Fluorination based on addition of molecular fluorine to conjugated enones
| Project/Area Number |
09672133
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | University of Shizuoka (1998)
Tohoku University (1997) |
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Principal Investigator |
SATO Masayuki University of Shizuoka, School of Pharmaceutical Sciences, Professor, 薬学部, 教授 (80004654)
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| Project Period (FY) |
1997 – 1998
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| Project Status |
Completed (Fiscal Year 1998)
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| Budget Amount *help |
¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1998: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1997: ¥2,300,000 (Direct Cost: ¥2,300,000)
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| Keywords | molecular fluorine / fluorination / α-fluoro carbonyl compound / γ-fluoro-β-ketoamide / 3-fluoro-2-quinolone / 3-fluoro-2-pyrone / 位置選択的フッ素化 / 含フッ素有機化合物 / α-フルオロケトン / ビシナ-ルジフルオロ化合物 / 5,6-ジフルオロウラシル / 位置選択的フッ素導入法 |
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| Research Abstract |
Introduction of fluorine atoms in specific site of molecules is very important task from both chemical and pharmaceutical points of view. Though molecular fluorine is the most economical as the electrophilic fluorinating reagent, it is normally regarded as being too reactive for site-specific fluorination. We studied efficient fluorination of organic molecules based on addition of molecular fluorine to conjugated enones. We found that 4-methoxy- or 4-chloro- 2-pyrones are selectively fluorinated at the 3- or 5-position by molecular fluorine at a low temperature. We also found that fluorination of α-hydroxymethylene carbonyl compounds affords a-fluoro carbonyl compounds in high yields. By this fluorination method, 3-fluoro-2-quinolones are also synthesized. 3-Fluoro-2-quinolones are alternatively synthesized cyclization of α-fluoroacetoasetanilides obtained by fluorination of acetoasetanilides with molecular fluorine. Reaction of diketene with molecular fluorine followed by treatment of the resulting fluoride with anilines produced γ-fluoroacetoasetanilides, which on cyclization afforded 4-fluoromethyl- 2-quinolones.
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Report
(3 results)
Research Products
(3 results)
