Development of novel synthetic reactions based on mutual cooperation of nitrogen-oxygen bonds and multiple bonds
| Project/Area Number |
26460024
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Multi-year Fund |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Osaka City University (2016)
Kobe Pharmaceutical University (2014-2015) |
|---|
Principal Investigator |
MIYATA Okiko 大阪市立大学, 大学院理学研究科, 客員教授 (90102110)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
品田 哲郎 大阪市立大学, 大学院理学研究科, 教授 (30271513)
|
|---|
| Co-Investigator(Renkei-kenkyūsha) |
UEDA Masafumi 神戸薬科大学, 薬学部, 准教授 (00340935)
MIYOSHI Tetsuya 神戸薬科大学, 薬学部, 助教 (10549992)
|
|---|
| Project Period (FY) |
2014-04-01 – 2017-03-31
|
| Project Status |
Completed (Fiscal Year 2016)
|
| Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2016: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
|
|---|
| Keywords | アルコキシアミン / アルコキシアアミド / オキシムエーテル / 極性転換反応 / ベンゾフラン / インドール / イソキサゾール / ケトン / ヒドロキシアミン / シグマトロピー転位 / 付加反応 / 連続反応 / ビニル化 / イソキサゾリジン / ヒドラゾン / カルボニル / アミン / 求核付加反応 / アルデヒド / チオフェン / フラン |
|---|
| Outline of Final Research Achievements |
Aiming to the development of useful methods for the synthesis of biologically active compounds, we have developed new synthetic reactions in which functional groups and multiple bonds mutually cooperate. Alkoxyamines, alkoxyamides, and oxime ethers having nitrogen and oxygen bonds were selected as substrates in this study. As a result, various new carbon-carbon forming reactions featured by the polarity inversion of carbonyl functionality and unprecedented cascade reactions were developed. Treatment of N-alkoxyenamines with triarylaluminum reagents afforded alfa-arylcarbonyls. Alkoxyamides with an alkenyl or alkynyl group underwent cyclization-rearrangement reaction to give isoxazole derivatives. Oxime ethers enabled to be converted to substituted benzofuropyrroles by triethylborane-mediated radical addition-rearrangement-cyclization-lactamization. Under the same conditions, hydrazones were transformed to indoleacetic acid derivatives.
|
Report
(4 results)
Research Products
(29 results)
