Synthesis of Condensed Heteroaromatics through Metalation of Ethynylaromatics
| Project/Area Number |
09672135
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Tohoku University |
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Principal Investigator |
SAKAMOTO Takao Faculty of Pharmaceutical Sciences, Tohoku University, Professor, 薬学部, 教授 (00006347)
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| Co-Investigator(Kenkyū-buntansha) |
KONDO Yoshinori Faculty of Pharmaceutical Sciences, Tohoku University, Associate Professor, 薬学部, 助教授 (90162122)
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| Project Period (FY) |
1997 – 1998
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| Project Status |
Completed (Fiscal Year 1998)
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| Budget Amount *help |
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 1998: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1997: ¥2,700,000 (Direct Cost: ¥2,700,000)
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| Keywords | ethynyl aromatics / metalation reaction / palladium catalyst / cross-coupling reaction / naphthyridines / indoles / carbolines / cyclization reaction / チエノピリジン |
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| Research Abstract |
Lithiation reaction of ethynylanilines obtained from the palladium-catalyzed crosscoupling reaction of N-(2-iodophenyl) carbamate with terminal acetylenes followed by substitution reaction with electrophiles and cyclization reaction gave 7-substituted indole derivatives. Using this method, synthesis of indoles with oxygen-bearing substituents at the benzene moiety was achieved. Lithiation reaction of bromopyridines and electro-philic substitution reaction with N,N-dimethylformamide gave o-bromopyridinecarbo-aldehydes which were cyclized to naphthyridines and their N-oxides. Lithiation reaction of 3-ethynylindoles prepared by the palladium-catalyzed reaction from the 3-iodoindoles with terminal acetylenes followed by substitution reaction with ethyl formate gave 2-formy derivatives, which were cyclized to beta-carbolines and their N-oxides.
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Report
(3 results)
Research Products
(6 results)
