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Synthsis of Bioactive Heterocyclic Medium Ring Using Selective Photo-cycloaddition

Research Project

Project/Area Number 07651063
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKagoshima University

Principal Investigator

SHIMO Tetsuro  Kagoshima Univ. , Fac. of Eng. , Associate Professor, 工学部, 助教授 (80041565)

Co-Investigator(Kenkyū-buntansha) UEMURA Hisako  Kagoshima Univ. , Fac. of Eng. , Associate, 工学部, 助手 (20041535)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1996: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1995: ¥1,000,000 (Direct Cost: ¥1,000,000)
KeywordsPhotocycloaddition / 3 (2H) -Furanone / 2-Pyrone / Cyclobutane / Frontier MO / Excited Triplet State / Medium-ring Ether / Hetero Macrocycle
Research Abstract

Photo-[2+2] cycloaddition reactions of conjugated heterocycles were investigated and the addition selectivities were analyzed by MO method. We next utilyzed some adducts for synthesis of medium-ring ethers.
1.3 (2H) -Furanone has a simple skeleton composed of cyclopentenone system. To estimate the regio-and stereoselective [2+2] photocycloaddition reactions (cyclobutane-ring formation) of the triplet furanones with alkenes, the main factors were analyzed by PM 3-CI method.
2.2-Pyrone has also a simple skeleton composed of 2,4-cyclohexadienone system. To elucidate the peri-, site- and regoselectivities of [2+2] cycloadditions of the triplet 2-pyrones with alkenes, the main factors were also analyzed.
3. Di-2-pyrones tethered by methylene chain were synthesized and the intramolecular photo-dimerization reactions were investigated. The siteselective [2+2] cycloaddition depended on the methylene chain length. Intermolecular photoreactions of di-2-pyrones with di-alkenes were also carried out to give macrocyclic compounds which have two cyclobutane rings in each products.
4. Photo-[2+2] cycloadducts of 3 (2H) - furanones with acetylenes thermally gave seven-membered ring ethers.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (4 results)

All Other

All Publications (4 results)

  • [Publications] Tetsuro Shimo: "Intramolecular Photocycloadditions of 6,6'-Dimethvl-4,4'-polymethylenedioxydi-2-pyrones" Journal of Heterocyclic Chemistry. 32. 727-730 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Shimo, S.Ueda, T.Suishu, K.Somekawa: "Intramolecular Photocycloadditions of 6,6'-Dimethyl-4,4'-polymethlenedioxy-di-2-pyrones" J.Heterocyclic Chem. 32. 727-730 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tetsuro Shimo: "Intramolecular Photocycloadditions of 6,6'-Dimethyl-4,4'-polymethylenedioxydi-2-pyrones" Journal of Heterocyclic Chemistry. 32. 727-730 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] Tetsuro Shimo: "Intramolecular Photocycloadditions of 6,6′-Dimethyl-4,4′-polymethylenedioxydi-2-pyrones" Journal of Heterocyclic Chemistry. 32. 727-730 (1995)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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