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Ring Transformations of Small-Ring Compounds Utilizing Chemical Properties of Heteroatoms

Research Project

Project/Area Number 01470089
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionOsaka University

Principal Investigator

OHSHIRO Yoshiki  Osaka University, Faculty of Engineering, Professor, 工学部, 教授 (70028984)

Co-Investigator(Kenkyū-buntansha) HIRAO Toshikazu  Osaka University, Faculty of Engineering, Assistant Professor, 工学部, 助手 (90116088)
KOMATSU Mitsuo  Osaka University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (60029197)
Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥7,900,000 (Direct Cost: ¥7,900,000)
Fiscal Year 1990: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1989: ¥6,400,000 (Direct Cost: ¥6,400,000)
KeywordsHeteroatom / Small Ring Compound / Ring Transformation / Cyclopropane / Three-Membered Ring / Ring Enlargement / Heterocyclic Compound / 環拡大付加 / シリルシクロプロパン / 高歪み三員環 / ヘテロ環合成 / ヘテロ環化合物
Research Abstract

Purpose of this study is to develop novel ring transformations utilizing large ring strain of small ring compounds and chemical properties of heteroatoms in or adjacent to the rings. Among them, onlyfunctionalized cylopropanes and three-membered heterocycles were studied to clarify their natures and to apply them to new synthetic reactions.
1. Basic or acidic treatment of dibromocylopropane carboxylate afforded bromobutenolides.
2. Synthetic methods of dihalocyclopropyl isocyanates were established and basic treatment of a urea derivative gave an imidazolinone ring.
3. Highly effective carboxylation was performed by the reaction of 1-cyano-1-trimethylsilyl-cyclopropane with carbon dioxide under mild conditions, at room temperature and ambient pressure, in the presence of cesium fluoride as desilylating agent.
4. Formation of allene derivative from 1-bromo-1-trimethylsilylcyclopropane via an allyl cation intermediate was found upon treatment with silver tetrafluoroborate.
5. Ring enlargement of a diaziridinone to diazetidinones was successful in the reaction with acetylides.
6. Diaziridinone reacted with hydroxyketones to give 1:1 ring-opened adducts which gave nitrogen-containing medium-sized heterocycles when treated with an acid.
7. Functionalized pyrazolinones or novel spiro heterocycles were prepared by ring-expanding addition of diaziridinone with compounds having an active methylene.
8. Pyrrolotriazine derivatives were synthesized by the reaction of diaziridinones with pyrrole derivatives.

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] Y.Ohshiro 他: "Ring Enlargement of Diaziridinone: PyrazolineーForming Reaction with αーMetallated Nitrile" Tetrahedron Lett.37. 5327-5330 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y.Ohshiro 他: "Ring Enlargement of Diaziridinone to Diazetidinone by Reaction with Acetylide"

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y.Ohshiro 他: "Novel Synthesis of Pyrrolotriazine Derivative from Diaziridinone and Pyrroles"

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y.Ohshiro 他: "Synthesis of Novel Spiroheterocycle by Ring Enlargement of Diaziridinone with Active Methylene Compound"

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y.Ohshiro 他: "Carboxylation of Silylcyclopropane"

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y.Ohshiro 他: "Preparation of Dihalocyclopropyl Isocyanates and Their Application to Heterocyclic Synthesis"

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y.Ohshiro 他: "Synthesis or βーBromobutenolide from 2,2ーDibromocycloーpropanecarboxylate"

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y. Ohshiro et al.: "Ring Enlargement of Diaziridinone : Pyrazolinone-Forming Reaction with alpha-metalated Nitriles" Tetrahedron Lett.37. 5327-5330 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y. Ohshiro et al.: "Ring Enlargement of Diazirizinone to Diazetidinone by Reaction with Acetylide"

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y. Ohshiro et al.: "Novel Synthesis of Pyrrolotriazine Derivative from Diaziridinone and Pyrroles"

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y. Ohshiro et al.: "Synthesis of Novel Spiroheterocycles by Ring Enlargement of Diaziridinone with Active Methylene Compound"

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y. Ohshiro et al.: "Carboxylation of Silylcyclopropane"

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y. Ohshiro et al.: "Preparation of Dihalocyclopropyl Isocyanates and Their Application to Heterocyclic Synthesis"

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y. Ohshiro et al.: "Synthesis of b-Bromobutenolide from 2, 2-Dibromocyclopropane Carboxylate"

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Y.Ohshiro他: "Ring Enlargement of Diaziridinone:PyrazolineーForming Reaction with αーMetalated Nitrile" Tetrahedron Lett.37. 5327-5330 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Y.Ohshiro他: "Ring Enlargement of Diazridinone to Diazetidinone by Reaction with Acetylide" Chem.Lett.

    • Related Report
      1990 Annual Research Report
  • [Publications] Y.Ohshiro他: "Novel Synthesis of Pyrrolotriazine Derivative from Diaziridinone and Pyrroles" Tetrahedron Lett.

    • Related Report
      1990 Annual Research Report
  • [Publications] Y.Ohshiro他: "Synthesis of Novel Spiroheterocycle by Ring Enlargement of Diaziridinone with Active Methylene Compound" J.Chem.Soc.,Chem.Comm.

    • Related Report
      1990 Annual Research Report
  • [Publications] Y.Ohshiro他: "Carboxylation of Silylcyclopropane" Chem.Lett.

    • Related Report
      1990 Annual Research Report
  • [Publications] Y.Ohshiro他: "Synthesis and Application of Halocyclopropyl Isocyanate" J.Org.Chem.

    • Related Report
      1990 Annual Research Report
  • [Publications] Y.Ohshiro et al.: "Synthesis of β-Bromobutenolide from 2,2-Dibromocyclo-propanecarboxylate" Chem.Lett.

    • Related Report
      1989 Annual Research Report
  • [Publications] Y.Ohshiro: "Preparation of Dihalocyclopropyl Isocyanates and Their Application to Heterocyclic Synthesis" J.Org.Chem.

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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