Herein, we report direct synthesis of 1-N-vinyl-1,2,3-triazoles via silver-mediated three-component cycloaddition reaction of phenylacetylenes, trimethylsilylazide, and 1,3-dicarbonyl compounds. The synthetic protocol proceeds with operational simplicity, good substrate and functional group compatibility, and easily available feedstocks, and without the need for pre-installation of vinylazide precursors, and offers a practical method for the efficient elaboration of triazole derivatives.
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http://dx.doi.org/10.1039/c9ob00686a | DOI Listing |
Org Lett
April 2022
Institute of Chemistry, Academia Sinica, Taipei 11529, Taiwan.
We report an efficient and mild tandem catalytic process for the synthesis of functionalized pyrrole-3-carbaldehydes. These compounds were obtained by a one-pot three-component reaction of 5-bromo-1,2,3-triazine, terminal alkynes, and primary amines via a palladium-catalyzed Sonogashira coupling reaction, and then annulation through a silver-mediated reaction of the resulting alkynyl 1,2,3-triazines allowed for access to the multifunctionalized pyrrole-3-carbaldehydes.
View Article and Find Full Text PDFOrg Biomol Chem
May 2019
School of Chemistry and Chemical Engineering, South China University of Technology, 381 Wushan Rd, Guangzhou 510640, People's Republic of China.
Herein, we report direct synthesis of 1-N-vinyl-1,2,3-triazoles via silver-mediated three-component cycloaddition reaction of phenylacetylenes, trimethylsilylazide, and 1,3-dicarbonyl compounds. The synthetic protocol proceeds with operational simplicity, good substrate and functional group compatibility, and easily available feedstocks, and without the need for pre-installation of vinylazide precursors, and offers a practical method for the efficient elaboration of triazole derivatives.
View Article and Find Full Text PDFStarting from a primary amine-tethered alkyne , a copper-catalyzed three-component tandem amination/cyanation/alkylation sequence gives α-CN pyrrolidine in good yield and regioselectivity. Also, a silver mediated tandem amination/oxidation of a secondary amine-tethered alkyne produces functionalized pyrrole in good yield. All reactions were conducted in one pot without any protection/deprotection steps.
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