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Molecules 2016, 21(1), 19; doi:10.3390/molecules21010019

Isocyanide-Based Multicomponent Reactions for the Synthesis of Heterocycles

Department of Neurology, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA
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Author to whom correspondence should be addressed.
Academic Editor: Romano V. A. Orru
Received: 10 October 2015 / Revised: 2 December 2015 / Accepted: 17 December 2015 / Published: 23 December 2015
(This article belongs to the Special Issue MCRs and Related One-Pot Organic Synthesis)

Abstract

Multicomponent reactions (MCRs) are extremely popular owing to their facile execution, high atom-efficiency and the high diversity of products. MCRs can be used to access various heterocycles and highly functionalized scaffolds, and thus have been invaluable tools in total synthesis, drug discovery and bioconjugation. Traditional isocyanide-based MCRs utilize an external nucleophile attacking the reactive nitrilium ion, the key intermediate formed in the reaction of the imine and the isocyanide. However, when reactants with multiple nucleophilic groups (bisfunctional reactants) are used in the MCR, the nitrilium intermediate can be trapped by an intramolecular nucleophilic attack to form various heterocycles. The implications of nitrilium trapping along with widely applied conventional isocyanide-based MCRs in drug design are discussed in this review. View Full-Text
Keywords: Ugi reaction; heterocycles; nitrilium trapping Ugi reaction; heterocycles; nitrilium trapping
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Váradi, A.; Palmer, T.C.; Notis Dardashti, R.; Majumdar, S. Isocyanide-Based Multicomponent Reactions for the Synthesis of Heterocycles. Molecules 2016, 21, 19.

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