Suzuki cross-coupling reactions of 3-pyrroleboronic acid derivatives with haloaromatics and the reverse process i.e., the coupling of 3-iodo(bromo)pyrroles with arylboronic acids have been investigated as a potential key step in the synthesis of (-)-rhazinilam and analogues. It was found that 3-iodo-2-formyl-1-tosylpyrroles efficiently coupled with a variety of arylboronic acids in the presence of PdCl 2 (dppf) as catalyst. This catalytic system is compatible with a broad spectrum of arylboronic acids -electron-rich, electron-poor, hindered, heterocyclic -which easily coupled with the pyrrole substrate.Résumé : Nous avons étudié les réactions de couplage de Suzuki entre les acides 3-pyrroleboroniques et divers aromatiques halogénés ainsi que les réactions inverses de couplage entre les 3-iodo(bromo)-pyrroles avec des acides boroniques aromatiques. Cette réaction de couplage pourrait être une étape clé dans la synthèse du (-)-rhazinilame. Nous avons découvert que les 3-bromo-et 3-iodo-2-formyl-1-tosylpyrroles pouvaient être couplés efficacement avec un grand nombre d'acides boroniques en utilisant PdCl 2 (dppf) comme catalyseur. Ce catalyseur permet d'introduire facilement une grande diversité d'acides arylboroniques (riches ou pauvres en électrons, encombrés ou hétérocycliques) en position 3 du pyrrole.
H(3)R inverse agonists based on an aminopropoxy-phenyloxazoline framework constitute highly valuable druglike lead compounds that display efficacy in a mouse model of recognition memory.
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