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Updated: Jan 5, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Intermolecular Hetero-Diels-Alder Reactions of Photogenerated aza-ortho-Quinone Methides with Aldehydes
Dong Liang1, Li Rao1, Cong Xiao1
1CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides & Chemical Biology Ministry of Education, College of Chemistry , Central China Normal University , 152 Luoyu Road , Wuhan , Hubei 430079 , China.
Abstract:
A visible-light-driven, perfluoroalkyl radical-mediated strategy for in situ formation of aza-o-QMs from readily available precursors is reported. Combination of this method with a Brønsted base thus enables an efficient and highly diastereoselective HDA reaction between such photogenerated aza-o-QMs and π-electron-poor systems, aldehydes, providing high yielding and rapid access to valuable, diversely substituted dihydrobenzoxazines. DFT calculation elucidated the origins of stereochemistry of the products and disclosed the concerted property of the process.
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