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Palladium-Catalyzed Imidoylation-Triggered [2 + 2 + 1] Cyclization of Internal Alkyne with Isocyanides

Keke Huang, Jin‐Biao Liu, Zhifeng Chen, Yuchao Wang, Sarita Yadav, Guanyinsheng Qiu

2020Organic Letters22 citationsDOI

Abstract

In this work, a palladium-catalyzed [2 + 2 + 1] cyclization of internal alkynes with double isocyanides is described. This facile procedure is efficient for synthesizing various pyrrolo[3,2-c]quinolin-2-amines. The reaction worked well with a broad reaction scope. In the process, it is believed that sequential double isocyanide insertion, 6-exo-dig cyclization of alkyne, and addition of an imino group are involved.

Topics & Concepts

AlkyneChemistryPalladiumIsocyanideCatalysisScope (computer science)Combinatorial chemistryMedicinal chemistryOrganic chemistryComputer scienceProgramming languageCatalytic C–H Functionalization MethodsSynthesis and Characterization of PyrrolesCatalytic Alkyne Reactions