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Development of Generation Method of Unstable Chemical Species Using Carbon Monoxide

Research Project

Project/Area Number 10555317
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 有機工業化学
Research InstitutionKansai University

Principal Investigator

SONODA Noboru  Kansai University, Faculty of Engineering, Professor, 工学部, 教授 (20083983)

Co-Investigator(Kenkyū-buntansha) NISHIYAMA Yutaka  Kansai University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (30180665)
Project Period (FY) 1998 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥13,500,000 (Direct Cost: ¥13,500,000)
Fiscal Year 1999: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1998: ¥10,000,000 (Direct Cost: ¥10,000,000)
KeywordsCarbon Monoxide / Selenium / Selenium Carbon Monoxide / Indol / Quinazolinone / ニトロ化合物 / ナイトレン
Research Abstract

We investigated the new generation method of unstable chemical species by the use of the characteristics of carbon monoxide and the utilization of these unstable species in organic synthesis. In the course of this study, we found that nitre or nitrenoid species were generated smoothly by the reduction of aromatic nitro compounds with carbon monoxide in the presence of a catalytic amount of selenium. When 0-nitrostyrenes were treated with carbon monoxide in the presence of a catalytic amount of selenium, deoxyganation of nitro group followed by intramolecular cyclization proceeded efficiently to give the corresponding indols in moderate to good yields. On the reaction of 0-nitrobenzoylamides with carbon monoxide, 4(3H)-quinazolinones were synthesized in moderate to good yields. In addition, we have also developed the rhenium complexes having ligand of carbon monoxide acts as a catalyst on the Friedel-Craft alkylation of arenes with alkyl halides, Aldol type reaction of enol silyl ethers with carbonyl compounds and allylation of carbonyl compounds with allyic stannanes.

Report

(3 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • Research Products

    (15 results)

All Other

All Publications (15 results)

  • [Publications] Noboru Sonoda et al.: "Regioselective Alkylation of 1-Alkoxy-3-phenylseleno-1-alkanes"Synlett. (5). 611-613 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Noboru Sonoda et al.: "Synthesis of Indoles : Selenium-Catalyzed Reductive N-Heterocyclization of 2-Nitrostyrenes with Carbon Monoxide"Tetrahedron Letters. 40. 5717-5720 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Noboru Sonoda et al.: "Catalytic Use of Organostannyl Radical : The Reaction of 1, 2, 3-Selenadiazole with Olefins in the Presence of a Catalytic Amount of Tributyltin Hydride"Tetrahedron Letters. 40. 6293-9296 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Noboru Sonoda et al.: "New Synthetic Method of Diorganyl Selenides : Palladium-Catalyzed Reaction of PhSeSnBu_3 with Aryl and Alkyl Halides"Organic Letters. 1(11). 1725-1727 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Noboru Sonoda et at.: "Reductive Coupling of Carbonyl Compounds Using Lanthanum Metal"Heteroatom Chemistry. 11(1). 81-85 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Nishiyama, Y. Kishimoto, K. Itoh and N. Sonoda: "Regioselective Alkylation of 1-Alkoxy-3-phenylseleno-1-alkanes"Synlett. (5). 611-613 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Nishiyama, R. Maema, K. Ohno, M. Hirose and N. Sonoda: "Synthesis of Indoles : Selenium-Catalyzed Reducitve N-Heterocyclization of 2-Nitrostyrenes with Carbon Monoxide"Tetrahedron Lett.. 40. 5717-5720 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Nishiyama, Y. Hada, M. Anjiki, S. Hanita and N. Sonoda: "Catalytic Use of Organostannyl Radical : The Reaction of 1,2,3-Selenadiazole with Olefins in the Presence of a Catallytic Amount of Tributyltin Hydride"Tetrahedron Lett.. 40. 6293-6296 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Nishiyama, K. Tokunaga and N. Sonoda: "New Synthetic Method of Diorganyl Selenides : Palladium-Catalyzed Reaction of PhSeSnBuィイD23ィエD2 with Aryl and Alkyl Halides"Org. Lett.. 1(11). 1725-1727 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Nishino, Y. Nishiyama, and N. Sonoda: "Reductive Coupling of Carbonyl Compounds Using Lanthanum Metal"Heteroatom Chem.. 11(1). 81-85 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Noboru Sonoda et al.: "Regioselective Alkylation of 1-Alkoxy-3-phenylseleno-1-alkanes"Synlett. 611-613 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Noboru Sonoda et al.: "Synthesis of Indoles:Selenium-Catalyzed Reductive N-Heterocyclization of 2-Nitrostyrenes with Carbon Monoxide"Tetrahedron Letters. 40. 5717-5720 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Noboru Sonoda et al.: "Catalytic Use of Organostannyl Radical:The Reaction of 1,2,3-Selenadiazole with Olefins in the Presence of a Catalytic Amount of Tributyltin Hrdride"Tetrahedron Letters. 40. 6293-6296 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Noboru Sonoda et al.: "New Synthetic Method of Diorganyl Selenides:Palladium-Catalyzed Reaction of PhSeSnBu_3 with Aryl and Alkyl Halides"Organic Letters. 1(11). 1725-1727 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Noboru Sonoda et al.: "Reductive Coupling of Carbonyl Compounds Using Lanthanum Metal"Heteroatom Chemistry. 11(1). 81-85 (2000)

    • Related Report
      1999 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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