| Project/Area Number |
22790027
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kobe Pharmaceutical University |
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Principal Investigator |
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| Project Period (FY) |
2010 – 2011
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| Project Status |
Completed (Fiscal Year 2011)
|
| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2010: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | 複素環 / 環化反応 / ヨウ素 / 芳香化 / ピラゾール / イソキサゾール / ピロール / 酸化 / プロリン / ヨード環化反応 |
|---|
| Research Abstract |
Iodocyclization is one of the most attractive methods for the construction of functionalized molecular architecture. This reaction can create not only the ring skeleton but also the iodo functionality for further transformation. In addition, iodinating reagents are relatively inexpensive and are ideal for achieving environmentally friendly reactions. I have developed a new method of iodocyclization based on reagent-controlled oxidative aromatization. This strategy takes advantage of the dual nature of iodine as both an iodinating and an oxidizing agent. The revealed approach enabled "product switch"and enhanced the flexibility of the synthetic pathway toward pyrazoles, isoxazoles, and pyrolles. In addition, the iodo moiety of the cyclized product could create further diversity. The utility of this methodology was demonstrated in the synthesis of valdecoxib and its 2, 5-dihydro analogs. During the elaborating process, fortunately, an efficient approach to benzoxazoles via tandem migration-carboalkoxylation of o-isocyanophenyl acetals has been developed.
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