Development of Novel Sythesis and Molecular Design of Biologically Active Fluorine Compounds Using Electrode Electron-Transfer Reactions
| Project/Area Number |
04650765
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Tokyo Institute of Techology |
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Principal Investigator |
FUCHIGAMI Toshio Tokyo Institute of Technology, Interdisciplinary Graduate School of Science and Engineering Associate Professor, 大学院・総合理工学研究科, 助教授 (10016701)
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| Co-Investigator(Kenkyū-buntansha) |
昆野 昭則 東京工業大学, 大学院総合理工学研究科, 助手 (50205572)
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| Project Period (FY) |
1992 – 1993
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| Project Status |
Completed (Fiscal Year 1993)
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| Budget Amount *help |
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1993: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1992: ¥1,300,000 (Direct Cost: ¥1,300,000)
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| Keywords | Monofluoro beta-lactam / 4-Thiazolidinone / Biologically active compounds / Regioselectivity / Anodic oxidation / Organic electrochemistry / Fiuoroheterocycles / Chiral compounds / 部分フッ素化 / 陽極酸化 / 有機電気化学 / フッ素化合物 / モノフルオロβーラクタム |
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| Research Abstract |
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.
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Report
(3 results)
Research Products
(12 results)
