Unsymmetrical Hantzsch coupling reaction using a basic isoreticular metal-organic framework (IRMOF-۳)

MOFs are highly tunable, porous materials that are ideal for catalysis due to abandoned active catalytic sites and large surface areas. Metal–organic frameworks (MOFs) have emerged as efficient and reusable heterogeneous catalysts in organic transformations, with particular success in promoting multicomponent reactions, such as the Hantzsch reaction. Their high surface area, tunable active sites, and structural stability enable enhanced reaction rates, selectivity, and ease of product separation. Given the chemical and biological significance of polyhydroquinolines, the synthesis of compound ۴ was investigated using various catalysts. Under the reaction conditions involving dimedone, aldehydes, a β-diketone, and ammonium acetate (NH۴OAc), both unsymmetrical polyhydroquinolines (۴a) and symmetrical dihydropyridines (۵ and ۶) were obtained. For the model reaction, dimedone, benzaldehyde, ammonium acetate, and methyl acetylacetonate were selected as standard substrates. Different conditions were tested to optimize the yield of the target compound ۴a. Specifically, IRMOF-۳ was evaluated for its catalytic performance in the unsymmetrical Hantzsch coupling, where ۴a was the main product and ۵ and ۶ were side products.

کلیدواژه ها:

Metal–organic frameworks (MOFs) ، Hantzsch reaction ، Multicomponent reactions