The Université Euromed de Fès (UEMF) is pleased to inform the public of the doctoral thesis defense in ’’Organic Chemistry’’

The thesis defense will take place on Tuesday, February 20, 2024 at 3:00 PM at UEMF

Location: The Main Hall of the Incubator (LOC001994) The thesis will be presented by Ms. Sarah Nassiri

On the theme:

“ Regioselective functionalizations of pyrazolopyridine N-oxides via palladium-catalyzed C-H activation reactions ”

Abstract

The activation of C-H bonds has emerged as an attractive approach for advancing the synthesis of novel heterocyclic systems with potential applications across diverse fields, particularly in biology and pharmacy.

The primary aim of this PhD thesis was to develop innovative strategies for the selective functionalization of nitrogen-containing heterocycles through C-H activation reactions, employing transition metal catalysis.

In the first part, we developed a synthesis methodology enabling the regioselective functionalization at the ortho position of the N-oxide function in 7-azaindazole derivatives. The reaction goes through an oxidative arylation reaction, with various arenes and heteroarenes as coupling partners. This approach enables precise control over the position of functionalization through optimized reaction conditions, which is crucial to design new compounds with enhanced properties whatever the domains of application.

In the second part of our research, we conducted a series of experiments to perform a regioselective oxidative alkenylation on the pyridine moiety of 4-azaindazole and 7-azaindazole. Using the N-oxide function as an ortho directing group allowed us to exert control over the position of functionalization.

In the last part, we presented our work aimed at establishing optimal conditions for a direct arylation reaction on various 7-azaindazole analogues. The use of the N-oxide function favoured the regioselectivity of the reaction towards the C6 position.

Summary

C-H activation reactions now represent an attractive approach for the development of new heterocyclic systems that can have applications in various fields, particularly in biology and pharmacy.

The objective of this thesis is the development of new strategies to selectively functionalize nitrogen-containing heterocycles through C-H activation reactions using transition metal-based catalysis.

In the first part, we developed a synthesis methodology enabling the regioselective functionalization at the ortho position of the N-oxide function in 7-azaindazole derivatives through an oxidative arylation reaction, using various arenes and heteroarenes as coupling partners. This strategy allows control over the position of functionalization by using optimized reaction conditions, which is essential for designing new compounds with enhanced properties regardless of the application domains.