efforts toward the synthesis of indolines and 3,4-dihydroquinolines. Chapter 3 describes the efforts towards the demethylation of N-methyltetrahydroquinolines, a long-standing challenge for this research program. It focuses on various strategies employed to access the desired demethylated tetrahydroquinoline as well as the fortuitous synthesis of 2-aryl tetrahydroquinolines that came as a result of these experiments. This chapter also briefly addresses the efforts toward the synthesis of the natural products, Incargranine B and Seneciobipyrrolidine. Chapter 4 closes this document with the preliminary efforts and future directions toward the functionalization of diarylamines through the use of aniline N-oxides. | |
| Advisor | Chain, William J. | |
| Degree | Ph.D. | |
| Department | University of Delaware, Department of Chemistry and Biochemistry | |
| Unique Identifier | 1523096101 | |
| URL | https://udspace.udel.edu/handle/19716/36241 | |
| Language | en | |
| Publisher | University of Delaware | |
| URI | https://www.proquest.com/pqdtlocal1006271/dissertations-theses/cyclizations-aniline-n-oxides-give/docview/3205527602/sem-2?accountid=10457 | |
| Keywords | Aniline N-oxide | |
| Keywords | Polonovski–Povarov reaction | |
| Keywords | Tetrahydroquinoline | |
| Keywords | Seneciobipyrrolidine | |
| Title | Cyclizations of aniline N-oxides to give tetrahydroquinoline and related polycyclic scaffolds | |
| Type | Thesis |