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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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | diazonaphthoquinones / diazo compounds / Rh / Pd / carbene / ジアゾキノン / ジアゾ化合物 / ナフトフラン / クロスカップリング / ジアゾナフトキノン / ベンゾナフトピラノン / ジアゾ移動反応 / グアニジノジアゾニウム塩 |
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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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Report
(4 results)
Research Products
(21 results)
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[Journal Article] Synthetic study of kosinostatin aglycone: Synthesis of BCDE rings using alkoxycarbonylmethylation of diazonaphthoquinone2014
Author(s)
Kitamura, M.; Kubo, K.; Yoshinaga, S.; Matsuzaki, H.; Ezaki, K.; Matsuura, T.; Matsuura, D.; Fukuzumi, N.; Araki, K.; Narasaki, M.
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Journal Title
Tetrahedron Lett.
Volume: 55
Issue: 23
Pages: 1653-1656
DOI
Related Report
Peer Reviewed / Acknowledgement Compliant
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