7542-60-1Relevant academic research and scientific papers
Insertion of Isocyanides into N?Si Bonds: Multicomponent Reactions with Azines Leading to Potent Antiparasitic Compounds
Kishore, Kranti G.,Ghashghaei, Ouldouz,Estarellas, Carolina,Mestre, M. Mar,Monturiol, Cristina,Kielland, Nicola,Kelly, John M.,Francisco, Amanda Fortes,Jayawardhana, Shiromani,Mu?oz-Torrero, Diego,Pérez, Belén,Luque, F. Javier,Gámez-Monta?o, Rocío,Lavilla, Rodolfo
, p. 8994 - 8998 (2016)
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.
