A novel Zn(OAc)-catalyzed three-component tandem cyclization reaction of isocyanides, α-diazoketones and anhydrides has been developed. The reaction demonstrates the wide scope of substrates and provides a novel and efficient strategy for the synthesis of polysubstituted maleimides from readily available substrates in a single step.
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http://dx.doi.org/10.1039/c9cc05802h | DOI Listing |
J Org Chem
January 2025
State Key Laboratory of Macromolecular Drugs and Large-Scale Manufacturing, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, P. R. China.
The Pd-catalyzed multicomponent tandem reaction of β-ketonitriles, arylboronic acids and DMSO was efficiently developed, enabling access to a variety of poly substituted pyridines. The protocol shows excellent chemoselectivity, generating nicotinonitriles or symmetrical tetrasubstituted pyridines under different conditions by tandem cyclization of enaminone intermediates with β-ketonitriles or enolates, respectively, and does not require extra ammonias. This method boasts notable advantages, such as the use of commercially available or easily prepared substrates, simple conditions, a broad substrate scope, and good functional group tolerance.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China.
A visible-light-induced deoxygenative alkylation/cyclization of acrylamides with alcohols activated by CS has been developed by using xanthate salts as alkyl radical precursors in the presence of tricyclohexylphosphine. It proceeds through a tandem radical addition/cyclization process, and this protocol provides a reliable and practical approach to building the skeleton of 3,3-disubstituted oxindoles in moderate to good yields. Notable features of this reaction include readily available starting reagents, broad substrate scope and mild reaction conditions.
View Article and Find Full Text PDFJ Med Virol
December 2024
Division of Life Sciences and Medicine, University of Science and Technology of China, Hefei, China.
SARS-CoV-2 continues to mutate, leading to breakthrough infections. The development of new vaccine strategies to combat various strains is crucial. Protein cyclization can enhance thermal stability and may improve immunogenicity.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry, Indian Institute of Technology Delhi, New Delhi 110016, India.
We report a visible-light-assisted tandem oxidative 5--dig cyclization of 1,6-enynes for the synthesis of aminated C-3 aryloylated benzofuran, furopyridine, benzothiophene, and indole derivatives. The nitrogen-centered radical generated in situ from -aminopyridinium salt initiates the consecutive formation of C-N, C-C, and C-O bonds. The methodology exhibits good functional group tolerance and regioselectivity, furnishing products in good to excellent yields at room temperature.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
School of Chemistry and Chemical Engineering, Northwestern Polytechnical University (NPU), Xi'an, 710072, China.
The cleavage of carbon-carbon bonds and their subsequent reassembly into highly functionalized and useful molecules in an atom-efficient manner has always been a central focus in the realm of organic synthesis. In this report, we describe the construction of highly functionalized naphthol esters via a tandem reassembly process, driven by Ullmann-type coupling of enaminones and 1,3-dicarbonyl compounds. Mechanistic investigations suggest the involvement of C(sp)-C(sp) coupling, cyclization, two acyl migrations, aromatization, and additional transformations within this tandem sequence.
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