Efficient Synthesis of Rhodanine-Based Amides via Passerini Reaction using Tetramethylguanidine-Functionalized Silica Nanoparticles as Reusable Catalyst

Abstract

Novel rhodanine-based amide derivatives were prepared in good yields via Passerini reaction of rhodanine- N -acetic acid with aromatic aldehydes and tert -butyl isocyanide in the presence of tetramethylguanidine immobilized on silica nanoparticles (TMG-SiO 2 NPs) as a heterogeneous base catalyst. The synthesized compounds were evaluated for their antibacterial effects against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis . ]]>

Diastereoselective synthesis of novel 2,5-dioxopyrrolidine derivatives via biocatalytic domino reactions

“…These results implied that 25 mg of NBC was enough to catalyze this reaction. Moreover, when 25 mg of Fe 3 O 4 nanoparticles, baker's yeast, and free ANL were used in the reaction, the yield was calculated (Table 1, entries [11][12][13].…”

“…Subsequently, this three-component reaction was investigated in various solvents such as H 2 O, ethanol, dioxane, and MeCN at 60 • C using 25 mg of NBC (Table 1, entries [12][13][14][15]. As indicated in Table 1, dioxane was chosen as the most suitable solvent for this reaction at 60 • C in the presence of 25 mg of NBC.…”

Synthesis and antibacterial activity evaluation of novel rhodanine based amide derivatives

“…On the other hand, rhodanine (2-thioxothiazolidin-4-one) as a privileged scaffold is found in a variety of biologically active compounds especially with antiviral [10], antibacterial [11], antifungal [12], antitubercular [13], anticancer [14], anticonvulsant [15], and hypnotic activities [16]. Therefore, following our interest in isocyanide-based reactions and our studies towards the development of new directions for the synthesis of novel organic compounds with biological activities [17][18][19], we herein report the multi-component reaction of aromatic aldehydes 1 with aniline 2, rhodanine-N-acetic acid 3 and isocyanides 4 in THF as a suitable procedure affording rhodanine-based amides 5 in good yields (Figure 1). The synthesized amides were also screened for their antibacterial activity by the disc diffusion method.…”