Pd- or Ni-catalyzed C-H arylation of 4-nitroimidazole derivatives directed by a manipulable nitro group was developed. The reaction tolerates a wide range of substituted aryl halides and 4-nitroimidazoles. The experiments indicated that the nitro group has influence on regioselectivity of the reaction. In addition, we have shown that the efficiency of the Suzuki-Miyaura cross-coupling reaction of nitroimidazoles is slightly lower in comparison to the direct C-H arylation. The exploration of the chemical potential of the nitro group and a putative reaction mechanism are discussed.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo5025927 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Comparative Study of Trifunctionalization for Enhanced Energy and Thermal Stability in Zwitterionic Fused Triazole Skeletons.
Org Lett
January 2025
School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 10081, China.
In this work, two energetic compounds 5-(3-iminio-6-nitro-3H-[1,2,4]triazolo[4,3-][1,2,4]triazol-2(7)-yl)tetrazol-1-ide () and 3-nitro-7-(2-tetrazol-5-yl)-7-[1,2,4]triazolo[4,3-][1,2,4]triazol-6-amine () were successfully synthesized from the same compound 3,6,7-triamino-7-[1,2,4]triazolo[4,3-][1,2,4]triazolium (). Both compounds contain three explosophores, amino, nitro, and tetrazole, on the fused ring. Through different functional group arrangements, possesses higher density and good thermal stability.
View Article and Find Full Text PDFReplacement of fishmeal with Quinoa Husk (Chenopodium quinoa) for mitigating multiple stresses in Pangasianodon Hypophthalmus.
Sci Rep
January 2025
ICAR-National Institute of Abiotic Stress Management, Baramati, Pune, 413115, India.
The fishmeal is boon for aquaculture production in this recent pollution and climate change era. However, the demand of fishmeal is enhancing in many folds which needs to find alternative to fishmeal in cheap price. The present investigation addresses these issues with quinoa husk (QH).
View Article and Find Full Text PDFThe substituent effect on the heat-induced pyrolysis mechanism of energetic materials: a case of reactive molecular dynamics simulations on nitrobenzene compounds.
Phys Chem Chem Phys
January 2025
School of Environment and Safety Engineering, North University of China, Taiyuan, 030051, China.
The initial decomposition reactions of 1,3,5-trinitrobenzene (TNB), picric acid (PA), 2,4,6-trinitrotoluene (TNT), 2,4,6-trinitroaniline (TNA) and 2,4,6-trinitrophenylmethylnitramine (Tetryl) were studied using ReaxFF-lg molecular dynamics simulations, and the substituent effect on the thermal decomposition behaviours of nitrobenzene compounds was evaluated through the reactant number, initial decomposition pathway, products and cluster analysis. The results show that the introduction of substituents could promote the decomposition of the reactants, increase the frequency of the nitro-nitrito isomerization reaction and intermolecular H or O atom transfer reaction, and reduce the frequency of the direct nitro dissociation reaction. Notably, these effects were most obvious in the case of TNT.
View Article and Find Full Text PDFSystematic Approach to Negative Fukui Functions: Its Association with Nitro Groups in Aromatic Systems.
Int J Mol Sci
January 2025
Departamento de Química y Biología, Facultad de Ciencias Naturales, Universidad de Atacama, Av. Copayapu 485, Copiapó 1530000, Chile.
Fukui functions are related to electron densities, and their interpretation permits the determination of reactivity of atomic centres. However, negative values cannot be interpreted by an "electron density based" model and represent a phenomenon that has been little investigated and understood. Previous works in the literature suggest that they are related to nodes in the wave function.
View Article and Find Full Text PDF-Butyl Hypochlorite: A Reagent for the Synthesis of Chlorinated Oxindole and Indole Derivatives.
Molecules
December 2024
College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, China.
-Butyl hypochlorite was employed as a versatile reagent for chlorooxidation of indoles, chlorination of 2-oxindoles, and decarboxylative chlorination of the indole-2-carboxylic acids. Four types of products including 2-chloro-3-oxindoles, 2,2-dichloro-3-oxindoles, 3,3-dichloro-2-oxindoles, and 2,3-dichloroindoles could be selectively obtained in moderate to excellent yields by switching the substrates. Various synthetically useful functional groups, such as halogen atoms, cyano, nitro, and methoxycarbonyl groups, remain intact during the reactions.
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!