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PHOTOCHEMICAL SYNTHESES OF HETEROCYCLIC COMPOUNDS.

Research Project

Project/Area Number 06672107
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
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) ODA Kazuaki  HEALTH SCIENCES UNIVERSITY OF HOKKAIDO,FACULTY OF PHARMACEUTICAL SCIENCES,INSTRU, 薬学部, 助手 (80094829)
TAKECHI Haruko  HEALTH SCIENCES UNIVERSITY OF HOKKAIDO,FACULTY OF PHARMACEUTICAL SCIENCES,ASSIST, 薬学部, 講師 (70094836)
Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1995: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1994: ¥900,000 (Direct Cost: ¥900,000)
Keywordsphotoreaction / arenecarbothioamide / benzannulation / thietane / furan / photocyclization / thiobarbiturate / heterocycles / ベンゼン環形成反応 / 四環縮合型インドール誘導体 / チオバルビツレート誘導体
Research Abstract

Photoreaction of arenecarbothioamides with substituted furans.
As part of our continuing program to investigate photochemistry of the nitrogen-thiocarbonyl systems, the photoreactions of arenecarbothioamides with carbon-carbon 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. In the case of 5-membered heteroaromatics (furan, thiophene, or 1-phenylsulfonylpyrrole), arenecarbothioamides gave regioselectively the corresponding 3-aroyl derivatives in good yields as major reaction. But in a case of 2-alkoxyfuran, henzannulation reaction occurred in preference to aroylation, giving benzo-fused heteroaromatics such as benzofuran, benzothiophene, isoquinoline, and quinoline, In photoreaction of thiobenzamide with certain furans, both transformation of furans to pyrroles and benzannulation occurred in preference to benzoylation.
In photoreaction of thiobenzamide with 2-vinylfuran analogues, tetracyclic indole derivative was obtained. This photoreaction would provide a new and convenient single-step convergent annulation approach for the construction of a multicyclic indole system.
(2) Photoreaction of thiobarbiturates.
Intermolecular photoreaction of mono-, di-, and tri-thiobarbiturate 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.

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] K.Oda, H.Tsujita, K.Ohno, and M.Machida: "Photochemistry of the nitrogen-thiocarbonyl systems. Part. 24. Photoreactions of thiobenzemide with various substituted furans : regioselective β-benzoylation and transformation of furans to other aromatic compounds." J.Cgem. Soc., Perkin Trans. 1. 2931-2935 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Takechi and M.Machida: "Intramolecular photoreaction of thiobarbiturates with an alkenyl group in their N-side chain. Regioselective synthesis of fused pyrimidine derivatives through photocycloaddition of mono-and di-thiobarbiturates." Heterocycles. 42. 117-120 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K.Oda, H.Tsujita, M.Sakai, and M.Machida: "Photoreaction of thiobenzamide with 2-vinylfuran analogues. Facile synthesis of tetracyclic indole system." Heterocycles. 42. 121-124 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K.Oda, R.Hiratsuka, and M,Machida: "The regioselective photoinduced aroylation at the 3-position of pyrrole derivatives." Heterocycles. 43. 463-470 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kazuaki Oda and Minoru Machida: "Benzannulation of heteroaromatics by photoreaction of arenecarbo-thioamides with 2-methoxyfuran" J.Chem.Soc., Chem.Commun.12. 1477-1478 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kazuaki Oda, Hisao Tsujita, Kosei Ohno, and Minoru Machida: "Photochemistry of the nitrogen-thiocarbonyl systems. Part.24. Photoreactions of thiobenzamide with various substituted furans : regioselective beta-benzoylation and transformation of furans to other aromatic compounds" J.Chem.Soc., Perkin Trans.1.(11). 2931-2935 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Haruko Takechi and Minoru Machida: "Intramolecular photoreaction of thiobarbiturates with an alkenyl group in their N-side chain. Regio-selective synthesis of fused pyrimidine derivatives through photocycloaddition of mono- and di-thio-barbiturates" Heterocycles. 42 (1). 117-120 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kazuaki Oda, Hisao Tsujita, Masayuki Sakai, and Minoru Machida: "Photoreaction of thiobenzamide with 2-vinylfuran analogues. Facile synthesis of tetra-cyclic indole system" Heterocycles. 42 (1). 121-124 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kazuaki Oda, Rin Hiratsuka, and Minoru Machida: "The regioselective photoinduced aroylation at the 3-position of pyrrole derivatives" Heterocycles. 43 (2). 463-470 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kazuaki Oda: "Photoreactions of thiobenzamide with various substituted furans." J. Chem. Soc. Perkin Trans. 1.2931-2935 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Haruko Takechi: "Intramolecular photoreaction of thiobarbiturates with an alkenyl group in their N-side chain." Heterocycles.42. 117-120 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Kazuaki Oda: "Photoreaction of thiobenzamide with 2-vinylfuran analogues." Heterocycles.42. 121-124 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Kazuaki Oda: "The regioselective photoinduced aroylation at the 3-position of pyrrole derivatives." Heterocycles.43. 463-470 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] K.Oda,M.Machida: "Benzannulation of Heteroaromatics by Photoreaction of Arenecarbothioamides with 2-Methoxyfuran" J.Chem.Soc.,Chem.Commun.1477-1478 (1994)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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