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Preparation, Structure and Reactions of Novel Tellurium-Containing Heterocycles

Research Project

Project/Area Number 12672073
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionHokuriku University

Principal Investigator

SASHIDA Haruki  Hokuriku University, Faculty of Pharmaceutical Sciences, Lecturer, 薬学部, 助教授 (70102746)

Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 2001: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2000: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordstellurium / 1-benzotellurepine / 1-benzotelluropyrylium Salt / 2-benzotelluropyrylium Salt / tellurochromen-4-one / tellurochromene / isotellurochromene / Te-Li exchange / 1-ペンゾセレノピリリウム塩 / イソセレノクロメン / 2-ベンゾセレノピリリウム塩 / 1-ベンゾスタネピン / 1-ベンゾスチベピン / 1-ベンゾボレピン / 1-ベンゾシレピン / 1-ベンゾセレノピリリウム塩 / セレノクロメン
Research Abstract

1. The treatment of 1-benzotellurepines, novel seven-membered heterocycles, with t-BuLi followed by addition of a metal reagent (Cl_2SnBu_2, Cl_2SbPh and Cl_2SiMe_2) afforded the corresponding 1-benzostannepines, 1-benzostibepines and 1-benzosilepines, respectively, in one pot via the tellurium-lithium exchange.
2. The 1-benzostannepines, which were prepared from (Z)-1-(o-bromophenyl) but-1-ene-3-ynes, were easily converted into the 1-benzostibepines and the 1-benzoborepines by tin-antimony and tin-boron exchange reactions in moderate to good yields, respectively.
3. The general preparation of the unsubstituted and 2-substituted 1-benzoselenopyrylium salts from the selenochromen-4-ones via the selenochlomenes is investigated.
4. The reactions of the stable 1-benzoselenopyrylium salts with several nucleophiles and also LiAlH_4 reduction are described ; comparison of the behavior of 1-benzotelluropyrylium salts is made.
5. The treatment of the 1-benzoselenopyrylium salts with an alkyl(phenyl … More )magnesium halide resulted in nucleophilic addition at the C-4 position to give the corresponding 2,4-disubstituted 4H-selenochromenes in good yields, respectively. The obtained selenochromenes were men easily converted into the 2,4-disubstituted 1-benzoselenopyrylium salts.
6. The treatment of the tellurochromen-4-ones with several Grignard reagents gave the 4-substituted 4-hydroxy-4H-tellurochromenes in good yields, respectively. The obtained compounds were readily transformed into the 2,4-disubstituted 1-benzotelluropyrylium salts.
7. The regioselective and stereospecific intramolecular ring closure reactions of o-ethynylbenzyl tellurols and o-ethynylbenzyl selenols, which were readily. generated by the reaction of the o-ethynylbenzyl bromides with sodium hydrogen telluride (NaHTe) or sodium hydrogen selenide (NaHSe), produced the isotellurochromenes and isoselenochromenes together with (Z)-1-methylidene-2-tellurahidans and (Z)-1-methylidene-2-selenaindans, respectively. The obtained isochromenes and were transformed into the corresponding 2benzopyrylium tetratluoroborates, respectively. An X-ray structural analysis of the 2-tert-butyl denvatives is also described. Less

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (26 results)

All Other

All Publications (26 results)

