Synthesis of Isoquinoline/Quinoline/Carboline-Substituted Methylamine Derivatives by an Interrupted Ugi Three-Component Reaction

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Abstract
A hexafluoroisopropanol (HFIP)-promoted Ugi three-component reaction of electron rich aryl, alkenyl or heteroaryl group-tethered isocyanides, aldehydes and amines was developed for the rapid and general synthesis of a wide range of isoquino-line/quinoline/carboline-substituted methylamine and α-amino acid derivatives. In this reaction, the in situ formed nitrilium was intramolecularly trapped by the nucleophiles tethered at isocyanides to form the corresponding heterocyclic framework, wherein an obviously gem-disubstituent (Thorpe-Ingold) effect was observed.
Funding Information
  • National Natural Science Foundation of China (22171168)

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