from first principles PP-I-1

PP-III-13Isoquinoline Derivatives via Stepwise Regioselective sp2 and sp3 C−H BondFunctionalizationsBoudiar T., Achard M., Kabouche Z., Doucet H., Bruneau C.Centre de Recherche en Biotechnologies, BPE 73, Ali Mendjli, Nouvelle Ville,25000 Constantine, Algeriaboudiar_tarek@yahoo.frConsidering the importance of cyclic amines and alkaloids in industry as dyes and aspharmaceutical and agrochemical drugs, straightforward and environmentally benignapproaches for the preparation of these compounds still represents a challenging task forchemists. Among them, tetrahydroisoquinoline (THIQ) derivatives constitute an importantclass of compounds with numerous biological properties such as anti-HIV, antitumor, andantipsychotic activities. They are actually produced by multistep methods, and new directsynthetic routes to access THIQ derivatives are highly desired and at the center of activeresearch activities. Main THIQ derivatives arise from the functionalization at position 1 viacross dehydrogenative coupling (CDC) or at position 3 with multistep syntheses.In contrast,functionalization at position 4 is scarce. In recent years, C−H bond functionalizationinvolving activation of inert C−H bonds to allow direct C−C coupling has attractedconsiderable attention since this type of reaction minimizes the reaction steps and thereforethe number of purification processes and the production of wastes and fullfills the criteria ofsustainability.In our laboratory, we have recently described, on the one hand, the first ruthenium-catalyzedC(β)−H functionalization of various cyclic amines and highlighted the formation of reactiveenamine intermediates via hydrogen autotransfer processes and, on the other hand, theregioselective palladium-catalyzed C(5) functionalization of five-membered heterocycles.164