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

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Date
2007-08-16
Authors
Gaddam, Vikram
Meesala, Ramu
Nagarajan, Rajagopal
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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. © Georg Thieme Verlag Stuttgart.
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Keywords
Aminoanthraquinones, Chromanoquinolonaphthaquinones, Cycloaddition, Ene-type cyclization, Naphthoacridine-5,14-dione
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Synthesis