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Electrophilic Halogen Reagents-mediated Halogenation: Synthesis of Halogenated Dihydro-1,3-oxazine Derivatives

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Abstract

Halogenation of N-cinnamylbenzamides and N-[(2H-chromen-3-yl)methyl]benzamides using electrophilic halogen source was reported. Various halogenated dihydro-1,3-oxazine derivatives(45 examples) were synthesized in high to excellent yields(up to 98% yields), as well as halogenated dihydrochromeno-1,3-oxazine derivatives(56 examples, up to 96% yields). The properties of mild conditions, metal-free and high efficiency of the reaction made it a promising strategy in future applications for the construction of carbon-halogen(fluorine, F; chlorine, Cl; bromine, Br; iodine, I) bond and 1,3-oxazine derivatives.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (No.22108264).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Department of Pharmacy, College of Life Sciences, China Jiliang University, Hangzhou, 310018, P. R. China

    Liang Qi, Xueqing Wang & Yifeng Zhou

  2. School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, P. R. China

    Yuji Qin & Weiwei Zhu

  3. School of Basic Medical Science, Lanzhou University, Lanzhou, 730000, P. R. China

    Hongli Chai

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  1. Liang Qi
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  2. Yuji Qin
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Correspondence to Weiwei Zhu or Yifeng Zhou.

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40242_2022_2289_MOESM1_ESM.docx

Electrophilic Halogen Reagents-mediated Halo-heterocyclizations: Synthesis of Halogenated Dihydro-1,3-oxazine Derivatives

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Qi, L., Qin, Y., Wang, X. et al. Electrophilic Halogen Reagents-mediated Halogenation: Synthesis of Halogenated Dihydro-1,3-oxazine Derivatives. Chem. Res. Chin. Univ. 39, 933–947 (2023). https://doi.org/10.1007/s40242-022-2289-1

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