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

Kishore, KG; Ghashghaei, O; Estarellas, C; Mar Mestre, M; Monturiol, C; Kielland, N; Kelly, JM; ... Lavilla, R; + view all (2016) Insertion of Isocyanides into N-Si Bonds: Multicomponent Reactions with Azines Leading to Potent Antiparasitic Compounds. Angewandte Chemie - International Edition , 55 (31) pp. 8994-8998. 10.1002/anie.201604109. Green open access

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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.

Type: Article
Title: Insertion of Isocyanides into N-Si Bonds: Multicomponent Reactions with Azines Leading to Potent Antiparasitic Compounds
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/anie.201604109
Publisher version: https://doi.org/10.1002/anie.201604109
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: Science & Technology, Physical Sciences, Chemistry, Multidisciplinary, Chemistry, azines, isocyanides, multicomponent reactions, silicon, trypanosomiasis, TRYPANOSOMA-CRUZI, DRUG DISCOVERY, CHEMISTRY, HETEROCYCLES, ISONITRILES, ALDEHYDES, CATALYSTS, SALTS, ALKYL
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10062138
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