Russian Chemical Bulletin

, Volume 47, Issue 8, pp 1553–1560 | Cite as

3,4-Diacetylhexane-2,5-dione—an effective synthon for synthesis of substituted azulene heteroanalogs by cyclocondensation reactions

  • E. P. Olekhnovich
  • S. L. Boroshko
  • Yu. N. Tkachenko
  • A. F. Pozharskii
  • E. B. Tsupak
  • Yu. A. Zhadanov
  • L. P. Olekhnovich
Organic Chemistry

Abstract

The one-pot method for the synthesis of 4,8-dialkoxy-6-aryl-1,3-dimethylcyclohepta [c]furanium perchlorates has been developed. The method is based on the cyclocondensation of 3,4-diacetylhexane-2,5-diones with aromatic aldehydes and trialkyl orthoformates under the action of a 16% perchloric acid solution in acetic anhydride. Under similar conditions, with hydrogen sulfide, cyclohepta[c]thiophenium perchlorates have been obtained, while cyclohepta[c]pyrrolium perchlorates have been prepared with arylamines, ammonium acetate, or aliphatic amine acetates. A heteroanalog of azulene, 4,8-diethoxy-1,3-dimethyl-2-azaazulene, has been obtained for the first time. Hydrolysis of aza- and thiaazulenium salts gives the corresponding cyclohepta[c]pyrrol-4-ones and cyclohepta [c]thiophen-4-ones.

Key words

3,4-diacetylhexane-2,5-diones ammonium acetate primary amines hydrogen sulfide 3,4-diacetyl-1,3-dimethylpyrroles(-thiophenes,-furans) perchloric acid triethyl orthoformate cyclohepta[c]pyrrolium -thiophenium -furanium perchlorates 4,8-diethoxy-1,3-dimethyl-2-azaazulene 2-aryl-1,3,6-trimethylcyclopenta[c]pyrrol-4-one 

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Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • E. P. Olekhnovich
    • 1
  • S. L. Boroshko
    • 2
  • Yu. N. Tkachenko
    • 2
  • A. F. Pozharskii
    • 2
  • E. B. Tsupak
    • 2
  • Yu. A. Zhadanov
    • 2
  • L. P. Olekhnovich
    • 2
  1. 1.Scientific-Research Institute of Physical and Organic ChemistryRostov State UniversityRostov-on-DonRussian Federation
  2. 2.Department of ChemistryRostov State UniversityRostov-on-DonRussian Federation

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