Diazo compounds have been employed as the nucleophile in a silver-catalyzed three-component reaction with amines and 2-alkynylbenzaldehydes. Various 3-benzazepines were prepared in a one-pot manner based on a cascade imine--yne cyclization/nucleophilic addition/1,2-aryl migration process. Moreover, this Ag(I)-mediated reaction also provides a practical route to diazo-containing dihydroisoquinolines under slightly modified conditions.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.5b02159 | DOI Listing |
RSC Adv
January 2025
Institute of Chemistry, Vietnam Academy of Science and Technology (VAST) 18 Hoang Quoc Viet, Cau Giay Hanoi Vietnam
Podophyllotoxin, along with its numerous derivatives and related compounds, is well known for its broad-spectrum pharmacological activity, especially for anticancer potential. In this study, several isatin-podophyllotoxin hybrid compounds were successfully synthesized with good yields through microwave-prompted three-component reactions of 2-amino-1,4-naphthoquinone, various substituted isatins, and tetronic acid. Their cytotoxicity was assessed against four types of human cancer cell lines, HepG2 (hepatoma carcinoma), MCF7 (breast cancer), A549 (non-small lung cancer), and KB (epidermoid carcinoma), alongside nontumorigenic HEK-293 human embryonic kidney cells.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.
The synthesis of perfluoroalkylated fullerenes (PFAFs) holds significant importance due to their enhanced molecular stability, increased lipophilicity, and high electron affinity. Herein, we report a copper-catalyzed multicomponent reaction conducted under aerobic conditions, which enables the production of highly soluble PFAFs with half-wave reduction potentials similar to those of C. Furthermore, the challenges posed by C-F coupling in carbon signal assignment were addressed through fluorine-decoupled carbon spectroscopy, facilitating precise structural characterization of the perfluoroalkyl moieties.
View Article and Find Full Text PDFRSC Adv
January 2025
Department of Organic Chemistry, Faculty of Chemistry, Alzahra University Vanak Tehran 1993893973 Iran
In this work, we present an efficient strategy for the straightforward synthesis of functionalized 1,6-dihydropyridine derivatives a three-component reaction of 3-vinylchromones, aromatic aldehydes, and ammonium acetate. A tandem procedure including NH aldimine formation/Michael-type addition/opening of the pyrone ring/isomerization/6π-electrocyclization/[1,5]-H shift allows rapid access to a series of dihydropyridines bearing an -hydroxybenzoyl and a benzoyl scaffold in good yields. Readily available precursors, simple heating conditions, and operational simplicity are some highlighted advantages of this transformation.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, China.
The absolute and relative configurations of bioactive chiral molecules are typically relevant to their biological properties. It is thus highly important and desirable to construct all possible stereoisomers of a lead candidate or a given bioactive natural compound. Synergistic dual catalysis has been recognized as a reliable synthetic strategy for a variety of predictable stereodivergent transformations.
View Article and Find Full Text PDFSci 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 PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!