A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1,2-]pyridin-3-yl)alkane-1,2-diones (3) in good yields (32-88%) from 2-phenylimidazo[1,2-]pyridines (1) and terminal alkynes (2) has been established with a wide range of substrate scope. A tandem reaction sequence containing gold-catalyzed double oxidations of terminal alkynes to generate glyoxals, nucleophilic addition of 2-phenylimidazo[1,2-]pyridines to glyoxals to yield α-hydroxyl ketones, and oxygenation of the α-hydroxyl ketones to afford the final products 3 under air atmosphere is involved in this method. Simple operation, mild reaction conditions, and widely available substrates make this strategy more affordable.
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http://dx.doi.org/10.1039/d1ob01507a | DOI Listing |
Sci Rep
January 2025
Department of Chemistry, Yazd University, Yazd, Iran.
A new humic acid-based nanomagnetic copper(II) composite was prepared and used as an eco-friendly recoverable catalyst for synthesizing 1,4-disubstituted 1,2,3-triazoles. The synthesis was done via the three-component click reaction of alkyl halide, sodium azide, and terminal alkyne with good to excellent yield. A simple magnetic copper acetate composite, FeO@HA-Cu(OAc), was prepared using humic acid and characterized by SEM, TEM, XRD, EDX, EDS-mapping, VSM, TGA, AAS, and FT-IR.
View Article and Find Full Text PDFOrg Lett
January 2025
Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou, Guangdong 511436, China.
Presented herein is a nickel-catalyzed chemo- and regioselective three-component tandem carboamination and cyclization of terminal alkynes with organoboronic acids and anthranils for facile and modular access to 2,3-substituted quinolines. In this process, anthranil has dual roles: serving as an electrophilic aminating reagent and a redox buffer to suppress the generation of an off-cycle Ni(0) complex. Moreover, the anionic acetylacetonate (acac) ligand was found to be vital to ensure a productive Ni(I)-Ni(III)-Ni(I) catalytic cycle.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Instituto Universitario de Tecnología Química, Universitat Politècnica de València-Consejo Superior de Investigaciones Científicas, Universitat Politècnica de València, Av. De los Naranjos s/n, 46022 Valencia, Spain.
Due to their conductive properties and optoelectronic tunability, MXenes have revolutionized the area of electrocatalysis and active materials in supercapacitors. In comparison, there are only a few reports on MXenes as thermal catalysts for general organic reactions. Herein, the unprecedented catalytic activity of TiC MXene for the hydroamination of alkynes is reported, overcoming the limitations of poor activity, lack of selectivity, and stability, which are generally encountered in the solid catalysts known so far.
View Article and Find Full Text PDFInt J Biol Macromol
January 2025
Department of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, China. Electronic address:
Zein and its complexes have been considered as promising carriers for encapsulating and delivering various biological active ingredients, however, there still have some issues about Zein-based drug delivery systems should be considered, including poor colloidal stability, low drug encapsulation efficiency as well as rapid initial drug release, and uncontrollable release. In this work, we reported for the first time that hyperbranched polymers (HPG) functionalized Zein with terminal alkyne (Zein-HPG-PA) can be used for loading anticancer agent curcumin (CUR) via a facile phenol-yne click reaction. The resultant product (Zein-HPG-PA@CUR) displays high drug loading capacity, small particle size and excellent water dispersibility.
View Article and Find Full Text PDFAsian J Org Chem
January 2025
Department of Medicinal Chemistry, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, 160 Frelinghuysen Road, Piscataway, New Jersey 08854, USA.
A one-pot process was developed to synthesize in moderate to high yield a series of 2-substituted indoles and 7-azaindoles starting from 2-iodo--mesylarylamines and terminal alkynes in the presence of CuO in DMF at 90-120 °C. Without isolation of any intermediate, our optimized conditions enabled the introduction of ester, phenyl, hydroxymethyl, hydroxyethyl, -Boc-aminomethyl, and methyl at the 2-postion of indoles and 7-azaindoles. The reaction tolerates a variety of substrates containing halogens, or acid- or base-sensitive functional groups without requiring a Pd catalyst, a ligand, or a base.
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