Synthesis of the naphthalenone, dihydroquinoline, and dihydrofuran derivatives

Güngör F. Ş., Anaç O., Sezer Ö.

Helvetica Chimica Acta, vol.94, no.6, pp.1115-1129, 2011 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 94 Issue: 6
  • Publication Date: 2011
  • Doi Number: 10.1002/hlca.201000386
  • Journal Name: Helvetica Chimica Acta
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1115-1129
  • Istanbul Technical University Affiliated: Yes


The reactions of enaminones with dimethyl diazomalonate were investigated in the presence of copper(II) acetylacetonate. From the reaction of (E)-3-[methyl(phenyl)amino]-1-phenylprop-2-en-1-one (6c), dimethyl 2-[methyl(phenyl)amino]-4-oxonaphthalene-1,1-(4H)-dicarboxylate, was unexpectedly obtained as the major product. Quinoline derivatives were formed as the major products in the case of N-methyl-p-anisidino and N-methyl-p-toluidino enaminones. The reactions of acetyl enaminones were also realized, and quinoline derivatives were isolated as the major products. 3H- and 5H-dihydrofurans were also formed as side products in these reactions. These results differ from those reported earlier on the reactions of tertiary enaminones with carbenes/metal carbenes. © 2011 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.