Visible-Light-Induced Chemodivergent Synthesis of Tetracyclic Quinazolinones and 3-Iminoisoindoliones via the Substrate Control Strategy

Huang, Fang‐Ping; Qin, W.; Pan, Xin-Yao; Yang, Kun; Wang, Kai; Teng, Qing‐Hu

doi:10.1021/acs.joc.3c02501

articleThe Journal of Organic ChemistryMar 19, 2024Closed access

Visible-Light-Induced Chemodivergent Synthesis of Tetracyclic Quinazolinones and 3-Iminoisoindoliones via the Substrate Control Strategy

FHFang‐Ping Huang WQW. Qin XPXin-Yao Pan KYKun Yang KWKai Wang

Guilin University of Technology

PubMed

Indexed incrossrefpubmed

Abstract

A visible-light-induced chemodivergent synthesis of tetracyclic quinazolinones and 3-iminoisoindoliones has been developed. This chemodivergent reaction afforded two kinds of different products by substrate control. A detailed investigation of the reaction mechanism revealed that this consecutive photoinduced electron transfer (ConPET) cascade cyclization involved a radical process, and the aryl radical was the crucial intermediate. This method employed 4-DPAIPN as a photocatalyst and i-Pr2NEt as a sacrificial electron donor leading to metal-free conditions.

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Topics & keywords

Topics

Keywords

Chemistry
Substrate (aquarium)
Visible spectrum
Photoinduced electron transfer
Combinatorial chemistry
Electron transfer
Photocatalysis
Photochemistry

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