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Synthesis of Medium Sized Hetero-Cyclic Compounds by Ylide Rearrangement

Research Project

Project/Area Number 08672437
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

SATO Yoshiro  Nagoya City University Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (80080183)

Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 1997: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1996: ¥1,800,000 (Direct Cost: ¥1,800,000)
Keywordsammonium ylide / sulfonium ylide / [2,3]sigmatropic rearrangement / Sommelet-Hauser rearrangement / Stevens rearrangement / organosilicon compound / organotin compound / fluoride ion / Sommelet-Hauser転位 / [2,3]シグマトロピー転位 / フッ素化合物
Research Abstract

Many new types of medium sized hetero-cyclic compounds were synthesized by [2,3] sigmatropic rearrangement of alpha-aryl cyclic ammonium methylides or sulfonium methylides which were generated by fluoride ion-induced desilylation of alpha-aryl-[(trimethylsilyl)methyl]-cyclic ammonium or sulfonium salts in DMF or DMSO at room temperature.
The results have been published in J.Org.Chem. (2 articles) and J.Chem.Soc., Perkin Trans 1.(4 articles).

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (24 results)

All Other

All Publications (24 results)

  • [Publications] Yasuhiro Maeda: "Reaction of N,N-Dimethyl-N-[(trialkylstannyl)methyl]benzylammonium Iodides with Organoithium Compounds" J.Org.Chem.61. 5188-5190 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Ken Narita: "Rearrangement of 2-Benzocycloammonium N-Methylides" J.Org.Chem.62. 2544-2549 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Chen Zhang: "Generation and Reaction of Benzylammonium N-Methylides with N-Cyanomethyl or N-[(Ethoxycarbonyl)alkyl]Groups" J.Chem.Soc.Perkin Trans.1. 25-28 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tomoko Kitano: "Synthesis of 3,4,6,7-Tetrahydro-1H-5,2-benzoxathionins by S-Ylide Rearrangement" J.Chem.Soc.Perkin Trans.1. 715-720 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Yasuhiro Maeda: "Mechanism of the Stevens Rearrangement of Ammonium Ylides" J.Chem.Soc.,Perkin Trans.1. 1491-1493 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Nobuhiko Kawanishi: "Rearrangement of cis-and trans-1-Methy1-2-(2-thienyl)pyrrolidinium 1-Methylides in a Non-basic Medium" J.Chem.Soc.,Perkin Trans.1. 3013-3016 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Yasuhiro Maeda and Yoshiro Sato: "Reaction of N.N-Dimethyl-N-[(trialkylstannyl)methyl]benzylammonium Iodides with Organolithium Compounds" J.Org.Chem.61. 5188-5190 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Ken Narita, Naohiro Shirai, and Yoshiro Sato: "Rearrangement of 2-Benzocycloammonium N-Methylides" J.Org.Chem.62. 2544-2549 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Chen Zhang, Yasuhiro Maeda, Naohiro Shirai and Yoshiro Sato: "Generation and Reaction of Benzylammonium N-Methylides with N-Cyanomethyl or N-[(Ethoxycarbonyl)alkyl]Groups" J.Chem.Soc.Perkin Trans.1. 25-28 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tomoko Kitano, Naohiro Shirai and Yoshiro Sato: "Synthesis of 3,4,6,7-Tetrahydro-1H-5,2-benzoxathionins by S-Ylide Rearrangement" J.Chem.Soc.Perkin Trans.1. 715-720 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Yasuhiro Maeda and Yoshiro Sato: "Mechanism of the Stevens Rearrangement of Ammonium Ylides" J.Chem.Soc.Perkin Trans.1. 1491-1493 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Satoshi Doi, Naohiro Shirai, and Yoshiro Sato: "Abnormal Products in Bischler-Napieralski Isoquinoline" J.Chem.Soc.Perkin Trans.1. 2217-2221 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Nobuhiko Kawanishi, Kazuhiko Fujiwara, Naohiro Shirai, Yoshiro Sato, Keiichiro Hatano and Yukihisa Kurono: "Rearrangement of cis-and trans-1-Methyl-2-(2-thienyl)pyrrolidinium 1-Methylides in a Non-basic Medium" J.Chem.Soc., Perkin Trans.1. 3013-3016 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tomoko Kitano and Yoshiro Sato: "Synthesis of 6,7,9,10-tetrahydro-4H-thieno [3,2-f] [1,4] oxathionine and 4,7,8,10-tetrahydro-5H-thieno [2,3-f] [1,4] oxathionine by S-ylide rearrangement" J.Chem.Soc., Perkin Trans.1. (in press). (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Yasuhiro Maeda and Yoshiro Sato: "Synthesis of N,N-Cimethyl-2(tributylstannyl)methyl-5-substituted benzylamines as a Quinodimethane Precursor by the Reaction of N,N-Cimethyl-N-(tributylst)methyl-4-substituted benzylammonium Salts with Lithium Diisopropylamide" Chem.Pharm.Bull.46. 508-511 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Chen Zhang, Yasuhiro Maeda and Yashiro Sato: "Reaction of N,N-Dialkyl-N-(trimethylsilylmethyl)-gamma-substituted allylammonium Salts with Caesium Fluoride" Chem.Pharm.Bull.(in press). (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Yasuhiro Maeda: "Reaction of N,N-Dimethyl-N-[(trialkylstannyl) methyl] benzylammonium Iodides with Organoithium Compounds" J.Org.Chem.61. 5188-5190 (1996)

    • Related Report
      1997 Annual Research Report
  • [Publications] Ken Narita: "Rearrangement of 2-Benzocycloammonium N-Methylides" J.Org.Chem.62. 2544-2449 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Chen Zhang: "Generation and Reaction of Benzylammonium N-Methylides with N-Cyanomethyl or N-[(Ethoxycarbonyl) alkyl] Groups" J.Chem.Soc.Perkin Trans.1,. 25-28 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Tomoko Kitano: "Synthesis of 3,4,6,7-Tetrahydro-1H-5,2-benzoxathionins by S-Ylide Rearrangement" J.Chem.Soc.Perkin Trans.1,. 715-720 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yasuhiro Maeda: "Mechanism of the Stevens Rearrangement of Ammonium Ylides" J.Chem.Soc.,Perkin Trans.1,. 1491-1493 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Nobuhiko Kawanishi: "Rearrangement of cis-and trans-1-Methyl-2-(2-thienyl) pyrrolidinium1-Methylides in a Non-basic Medium" J.Chem.Soc.,Perkin Trans.1,. 3013-3016 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yasuhiro Maeda: "Reaction of N, N-dimethyl-N-[(trialkylstannyl) methyl] benzylammonium iodides with organolithium compounds" The Journal of Organic Chemistry. 61. 5188-5190 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Chen Zhang: "Generation and reaction of benzylammonium N-methylides with N-cyano-methyl or N-[(ethoxycarbonyl) alkyl] groups" Journal of the Chemical Society, Perkin Transaction 1. 25-28 (1997)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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