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Updated: May 12, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Indium-catalyzed formal [4 + 1 + 1]/[4 + 1] isocyanide-based annulation for construction of polyfunctionalized
Issa Zarei1, Hormoz Khosravi1, Frank Rominger2
1Peptide Chemistry Research Institute, K. N. Toosi University of Technology, P.O. Box 19697-64499, Tehran, Iran. balalaie@kntu.ac.ir.
Abstract:
A distinctive catalytic reaction involving multiple isocyanide insertions on ambiphilic quinolines has been introduced to synthesize intricate polyheterocyclic scaffolds (21 examples, up to 71% yield) through the formation of several C-C, C-O, and C-N bonds. Our findings indicate that these reactions can switch between two cycloadditions ([4 + 1 + 1] and [4 + 1]) depending on the isocyanide structure and the solvent used. Finally, furo[2,3-b]quinoline-2,3-diamine examples, as some of the novel products, exhibit strong solvatochromism in various solvents.
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