The behavior of dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles under Vilsmeier-Haack conditions

L. D. Patsenker, I. G. Ermolenko, O. N. Lyubenko, I. A. Fedyunyaeva, N. A. Popova, O. S. Galkina, A. V. Mazepa, B. M. Krasovitskii

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Abstract

It has been shown that dimethylamino-substituted 2,5-diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles undergo heterocyclization under Vilsmeier-Haack conditions with the participation of the dimethylamino group to form quinazolinium salts. The oxazole ring can also be formylated at the free 4 position. In alkaline medium the quinazolinium ring is readily hydrolyzed with desalkylation.

Original languageEnglish
Pages (from-to)525-533
Number of pages9
JournalChemistry of Heterocyclic Compounds
Volume39
Issue number4
DOIs
StatePublished - Apr 2003
Externally publishedYes

Keywords

  • 2,5-diaryl-1,3,4-oxadiazoles
  • 2,5-diaryloxazoles
  • Dimethylamino-substituted
  • Heterocyclization
  • Hydrolysis
  • Quinazolinium salts
  • Vilsmeier reaction

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