Synthesis of 5-ethynyl-l,4-naphthoquinone and its derivatives

  • M. S. Shvartsberg
  • A. A. Moroz
  • N. V. Ivashkina
  • S. B. Cherepanov
Organic Chemistry

Conclusion

  1. 1.

    Synthesis of 5-acetylenyl-l,4-naphthoquinones including 5-ethynyl-l,4-naphthoquinone was carried out starting from 5-iodo derivatives of 1,4-dimethoxynaphthalene and naphthoquinone.

     
  2. 2.

    5-Acetylenyl-l,4-naphthoquinones containing an amino group on the quinone ring are capable of nucleophilic addition of secondary amines at the triple bond.

     
  3. 3.

    Oxidative amination of 5-phenylethynyl-l,4-naphthoquinone by diethylamine results in 3- and 2-diethylamino derivatives in R:1 ratio. The orienting effect of the substituent in position 5 increases in the series: nitro- < phenylethynyl- < amino group.

     

Keywords

Quinone Secondary Amine Naphthoquinone Triple Bond Diethylamine 

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Literature cited

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Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • M. S. Shvartsberg
    • 1
    • 2
    • 3
  • A. A. Moroz
    • 1
    • 2
    • 3
  • N. V. Ivashkina
    • 1
    • 2
    • 3
  • S. B. Cherepanov
    • 1
    • 2
    • 3
  1. 1.Institute of Chemical Kinetics and Combustion, Siberian BranchAcademy of Sciences of the USSRNovosibirsk
  2. 2.Novosibirsk State UniversityUSSR
  3. 3.Kemerovo State UniversityUSSR

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