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April 24, 2026European Journal of Organic Chemistry0 citations

Visible‐Light‐Catalyzed Ring‐Opening Halogenation of Spiro‐Dihydroquinazolinones Using Perhalogenated Methanes as Halogen Sources

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HYHao YanTWTao WangJZJin-Yang Zhan

Key Points

  • This research aims to explore a visible-light-catalyzed method for brominating and chlorinating specific compounds.
  • Used visible-light to catalyze halogenation reactions.
  • Utilized perhalogenated methanes as halogen sources.
  • Investigated the outcomes of different substitutions on quinazolin-4(3H)-ones.
  • Achieved moderate yields of bromoalkyl and chloroalkyl-substituted compounds.
  • Reported functional-group tolerance during the reactions.
  • Proposed a radical mechanism involving nitrogen-centered radicals.

Abstract

Visible‐light‐catalyzed aromatization‐driven deconstructive bromination and chlorination of spiro‐dihydroquinazolinones are described, with perhalogenated methanes serving as halogenating agents. A series of remotely and site‐specifically bromoalkyl‐ and chloroalkyl‐substituted quinazolin‐4(3H)‐ones were obtained with moderate yields and functional‐group tolerance. A radical pathway involving nitrogen‐centered‐radical‐induced C─C bond cleavage and carbon–halogen bond formation is proposed for this transformation.

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Cite This Study

Yan et al. (2026) studied this question.

synapsesocial.com/papers/69eb08ef553a5433e34b3a24https://doi.org/10.1002/ejoc.202501240
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