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Digital archive of theses discussed at the University of Pisa

 

Thesis etd-09152023-084101


Thesis type
Tesi di laurea magistrale LM5
Author
GALLORINI, GIULIO
URN
etd-09152023-084101
Thesis title
Development of ring-opening reactions of cyclic aminals with carbon nucleophiles
Department
FARMACIA
Course of study
CHIMICA E TECNOLOGIA FARMACEUTICHE
Supervisors
relatore Pineschi, Mauro
correlatore Comparini, Lucrezia Margherita
Keywords
  • aminals
  • diamines
  • Grignard reagents
  • copper catalysis
  • alkynylation
Graduation session start date
04/10/2023
Availability
Withheld
Release date
04/10/2026
Summary
Some bicyclic compounds in study in Prof. Pineschi laboratory revealed to be biologically active as GLP-1 (Glucagon Like Peptide 1) secretagogues, an incretine hormone secreted from ileum and colon cells, controlling glycaemia with a multifactorial insulinotropic action. During some late-stage modifications, aimed at expanding the compounds library, an unusual reactivity of these heterocycles with Grignard reagents was observed. In fact, the organometallic reagent attacked the gem-diamine carbon atom, determining the formation of a new C-C bond and contemporary ring opening of the bicycle. As this kind of reactivity was not present in the literature, the main aim of this thesis was that of exploiting this phenomenon as a novel synthetic strategy to prepare alkylated diamines, which are important structural motifs found in natural products, medicine, and ligands in transition metal catalysis and organocatalysis. Importantly, substituted 1,2- and 1,3-diamines are frequently difficult to produce following standard procedures, especially in enantioenriched fashion. In fact, after a fine tuning of the reaction conditions, one of the latest target of our work was about the development of an enantioselective synthesis of these compounds. Meanwhile, most of our efforts were devoted to expanding our knowledge about these systems, performing the reaction on several new gem-diamine scaffolds and Grignard reagents, by varying the reaction conditions, in order to further investigate the reactivity of these peculiar ring-opening reactions.
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