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1997 Fiscal Year Final Research Report Summary

Synthetic Study Using a New Active Reaction Species, Nitrosoketene

Research Project

Project/Area Number 08672405
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

KATAGIRI Nobuya  Tohoku University, Faculty of Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (60089787)

Co-Investigator(Kenkyū-buntansha) SUGIHARA Takumiti  Tohoku University, Faculty of Pharmaceutical Sciences, Instructor, 薬学部, 助手 (40222054)
Project Period (FY) 1996 – 1997
Keywordsnitrosoketene / FT-IR spectrum / cyclic nitrone / 1,3-dipolar cycloaddition / asymmetric synthesis / modified amino acid / isonitroso Meldrum's acid / cyclopentenylglycine
Research Abstract

Previously, we reported that heating of isonitroso Meldrum's acid with ketones in a aprotic solvent to give cyclic nitrones. This reaction involves the 1,3-cycloaddition of ketone with nitrosoketene derived from isonitroso Meldrum's acid. In this research project, we synthesized chiral cyclic nitrones from the reaction of nitrosoketene with various chiral ketones, and achieved the asymmetric synthesis of modified amino acids via asymmetric 1,3-dipolar cycloaddition of the nitrones. Thus, reaction of nitrosoketene with (+)-nopinone or (+)-camphenilone gave a chiral nitrone as a single isomer whereas l-menthone reacted with nitrosokene to give two isomers of chiral nitrones. One of these isomers was used for the EPC synthesis of modified amino acids such as allylglycine and cyclopentenylglycine. Furthermore, we first succeeded the detection of nitrosoketene using FT-IR spectroscopy under collaboration with American researchers. Thus, we found that nitrosoketene was gradually generated from isonitroso Meldrum's acid above 80゚C and then decomposed about 160゚C,and that life time of nitrosoketene was 4 h at 90゚C.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Nobuya Katagiri, et al: "Symthesis of Chiral Cyclic Nitrones via nitrosoketene Intermediate and thair use for the Complete EPC Syntheses of Nonprotaine genic Amino Acids" Tetcahedron Letters. 37. 1801-1804 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nobuya Katagiri, et al: "The first Enantionmerically Pure Synthesis of (2S,I'S)-(Cyclopent-2-emyl) glycine by Boron Trigluoride Medisted Asymmetric 1,3-Dipolar Cycoaddition" J.Chem.Soc.,Chem.Commun.2137-2138 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nobuya Katagiri, et al: "Systhesis of Chiral Spiro3-Oxazolin-5-one 3-Oxide(Chiral Nitrones) via A Nitylsketine Intermediate and their Asymmetric1,3-Dipolar Cycoadditions Landing to the EPC Synthesis of Modified AmmeAids" Tetcahedron. 53. 5725-5746 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroshi Matsue and Nobuya Katagiri, et al: "FT-IR and Ab initio Studies of Gase gous Nitrosoketene via Pyrolyses of Isonitroso Mcidrum's Acid" J.Phys.Chem.,A. 101. 3936-3941 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nobuya Katagiri, et al: "Reaction of 5-Hydroxyimino-1,3-dioxine-4,6-dione(Isonitroso Melxrum's Acid) with Carbodiimides to Give Parabanic Acids" Heterocycles. 46. 503-508 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nobuya Katagiri, et al: "Methylation of 5-Isonitroso-1,3-dioxine-4,6-diones with Diezomethane and Some Reactions of Its Products" Heterocycles. 47. 383-390 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] N.Katagiri, M.Okada, C.Kaneko, and T.Furuya: "Synthesis of Chiral Cyclic Nitrones via a Nitrosoketene Intermediate and Their Use for the Complete EPC Synthesis of Nonproteingenic Amino Acids" Tetrahedron Lett.39. 1801-1804 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] N.Katagiri, M.Okada, Y.Morishita, and C.Kaneko: "The first enantiomerically puresynthesis of Nonproteinogenic Amino Acids (2S,1'S)-(cyclopent-2-enyl) glycine by boron trifluoride-mediated asymmetric 1,3-dipolar cycloaddition" J.Chem.Soc.Chem.Commun.2137-2134 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] N.Katagiri, M.Okada, Y.Morishita, and C.Kaneko: "Synthesis of Chiral Spiro 3-Oxazolin-5-one 3-Oxides (Chiral Nitrones) via a Nitrosoketene Intermediate and Their Asymmetric 1,3-Dipolar Cycloadditions Leading to the EPC Synthesis of Modified Amino Acids" Tetrahedron. 53. 5725-5746 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Matsui, E.J.Zukerman, N.Katagiri, C.Kaneko, S.Ham, and D.M.Birney: "FTIR and Abinitio Studies of Gaseous Nitrosoketene via Pyrolysis of Isonitroso Meldrum's Acid" J.Phys.Chem.A. 101. 3936-3941 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] N.Katagiri, Y.Morishita, and C.Kaneko: "Reaction of 5-Hydroxyimino-1,3-dioxine-4,6-dione (Isonitroso Meldrum's Acid) with Carbodiimides to Give Parabanic Acids" Heterocycles. 46. 503-508 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] N.Katagiri, Y.Morishita, and C.Kaneko: "Methylation of 5-Isonitroso-1,3-dioxine-4,6-diones with Diazomethane and Some Reactions of Its Products" Heterocycles. 47. 383-390 (1998)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1999-03-16  

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