Novel extensions of the tert-amino effect: Formation of phenanthridines and diarene-fused azocines from ortho-ortho′-functionalized biaryls

Ágnes Polonka-Bálint, Caterina Saraceno, Krisztina Ludányi, Attila Bényei, Péter Mátyus

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Phenanthridines and azocines fused to two benzene rings or one benzene and one pyridazinone ring, which are otherwise difficult to access, were prepared via two new extensions of the tert-amino effect. The synthetic pathway includes three steps: i) Suzuki reaction of an ortho-functionalized phenylboronic acid with ortho-disubstituted benzenes or pyridazinones; ii) the Knoevenagel condensation reaction of the biaryl aldehydes formed with active methylene compounds to obtain vinyl derivatives or, through their cyclization, phenanthridines via a tert-amino effect; and iii) thermal isomerization of vinyl or phenanthridinium compounds to fused azocines via another type of tert-amino effect.

Original languageEnglish
Pages (from-to)2846-2850
Number of pages5
JournalSynlett
Issue number18
DOIs
Publication statusPublished - Nov 14 2008

Keywords

  • Dibenzazocines
  • Nonbonding interactions
  • Pyridazinobenzazocines
  • Suzuki reaction
  • tert-amino effect

ASJC Scopus subject areas

  • Organic Chemistry

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