xxv, 468 p. : ill. (some col.) A print copy of this thesis is available through the UO Libraries. Search the library catalog for the location and call number. / 1,2-Dihydro-1,2-azaborine is a six-membered aromatic heterocycle that is related to the quintessential aromatic molecule, benzene, via the replacement of a CC fragment in benzene with an isoelectronic BN bond-pair. Like the benzene motif, 1,2-dihydro-1,2-azaborine derivatives could provide opportunities in fields ranging from medicine to materials. Recent breakthroughs in the synthesis of 1,2-dihydro-1,2-azaborine have led to a burgeoning interest in this relatively unexplored heterocycle. This dissertation describes the synthesis, characterization, and potential applications of novel 1,2-dihydro1,2-azaborines. Chapter I reviews the chemistry of monocyclic and polycyclic BN-heterocycles over the last fifty years. Chapter II introduces the synthesis of numerous boron-substituted 1,2-dihydro-1,2-azaborine derivatives from a versatile precursor. Chapter III discusses the first successful synthesis of the parent 1,2-dihydro-1,2-azaborine, which is isoelectronic with benzene itself. An examination of the chemistry of 1,2-dihydro-1,2-azaborine provides a direct comparison of its properties relative to benzene. Chapter IV discusses the synthesis and characterization of 1,2-dihydro-1,2-azaborines incorporated into phenylacetylenic scaffolds. Chapter V discusses unrelated work on nitrated lipids, which was performed under the guidance of Professor Bruce Branchaud. The chapter introduces the importance of nitrated lipids in a biological context and details the synthetic achievements in this field. This dissertation includes previously published and unpublished co-authored material. / Committee in charge: Michael Haley, Chairperson, Chemistry; Shih-Yuan Liu, Advisor, Chemistry; David Tyler, Member, Chemistry; Raghuveer Parthasarathy, Outside Member, Physics

Le but principal de ce travail a été de développer de nouvelles méthodologies pour la synthèse de molécules d'intérêt biologique, telles que des azafluorénones, et des précurseurs d'analogues de la variolines B. Tout d'abord, nous avons synthétisé des diarylcétones, précurseurs pour nos cibles, par une séquence déprotocupration-aroylation. Ensuite, nous les avons impliquées dans une étape de couplage pallado-catalysé : les substrats ont subi une C-H activation pour aboutir aux azafluorénones. Nous nous sommes tournés par la suite vers la synthèse d'azafluorénones substituées. Ces dernières ont été synthétisées par un processus auto-tandem en combinant le couplage de Suzuki ou le couplage de Heck avec la cyclisation intramoléculaire catalysée par le palladium. Certaines de ces molécules ont été évaluées pour leurs propriétés biologiques et ont révélé des bonnes activités cytotoxique, antimalariale, antibactérienne et antifongique. Enfin, nous avons réussi à synthétiser des précurseurs d'analogues de variolines en seulement trois étapes à partir d'un produit commercial. / The main purpose of this work was to develop new methodologies for the synthesis of molecules of biological interest, such as azafluorenones and precursors of variolin B analogs. First, we synthesized diarylketones, precursors for our targets, via a deprotocupration-aroylation sequence. Then, we involved them in a pallado-catalyzed coupling step: some substrates underwent C-H activation to provide azafluorenones. Next, we turned our attention to the synthesis of substituted azafluorenones. The latter were synthesized by a tandem process combining Suzuki coupling or Heck coupling with intramolecular cyclization catalyzed by palladium. Some of these molecules were biologically evaluated and showed good biological activities: cytotoxic, antimalarial, antibacterial and antifungal. Finally, we succeeded in synthesizing precursors of variolin analogues in only three steps from a commercial product.