Development of Novel Sythesis and Molecular Design of Biologically Active Fluorine Compounds Using Electrode Electron-Transfer Reactions

生物活性氟化合物的直接转化法和分子转化法在安全性、选择性和有效性等方面有许多优点。从这一点出发，我们已经开发出非常有效的方法，通过阳极氧化作为关键步骤制备含氟β-内酰胺。1. 4-噻唑烷酮的高区域选择性阳极氧化单取代反应及其在单氟β-内酰胺合成中的应用：我们成功地进行了4-噻唑烷酮（1）在氟离子存在下的高效和区域选择性单取代反应。这是含硫杂环化合物阳极氧化的第一个成功实例。发现由氟化1衍生的砜的热分解以优异的产率提供单氟β-内酰胺。β-内酰胺类药物的区域选择性阳极单氧化：我们首次成功地进行了β-内酰胺类药物的阳极部分氧化。发现α-苯硫基β-内酰胺以优异的产率和高的电流效率被高度区域选择性地单氟化。我们已经证明，这种新的阳极法是上级比传统的化学方法。因此，我们几乎完成了我们的预定项目。

Methods of direct fluorination and mlecular conversion for the development of biologically active fluorine compounds have many roblems in the safety, selectivity, and efficiency. From this point, we have developed very efficient methods of the preparation of fluorine-containing beta-lactams via anodic fluorination as a key step.1. Highly Regioselective Anodic Monofluorination of 4-Thiazolidinones and Its Application to the Synthesis of Monofluoro beta-Lactams : We have successfully carried out efficient and reioselective monofluorination of 4-thazolidinones (1) by the anodc oxidation of 1 in the presence of fluoride ions. This is the first successful example of anodic fluorination of sulfur-containing heterocycles. It was found that thermolysis of the sulfones derived from fluorinated 1 provided monofluoro beta-lactams in excellent yields.2. Regoselective Anodic Monofluorination of beta-Lactams : We have successfully performed anodc partial fluorination of beta-lactams for the first time. It was found that alpha-phenylsulfenyl beta-lactams were monofluorinated highly regioselectively in excellent yields and with high current efficiencies. We have shown that this new anodic method is superior to conventional chemical methods. Thus, we ave almost achieved our roposed projects.