AROMATIZATION WITH DEARYLATION ON HANTZSCH CYCLOCONDENSATION OF 4-(DIMETHYLAMINO)BENZALDEHYDE, CYCLOHEXANE-1,3-DIONES, AND SOME 1,3-[N,C]-DINUCLEOPHILES

Authors

  • И. Б. Дзвинчук Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • Н. А. Толмачoва Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • А. Н. Чернега Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094
  • М. О. Лозинский Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 02094

DOI:

https://doi.org/10.1007/6826

Keywords:

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

Abstract

he 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).

How to Cite
Dzvinchuk, I. B.; Tolmachova, N. A.; Chernega, A. N.; Lozinskii, M. O.  Chem. Heterocycl. Compd. 2009, 45, 194. [Khim. Geterotsikl. Soedin. 2009, 244.]

For this article in the English edition see DOI 10.1007/s10593-009-0250-6


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Published

2022-05-25

Issue

No. 2 (2009)

Section

Original Papers