Microwave assisted, sequential two-step, one-pot synthesis of novel imidazo[1,2-a]pyrimidine containing tri/tetrasubstituted imidazole derivatives

Turk J Chem. 2021 Feb 17;45(1):219-230. doi: 10.3906/kim-2009-40. eCollection 2021.

Abstract

A series of novel imidazo[1,2- a ]pyrimidine containing tri/tetrasubstituted imidazole derivatives (1-10) has been synthesized via sequential two-step, one-pot, multicomponent reaction using imidazo[1,2- a ]pyrimidine-2-carbaldehyde, benzil, primary amines, and ammonium acetate catalyzed by p -toluenesulfonic acid under microwave-assisted conditions. The results showed that target compounds can be obtained from a wide range of primary amines bearing different functional groups with moderate to good yields (46%-80%) under optimum reaction conditions. This method provides a green protocol for imidazo[1,2- a ]pyrimidine containing tri/tetrasubstituted imidazole derivatives due to ethyl alcohol as a green solvent, microwave irradiation as a greener heating method and one-pot multicomponent reaction as a green technique. The synthesized compounds have been elucidated using various spectroscopic tools such as FT-IR, 1H NMR, 13 C NMR, and MS.

Keywords: 2- a ]pyrimidine; Imidazo[1; microwave synthesis; one-pot reaction; p -toluenesulfonic acid; sequential; tri/tetrasubstituted imidazole.