Ultrasound assisted synthesis of hybrid quinoline-imidazole derivatives: a green synthetic approach

Abstract

A green, straightforward and efficient study for obtaining hybrid quinoline-imidazole derivatives under ultrasound (US) irradiation as well as under conventional thermal heating (TH) has been presented. The reaction pathway involves only two steps: the N-alkylation of imidazole ring and a Huisgen [3 + 2] dipolar cycloaddition reaction of ylides to dimethyl acetylenedicarboxylate (DMAD). For both types of reactions, a green workup procedure under US irradiation has been presented. Under US irradiation, the N-alkylation of nitrogen atoms from the imidazole nucleus has outstanding benefits in terms of reaction time, energy consumption and yields, and can thereby be considered an environmentally friendly method. Forty new hybrid quinoline-imidazole compounds have been synthesized: 18 salts, 8 dihydro-benzopyrrolo imidazolo quinoline, 9 benzopyrrolo-imidazolo quinoline and 5 dihydro-pyrroloquinoxaline quinoline cycloadducts.