A rhodium-catalyzed regioselective C-H activation/cyclization of azoxy compounds with alkynes has been disclosed to construct a variety of 2H-indazoles. A [4 + 1]-cycloaddition rather than a normal [4 + 2] mode is observed in the process of cyclative capture along with an oxygen-atom transfer and a C≡C triple bond cleavage. This protocol features a broad substrate scope, a good functional group tolerance, and an exclusive regioselectivity.
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http://dx.doi.org/10.1021/acs.orglett.7b00982 | DOI Listing |
Molecules
November 2024
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russia.
In this study, the electrochemical coupling of nitrosoarenes with ammonium dinitramide is discovered, leading to the facile construction of the nitro--azoxy group, which represents an important motif in the design of energetic materials. Compared to known approaches to nitro--azoxy compounds involving two chemical steps (formation of azoxy group containing a leaving group and its nitration) and demanding expensive, corrosive, and hygroscopic nitronium salts, the presented electrochemical method consists of a single step and is based solely on nitrosoarenes and ammonium dinitramide. The dinitramide salt plays the roles of both the electrolyte and reactant for the coupling.
View Article and Find Full Text PDFNat Commun
September 2024
Key Laboratory of Engineering Biology for Low-carbon Manufacturing, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, 32 West 7th Avenue, Tianjin, 300308, China.
Enzymes are making a significant impact on chemical synthesis. However, the range of chemical products achievable through biocatalysis is still limited compared to the vast array of products possible with organic synthesis. For instance, azoxy products have rarely been synthesized using enzyme catalysts.
View Article and Find Full Text PDFJ Org Chem
October 2024
Biochemistry and Chemical Biology Research Laboratory, Chemistry Department, Sharif University of Technology, Tehran 11365-11155, Iran.
Azoxy arenes are valuable compounds in different areas of chemistry, such as organic chemistry, medicinal chemistry, and natural product chemistry. Despite their value, the regioselective synthesis of unsymmetric azoxybenzenes has remained a real challenge in the field. Herein, the product selectivity in oxidative homocoupling of anilines into symmetric azoxybenzenes was first achieved by an asparagine-functionalized CQD catalyst.
View Article and Find Full Text PDFBiosci Biotechnol Biochem
August 2024
Department of Agricultural, Life, Environmental Sciences, Faculty of Agriculture, Tottori University, Tottori, Japan.
Virulence pathways in pathogenic bacteria are regulated by quorum sensing mechanisms, particularly biofilm formation through autoinducer (AI) production and sensing. In this study, the culture filtrate extracted from an edible mushroom, Agaricus subrutilescens, was fractionated to isolate a compound that inhibits biofilm formation. Four gram-negative bacteria (Klebsiella pneumoniae, Escherichia coli, Proteus mirabilis, and Enterobacter cloacae) and two gram-positive bacteria (Enterococcus faecalis and Staphylococcus aureus) were used for the bioassay.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
New Cornerstone Science Laboratory, State Key Laboratory for Physical Chemistry of Solid Surfaces, Collaborative Innovation Center of Chemistry for Energy Materials, and National & Local Joint Engineering Research Center of Preparation Technology of Nanomaterials, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
A full selectivity control over the catalytic hydrogenation of nitroaromatics leads to the production of six possible products, i.e., nitroso, hydroxylamine, azoxy, azo, hydrazo or aniline compounds, which has however not been achieved in the field of heterogeneous catalysis.
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