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Developments of New Organic Synthetic Reactions Using Inorganic Supports

Research Project

Project/Area Number 62850148
Research Category

Grant-in-Aid for Developmental Scientific Research

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionFaculty of Engineering, Kobe University

Principal Investigator

HOJO Masaru  Fac. of Eng., Kobe Univ., Dept. of Ind. Chem., Professor, 工学部, 教授 (60031043)

Co-Investigator(Kenkyū-buntansha) KAMITORI Yasuhiro  Fac. of Eng., Kobe Univ., Dept. of Ind. Chem., Associate Professor, 工学部, 助教授 (10135816)
Project Period (FY) 1987 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥6,500,000)
Fiscal Year 1989: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1988: ¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 1987: ¥2,800,000 (Direct Cost: ¥2,800,000)
KeywordsOrganic Synthesis Using Inorganic Supports / Substitution at Olefinic Carbons / Fluorine-Containing Heterocycles / Acylation of Aldehyde Hydrazones / Fluorine-Containing Oxadiazines / Fluorine-Containing Thiadiazines / Fluorine-Containing Naphthooxazines / Ether Exchange Reactions at Olefinic Carbon Atoms / 含フッ素ヘテロ環化合物 / アルデヒドヒドラゾンのアミル化 / オレフイン炭素上でのエ-テル交換反応 / アルデヒドヒドラゾンのトリフルオロアセチル化 / 含フッ素αージケトン / 含フッ素ピペラジン / 含フッ素キノキサリン / 含フッ素チオフェン
Research Abstract

In these ten years we have been engaged in the study of development of new synthetic organic reactions with the use of silica gel as a useful catalyst. Another important recent project in our laboratory is electrophilic and nucleophilic substitution reactions at olefinic carbon atoms. The present study was undertaken to combine the both projects and to develop new synthetic methods for the syntheses of various fluorine-containing heterocycles which are otherwise difficultly accessible. The results are as follows. (1) Ethyl vinyl ether was trifluoroacetylated at the beta-position and then converted to allyl beta-trifluoroacetylvinyl ethers by reaction with various allyl alcohols in the presence of silica gel. The products were submitted to Claisen rearrangement with the use of silica gel to yield 3-allyl-1,1,1-trifluoroacetylacetones, from which various fluorine-containing heterocycles were obtained. (2) Various aldehyde hydrazones were successfully trifluoro- acetylated at the azomethine carbons and then converted by novel cyclization to fluorine- containing oxadiazines in the presence of silica gel. From these oxadiazines various fluorine-containing heterocycles such as thiadiazines, imidazoles, pyrazoles, quinoxalines, pyrazines, thiophenes, furans and pyrroles were obtained. (3) 2,4-Bistrifluoroacetyl- 1-dimethylaminonaphthalene was successfully converted with the use of silica gel as catalyst into fluorine-containing [1,2-d][1,3]oxazine.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (24 results)

All Other

All Publications (24 results)

