A ligand-free copper-catalyzed tandem azide-alkyne cycloaddition (CuAAC), Ullmann-type C-N coupling, and intramolecular direct arylation has been described. The designed strategy resulted in the synthesis of a novel trazole-fused azaheterocycle framework. The reaction gave good yields (59-77%) of 1,2,3-triazole-fused imidazo[1,2-a]pyridines in a single step.
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http://dx.doi.org/10.1021/ol401655r | DOI Listing |
J Org Chem
December 2024
Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China.
A one-pot, three-component synthesis of indole-benzofuran bis-heterocycles from terminal alkynes, salicylaldehydes, and indoles has been developed via copper-catalyzed tandem annulation. This catalytic system utilizes readily available starting materials, enabling predictable synthesis of indole-benzofuran bis-heterocycles with broad substrate versatility, excellent regiocontrol, and gram-scale amenability. The reaction proceeds via a sequential pathway involving A3 coupling, 1,4-conjugate addition, and 5-- cyclization.
View Article and Find Full Text PDFChem Commun (Camb)
October 2024
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
Copper(I)-catalyzed (4+3)-cycloaddition of 4-indolylcarbinols with aziridines has been accomplished to furnish azepinoindoles. The chirality transfer, substrate scope, functional group tolerance, natural product modification and tandem C-C/C-N bond formation are the important practical features.
View Article and Find Full Text PDFOrg Biomol Chem
October 2024
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P. R. China.
The first successful copper-catalyzed decarboxylative cyclization reaction of ethynylbenzoxazinones and thiols has been developed. A rarely studied α-addition process to a copper-allenylidene intermediate promoted this reaction. Using this protocol, a range of 2-thiomethylene indole compounds have been obtained.
View Article and Find Full Text PDFJ Org Chem
August 2024
Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
Asymmetric total synthesis of (-)-fasicularin was achieved in nine steps from a commercially available inexpensive material, by leveraging (1) an aryl radical-mediated, copper-catalyzed Sonogashira-type cross-coupling, (2) a Au-catalyzed tandem intramolecular alkyne hydroamination/iminium formation/intramolecular allylation, and (3) a tandem hydrogenation/hydrogenolysis/intramolecular reductive amination as key transformations.
View Article and Find Full Text PDFJ Org Chem
July 2024
School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou, Henan 450001, P. R. China.
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