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Development of one-pot synthetic method of five-membered heterocycles from olefins.

Research Project

Project/Area Number 02554022
Research Category

Grant-in-Aid for Developmental Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionHIROSHIMA UNIVERSITY

Principal Investigator

OTSUBO Tetsuo  Hiroshima Univ. Fac. of Prof., 工学部, 教授 (80029884)

Co-Investigator(Kenkyū-buntansha) ASO Yoshio  Hiroshima Univ. Fac. of Eng. Assit, 工学部, 助手 (60151065)
OGURA Fumio  Hiroshima Univ. Fac. of Eng. Prof, 工学部, 教授 (90028150)
Project Period (FY) 1990 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥6,000,000 (Direct Cost: ¥6,000,000)
Fiscal Year 1992: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1991: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1990: ¥5,300,000 (Direct Cost: ¥5,300,000)
KeywordsHeterocycle / Heteroatom / Organotellurium / Addition Reaction / Cyclization Reaction / 五員環複素環 / ヘテロ元素 / テルル化合物
Research Abstract

This project deals with development of useful reactions using organotellurium agents such as benzenetellurinyl acetate, trifluoroacetate, and trifluoromethanesulfonate. These benzenetellurinic mixed anhydrides can behave as a nucleophile towards olefins to effect oxytellurinylation in combination with alcohol, aminotellurinylation with ethyl carbamate, and amidotellurinylation with acetonitrile. These reactions are applicable to cyclofunctionalization of olefins to cyclic ethers or amines. In addition, it has turned out that the aminotellurinylation and amidotellurinylation at a high temperature are followed by an intramolecular cyclization with elimination of the introduced phenyltellurinyl group to give 2-oxazolidinones and 2-oxazolines, respectively. A similar reaction of acetylenes gives oxazoles via an addition. This provides a convenient one-pot synthesis of five-membered heterocycles from olefins and acetylenes.

Report

(4 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • 1990 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] T FUKUMOTO et al.: "Benzenetellurinic mixed anhydrides as mild oxidizing agents." Chemistry Letters. 2269-2272 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T ABE,et al.: "Oxygen-induced transmetallation of organoboranes with diphenyl ditelluride." Chemistry Letters. 1671-1674 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T OTSIBO,et al.,: "Novel organic syntheses using benzenetellurinic mixed anhydride." Asahigarasu Research Report,. 56. 89-94 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K SASAKI,et al.: "Nucleophilic reactions of acetals,alkyl sulfonates,and oxiranes with diibutylaluminium benzenetellurolate." Chemistry letters. 415-418 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T FUKUMOTO,et al.: "Stereoselective addition reactions of alkynes with benzenetellurinyl trifluoromethanesulfonate in acetonitrile:organotellurium-mediated one-pot synthesis of oxazoles from internal alkynes." Journal of the Chemical Society,Chemical communications. 1070-1072 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] F OGURA,et al.: "New synthetic reactions using some organotelluriums." Phosphorus,Sulfur,and Silicon. 67. 223-238 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fukumoto et al: "Benzenetellurinic mixed anhydrides as mild oxidizing agents." Chem. Lett.2269-2272 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Abe et al.: "Oxygen-induced trans-metallation of organoboranes with diphenyl ditelluride." Chem. Lett.1671-1674 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Otsubo et al.: "Novel organic syntheses using benzenetellurinic mixed anhydride." Asahigarasu Research Report. Vol.56. 89-94 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Sasaki et al.: "Nucleophilic reactions of acetals, alkyl sulfonates, and oxiranes with dibutylaluminium benzenetellurolate." Chem. Lett.415-418 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fukumoto et al.: "Stereoselective addition reactions of alkynes with benzenetellurinyl trifluoromethane-sulfonate in acetonitrile: Organo-tellurium-mediated one-pot synthesis of oxazoles from internal alkynes." J. Chem. Soc., Chem. Commun.1070-1072 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] F.Ogura et al.: "New synthetic reactions using some organotelluriums." Phosphorus, Sulfur, and Silicon. Vol.67. 223-238 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fukumoto et al.: "Stereoselective addition reactions of alkynes with benzenetellurinyl trifluoromethanesulfonate in acetonitrile:organotellurium-mediated one-pot synthesis of oxazoles from internal alkynes." Journal of the Chemical Society,Chemical Communications.1070-1072 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] F.Ogura et al.: "New synthetic reactions using some organotelluriums" Phosphorus,Sulfur,and Silicon. 67. 223-238 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Sasaki et al.: "Nucleophilic reactions of acatals,alkyl sulfonates,and oxiranes with diisobutylaluminium benzenetellurolate." Chemistry Letters. 415-418 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] T.Abe et al.: "OxygenーInduced Transmetallation of Organoboranes with Diphenyl Ditelluride" Chemistry Letters. 1671-1674 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Fukumoto et al.: "Benzenetellurinic Mixed Anhydrides as Mild Oxidizing Agents." Chemistry Letters. 2269-2272 (1990)

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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