| Project/Area Number |
10555314
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| Research Category |
Grant-in-Aid for Scientific Research (B).
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| Allocation Type | Single-year Grants |
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| Section | 展開研究 |
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| Research Field |
有機工業化学
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| Research Institution | HOKKAIDO UNIVERSITY |
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Principal Investigator |
TOKUDA Masao Hokkaido Univ.Grad.School of Eng., Prof., 大学院・工学研究科, 教授 (80001296)
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| Co-Investigator(Kenkyū-buntansha) |
佐々木 皇美 通産省, 工業技術院北海道工業技術研究所・資源エネルギー基礎工学部, 技官(研究職)
SENBOKU Hisanori Hokkaido Univ.Grad.School of Eng., Inst., 大学院・工学研究科, 助手 (50241360)
ORITO Kazuhiko Hokkaido Univ.Grad.School of Eng., Asso.Prof., 大学院・工学研究科, 助教授 (20109482)
佐々木 〓美 通産省, 工技院・北海道工業技術・研究所資源エネルギー基礎工学部, 技官
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| Project Period (FY) |
1998 – 2000
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| Project Status |
Completed (Fiscal Year 2000)
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| Budget Amount *help |
¥10,800,000 (Direct Cost: ¥10,800,000)
Fiscal Year 2000: ¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1999: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1998: ¥4,000,000 (Direct Cost: ¥4,000,000)
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| Keywords | Anti-inflammatory Agent / Ibuprofen / Naproxen / Loxoprofen / Fixation of Carbon Dioxide / Electroorganic Synthesis / Carboxylation / Microwave Irradiation / インドプロフェン / シクロプロフェン / フルルビプロフェン / ハロゲン化ビニル / ビニルトリフラート |
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| Research Abstract |
1. Synthesis of Anti-inflammatory Agents and Their Precursors
(1)Electrochemical carboxylation of vinyl halides -2-Aryl-2-propenoic acids were prepared in high yields by electrolysis of the corresponding aryl-substituted vinyl bromides in DMF in the presence of atmospheric pressure of carbon dioxide with a platinum cathode and a magnesium anode. 2-Aryl-2-propenoic acids, precursors of various anti-inflammatory agents such as ibuprofen, naproxen, and ketoprofen, were actually prepared in high yields by using this electrochemical carboylation and can readily be transformed into anti-inflammatory active compounds by enantioselectiev hydrogenation.
(2)Electrochemical carboxylation of aryl methyl ketones -Similar electrochemical carboxylation of aryl methyl ketones gave 2-aryl-2-hydroxypropanoic acids, precursors of anti-inflammatory agents, in high yields. This method was found to be very useful for a synthesis of loxoprofen.
(3)Electrochemical carboxylation of substituted benzyl halides -Sim
… More
ilar electrochemical carboxylation of 1-aryl-1-haloethanes gave a racemic mixture of anti-inflammatory agents in high yields.
2. Use of Supercritical Carbon Dioxide in the Synthesis of Anti-inflammatory Agents
Electrochemical fixation of carbon dioxide to vinyl bromides, aryl methyl ketones, and benzylic halides took place efficiently to give various anti-inflammatory agents when supercritical carbon dioxide was used both as a reagent and-a reaction medium.
3. Synthesis of Useful Carboxylic Acids by Electrochemical Carboxylation
Electrochemical carboxylation of aryl-substituted vinyl triflates, aliphatic vinyl triflates, and phenyl-substituted alkenes gave the corresponding α, β-unsaturated acids, β-keto carboxylic acids, and 2-phenylsuccinic acids in high yields.
4. Highly Efficient and Stereoselective Synthesis of Vinyl Halides by Microwave-induced Reaction
Highly efficient and stereoselective synthesis of(E)-and(Z)-vinyl halides, which are starting compounds for a synthesis of anti-inflammatory agents, was achieved in a short reaction time(1-2 min)by using microwave-induced reaction. Less
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