Insertion of Isocyanides into N-Si Bonds: Multicomponent Reactions with Azines Leading to Potent Antiparasitic Compounds.


Kishore, KG; Ghashghaei, O; Estarellas, C; Mestre, MM; Monturiol, C; Kielland, N; Kelly, JM; Francisco, AF; Jayawardhana, S; Muñoz-Torrero, D; Pérez, B; Luque, FJ; Gámez-Montaño, R; Lavilla, R; (2016) Insertion of Isocyanides into N-Si Bonds: Multicomponent Reactions with Azines Leading to Potent Antiparasitic Compounds. Angewandte Chemie (International ed in English), 55 (31). pp. 8994-8. ISSN 1433-7851 DOI: https://doi.org/10.1002/anie.201604109

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Abstract

: 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.<br/>

Item Type: Article
Faculty and Department: Faculty of Infectious and Tropical Diseases > Dept of Pathogen Molecular Biology
PubMed ID: 27314630
Web of Science ID: 383253700036
URI: http://researchonline.lshtm.ac.uk/id/eprint/2551446

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