One-pot preparation of heterocycles with diaryliodoniums under transition-metal-free conditions
| Project/Area Number |
15K05418
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Chiba University |
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Principal Investigator |
Togo Hideo 千葉大学, 大学院理学研究院, 教授 (60217461)
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| Project Period (FY) |
2015-04-01 – 2018-03-31
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| Project Status |
Completed (Fiscal Year 2017)
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| Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
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| Keywords | ジアリールヨードニウム / クマリン / キノリン / クロメン / １工程合成反応 / 環化反応 / ジアリールヨードニウム塩 / ラジカル反応 / O-アリール化反応 / 3-アリールプロピン酸 / N-(プロパルギル)トシルアミド / キノリン誘導体 / ヨード環化反応 / NIS / N-アリール化反応 / ヨウ素 / ワンポット合成 |
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| Outline of Final Research Achievements |
Treatment of 3-aryl-2-propyn-1-ols with diaryliodonium salts, followed by the reaction with NIS and BF3 gave 4-aryl-3-iodochromenes, treatment of N-tosyl 3-aryl-2-propynyl-1-amines with diaryliodonium salts, followed by the reaction with NIS and BF3 gave 4-aryl-3-iodoquinolines, and treatment of 3-aryl-2-propynoic acids with diaryliodonium salts, followed by the reaction with TBAB and Na2S2O8 gave 4-aryl-3-bromocoumarins in good yields, respectively. Those preparation methods are one-pot reactions of chromene, quinoline, and coumarin units. Moreover, those obtained 4-aryl-3-iodochromenes, 4-aryl-3-iodoquinolines, and 4-aryl-3-bromocoumarins were transformed to various 4-arylcoumarine derivatives and 4-arylquinoline derivatives by their oxidation, reduction, and coupling reaction with Pd complex.
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Report
(4 results)
Research Products
(34 results)
