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0 202506007

DOI: https://doi.org/10.6023/cjoc202506007

REVIEW

Recent Advances on the Functionalization of Azlactones at Different Reactive Sites

  • Jiang Zhijie ,
  • Chen Jinxiu ,
  • Zhu XiaoFei ,
  • Deng Xinhao ,
  • Yan Qiongjiao ,
  • Wang Wei ,
  • Zhou Hui
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  • aCollege of Biological Food and Chemistry, Shaanxi Xueqian NormalUniversity, Xi'an 710100
    bDepartment of Chemistry, Central China Normal University, Wuhan 430079
    cPharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 43020
    dPingwu High School, Mianyang, 621000
†These authors contributed equally to this work.

Received date: 2025-07-15

  Revised date: 2025-08-19

  Online published: 2025-09-12

Supported by

Natural Science Foundation of Hubei Province (2025AFB675) and 2024 Shaanxi Higher Education Institutions Outstanding Young Talents Support Program (2025QJ-02(内)).

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Abstract

Azlactones constitute a crucial precursor for the preparation of α,α-disubstituted amino acids, N,O-acetal derivatives, many heterocyclic compounds, finding increasingly widespread applications in organic chemistry. Recent advances in functionalization of azlactone have enabled the synthesis of a large number of important organic compounds. Notably, asymmetric transformations of azlactone have facilitated the preparation of valuable chiral compounds, attracting growing interest among researchers in this field. Focusing on the multi-active-site nature of azlactone, this review classifies its participation in diverse organic reactions, including C-2, C-4, and C-5 functionalizations and multi-site cycloaddition reactions. Meanwhile, our research group has recently developed a novel method for the inβsitu formation of azlactones via the intramolecular cyclization of N-hydroxyphthalimide esters, which yields a various of chiral unnatural amino acids. This strategy complements existing azlactone functionalization reactions, thereby promoting the robust development of this field. Finally, the challenges and opportunities in this field are critically assessed, providing insights to direct future research and innovation.

Key words： azlactones; reactive site; functionalization; amino acids; asymmetric transformation

Cite this article

Jiang Zhijie , Chen Jinxiu , Zhu XiaoFei , Deng Xinhao , Yan Qiongjiao , Wang Wei , Zhou Hui . Recent Advances on the Functionalization of Azlactones at Different Reactive Sites[J]. Chinese Journal of Organic Chemistry, 0 : 202506007 . DOI: 10.6023/cjoc202506007

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