分子碘催化4-羟基香豆素3位烷基化反应研究
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摘要
分子碘作为一种重要的有机化学反应催化剂,已经在有机化学及药物化学等领域有着广泛应用。分子碘作为一种特殊的lewis酸,它具有一般质子酸和重金属盐所不具有的催化特性,例如它具有高选择性、高收率、反应条件温和、操作简单、反应时间短等优点。本论文在第一部分综述了分子碘催化的有机化学反应进展。
本文研究了分子碘催化的4-羟基香豆素3位烷基化反应。通过条件优化我们发现在50℃下,以硝基甲烷为溶剂,4-羟基香豆素和各种取代苄醇能顺利发生烷基化反应,以中等到优秀的收率合成了相应的3位烷基化的4-羟基香豆素类衍生物产物;我们应用旋光纯的二芳基炔丙醇对反应机理进行了探索,提出了基于碳正离子中间体的可能的反应机理;我们将该反应应用于药物合成研究中,以44%的产率合成了抗凝血药物Coumatetraly;我们还利用这个反应,发展了一种两步一锅法合成多取代香豆素并吡喃类化合物的新方法。
Molecular iodine-catalyzed reactions have been used widely in organic chemistry and pharmaceutical chemistry as one of the most important catalysts in organic synthesis. Molecular iodine is kind of a special Lewis acid, which has distinctive catalytic properties comparing with usual protonic acids and slats of heavy metals. For example, iodine-catalyzed reactions are in high selectivity and yield in shorter reaction time. Moreover, the reaction can proceed in mild condition with simple operation. In this thesis, new development of molecular iodine-catalyzed reaction in organic chemistry has been summarized.
In this thesis, molecular iodine-catalyzed C3-alkylation of 4-hydroxycoumarins is reported. Corresponding C3-alkylated 4-hydroxycoumarin derivatives are obtained in good to excellent yields in optimized condition, by the alkylation reaction of 4-hydroxycoumarins with secondary benzyl alcohols at 50℃, using MeNO_2 as the solvent. We also use enantiomeric pure diaryl-propargyl alcohol in this method to probe the reaction mechanism of this I_2-catalyzed alkylation reaction. A possible mechanism based on carbonium ion intermediate is proposed. Applying this reaction condition in drug synthesis, anticoagulated blood drug coumatetraly is obtained in 44% yield. By using this reaction as the key step, multi-substituted pyranocoumarins can easily be synthesized in a new one-pot procedure.
本文研究了分子碘催化的4-羟基香豆素3位烷基化反应。通过条件优化我们发现在50℃下,以硝基甲烷为溶剂,4-羟基香豆素和各种取代苄醇能顺利发生烷基化反应,以中等到优秀的收率合成了相应的3位烷基化的4-羟基香豆素类衍生物产物;我们应用旋光纯的二芳基炔丙醇对反应机理进行了探索,提出了基于碳正离子中间体的可能的反应机理;我们将该反应应用于药物合成研究中,以44%的产率合成了抗凝血药物Coumatetraly;我们还利用这个反应,发展了一种两步一锅法合成多取代香豆素并吡喃类化合物的新方法。
Molecular iodine-catalyzed reactions have been used widely in organic chemistry and pharmaceutical chemistry as one of the most important catalysts in organic synthesis. Molecular iodine is kind of a special Lewis acid, which has distinctive catalytic properties comparing with usual protonic acids and slats of heavy metals. For example, iodine-catalyzed reactions are in high selectivity and yield in shorter reaction time. Moreover, the reaction can proceed in mild condition with simple operation. In this thesis, new development of molecular iodine-catalyzed reaction in organic chemistry has been summarized.
In this thesis, molecular iodine-catalyzed C3-alkylation of 4-hydroxycoumarins is reported. Corresponding C3-alkylated 4-hydroxycoumarin derivatives are obtained in good to excellent yields in optimized condition, by the alkylation reaction of 4-hydroxycoumarins with secondary benzyl alcohols at 50℃, using MeNO_2 as the solvent. We also use enantiomeric pure diaryl-propargyl alcohol in this method to probe the reaction mechanism of this I_2-catalyzed alkylation reaction. A possible mechanism based on carbonium ion intermediate is proposed. Applying this reaction condition in drug synthesis, anticoagulated blood drug coumatetraly is obtained in 44% yield. By using this reaction as the key step, multi-substituted pyranocoumarins can easily be synthesized in a new one-pot procedure.
引文
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