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Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate
Molbank Pub Date : 2020-11-20 , DOI: 10.3390/m1167 Serigne Abdou Khadir Fall , Saïd Achamlale , Younas Aouine , Asmae Nakkabi , Hassane Faraj , Anouar Alami
Molbank Pub Date : 2020-11-20 , DOI: 10.3390/m1167 Serigne Abdou Khadir Fall , Saïd Achamlale , Younas Aouine , Asmae Nakkabi , Hassane Faraj , Anouar Alami
The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performed by 1D and 2D-NMR experiments, infrared spectroscopy, and elemental analysis.
中文翻译:
[(4-{(9H-咔唑-9-基)甲基} -1H-1,2,3-三唑-1-基)(苯甲酰胺基)甲基]二膦酸酯
合成标题化合物[(4-{(9H-咔唑-9-基)甲基} -1H-1,2,3-三唑-1-基)(苯甲酰胺基)甲基]膦酸二乙酯,收率高,收率高。通过α-叠氮基二乙基氨基甲基膦酸酯与杂环炔烃9-(prop-2-yn-1-yl)-9H-咔唑之间的1,3-偶极环加成反应实现区域选择性。通过“点击化学”的环化反应在水/乙醇溶剂混合物(50/50)中,在五水合硫酸铜和催化性抗坏血酸钠的存在下进行。通过1D和2D-NMR实验,红外光谱和元素分析对所得的1,4-区域异构体的结构进行表征。
更新日期:2020-11-20
中文翻译:
[(4-{(9H-咔唑-9-基)甲基} -1H-1,2,3-三唑-1-基)(苯甲酰胺基)甲基]二膦酸酯
合成标题化合物[(4-{(9H-咔唑-9-基)甲基} -1H-1,2,3-三唑-1-基)(苯甲酰胺基)甲基]膦酸二乙酯,收率高,收率高。通过α-叠氮基二乙基氨基甲基膦酸酯与杂环炔烃9-(prop-2-yn-1-yl)-9H-咔唑之间的1,3-偶极环加成反应实现区域选择性。通过“点击化学”的环化反应在水/乙醇溶剂混合物(50/50)中,在五水合硫酸铜和催化性抗坏血酸钠的存在下进行。通过1D和2D-NMR实验,红外光谱和元素分析对所得的1,4-区域异构体的结构进行表征。