Graphical Various arylacylated oxindoles are synthesized from the visible-light- promoted tandem reaction of N-arylsulfonyl-acrylamides with α-oxocarboxylic acids. The products are obtained under mild conditions. A visible-light-promoted radical tandem reaction of N-arylsulfonyl-acrylamides with α-oxocarboxylic acids is described. It undergoes decarboxylation, Smiles rearrangement, and intramolecular cyclization under mild reaction conditions, providing a series of arylacylated oxindoles with potential pharmacological activities.
Ugi-Smiles reactions play an important role in the field of organic synthesis and pharmaceutical chemistry. However, due to their low reactivity, less electrophilic aliphatic aldehydes have never been used as substrates. To expand the range of substrates for the reaction, a bis(N-(pyridin-2-ylmethyl)aminomethyl substituted Tröger's base derivative was used to promote the Ugi-Smiles reaction involving aliphatic aldehydes. With the facilitation of the catalyst, the reaction of isocyanides, malononitrile, aldehydes, and low-reactive, unfunctionalized 1H-benzo[d]imidazole-2-thiols proceeded smoothly to afford thioimidazolidinones in high yields under mild conditions. Both experimental and theoretical calculations showed that the catalyst's high catalytic activity may be due to its appropriate cavity size and alkalinity, as well as its multiple catalytic active sites.
This study presents a novel method using a gold-inlaid iron-based nanoenzyme (Au@MIL-53(Fe)) to rapidly detect phoxim, a neurotoxic organophosphate pesticide, in animal feed. The porous structure of MIL-53(Fe) acts as small-molecular ionic isolation lattices (SMILES), creating a solid-matrix surface confinement induced fluorescence enhancement (SSCIFE) environment for gold nanoclusters (AuNCs), enabling stable fluorescence at 642 nm and 435 nm. Additionally, it catalyzes TMB oxidation by hydrogen peroxide for colorimetric detection. Ascorbic acid 2-phosphate (AAP) is hydrolyzed by acid phosphatase (ACP) to ascorbic acid (AA), altering fluorescence and color signals. Phoxim inhibits ACP, modulating these signals and restoring the TMB color shift. The detection limits are 1.10 ng/mL (fluorescence), 1.02 ng/mL (colorimetry), and 1.04 ng/mL (smartphone colorimetric platform), respectively. The recovery rate of this method in feed is 84% ~ 116%. It offers a rapid, sensitive, and reliable solution for pesticide monitoring and food safety assurance.
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