The University Euromed of Fez (UEMF) has the pleasure to inform the the public of the doctoral thesis in ’’Organic Chemistry”

 

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

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

Under the title:

“ Regioselective functionalizations of N-oxides of pyrazolopyridines via palladium-catalyzed CH-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 proceeds through an oxidative arylation, with various arenes and heteroarenes as coupling partners. This approach enables precise control over the site of functionalization through optimized reaction conditions, which is crucial for designing new compounds with enhanced properties regardless of the fields of application.

In the second part of our research, we conducted a series of experiments to perform a regioselective oxidative alkenylation on the pyridine ring of 4-azaindazole and 7-azaindazole. Using the N-oxide function as an ortho-directing group allowed us to exert control over the site 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 favored the regioselectivity of the reaction toward the C6 position.

 

Abstract

 

C–H activation reactions are now an attractive approach for the development of new heterocyclic systems that can have applications in diverse fields, notably in biology and pharmacy.

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

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