  • [Publications] Haruki Sashida: "An alternative route for the preparation of 1-benzostannepines, 1-benzostibepines and 1-benzosilepines via Te-Li exchange of 1-benzotellurepines"Heterocycles. 53. 49-53 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida, Atsuhiro Kuroda: "An alternative general preparation of 2-alkyl-1-beuzostannepines and their conversion into 1-benzostibepines and 1-benzoborepines via a tin-metal exchange"J. Chem. Soc., Perkin Trans. 1. 1965-1969 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida, Hiroshi Minamida: "A facile preparation of 1-benzoselenopyrylium salts"J. Chem. Res.(S). 569-571 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida, Hiroshi Minamida, Kenji Yamamoto: "Reactions of 1-benzoselenopyrylium salts with nucleophiles : formation of functionalised selenochromenes"J. Chem. Res.(S). 572-575 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida: "Syntheses of tellurium-containing heterocycles by intramolecular hydrotelluration of tellurols to a triple bond"Reviews on Heteroatom Chemistry. 22. 59-78 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 指田 春喜: "テルロールおよび関連化合物の分子内三重結合への環化付加による複素環合成"有機合成化学協会誌. 59. 355-362 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida, Masahiro Yoshida, Hiroshi Minamida, Masanori Teranishi: "Reaction of 1-benzoselenopyrylium salts with Grignard reagents : Formation of 2,4-disubstituted selenochromenes and their conversion into the corresponding 1-benzoselenopyrylium salts"J. Heterocyclic Chem.. 39(in press). (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida, Kazuo Ohyanagi, Mao Minoura, Kin-ya Akiba: "Studies on tellurium-containing heterocycles. Part 18. Preparation and structure of 2-benzotelluropyrylium salts and 2-benzoselenopyrylium salts"J. Chem. Soc., Perkin Transactions 1. 606-612 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida, Masahiro Yoshida: "A simple and practical preparation of 2,4-disubstituted 1-beuzotelluropyrylium salts"Heterocycles. 57. 649-656 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida: "An alternative route for the preparation of 1-benzostannepines, 1-benzostibepines and 1-benzosilepines via Te - Li exchange of 1-benzotellurepine"Heterocycles. 53. 49-53 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida. Atsuhiro Kuroda: "An aternative general preparation of 2-alkyl-1-benzostannepines and their novel conversion into 1-benzostibepines and 1-benzoborepines via a tin-metal exchange"J. Chem. Soc., Perkin Trans.. 1. 1965-1969 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida, Hiroshi Minamida: "A facile preparation of 1-benzoselenopyrylium"J. Chem. Res. (S). 569-571 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida, Hiroshi Minamida, Kenji Yamamoto: "Reaction of 1-benzoselenopyrylium salts with nucleophiles : formation of functionalized selenochromenes"J. Chem. Soc., Res. (S). 572-575 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida: "Synthesis of tellurium-containing heterocycles by intramolecular hydrotelluration of tellurols to a triple bond"Reviews on Heteroatom Chemistry. 22. 59-78 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida, Masahiro Yoshida, Hiroshi Minamida, Masanori Teranishi: "Reaction of 1-benzoselenopyrylium salts with Grignard reagents : formation of 2,4-disubstituted selenochromenes and their conversion into the corresponding 1-benzoselenopyrylium salts"J. Heterocycl. Chem.. 39 (in press). (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida. Kazuo Ohyanagi, Moa Minoura, Kin-ya Akiba: "Studies on tellurium-containing heterocycles. Part. 18. Synthesis and structure of 2-benzotelluropyrylium salts and 2-benzoselenopyrylium salts"J. Chem. Soc., Perkin Trans.. 1. 606-612 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruki Sashida, Masahiro Yoshida: "A simple and practical preparation of 2,4-disubstituted 1-benzotelluropyrylium salts"Heterocycles. 57. 649-656 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 指田 春喜: "テルロールおよび関連化合物の分子内三重結合への環化付加による複素環合成"有機合成化学協会誌. 59. 355-362 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Haniki Sashida, Masahiro Yoshida, Hiroshi Minamida, Masanori Teranishi: "Reaction of 1-Benzoselenopyrylium Salts with Grignard Reagents : Formation of 2,4-Disubstituted Selenochromenes and Their Conversion into the Corresponding 1-Benzoselenopyrylium Salts"J.Heterocyclic Chem.. 39(in press). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Haniki Sashida, Kazuo Ohyanagi, Mao Mrnoura, Kin-ya Akiba: "Studies on Tellurium-Containing Heterocycles. Part 18. Preparation and Structure of 2-Benzotelluropyrylium Salts and 2-Benzoselenopyrylium Salts"J.Chem.Soc., Perkin transactions 1. 606-612 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Haruki Sashida, Masahiro Yoshida: "A Simple and Practical Preparation of 2,4-Disubstituted 1-Benzotelluropyrylium Salts"Hetelocycles. 57(in press). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Haruki Sashida: "An alternative route for the preparation of 1-benzostannepines, 1-benzostibepines and 1-benzosilepines via Te-Li exchange of 1-benzotellurepines"Heterocycles. 53. 49-53 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Haruki Sashida and Atsuhiro Kuroda: "An alternative general preparation of 2-alkyl-1-benzostannepines and their conversion into 1-benzostibepines and 1-benzoborepines via a tin-metal exchange"J.Chem.Soc.,Perkin Trans.1. 1965-1969 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Haruki Sashida and Hiroshi Minamida: "A facile preparation of 1-benzoselenopyrylium salts"J.Chem.Res.(S). 569-571 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Haruki Sashida,Hiroshi Minamida and Kenji Yamamoto: "Reactions of 1-benzoselenopyrylium salts with nucleophiles : formation of functionalised selenochromenes"J.Chem.Res.(S). 572-575 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Haruki Sashida: "Syntheses of tellurium-containing heterocycles by intramolecular hydrotelluration of tellurols to a triple bond"Reviews on Heteroatom Chemistry. 22. 59-78 (2001)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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