  • [Publications] Y.Kamitori: "Electrophilic Substitution at Azomethine Carbon Atoms.Reaction of Aromatic Aldehyde Hydrazone with Trifluoroacetic Anhydride" J.Org.Chem.53. 129-134 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Y.Kamitori: "Electrophilic Substitution Reaction at Azomethine Carbon Atom.Acylation of Aliphatic Aldehyde Hydrazones." J.Org.Chem.53. 519-526 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Hojo: "Acid Catalyzed Cyclization of N,N-Dialky-2,4-bistrifluoroacetyll-naphthylamines to Naphtho[1,2-d][1,3]ozazines" Tetrahedron Lett.29. 4599-4602 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Hojo: "A Facile Synthesis of 2,4-Dialkoxy-,2-Alkoxy-4-Phenozy-,and2,4-Diphenoxy-6-trifouoromethy1-3,4-ditydro-2H-pyrans:Hetero-Diels-Alder Reactions of Trans-β-Trifluoroacetylvinyl Ethers with Various Vinyl Ethera" Synthesis. 215-217 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Hojo: "Aromatic Nucleophilic Nitrogen-Nitrogen Exchange Reaction of N,N-Dimethy1-2,4-bis(trifluoroacetyl)-1-naphthylamine with Amino Acid Deribatives:A Facile Syntheis of Fluorine-Containing 1H-Benzo[g]-indolines and 1H-Bienzo[g]indoles" Synthesis. 550-552 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Hojo: "O-N,S-N,and N-N Exchange Reactions at Olefinic Carbon Atoms:Facile Synthetic Method for β-Trifluoroacetylvinylamines" Tetrahedron Lett.30. 6173-6176 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Y. Kamitori: "Electrophilic Substitution at Azomethine Carbon Atoms. Reaction of Aromatic Aldehyde Hydrazone with Trifluoroacetic Anhydride" J. Org. Chem., 53 p.129-p.134, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Y. Kamitori: "Electrophilic Substitution Reaction at Azomethine Carbon Atom. Acylation of Aliphatic Aldehyde Hydrazones." J. Org. Chem., 53 p.519-p.526, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Hojo: "Acid Catalyzed Cyclization of N,N-Dialkyl-2,4-bistrifluoroacetyl-1-naphthylamines to Naphtho[1,2-d][1,3]oxazines" Tetrahedron Lett., 29 p.4599-p.4602, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Hojo: "A Facile Synthesis of 2,4-Dialkoxy-, 2-Alkoxy-4-Phenoxy-, and 2,4-Diphenoxy-6-trifluoromethyl-3,4-dihydro-2H-pyrans: Hetero-Diels-Alder Reactions of trans-beta-Trifluoroacetylvinyl Ethers with Various Vinyl Ethers" Synthesis p.215-p.217, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Hojo: "Aromatic Nucleophilic Nitrogen-Nitrogen Exchange Reaction of N,N-Dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine with Amino Acid Derivatives: A Facile Synthesis of Fluorine-Containing 1H-Benzo[g]・indolines and 1H-Benzo[g]indoles" Synthesis p.550-p.552, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Hojo: "O-N, S-N and N-N Exchange Reactions at Olefinic Carbon Atoms: Facile Synthetic Method for beta-Trifluoroacetylvinylamines" Tetrahedron Lett., 30 p.6173-p.6176, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Y.Kamitori: "Electrophilic Subsitution at Azomethine Carbon Atoms. Reaction of Aromatic Aldehyde Hydeazone with Trifluoroacetic Anhydride" J.Org.Chem. 53. 129-134 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Y. Kamitori: "Electrophilic Substitution Rraction at Azomethine Carbon Atom.Acylation of Aliphatic Aldehyde Hydrazones." J.Org.Chem.53. 519-526 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Hojo: "Acid Catalyzed Cyclization of N,N-Dialky1-2,4-bistirfluoroacety1-1-naphthylamines to Naphtho〔1,2-d〕〔1,3〕oxazines" Tetrahedron Lett.29. 4599-4602 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Hojo: "A Facile Synthesis of 2,4-Dialkoxy-,2-Alkoxy-4-Phenoxy-,and 2,4-Diphenoxy-6-trifluoromethy1-3,4-dihydro-2H-pyrans:Hetero-Diels-Alder Reactions of trans-β-Trifluoroacetylvinyl Ethers with Various Vinyl Ethers" Synthesis. 215-217 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Hojo: "Aromatic Nucleophilic Nitrogen-Nitrogen Exchange Reaction of N,N-Dimethyl-2,4-bis(trifluoroacetyl)-1-naphthy with Amino Acid Derivatives:A Facile Syntheis of Fluorine-Containing 1H-Benzo〔g〕-indolines and 1H-Benzo〔g〕indoles" Synthesis. 550-552 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Hojo: "O-N,S-N and N-N Exchange Reactions at Olefinic Carbon Atoms:Facile Synthetic Method for β-Trifluoroacetylvinylamines" Tetrahedron Lett.30. 6173-6176 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Masaru Hojo: Tetrahedron Lett.29. 4599-4602 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Masaru Hojo: J.Org.Chem.53. 2209-2213 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Yasuhiro Kamitori: J.Org.Chem.53. 519-526 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Yasuhiro Kamitori: J.Org.Chem.53. 129-135 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Masaru Hojo: Tetrahedron Lett.28. 6199-6200 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Masaru Hojo: Synthesis. 1013-1014 (1987)

    • Related Report
      1988 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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