Akademska digitalna zbirka SLovenije - logo
VSE knjižnice (vzajemna bibliografsko-kataložna baza podatkov COBIB.SI)
  • Dearomative reductive functionalisation reactions of azaarenes : a thesis submitted in partial fulfilment of the requirement for the degree of Doctor of Philosophy (DPhil)
    Marinič, Bruno
    Chapter 1: Introduction. The introduction gives an overview of the different strategies for the reduction of azaarenes, with a particular focus on transfer hydrogenation approaches for the synthesis ... of aliphatic N-heterocycles. The second half of the introduction presents a brief overview of relevant dearomative reductive functionalisation reactions of azaarenes published in recent years. Chapter 2: Single-point activation strategy for the reductive hydroxymethylation of pyridines. In this chapter a single-point activation strategy of pyridines is described that allowd for the use of a more electronically diverse range of substrates to undergo the dearomative reductive hydroxymethylation reaction. Additionally, a total synthesis of (+ -)-paroxetine is described, the target was prepared from a key dearomatized intermediate in 3 synthetic steps. Chapter 3: Expending the scope of electrophiles in the dearomative reductive functionalisation reactions of quinolines. In this chapter the dearomative reductive functionalisation of quinolinium salts to their tetrahydroquinoline analogues is described. Two sets of new reaction conditions are developed with formic acid acting as the terminal reductant under transition-metal-free conditions or rhodium catalysis with very low catalyst loadings. The scope of electrophiles was expanded from just formaldehyde to a wide range of electrophiles, including enones, imides, unsaturated esters and sulfones. Chapter 4: Expending the scope of electrophiles in the dearomative reductive functionalisation reaction of isoquinolines. In this chapter the dearomative reductive functionalisation of isoqunolinium salts to their tetrahydroisoquinoline counterparts is described. Analogously to the quinoline system, formic acid was used as the source of hydride and the reaction was possible under transition-metal-free conditions or rhodium catalysis with very low catalyst loadings. the scope of electrophiles that were intercepted by the enamine species generated in situ was further expanded to include enones, imides, unsaturated esters and sulfones, ß-nitrostyrens and aldehydes. Chapter 5: Dearomative annulation reactions of isoquinolines. In this chapter various dearomative annulation reactions of activated isoquinolines are presented. The reactivity of in situ genarated intermediates is exploited further to assemble complex tricyclic frameworks in a single step with excellent diastereselectivities. The formal [3+3] annulation with methyl vinyl ketone is explored in greater detail including model studies towards the synthesis of the natural products in the crinane-alkaloid family. Chapter 6: Experimental. This chapter contains the experimental procedures and spectroscopic data for all the compounds described in this thesis.
    Vrsta gradiva - disertacija ; neleposlovje za odrasle
    Založništvo in izdelava - Oxford : B. Marinič, 2023
    Jezik - angleški
    COBISS.SI-ID - 162103299

Nobena knjižnica v sistemu COBISS.SI nima izvoda tega gradiva.
loading ...
loading ...
loading ...

Vnos na polico