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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

2024Organic Letters14 citationsDOI

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
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 | Litcius