Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
A telescoped process under continuous flow conditions is described for the synthesis of -pyridyl-5-amino-1,2,3-triazole-4-carboxylate derivatives catalyzed by copper salts in a packed bed reactor. The synthetic approach takes first advantage of click chemistry, specifically relying on Cu(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC), to achieve the efficient and selective assembly of a triazole ring, followed by a copper-mediated C-H activation, that substitutes an inert C-H bond with a C-N bond, providing an environmentally acceptable and cost-effective strategy for synthesizing highly functionalized organic molecules.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC12068680 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.5c00453 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Multicomponent Reaction Integrating Selenium(II)-Nitrogen Exchange (SeNEx) Chemistry and Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC).
Angew Chem Int Ed Engl
April 2025
Shanghai Institute for Advanced Immunochemical Studies, ShanghaiTech University, Shanghai, 201210, China.
Multicomponent reactions (MCRs) are powerful tools for rapidly constructing compound libraries with sufficient molecular diversity and complexity. Herein, to fully leverage a third aspect of molecular diversity enabled by the selenium-nitrogen exchange (SeNEx) reaction between alkynes and benzoselenazolones, a novel CuI-catalyzed three-component reaction has been successfully developed. This reaction integrates SeNEx with CuAAC click chemistry, enabling rapid and regioselective synthesis of 1,4,5-trisubstituted 5-seleno-1,2,3-triazoles with high atom economy and good to excellent yields (65 examples, 50%-95%).
View Article and Find Full Text PDFCuI-catalyzed synthesis of multisubstituted pyrido[1,2-]pyrimidin-4-ones through tandem Ullmann-type C-N cross-coupling and intramolecular amidation reaction.
RSC Adv
August 2023
College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University No. 26 Hexing Road Harbin 150040 P. R. China
Various multi-substituted pyrido[1,2-]pyrimidin-4-ones were synthesized a one-pot tandem CuI-catalyzed C-N bond formation/intramolecular amidation reaction at 130 °C in DMF. This protocol features simple operation, broad substrate scope, good functional group tolerance and gram scale preparation, thus allowing practical and modular synthesis of pyrido[1,2-]pyrimidin-4-ones from readily available 2-halopyridine and ()-3-amino-3-arylacrylate ester in good to excellent yields.
View Article and Find Full Text PDFCopper-Catalyzed Tandem Reactions for Synthesis of Pyrazolo[5,1-a]isoquinolines with Heterocyclic Ketene Aminals as Ligands.
J Org Chem
January 2015
State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China.
A CuI-catalyzed tandem reaction of 5-(2-bromoaryl)-N-aryl-1H-pyrazol-3-amines with active acetonitrile derivatives to prepare pyrazolo[5,1-a]isoquinolines in good to excellent yields has been successfully developed under mild conditions with heterocyclic ketene aminals (HKAs) as new ligands. This is the first time HKAs have been used as ligands for copper-catalyzed coupling reactions.
View Article and Find Full Text PDFRecyclable copper catalyzed nitrogenation of biphenyl halides: a direct approach to carbazoles.
Chem Commun (Camb)
April 2013
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.
A novel A21-CuI catalyzed direct nitrogenation of biphenyl halides for the direct synthesis of carbazoles via a direct C-H amination process has been developed. A recyclable and inexpensive Cu-catalyst was successfully employed in N-heterocyclic compound synthesis via tandem azidation and C-H amination, which makes this protocol very practical and easy to handle.
View Article and Find Full Text PDFSkeletal diverse synthesis of N-fused polycyclic heterocycles via the sequence of Ugi-type MCR and CuI-catalyzed coupling/tandem Pictet-Spengler reaction.
J Org Chem
February 2012
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226 001, India.
Several diversity-oriented syntheses of N-fused polycyclic heterocycles have been demonstrated but most of them are based on point diversity within the same library and usually involve time-consuming sequential multistep syntheses, which also suffer from low yields and/or poor precursor scopes. We have developed a new strategy for the syntheses of skeletal diverse N-fused polycyclic compounds via an Ugi-type MCR followed by a CuI-catalyzed coupling reaction or tandem Pictet-Spengler reaction. This two-step sequence provides eight distinct skeleton of fused {6-5-5-6}, {5-5-5-6}, {6-5-6-6}, and {5-5-6-6} ring systems that have applications in medicinal chemistry and chemical genetics too.
View Article and Find Full Text PDF