Reactions of Dimedone-β-Benzoylacrylic Acid Adduct with Nitrogen-Containing Binucleophiles

摘要

2-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1 -en-1 -yl)-4-oxo-4-phenylbutanoic acid (dimedone adduct with β-benzoylacrylic acid) reacted with ethylenediamine and benzidine to give bis-quinoline derivatives. In the reaction with tryptamine a product containing hexahydroquinoline and indole fragments was obtained, while the reaction with phenylhydrazine hydrochloride afforded pyridazine derivative. The reactions with o- and p-phenylenediamines involved retro-Michael decomposition of the initial adduct and formation of enamino derivatives of dimedone.