2013 Fiscal Year Final Research Report
Development of the synthesis of heterocycle-fused naphthoquinones toward specific substrate for DT-diaphorase
| Project/Area Number |
24790116
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Drug development chemistry
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| Research Institution | Kinki University |
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Principal Investigator |
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| Project Period (FY) |
2012-04-01 – 2014-03-31
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| Keywords | 生物活性物質 / インドール / キノン / タンデム反応 |
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| Research Abstract |
A concise method for the synthesis of heterocycle-fused naphthoquinones such as 1H-benz[f]indole-4,9-dione was developed. This method employed Sonogashira coupling and tandem addition-elimination/intramolecular cyclization, and it enabled the preparation of versatile heterocycle-fused naphthoquinones from one substrate. However, introduction of C1 unit at 3-position was failed.
Alternatively, we developed direct methods for the synthesis of 3-substituted indoles from o-alkynylanilines by utilizing a copper-catalyzed tandem intramolecular cyclization/coupling reaction.
Moreover, we developed an efficient method for the transformation of indoles by utilizing a copper catalyst and molecular oxygen as the oxidant. The transformation involves a tandem oxidative process of 2-arylindoles. Our reaction afforded a variety of N-benzoyl anthranilic acids and benzoxazinones.
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