One‐Carbon Ring Expansion of Indoles and Pyrroles: A Straightforward Access to 3‐Fluorinated Quinolines and Pyridines
Huaixuan Guo, Shiqin Qiu, Peng Xu
Abstract
Abstract 3‐Fluorinated quinolines and pyridines are prevalent pharmacophores, yet their synthesis is often challenging. Herein, we demonstrate that dibromofluoromethane as bromofluorocarbene source enables the one‐carbon ring expansion of readily available indoles and pyrroles to structurally diverse 3‐fluorinated quinolines and pyridines. This straightforward protocol requires only a short reaction time of ten minutes and can be performed under air atmosphere. Preliminary investigations reveal that this strategy can also be applied to the synthesis of other valuable azines by using different 1,1‐dibromoalkanes as bromocarbene sources.
Topics & Concepts
Ring (chemistry)ChemistryPharmacophoreCombinatorial chemistryCarbon fibersOrganic chemistryStereochemistryMaterials scienceComposite numberComposite materialFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Biological Evaluation