| Project/Area Number |
08672440
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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 | HEALTH SCIENCES UNIVERSITY OF HOKKAIDO |
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Principal Investigator |
MACHIDA Minoru HEALTH SCIENCES UNIVERSITY OF HOKKAIDO,FACULTY OF PHARMACEUTICAL SCIENCES,PROFESSOR, 薬学部, 教授 (70094844)
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| Co-Investigator(Kenkyū-buntansha) |
TAKECHI Haruko HEALTH SCIENCES UNIVERSITY OF HOKKAIDO,FACULTY OF PHARMACEUTICAL SCIENCES,ASSIST, 薬学部, 講師 (70094836)
ODA Kazuaki HEALTH SCIENCES UNIVERSITY OF HOKKAIDO,FACULTY OF PHARMACEUTICAL SCIENCES,ASSOCI, 薬学部, 助教授 (80094829)
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| Project Period (FY) |
1996 – 1997
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| Project Status |
Completed (Fiscal Year 1997)
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| Budget Amount *help |
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1997: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1996: ¥1,100,000 (Direct Cost: ¥1,100,000)
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| Keywords | photocyclization / arenecarbothioamide / benzannulation / heterocycles / furan / indolizidine / thiobarbiturate / fused pyrimidine / フラン / ベンズアレネーション / グルタルチオイミド / 複素環化合物 / アリデヒド |
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| Research Abstract |
As part of our continuing program to investigate photochemistry of the nitrogen-thiocarbonyl systems, the photoreactions of arenecarbothioamides with carbon-car0000bon double bond (alkene) systems were studied. In particular, furans as a cycloalkadiene analogue (paterno-Buchi acceptor) showed interesting photochemical behavior towards arenecarbothioamide to afford various heterocyclic compounds.
1.Photoreaction of arenecarbothioamides with 2-alkoxyfurans.
In a case of 2-trimethylsiloxyfuran, benzannulation reaction occurred in preference to aroylation, giving arene-fused methyl p-aminobenzoates, accompanied by small amounts of alpha-aryl-pyrroles or alpha-arylthiophenes.
2.Intermolecular photoreaction of thiobenzamide with aldehydes.
Phenanthroimidazole and 4,5-diphenylimidazole derivatives were obtained. This photoreaction would provide a new and convenient one step synthesis of phenanthro-imidazole derivatives.
3.Intramolecular photoreaction of mono- and dithioglutarimides having an alkenyl group in their N-side chain.
Bicyclic compounds, indolizidine and quinolizidine derivatives, were obtained.
4.Photoreaction of thiobarbiturates.
Intermolecular photoreaction of mono-, di-, and trithiobarbiturate with alkenes gave efficiently thietanes. Similarly, intramolecular photoreaction of thiobarbiturates having an alkenyl group in their N-side chain gave fused pyrimidine derivatives through photocyclization. In addition, photoreaction of mono- and dithiobarbiturate having a benzylic hydrogen at their N-side chain also gave fused pyrimidine derivatives through Norrish type II reaction.
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