A novel atroposelective strategy for the synthesis of quinoline substrates

Mazzanti, Stefano (2018) A novel atroposelective strategy for the synthesis of quinoline substrates. [Laurea magistrale], Università di Bologna, Corso di Studio in Chimica industriale [LM-DM270], Documento ad accesso riservato.
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Among heterocyclic compounds, quinoline scaffold has become an important motif for the development of new pharmacological active compounds. Since the discovery of their antimalarial properties, a large variety of quinolines was found to have interesting physiological activities and displayed attractive applications for pharmaceutical industries. In accordance to the above-mentioned features, a number of methods were developed for their synthesis but enantioselective versions are still lacking in the literature. In the past decades, this question has become even more complex, with the emergence of the less common axial chirality. Within the growing number of articles about atropisomers, the discovery of new synthetic pathways for the synthesis of enantioenriched atropisomers and their use in drug discovery has become a challenging topic in the organic chemistry scenario. In this work, the development of a novel atroposelective strategy for the synthesis of quinoline substrates has been achieved, and in order to obtain high values of enantioselectivity and yields a screening of the reaction conditions has been performed. The design of such strategy has been developed combining an already established methodology for the synthesis of heteroaromatic compounds such as a well-known Friedländer-type quinoline synthesis with chiral Brønsted acid catalysis to obtain the C-C bond formation in an enantioselective fashion.

Tipologia del documento
Tesi di laurea (Laurea magistrale)
Autore della tesi
Mazzanti, Stefano
Relatore della tesi
Correlatore della tesi
Corso di studio
Ordinamento Cds
Parole chiave
Friedländer Arene-forming reactions atropisomers organocatalysis Bronsted acid catalysis quinolines
Data di discussione della Tesi
12 Ottobre 2018

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