We describe a general approach for the synthesis of complex aryl 1,2,4-triazoles. The electronic character of the C-H bonds and the triazole ring allows for the regioselective C-H arylation of 1-alkyl- and 4-alkyltriazoles under catalytic conditions. We have also developed the SEM and THP switch as well as trans-N-alkylation, which enable sequential arylation of the triazole ring to prepare 3,5-diaryltriazoles. This new strategy provides rapid access to a variety of arylated 1,2,4-triazoles and well complements existing cyclization methods.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4546932 | PMC |
| http://dx.doi.org/10.1021/jo3021677 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A deoxyfluoroalkylation-aromatization strategy to access fluoroalkyl arenes.
Chem Commun (Camb)
January 2025
Borch Department of Medicinal Chemistry, Purdue University, West Lafayette, IN, 47906, USA.
Fluoroalkyl arenes (Ar-R) are valuable substructures present in several FDA-approved drugs, patents, agrochemicals, and materials, and complementary strategies that enable access to a broad spectrum of Ar-R compounds benefit these applied fields. Herein, we report a deoxyfluoroalkylation-aromatization strategy to convert cyclohexanones into broad-spectrum Ar-R containing compounds. Generally, the fluoroalkyl sources were activated to participate in a 1,2-addition reaction followed by aromatization in a sequence that contrasts more common preparations of these Ar-R compounds, such as (i) transition-metal catalyzed cross-coupling reactions of aryl electrophiles and nucleophiles, and (ii) radical fluoroalkylation reactions of C-H bonds of arenes.
View Article and Find Full Text PDFFlanking Effect on the Folding of Telomeric DNA Sequences into G-Quadruplex Induced by Antimalarial Drugs.
J Phys Chem B
January 2025
School of the Chemical Science, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
The folding of the guanine repetitive region in the telomere unit into G-quadruplex (G4) by drugs has been suggested as an alternative approach for cancer therapy. Hydroxychloroquine (HCQ) and chloroquine (CQ) are two important drugs in the trial stage for cancer. Both drugs can induce the folding of telomere-guanine-rich sequences into G4 even in the absence of salt.
View Article and Find Full Text PDFUnderstanding the Reactivity of "Naked" Acyclic Carbene-like Species Featuring a Group 13 Element in the [4+1] Cycloaddition with Benzene.
Inorg Chem
January 2025
Department of Applied Chemistry, National Chiayi University, Chiayi 60004, Taiwan.
The chemical reactivity between benzene and the "naked" acyclic carbene-like (G13X) species, having two bulky N-heterocyclic boryloxy ligands at the Group 13 center, was theoretically assessed using density functional theory computations. Our theoretical studies show that (BX) preferentially undergoes C-H bond insertion with benzene, both kinetically and thermodynamically, whereas the (AlX) analogue favors a reversible [4 + 1] cycloaddition. Conversely, the heavier carbene analogues ((GaX), (InX), and (TlX)) are not expected to engage in a reaction with benzene.
View Article and Find Full Text PDFMimicking the Reactivity of LPMOs with a Mononuclear Cu Complex.
Eur J Inorg Chem
May 2024
Department of Chemistry, Carnegie Mellon University, Pittsburgh, Pennsylvania 15213, United States.
Lytic polysaccharide monooxygenases (LPMOs) are Cu-dependent metalloenzymes that catalyze the hydroxylation of strong C-H bonds in polysaccharides using O or HO as oxidants (monooxygenase/peroxygenase). In the absence of C-H substrate, LPMOs reduce O to HO (oxidase) and HO to HO (peroxidase) using proton/electron donors. This rich oxidative reactivity is promoted by a mononuclear Cu center in which some of the amino acid residues surrounding the metal might can accept and donate protons and/or electrons during O and HO reduction.
View Article and Find Full Text PDFElucidating Photochemical Conversion Mechanism of PDMS to Silica under Deep UV Light and Ozone.
J Phys Chem Lett
January 2025
School of Materials Science and Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.
Photochemistry-based silica formation offers a pathway toward energy-efficient and controlled fabrication processes. While the transformation of poly(dimethylsiloxane) (PDMS) to silica (often referred to as SiO due to incomplete conversion) under deep ultraviolet (DUV) irradiation in the presence of oxygen/ozone has experimentally been validated, the detailed mechanism remains elusive. This study demonstrates the underlying molecular-level mechanism of PDMS-to-silica conversion using density functional theory (DFT) calculations.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!