Base-catalyzed tandem carbon-carbon followed by nitrogen-nitrogen bond formations quantitatively converted N-alkyl-2-nitro-N-(2-oxo-2-aryl-ethyl)-benzenesulfonamides to 2H-indazoles 1-oxides under mild conditions. Triphenylphosphine or mesyl chloride/triethylamine-mediated deoxygenation afforded 2H-indazoles.
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http://dx.doi.org/10.1021/jo8018895 | DOI Listing |
Angew Chem Int Ed Engl
December 2024
School of Chemistry and Chemical Engineering, Northwestern Polytechnical University (NPU), Xi'an, 710072, China.
The cleavage of carbon-carbon bonds and their subsequent reassembly into highly functionalized and useful molecules in an atom-efficient manner has always been a central focus in the realm of organic synthesis. In this report, we describe the construction of highly functionalized naphthol esters via a tandem reassembly process, driven by Ullmann-type coupling of enaminones and 1,3-dicarbonyl compounds. Mechanistic investigations suggest the involvement of C(sp)-C(sp) coupling, cyclization, two acyl migrations, aromatization, and additional transformations within this tandem sequence.
View Article and Find Full Text PDFFood Res Int
November 2024
State Key Laboratory of Animal Nutrition and Feeding, Institute of Animal Sciences of Chinese Academy of Agricultural Sciences, Beijing 100193, China. Electronic address:
Livestock and poultry meat is one of the main consumption sources of fatty acids (FAs) in China. FAs are the main component of lipids and essential nutrients for the human body. The location of carbon-carbon double bond (CC) in unsaturated fatty acids (UFAs) significantly affects the nutrition and flavor quality of meat products.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.
The Suzuki-Miyaura biaryl cross-coupling is the pivotal technology for carbon-carbon coupling in pharmaceutical, polymer, and agrochemical fields. A long-standing challenge has been the development of efficient precursors for the decarbonylative cross-coupling of amide bonds. Herein, we report a highly chemoselective palladium-catalyzed Suzuki-Miyaura cross-coupling of -mesyl amides for the synthesis of biaryls by a tandem N-C(O)/C-C bond activation with high selectivity for decarbonylative cleavage.
View Article and Find Full Text PDFFood Chem
February 2025
Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation, East China University of Technology, 418 Guanglan Ave, Nanchang 330013, China. Electronic address:
The composition and ratio of unsaturated fatty acids in vegetable oils play a crucial role in determining their overall quality. In this study, we present a corona discharge ionization mass spectrometry (MS) method for the rapid differentiation of vegetable oil varieties and their geographical origins under environmental conditions. Abundant water dimer radical cations, (HO), were generated by the ionization setup, which effectively activated carbon‑carbon double bonds (C=C) to form epoxidized products.
View Article and Find Full Text PDFAnal Chem
November 2024
Department of Chemistry, National Taiwan University, Taipei, 10617, Taiwan.
The unsaturated lipids produced by human gut bacteria have an extraordinary range of structural diversity, largely because of the isomerism of the carbon-carbon double bond (C═C) in terms of its position and stereochemistry. Characterizing distinct C═C configurations poses a considerable challenge in research, primarily owing to limitations in current bioanalytical methodologies. This study developed a novel structural lipidomics workflow by combining MELDI (chloroperoxybenzoic acid epoxidation for lipid double-bond identification) with liquid chromatography-tandem mass spectrometry for C═C characterization.
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