A Rapid Intramolecular Imino Diels-Alder Reaction of Aminoanthraquinones with Citronellal or Prenylated Salicylaldehydes: Substituent Effect on Changing the Reaction Pathway from Diels-Alder to Ene-Type Cyclization

Abstract

The reaction of 1-aminoanthraquinone with citronellal or substituted prenylated salicylaldehyde catalyzed by triphenylphosphonium perchlorate (TPPP) is reported. The nature of the substituents in salicylaldehyde changes the reaction pathway from Diels-Alder to ene-type cyclization.

aminoanthraquinones - cycloaddition - naphthoacridine-5,14-dione - chromanoquinolonaphthaquinones - ene-type cyclization

References

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