Eco-friendly one-pot, three-component synthesis of novel derivatives of kojic acid by the Mannich-type reaction under solvent-free ball-milling conditions

Abstract

A novel series of aminokojic acid derivatives were efficiently synthesized by one-pot condensation of kojic acid, aromatic aldehydes and heteroaromatic amines in the presence of cerium(III) sulphate as an efficient and recyclable catalyst in ball-milling under solvent-free conditions at room temperature. This synthesis method offers several advantages, including a green and eco-friendly protocol, operational simplicity, mild reaction conditions, short reaction time, higher yields and easy workup procedures. The workup of these very clean reactions involves only a simple washing with acetone/cold water. The catalytic system can be reused several times with no loss of activity. Graphical Abstract O HO

Synthesis and application of novel 1,2,3‐triazolylferrocene‐containing ionic liquid supported on Fe3O4 nanocatalyst in the synthesis of new pyran‐substituted Betti bases

“…In continuation of our recent studies on the modification and development of multicomponent reactions, and the design and synthesis of ferrocene‐containing magnetic nanocatalysts and Betti bases, herein we introduce a new 1,2,3‐triazolylferrocene‐containing ionic liquid nanocatalyst stabilized on silica‐coated Fe 3 O 4 ([Fe 3 O 4 @SiO 2 @Triazol‐Fc][HCO 3 ]). We also report a simple and efficient protocol for the three‐component one‐pot synthesis of pyran‐containing Betti base derivatives catalysed by [Fe 3 O 4 @SiO 2 @Triazol‐Fc][HCO 3 ] at room temperature (Scheme ).…”

“…In continuation of our recent studies on the modification and development of multicomponent reactions, [43,44] and the design and synthesis of ferrocene-containing magnetic nanocatalysts [45][46][47][48] and Betti bases, [49][50][51][52][53] [46,47] Then, cycloaddition reaction of 4-chlorobutylferrocene, propargyl alcohol and sodium azide afforded (1-(4-ferrocenylbutyl)-1H-1,2,3-triazol-4-yl) methanol. Then the reaction of The absorption peaks at about 1079 cm −1 for all Fe 3 O 4 @SiO 2 core-shell magnetic nanoparticles are related to the asymmetric stretching vibrations of Si&bond;O&bond;Si.…”

“…In this context, the efficiency of the [Fe 3 O 4 @SiO 2 @Triazol-Fc][HCO 3 ] nanocatalyst was investigated in various solvents, at and further decrease or increase in catalyst quantity did not increase the yield of the product significantly. [51] (Continues)…”

“…A plausible mechanism to explain these three-component reactions is presented in Scheme 3. The acid-base interactions among the nanocatalyst, aldehyde and amine lead [51] to the efficient reaction of aldehyde and amine derivatives, followed by dehydration and formation of related imine. In the next step, the catalyst activates 2-naphthol or kojic acid and, consequently, nucleophilic attack to the imine produces the desired products.…”

One‐pot, Three‐component Synthesis of a Series of New Bis‐pyrrolo[2,3‐d]pyrimidines in the Presence of TPAB under Reflux Conditions

“…One‐pot, multicomponent reactions have many advantages such as simple isolation and purification steps, using green solvents, and more productivity with chemoselectivities and regioselectivities .…”