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Digital archive of theses discussed at the University of Pisa

 

Thesis etd-02172020-164607


Thesis type
Tesi di dottorato di ricerca
Author
MENICHETTI, ANDREA
URN
etd-02172020-164607
Thesis title
Development of synthetic methodologies to obtain new nitrogen-containing scaffolds
Academic discipline
CHIM/06
Course of study
SCIENZA DEL FARMACO E DELLE SOSTANZE BIOATTIVE
Supervisors
tutor Prof. Pineschi, Mauro
Keywords
  • acyl Mannich
  • azirdines
  • borylation
  • catalysis
  • decarboxylation
  • diabetes
  • NDA
  • photochemistry
  • ring-opening
  • vinylogous
Graduation session start date
10/03/2020
Availability
Withheld
Release date
10/03/2026
Summary
The organic chemistry play a pivotal role in the field of life sciences since every knowledge on this topic can be very useful in many scientific disciplines. For examples, the synthesis of new compounds as drug candidate or probes, and the researches of new synthetic methodologies can help the growth of medicine and new technologies.
This PhD thesis depicts the development of novel synthetic methodologies for the obtainment of nitrogen-containing compounds, that are known to have a crucial role in the field of pharmaceutical and biological science. Firstly, since the asymmetric synthesis of alkaloids has a remarkable relevance, an enantioselective alkylation of quinoline-type and isoquinoline-type substrates by using synergistic catalysis have been exploited obtaining highly enantioenriched diversely substituted compounds. Then, innovative ring-opening reactions of aziridines with diboron reagents have been attempted in order to have a versatile boron-based handle into the final product. Moreover, a library of novel heterobicycles have been generated by using an innovative four-linear-step synthesis allowing a hit-to-lead optimization in the field of research of novel treatments for diabetes. Finally, preliminary efforts in the field of photochemistry have been done for the borylation of haloarenes and the decarboxylation of aminoacids.
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