A highly diastereoselective tandem reaction of 2'-nitrochalcones is reported, involving Michael addition and a subsequent -substitution of the nitro group to produce 1-tetralones with two contiguous chiral centers. A related annulation reaction of 2'-nitrochalcones with potassium cyanide affording 1-indanones with a C3-quaternary chiral center is also demonstrated.
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http://dx.doi.org/10.1021/acs.joc.3c00134 | DOI Listing |
Chemphyschem
January 2025
University of Vigo, Dept. of Physical Chemistry, Lagoas-Marcosende, 36310, Vigo, SPAIN.
The aromaticity of a representative sample of pro-aromatic radicals and its nitro, amino, hydroxyl and imine substituted derivatives has been analysed by means of multicentre delocalization indices (MCI) and nuclear-independent chemical shifts (NICS). Because of their radical character, these compounds may exhibit conflicting α/ß aromaticity, so that the contribution of α and β electrons to the MCI and NICS has been analysed separately and their values qualitatively interpreted in terms of the 2n+1/2n rule. All the monocyclic radicals investigated show conflicting α/β aromaticity.
View Article and Find Full Text PDFNat Chem
January 2025
CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China.
Nitroarenes are readily accessible bulk chemicals and can serve as versatile starting materials for a series of synthetic reactions. However, due to the inertness of the C-NO bond, the direct denitrative substitution reaction with unactivated nitroarenes remains challenging. Chemists rely on sequential reduction and diazotization followed by the Sandmeyer reaction or the nucleophilic aromatic substitution of activated nitroarenes to realize nitro group transformations.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo 162-0041, Japan.
Nitroarenes are highly versatile building blocks in organic synthesis, playing a pivotal role in various reactions. Common transformations involving nitroarenes include nucleophilic aromatic substitution (SAr) reactions, where the nitro group functions both as a potent electron-withdrawing group that activates the aromatic ring and as a leaving group facilitating the substitution. Additionally, the direct transformation of nitro groups, such as reduction-driven syntheses of amines and carboxylic acids, as well as -substitution SAr reactions, have been extensively explored.
View Article and Find Full Text PDFToxicol Res (Camb)
February 2025
Department of Bioinformatics, Bharathidasan University, Tiruchirappalli, Tamil Nadu 620024, India.
Sugar substitutes are mostly artificial, man-made industrial products used as additives in food and beverages. Most of these substances flow through the digestive tract and food chains, becoming emerging organic contaminants in various abiotic and biotic environmental media. Here, we predict the mutagenicity and carcinogenicity of commonly used sugar substitutes using in silico based methods.
View Article and Find Full Text PDFRSC Adv
January 2025
Department of Chemistry, University of Kurdistan P. O. Box 66135-416 Sanandaj Iran +98 873324133 +98 8733624133.
Synthesis of 5-substituted 1-tetrazoles and reduction of a variety of nitro compounds presents a promising solution for the pharmaceutical and agricultural industries. However, the development of green catalysts with superior catalytic performance for this reaction remains a significant challenge. This research introduces a green protocol for the creation of ultrafine Cu(ii) metal immobilized on the surface of pectin hydrogel (HPEC), modified by a CoFeO/Pr-SOH magnetic nanocomposite, enabling the synthesis of tetrazoles and reduction of nitro compounds.
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