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

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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.