Yin Lu, Zhang Zhou, Huang Shuntao, Wang Zhuoyu, Huang Chao
Key Laboratory of Biomass Green Chemical Conversion of Yunnan Provincial Education Department, Yunnan Key Laboratory of Chiral Functional Substance Research and Application, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650504, PR China.
National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650504, PR China.
J Org Chem. 2024 Sep 20;89(18):13629-13640. doi: 10.1021/acs.joc.4c01827. Epub 2024 Sep 1.
A catalyst-free mild synthesis was reported to produce medium-ring oxazepane and oxazocine derivatives from aminomaleimides and -alkyl amines. The substrate and acidic additives were employed to cleave the C(sp)-N bond as a one-carbon synthon for C-C and C-O coupling, thus facilitating the [ + 1] cascade cyclization reaction, which enabled the construction of seven- and eight-membered ,-heterocycles at room temperature. The method exhibits abroad substrate scope and remarkable tolerance toward various functional groups (seven-membered 28 examples, eight-membered 8 examples, and activated -alkyl amine 12 examples) and utilization of natural products (2 examples).
据报道，一种无催化剂的温和合成方法可从氨基马来酰亚胺和烷基胺制备中环恶唑烷和恶唑嗪衍生物。利用底物和酸性添加剂裂解C(sp)-N键作为用于C-C和C-O偶联的一碳合成子，从而促进[+1]级联环化反应，该反应能够在室温下构建七元和八元的氮杂环。该方法具有广泛的底物范围，对各种官能团具有显著的耐受性（七元环28例，八元环8例，活化烷基胺12例）以及天然产物的应用（2例）。
