4.4 Article

Synthesis of 4(3H)-Quinazolinones by Visible-Light-Induced 2-Benzylaminobenzamides

Journal

CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 41, Issue 8, Pages 3083-3088

Publisher

SCIENCE PRESS
DOI: 10.6023/cjoc202104047

Keywords

visible-light; 2-benzylaminobenzamides; 4(3H)-quinazolinones

Funding

  1. Science and Technology Commission of Shanghai Municipality [18JC1410801]
  2. Medical Engineering Cross Fund of Shanghai Jiao Tong University [YG2019QNA38]

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An environmentally benign protocol of visible-light-induced reaction has been developed for the effective synthesis of 4(3H)-quinazolinones from 2-benzylaminobenzamides. The reaction proceeds well under metal-free, photocatalyst-free and mediator-free conditions, providing the corresponding quinazolinones in good to high yields. Mechanism studies suggest that a radical pathway might be involved in the reaction.
An environmental benign protocol of visible-light-induced reaction has been developed. The methodology allows effective synthesis of 4(3H)-quinazolinones from 2-benzylaminobenzamides in simple and mild reaction conditions. Just irradiation with a blue LED light at room temperature, the reaction proceeds well to provide the corresponding quinazolinones in good to high yields under metal-free, photocatalyst-free and mediator-free conditions. This protocol is demonstrated by its wide substrate scope, good functional group tolerance, operationally simple, and gram-scale reaction. Mechanism studies suggest that a radical pathway might be involved in current reaction.

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