Kerwin, Sean M.Navarro Salazar, Jennifer Tania2024-05-132024-05-132022-05Navarro Salazar, J. T. (2022). The synthesis and utility of novel N-alkynyl azoles (Unpublished thesis). Texas State University, San Marcos, Texas.https://hdl.handle.net/10877/18692N-Alkynyl azoles have attracted interest in the synthetic community due to the polarized nature of these alkynes and the presence of these nitrogen heterocycles in biologically interesting compounds. While enediynes undergo Bergman cyclization to reactive 1,4-benzyne diradical intermediates, the thermolysis of 1,2-dialkynylimidazoles affords cyclopentapyrazine carbene intermediates. In contrast to enediynes, whose cytotoxicity is linked to DNA cleavage by 1,4-benzyne diradicals, studies have disproved any correlation between the rate of carbene formation and the cytotoxicity of these 1,2dialkynylimidazoles. The generality of the novel thermal rearrangement of 1,xdialkynylazoles is investigated. Using a 6-step synthetic route, we confirm the preliminary structure assignment of a spirocyclic cyclopentapyrimidine product derived from a cyclopentapyrimidine carbene intermediate that is produced during the thermolysis of 1,5-diethynylimidazole. This work has application in a synthetic approach towards a similar thermolysis of 1,2-dialkynylpyrroles in a strategy to construct the core of lycoposerramine-R through intramolecular carbene trapping reactions.Text69 pages1 file (.pdf)en1,5-dialkynylimidazolespiro[cyclopenta[d]pyrimidine-5,5'-[1,4]dioxepane]lycoposerramine-RthermolysisN-alkynyl azoleThesis