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Visible-light driven synthesis of polycyclic benzo[d][1,3]oxazocine from 2-aminochalcone

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Abstract

Herein, we report a tandem cycloisomerization/nucleophilic addition/cyclization of 2-amino chalcone with bifunctional nucleophiles driven by visible light. This cascade process is realized by the irradiation of a blue LED at room temperature, which provides a concise route to structurally diverse benzo[d][1,3]oxazocine scaffolds. Mechanistic studies show that the reaction is initiated with the E to Z isomerization of a C–C double bond upon the irradiation of visible light, followed by cyclization/rearomatization to generate a transient quinolinium intermediate, which is trapped by the nucleophile and cyclized to produce the polycyclic benzo[d][1,3]oxazocine.

Graphical abstract: Visible-light driven synthesis of polycyclic benzo[d][1,3]oxazocine from 2-aminochalcone

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Article information


Submitted
03 Apr 2020
Accepted
09 May 2020
First published
13 May 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Visible-light driven synthesis of polycyclic benzo[d][1,3]oxazocine from 2-aminochalcone

Y. Gao, Y. Hou, L. Zhu, J. Chen, R. Li, S. Zhang, Y. He and W. Xie, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02416C

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