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Kishore, Kranti G.; Ghashghaei, Ouldouz; Estarellas, Carolina; Mestre, M. Mar; Monturiol, Cristina; Kielland, Nicola; Kelly, John M.; Francisco, Amanda Fortes; Jayawardhana, Shiromani; Muñoz-Torrero, Diego; Pérez, Belén; Luque, F. Javier; Gámez-Montaño, Rocío; Lavilla, Rodolfo
Angewandte Chemie (International ed.), July 25, 2016, Letnik: 55, Številka: 31Journal Article
Trimethylsilyl chloride is an efficient activating agent for azines in isocyanide‐based reactions, which then proceed through a key insertion of the isocyanide into a N−Si bond. The reaction is initiated by N activation of the azine, followed by nucleophilic attack of an isocyanide in a Reissert‐type process. Finally, a second equivalent of the same or a different isocyanide inserts into the N−Si bond leading to the final adduct. The use of distinct nucleophiles leads to a variety of α‐substituted dihydroazines after a selective cascade process. Based on computational studies, a mechanistic hypothesis for the course of these reactions was proposed. The resulting products exhibit significant activity against Trypanosoma brucei and T. cruzi, featuring favorable drug‐like properties and safety profiles. Insert here! Multicomponent reactions (MCRs) with isoquinolines and other azines that proceed through the insertion of an isocyanide into a N−Si bond are described. This novel activation mode enables a variety of transformations to take place with high selectivity under mild reaction conditions. Some of the products showed in vitro activity against the causative agents of trypanosomiasis. TMS=trimethylsilyl.
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