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SYNTHESES OF HETEROCYCLIC COMPOUNDS THROUGH PHOTOREACTION OF THIOCARBONYL SYSTEMS.

Research Project

Project/Area Number 08672440
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionHEALTH SCIENCES UNIVERSITY OF HOKKAIDO

Principal Investigator

MACHIDA Minoru  HEALTH SCIENCES UNIVERSITY OF HOKKAIDO,FACULTY OF PHARMACEUTICAL SCIENCES,PROFESSOR, 薬学部, 教授 (70094844)

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)
Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
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)
Keywordsphotocyclization / 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
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.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Haruko Takechi: "Photoreactions of thiobarbiturates.Intermolecular cycloaddition with alkenes and ring contraction reaction of trithiobarbiturate." Chem. Pharm. Bull.,. 45(1). 1-7 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kazuaki Oda: "Photoreaction of benzenecarbothioamide with aldehydes. Facile synthesis of tetracyclic imidazoles." Synth. Commun.,. 27(7). 1183-1189 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kazuaki Oda: "Intermolecular photoaddition reaction of arenecarbothioamides to 2-methoxy-and 2-trimethylsiloxy furans. Facile synthesis of arene-fused aminobenzoates by novel photoinduced benzannulation." Chem.Pharm.Bull.,. 45(4). (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kazuaki Oda: "Intermolecular photoaddition reaction of arenecarbothioamides to 2-methoxy-and 2-trimethylsiloxy furans. Facile synthesis of arene-fused aminobenzoates by novel photoinduced benzannulation." Chem.Pharm.Bull.,. 45(4). (1997)584-589

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Haruko Takechi and Minoru Machida: "Photoreaction of thiobarbiturates. Intermolecular cycloaddition with alkenes and ring contraction reaction of trithiobarbiturate." Chem.Pharm Bull.45(1). 1-7 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kazuaki Oda, Masayuki Sakai, Hisao Tusjita, and Minoru Machida: "Photoreaction of benzenecarbo-thioamide with aldehydes. Facile synthesis of tetracyclic imidazoles" Synthetic Commun.27(7). 1183-1189 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kazuaki Oda, Masayuki Sakai, and Minoru Machida: "Intermolecular photoaddition reaction of arenecarbothioamides to 2-methoxy- and 2-trimethyl-siloxyfurans. Facile synthesis of arene-fused aminobenzoates by novel photoinduced benzannulation." Chem.Pharm Bull.45(4). 584-589 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Haruko Takechi: "Photoreactions of thiobarbiturates. Intermolecular cycloaddition with alkenes and ring contraction raction of trithiobarbiturate" Chemi.Pharm.Bull.,. 45 (1). 1-7 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kazuaki Oda: "Photoreaction of benzenecarbothioamide with aldehydes. Facile synthesis of tetracyclic imidazoles" Synth.Commun.,. 27 (7). 1183-1189 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kazuaki Oda: "Intermolecular photoaddition raction of arenecarbothioamides to 2-methoxy-and 2-trimethylsiloxy furans. Facile synthesis of arene-fused aminobenzoates by novel photoinduced benzannulation" Chem.Pharm.Bull.,. 45 (4). 584-589 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Haruko Takechi: "Photoreactions of thiobarbiturates. Intermolecular cycloaddition with alkenes and ring contraction reaction of trithiobarbiturate." Chem.Pharm.Bull.45(1). 1-7 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kazuaki Oda: "Photoreaction of benzenecarbothioamide with aldehydes. Facile synthesis of tetracyclic imidazoles." Synth.Commun.(In press). (1997)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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