Date Thesis Awarded
5-2025
Access Type
Honors Thesis -- Access Restricted On-Campus Only
Degree Name
Bachelors of Science (BS)
Department
Chemistry
Advisor
Robert J. Hinkle
Committee Members
Jonathan Scheerer
Robert D. Pike
David Grandis
Abstract
Herein, we explore the scope and limitations of the BF3•Et2O-mediated alkyne aza-Prins reaction in tandem with an intramolecular Friedel-Crafts addition to synthesize tetracyclic molecules with both nitrogen and oxygen-containing heterocycles. We demonstrate its utility and versatility with the synthesis of numerous compounds containing a 7,8-dihydro-6H-chromeno[3,4-c]quinoline core. The use of aldehydes with varying electronic properties, ranging from both electron-donating to strongly electron-withdrawing, as well as varying substituents on the alkynyl substrates all afforded our desired target molecule in modest to good yields.
Recommended Citation
Kim, Katherine U., "Cascade Aza-Prins Reactions to Access Novel Fused Tetracyclic Heterocycles" (2025). Undergraduate Honors Theses. William & Mary. Paper 2316.
https://scholarworks.wm.edu/honorstheses/2316
