Acidic ionic liquids catalyzed three-component synthesis of 12-aryl-12H-indeno[1,2-b]naphtho[3,2-e]pyran-5,11,13-trione and 13-aryl-indeno[1,2-b]naphtha[1,2-e]pyran-12(13H)-one derivatives

Abstract

Synthesis of 12-aryl-12H-indeno[1,2-b]naphtho[3,2-e]pyran-5,11,13-trione derivatives by the three component reaction of 2-hydroxynaphthalene-1,4-dione, aldehydes, and 2H-indene-1,3-dione under solvent-free conditions at 70°C in the presence of catalytic amount of acidic ionic liquids such as triethylammonium hydrogensulfate ([Et3NH][HSO4]), triethylamine-bonded sulfonic acid ([Et3N–SO3H]Cl), 2-pyrrolidonium hydrogensulfate ([Hnhp][HSO4]), 3-methyl-1-sulfonic acid imidazolium chloride ([Msim]Cl), and 1-methylimidazolium hydrogensulfate ([Hmim][HSO4]) is described. In addition, 13-aryl-indeno[1,2-b]naphtha[1,2-e]pyran-12(13H)-one derivatives from the reaction of β-naphthol, aldehydes, and 2H-indene-1,3-dione under thermal solvent-free conditions in the presence of mentioned catalysts is reported.