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Synthesis and Biological Evaluation of Thiophene Derivatives containing a Silicon Atom

Research Project

Project/Area Number 07672295
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionScience University of Tokyo

Principal Investigator

HOSHINO Osamu  Science University of Tokyo, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (40084420)

Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 1996: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1995: ¥1,400,000 (Direct Cost: ¥1,400,000)
Keywordsvinylsilylmethylthiophene / silylated thiophene / (substituted methyl) silylmethylthiophene / MO calculation / PM3 method / intramolecular cyclization / Grignard reaction / biological evaluation / 2-ジクロロビニルシリルチオフェン誘導体 / 2-ジクロロビニルシリルフラン誘導体 / 3-ジクロロビニルシリルメチルチオフェン / 2-ヂメチルシリルチオフェン誘導体 / 2-クロロメチルジメチルシリルチオフェン誘導体
Research Abstract

(1) Synthesis of Vinylsilyl- and (Substituted methyl) silyl-methylthiophenes In 1995, it was found that vinylsilylmethylthiophenes were obtained by addition of thienylmethyl chlorides to a suspension of Mg and trichlorovinysilane in THF.In 1996, this method was developed to the synthesis of various vinylsilylmethylthiophene derivatives. Furthermore, chloromethylsilylmethylthiophenes were synthesized by the modified method, in which a mixture of thienylmethyl chlorides and chloro (chloromethyl) silane was added to a suspension Mg in THF.Chloromethylsilyl derivatives thus obtained were converted into the Grignard reagents in a usual manner, which were treated with dry ice or dialkyl carbonates to give the corresponding (substituted methyl) silylmethylthiophene derivatives in fair to good yield. Among them, the mass spectra of hydroxy -and alkoxycarbonylsilyl derivatives showed characteristic fragment peaks. Silylmethylthiophenes except dichlorosilylmethylthiophenes are stable at ambident … More temperature and all of them thus obtained are novel compounds.
(2) Attempts for Intramolecular Cyslization Intramolecular cyclization of vinylsilylmethylthiophenes under the conditions similar to those for vinylsilylmethylbenenes failed. In order to document this discrepancy in the cyclization, molecular orbital (MO) calculations of vinylsilylmethyl-benzenes and -thiophenes using PM3 method were done. The calculations suggested that in the transition state the over-lappings of the pi-orbital (HOMO) of the carbon atom at 2-position in thiophene and the pi-orbital (LUMO) of the terminal carbon atom of vinyl group are in anti-bonding. Although the cyclization of vinylsilylmethylthiophenes was unfruitful, a product, which was formed by the cyclization followed by the cleavage, was obtained by the cyclization of acetoxyethysilylmethylthiophene. The present findings can offer a novel information on the synthesis of heterocyclic compounds containing a silicon atom.
(3) Biological Evaluation This works are now in progress. Less

Report

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

    (26 results)

All Other

All Publications (26 results)

  • [Publications] Osamu Hoshino: "Reaction of 2-Silatetralins with Alkyl Halides and Ketones under Basic Conditions" Heterocycles. 40(2). 975-982 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Osamu Hoshino: "Synthesis of 6-Acyl-2,2-dimethyl-2-silatetralins" Heterocycles. 43(2). 381-388 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Osamu Hoshino: "Synthesis of Thiophene Derivatives bearing a Silicon Atom" Heterocycles. 44(1). 509-518 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Osamu Hoshino: "Synthesis 2-Siladecalin Derivatives" (発表予定).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Osamu Hoshino: "Synthesis and Reaction of 2-Silaoctalin Derivatives" (発表予定).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Osamu Hoshino: "A Comment on the Intramolecular Diels-Alder Reaction of Vinylsilylmethylthiophenes" (発表予定).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Osamu Hoshino: "Studies in Natural Products Chemistry,Vol.16 Stereoselective Synthesis(Part J)" Elsevier,Amsterdam, 757(503-546) (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Osamu Hoshino: "Isoquinolines Part 3" John Wiley & Sons,Inc.,New York, 552(225-543) (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Hoshino: "Reaction of 2-Silatetralins with Alkyl Halides and Ketones under Basic Conditions" Heterocycles. 40. 975-982 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Hoshino: "Synthesis of 6-Acyl-2,2-dimethyl-2-silatetralins" Heterocycles. 43. 381-388 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] O.Hoshino: "Synthesis of Thiophene Derivatives bearing a Silicon Atom" Heterocycles. 44. 509-518 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Osamu Hoshino: "Reaction of 2-Silatetralins with Alkyl Halides and Ketones under Basic Conditions" Heterocycles. 40(2). 975-982 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] Osamu Hoshino: "Synthesis of 6-Acyl-2,2-dimethyl-2-silatetralins" Heterocycles. 43(2). 381-388 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Osamu Hoshino: "Synthesis of Thiophene Derivatives bearing a Silicon Atom" Heterocylces. 44(1). 509-518 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Osamu Hoshino: "Synthesis of 2-Siladecalin Derivatives" (発表予定).

    • Related Report
      1996 Annual Research Report
  • [Publications] Osamu Hoshino: "Synthesis and Reaction of 2-Silaoctalin Derivatives" (発表予定).

    • Related Report
      1996 Annual Research Report
  • [Publications] Osamu Hoshino: "A Comment on the Intramolecular Diels-Alder Reaction of Vinylsilymethylthiophenes" (発表予定).

    • Related Report
      1996 Annual Research Report
  • [Publications] Osamu Hoshino: "Studies in Natural Products Chemistry,Vol.16 Stereoselective Synthesis (Part J)" Elsevier Amsterdam, 757(503-546) (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] Osamu Hoshino: "Isoquinolines Part 3" John Wiley ε Sons,Inc.,New York, 552(225-543) (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] Hiroshi Hara: "A Synthesis of 5-Silacyclotriveratrylenes" Heterocycles. 33(1). 43-46 (1992)

    • Related Report
      1995 Annual Research Report
  • [Publications] Osamu Hoshino: "Synthesis of 2-Silatetralin Derivatives bearing Ogygen Functional Groups" Heterocycles. 38(4). 883-896 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] Akihisa Hirokawa: "Radical Reaction of 1-(2-Bromoarylmethyl)-2-silatetralins: Formation of Polycyclic Organosilicon Compounds" Heterocycles. 38(5). 1103-1118 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] Osamu Hoshino: "Reaction of 2-Silatetralins with Alkyl Halides and Ketones under Basic Conditions" Heterocycles. 40(2). 975-982 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Osamu Hoshino: "Synthesis of 6-Acyl-2,2-dimethyl-2-silatetralins" Heterocycles. 43(2). 381-388 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Osamu Hoshino: "Synthesis of 2-Siladecahydronaphthalene Derivatives" 発表予定.

    • Related Report
      1995 Annual Research Report
  • [Publications] Osamu Hoshino: "Studies in Natural Products Chemistry, Vol. 16, Stereoselective Synthesis (Part J)" ELSEVIER-Amsterdam, 757(503-546) (1995)

    • Related Report
      1995 Annual Research Report

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

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