| 三组分串联反应合成苯并硫氮杂卓衍生物 |
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| 引用本文： | 张杰,吴庆国,贾纪萍,吴卓航,唐盈盈,耿梦囡,汤伟. 三组分串联反应合成苯并硫氮杂卓衍生物[J]. 化学试剂, 2022, 44(1): 153-159. DOI: 10.13822/j.cnki.hxsj.2022008524 |
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| 作者姓名： | 张杰 吴庆国 贾纪萍 吴卓航 唐盈盈 耿梦囡 汤伟 |
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| 作者单位： | 江苏农牧科技职业学院 动物药学院,江苏 泰州 225300 |
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| 基金项目： | 江苏省高校自然科学基金面上项目(21KJB150008)； |
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| 摘 要： | 以原位生成的芳基重氮盐为自由基源,在无过渡金属条件下,以单质硫作为硫源,利用碘化钾促进的2-(1H-吡咯-1-基)苯胺/单质硫/炔三组分自由基串联反应,经过自由基型的单质硫插入/加成/环化等过程,成功构建了20个苯并硫氮杂卓衍生物,通过1HNMR、13CNMR和HR-MS对产物的结构进行确证。反应产率为45%~73%,底物适用范围较广并具有良好的官能团兼容性。通过自由基捕获实验结合液质分析,推测了反应过程可能产生的中间体。
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| 关 键 词： | 单质硫 无过渡金属 三组分反应 自由基 苯并硫氮杂卓 |
Three-component Cascade Reaction to Synthesize Benzothiazepinones Derivatives |
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| ZHANG Jie,WU Qing-guo,JIA Ji-ping,WU Zhuo-hang,TANG Ying-ying,GENG Meng-nan,TANG Wei. Three-component Cascade Reaction to Synthesize Benzothiazepinones Derivatives[J]. Chemical Reagents, 2022, 44(1): 153-159. DOI: 10.13822/j.cnki.hxsj.2022008524 |
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| Authors: | ZHANG Jie WU Qing-guo JIA Ji-ping WU Zhuo-hang TANG Ying-ying GENG Meng-nan TANG Wei |
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| Affiliation: | (College of Animal Pharmacetical Sciences,Jiangsu Agri-animal Husbandry Vocational College,Taizhou 225300,China) |
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| Abstract: | Using aryldiazonium salt in-situ generated as radical source,an efficient KI promoted three-component radical series reaction of 1-(2-aminoaryl)pyrroles,elemental sulfur and alkyne for constructing of benzothiazepinones through radical insertion of sulfur,addition and cyclization under transition-metal-free conditions has been developed.Elemental sulfur acted as sulfur source.The structures of the corresponding products were characterized by 1HNMR,13CNMR and HR-MS.Twenty kinds of benzothiazepinones derivatives were obtained in 45%~73%yields with good functional group compatibility and the method had advantages of wide raw material sources.Through free radical capture experiment and LC-MS,the possible intermediate specie was speculated. |
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| Keywords: | elemental sulfur transition-metal-free three-component reaction radical benzothiazepinones |
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