Visible Light-Promoted Three-Component Reaction for the Synthesis of Pyrrolopyrazoles
Han‐Peng Pan, Shao‐Shuai Chen, Han Yang, Zhanhao Su, Yajie Chen, Mao-Bi Zhu, Ai‐Jun Ma, Xiang‐Zhi Zhang
Abstract
A visible light-enabled three-component cascade assembles pyrrolopyrazoles from arylalkynes, benzoquinones, and 5-aminopyrazole through a mechanistically validated carbonyl-alkyne metathesis/(3 + 2)-cycloaddition/1,2-aryl migration sequence. This protocol delivers pyrrolopyrazole heterocycles in up to 96% yield with excellent functional group tolerance. Preliminary biological screening identified promising antitumor activity in selected products, highlighting the potential value of this method. The proposed reaction mechanism is supported by control experiments.
Topics & Concepts
ChemistryComponent (thermodynamics)Visible spectrumCombinatorial chemistryPhotochemistryOptoelectronicsThermodynamicsPhysicsOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsCatalytic C–H Functionalization Methods