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Chemistry of Heterocyclic Compounds

, Volume 45, Issue 2, pp 194–200 | Cite as

Aromatization with dearylation on Hantzsch cyclocondensation of 4-(dimethylamino)benzaldehyde, cyclohexane-1,3-diones, and some 1,3-[N,C]dinucleophiles

  • I. B. DzvinchukEmail author
  • N. A. Tolmachova
  • A. N. Chernega
  • M. O. Lozinskii
Article

The Hantzsch three-component cyclization of 4-(dimethylamino)benzaldehyde, cyclohexane-1,3-diones, and some 1,3-[N,C]-dinucleophiles (5-amino-3-methyl-1-phenylpyrazole, 3,5-dimethoxyaniline, and 4-amino-1,3-dimethylpyrimidine-2,6-dione) proceeds in boiling acetic acid with the splitting off N,N-dimethylaniline and the formation of polycondensed heterocyclic sytems with a γ-unsubstituted pyridine ring (pyrazolo[3,4-b]quinoline, acridine, and pyrimido[4,5-b]quinoline).

Keywords

acridines pyrazolo[3,4-b]quinolines pyrimido[4,5-b]quinolines aromatization dearylation Hantzsch reaction 

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Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • I. B. Dzvinchuk
    • 1
    Email author
  • N. A. Tolmachova
    • 1
  • A. N. Chernega
    • 1
  • M. O. Lozinskii
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKievUkraine

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