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Generalization of New Synthetic Methods of Macrocyclic compounds Utilizing Characteristic Bonding Properties of Hypervalent Atom and Their Applications

Research Project

Project/Area Number 14540502
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOsaka Prefecture University

Principal Investigator

MATSUMURA Noboru  Osaka Prefecture University, Graduate School, Assoc.Professor, 大学院・工学研究科, 助教授 (40125274)

Co-Investigator(Kenkyū-buntansha) KAZUHIKO Mizuno  Osaka Prefecture University, Graduate School, Professor, 大学院・工学研究科, 教授 (10109879)
Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2003: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2002: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsTetraazathiapentalene / Hypervalent Sulfur / Macrocyclic Compound / Ring-Opening / Anion Receptor / Molecular Recognition
Research Abstract

We report new methods for the synthesis of novel macrocyclic compounds by utilizing characteristic bonding properties of hypervalent sulfur. The results are summarized as follows: 1)Treatment of 2,3-dimethyltetraazathiapentalene derivative (1)with 1 equiv. of p-xylilene diisothiocyanate in refluxing benzene gives the macrocyclic compound 2 which has two tetraazathiapentalene skeletons in the compound. 2)The reaction of compund 3 which has two pentalene rings in the molecule with p-xylilene diisothiocyanate affords macrocyclic compound 4 which has four tetraazathiapentalene rings, these rings being situated in a laminate form. 3)The reaction of 3 with 3,6,9-trioxaundecane-1,11-diisothiocyanate affords macrocyclic compound 5 which has having two rings containing oligoethyleneglycol chain and pentalene ring. 4)The reaction of 2,4 and 5 with NaBH_4 gives ring-expanded 26-35-membered macrocycles 6,7 and 8, respectively, via the reductive elimination of hypervalent sulfur. 5)Treatment of 2,4 and 5 with aqueous potassium hydroxide gives 4045 membered macrocyclic compound 9, 10 and 11, respectively, which have thiourea moieties via the elimnation of C=S^<IV> moiety. 6) The macrocyclic compound 6 -8 serve as an anionm receptor for H_2PO_4. The reactions described here would provide the useful methods for the variety of macrocyclic compounds.

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (7 results)

All Other

All Publications (7 results)

  • [Publications] Y.Okumura, S.Murakami, H.Maeda, N.Matsumura, K.Mizuno: "Synthesis and Dual Binding Character of Novel Macrocyclic Thiourea Derivatives"Tetrahedron Lett.. 44. 8183-8185 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Matsumura, A.Ito, M.Tomura, Y.Okumura, K.Mizuno: "Reaction of Tetraazathiapentalene and Thiadiazolo-pyrimidine Derivatives with Heterocumulene"J.Heterocycl.Chem.. (in press). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Okumura, S.Murakami, H.Maeda, N.Matsumura, K.Mizuno: "synthesis and Dual Binding Character of Novel Macrocyclic Thiourea Derivatives"Tetrahedron Lett.. 44. 8183-8185 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Matsumura, A.Ito, M.Tomura, Y.Okumura, K.Mizuno: "Reaction of Tetraazathiapentalene and Thiadiazolopyrimidine derivatives with Heterocumulene"J.Heterocycl.Chem.. (in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Okumura, S.Murakami, H.Maeda, N.Matsumura, K.Mizuno: "Synthesis and Dual Binding Character of Novel Macrocyclic Thiourea Derivatives"Tetrahedron Lett.. 44. 8183-8185 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] N.Matsumura, A.Ito, M.Tomura, Y.Okumura, K.Mizuno: "Reaction of Tetraazathiapentalene and Thiadiazolopyrimidine Derivatives with Heterocumulene"J.Heterocycl.Chem.. (in press). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] N.Matsumura, T.Konishi, H.Hayashi, M.Yasui, F.Iwasaki, K.Mizuno: "Synthesis and Properties of Novel Macrocyclic Compounds Bearing Thiourea Moieties by Use of Chemical Feature of Hypervalent Sulfur"J.Heterocyclic Chem.. 39. 189-202 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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