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Synthèse et fonctionnalisation des furo[3,2-b]- et [2,3-c]pyridines par voie organométallique

Abstract : The work described in this PhD thesis concerns a regioselective metalation study of two fused heterocycles : the furo[3,2-b]- et [2,3-c]pyridines. The influence of the lithiated agent on the reaction course and on the selectivity of the lithiation has been studied with several bases : n-BuLi, LTMP, LDA and [n-BuLi/LiDMAE]. From a fundamental point of view, this study allowed us to establish some rules concerning the functionalisation of fused heterocycles, and then, a chemical library of polyfunctionalised furo[3,2-b]- and [2,3-c]pyridines has been designed. Some of the compounds obtained in this way were engaged in metallo-catalysed coupling reactions. The difficulties we met during this work allowed us to discover a double functionalisation sequence of ?-deficient heterocycles via a cascade process combining the trapping of lithiated intermediates and the nucleophilic addition of some in-situ released species. The development of this sequence afforded direct access to difunctionalised pyrazines, pyridines and furo[3,2-b]pyridines
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Anthony Chartoire. Synthèse et fonctionnalisation des furo[3,2-b]- et [2,3-c]pyridines par voie organométallique. Autre. Université Henri Poincaré - Nancy 1, 2010. Français. ⟨NNT : 2010NAN10081⟩. ⟨tel-01746339⟩



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