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An efficient construction of imidazole ring by a CsCO-promoted annulation of amidoximes with terminal alkynes in DMSO has been developed. This protocol provides a simple synthetic route with high atom-utilization for the synthesis of 2,4-disubstituted imidazoles in good yields under transition-metal-free and ligand-free conditions. Internal alkynes can also undergo the annulation to give 2,4,5-trisubstituted imidazoles.
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http://dx.doi.org/10.3390/molecules25163621 | DOI Listing |
Org Biomol Chem
September 2024
Organic Synthesis & Catalysis Lab, Department of Chemistry, National Institute of Technology Warangal, Hanumakonda-506004, Telangana, India.
A metal-free, iodine-catalyzed protocol has been developed for constructing biologically significant 5-aroyl 1,2,4-oxadiazole scaffolds using aryl methyl ketones and amidoximes. The strategy produces structurally diverse 5-aroyl 1,2,4-oxadiazoles in good to excellent yields, with a broad substrate scope that includes drug derived substrates. The reaction proceeds through iodine/DMSO-mediated oxidation of aryl methyl ketones, followed by imine formation and subsequent cyclization to yield the desired products.
View Article and Find Full Text PDFOrg Biomol Chem
July 2023
Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China.
A simple and efficient one-pot intermolecular annulation reaction for the synthesis of 1,2,4-oxadiazoles from amidoximes and benzyl thiols has been developed, in which benzyl thiols act as not only reactants but also organo-catalysts. The control experiments proved that thiol substrates could facilitate the dehydroaromatization step. High yield, functional group diversity and transition metal-free, extra oxidant-free, and mild conditions are the important practical features.
View Article and Find Full Text PDFMolecules
August 2020
Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China.
An efficient construction of imidazole ring by a CsCO-promoted annulation of amidoximes with terminal alkynes in DMSO has been developed. This protocol provides a simple synthetic route with high atom-utilization for the synthesis of 2,4-disubstituted imidazoles in good yields under transition-metal-free and ligand-free conditions. Internal alkynes can also undergo the annulation to give 2,4,5-trisubstituted imidazoles.
View Article and Find Full Text PDF