Synthesis of novel fused azecine ring systems through application of the tert-amino effect

Petra Dunkel, György Túrós, Attila Bényei, Krisztina Ludányi, Péter Mátyus

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Abstract

Novel fused azecine ring systems were synthesized via the microwave-assisted thermal isomerization of terphenyl or biphenyl-pyridazine compounds possessing a vinyl and a tert-amino group, through application of a new extension of the tert-amino effect. Substrates for the ring closure were prepared from ortho-dihalobenzene or pyridazinone by consecutive Suzuki couplings with ortho-sec-amino- and formylphenylboronic acids, followed by Knoevenagel condensation of the aldehydes obtained.

Original languageEnglish
Pages (from-to)2331-2339
Number of pages9
JournalTetrahedron
Volume66
Issue number13
DOIs
Publication statusPublished - Mar 27 2010

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Keywords

  • Fused azecine ring systems
  • Microwave
  • Regioselective Suzuki coupling
  • tert-Amino effect

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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