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

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

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.

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Authors and Affiliations

  1. Scientific-Research Institute of Physical and Organic Chemistry, Rostov State University, 194/2 prosp. Stachki, 344090, Rostov-on-Don, Russian Federation

    E. P. Olekhnovich

  2. Department of Chemistry, Rostov State University, 7 ul. Zorge, 344090, Rostov-on-Don, Russian Federation

    S. L. Boroshko, Yu. N. Tkachenko, A. F. Pozharskii, E. B. Tsupak, Yu. A. Zhadanov & L. P. Olekhnovich

Authors
  1. E. P. Olekhnovich
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  2. S. L. Boroshko
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  3. Yu. N. Tkachenko
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  4. A. F. Pozharskii
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  5. E. B. Tsupak
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  6. Yu. A. Zhadanov
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  7. L. P. Olekhnovich
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1596–1603, August, 1998.

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Olekhnovich, E.P., Boroshko, S.L., Tkachenko, Y.N. et al. 3,4-Diacetylhexane-2,5-dione—an effective synthon for synthesis of substituted azulene heteroanalogs by cyclocondensation reactions. Russ Chem Bull 47, 1553–1560 (1998). https://doi.org/10.1007/BF02495609

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  • DOI: https://doi.org/10.1007/BF02495609

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