Efficient Syntheses of New Chromone- and Chromanequinoline Hybrids and their Aza-analogs

Abelmalek Bouraiou , Fabienne Berrée (1) , Sofiane Bouacida , Bertrand Carboni (1) , Abdelmadjid Debache (2) , Thierry Roisnel (1) , Ali Belfaitah (2)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 PHYSYNOR - Laboratoire des produits naturels d'origine végétal et de synthèse organique

Some novel chromone- and chromanequinoline hybrids and their aza-analogs were synthesized from 2-chloro- 3-quinolinecarboxaldehydes as starting materials. The cyclization of 2-hydroxychalcones in the presence of AcONa yielded chroman-4-ones, while, in the typical AFO conditions, the 2-corresponding quinolyl-3-hydroxyflavonols were obtained. These approaches were extended to 2-aminochalcones, which delivered the 3-hydroxy-2,3-dihydroquinolin- 4(1H)-one via an epoxy-ketone and 2-quinolyl-2,3-dihydroquinoline-4(1H)-one under microwave irradiation in the presence of silica gel impregnated with indium (III) chloride.

Mots clés: Quinoline; chalcones; flavonoid; quinolinone; bis-heterocycles; chromone; chromanequinoline; hybrids; azanalogues; aminochalcones

Domaines: Chimie organique

Abelmalek Bouraiou, Fabienne Berrée, Sofiane Bouacida, Bertrand Carboni, Abdelmadjid Debache, et al.. Efficient Syntheses of New Chromone- and Chromanequinoline Hybrids and their Aza-analogs. Letters in Organic Chemistry, 2011, 8 (6), pp.374-379. ⟨10.2174/157017811796064494⟩. ⟨hal-00736388⟩