Silver and rhodium-catalyzed cycloisomerization reactions leading to furoquinolines, pyranoquinolines and dibenzofurans

Among a variety of new synthetic transformations, transition-metal-catalyzed reactions are some of the most attractive methodologies for synthesizing heterocyclic compounds. In this context, two different cycloisomerization reactions are studied. We first developed an efficient and versatile access to pyranoquinoline and furoquinoline derivatives, thanks to a tandem silver-catalyzed acetalization /cycloisomerization reaction. The synthesized compounds presented interesting antimalarial activity when tested on a resistant strain of the parasite Plasmodium Falciparum. The antitumoral activity of some furoquinolines was also investigated within a project funded by the French National League Against Cancer. Interestingly, we noticed that the regioselectivity of the cyclization can be controlled depending on the type of silver catalyst used. The observed reaction regioselectivity, including also an interesting nitrogen effect, led us to develop a silver imidazolate polymer as a stable and new silver catalyst. We also described a rhodium-catalyzed benzannulation reaction of silyl-enol-ethers onto alkynes, leading to dibenzofurans derivatives. These heterocycles are well-known for their biological properties and their interest in therapeutic chemistry. Finally, we developed an original methodology for the synthesis of oxindole derivatives

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Source https://theses.hal.science/tel-00864994
Author Parker, Évelyne
Maintainer CCSD
Last Updated May 9, 2026, 15:40 (UTC)
Created May 9, 2026, 15:40 (UTC)
Identifier NNT: 2010LYO10306
Language fr
Rights https://about.hal.science/hal-authorisation-v1/
contributor Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS) ; Université Claude Bernard Lyon 1 (UCBL) ; Université de Lyon-Université de Lyon-École Supérieure de Chimie Physique Électronique de Lyon (CPE)-Institut National des Sciences Appliquées de Lyon (INSA Lyon) ; Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)
creator Parker, Évelyne
date 2010-12-16T00:00:00
harvest_object_id 74753b81-62f5-4eca-a60b-7fc29ee63733
harvest_source_id 3374d638-d20b-4672-ba96-a23232d55657
harvest_source_title test moissonnage SELUNE
metadata_modified 2026-03-31T00:00:00
set_spec type:THESE