2016 Fiscal Year Final Research Report
Synthesis of poly-substituted aromatic compounds from diazonaphthoquinone
| Project/Area Number |
26410054
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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 | Kyushu Institute of Technology |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Keywords | diazonaphthoquinones / diazo compounds / Rh / Pd / carbene |
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| Outline of Final Research Achievements |
The diazo-transfer reactions of 2-azido-1,3-dimethylimidazolinium chlorides (ADMC) to naphthols proceeded smoothly to give corresponding diazonaphthoquinones in high yields. We developed several synthetic methods of poly-substituted arenes by metal-catalyzed reaction of diazonaphthoquinones. 3-Aryloxycarbonyldiazonaphthoquinones were transformed to β-phenylnaphthalene lactones through Rh-catalyzed intramolecular formal C-H insertion reaction. This lactone formation was efficiently applied to the formal total synthesis of pradimicinone. Naphthofurans were selectivity synthesized from diaozonaphthoquinones and terminal alkynes catalyzed by Cu and Pd reagents.
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| Free Research Field |
organic synthesis
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