Formation and destruction of diazine ring under conditions of the Vilsmeier-Haack formylation of 4-dialkylaminonaphthalic acid derivatives

Leonid D. Patsenker, Inna G. Yermolenko, Yevgeniya Ye Artyukhova, Vyacheslav N. Baumer, Boris M. Krasovitskii

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

The quaternized 1,3-diazine ring formation qualified as a particular case of the t-amino effect has been found under conditions of the Vilsmeier-Haack formylation of 4-dialkylaminonaphthalic acid derivatives. The diazinium ring is hydrolyzed in alkaline media with dealkylation, and 3-dimethylamino-4-alkylamino derivatives are formed.

Original languageEnglish
Pages (from-to)7319-7323
Number of pages5
JournalTetrahedron
Volume56
Issue number37
DOIs
StatePublished - 8 Sep 2000
Externally publishedYes

Keywords

  • 4-dialkylaminonaphthalic acid derivatives
  • Diazine ring
  • Vilsmeier-Haack formylation

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