Synthesis of 6/5/3-Fused Tricyclic Scaffolds via Multistep Cascade Cyclization of α-Aryl Vinylsulfoniums with <i>para</i>-Quinamines and <i>para</i>-Quinols
Zhen‐Hua Wang, Dong-Qun Huang, Ping Wang, Lei Yang, Yong You, Jian‐Qiang Zhao, Yan-Ping Zhang, Wei‐Cheng Yuan
Abstract
Herein, we present a straightforward approach to access hydroindoline-5-one-based 6/5/3-fused polycyclic ring structures through multistep cascade reactions involving α-aryl vinylsulfoniums and para -quinamines. The reactions proceed smoothly under mild conditions to deliver the desired products in generally good isolated yields. This protocol is also applicable to the cascade cycloaddition reactions of α-aryl vinylsulfoniums and para -quinols, effectively generating complex tricyclic scaffolds. In addition, the scale-up synthesis and further derivatizations demonstrate the potential synthetic application of the protocol.
Topics & Concepts
TricyclicChemistryArylCascadeCombinatorial chemistryStereochemistryOrganic chemistryAlkylChromatographySulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods