Oxidation of 2- and 3-hydroxycarbazoles with Frémy's salt gave the corresponding ortho-carbazolequinones. These molecules react as carbodienophiles in Diels-Alder reaction with 1-acetoxy-1,3-butadiene and 1,3-cyclopentadiene to provide the novel benzocarbazolequinone structures 15, 16, 18 and 19.
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http://dx.doi.org/10.1248/cpb.52.1114 | DOI Listing |
Nat Commun
January 2025
College of Chemistry, Beijing Normal University, Beijing, 100875, P.R. China.
Developing donor-acceptor [n]cycloparaphenylenes (D-A [n]CPPs) with multiple emissions from different emissive states remains challenging yet crucial for achieving white-light emission in single-molecule. Here, we report our explorations into acceptor engineering of quinone-based D-A [10]CPPs (Nq/Aq/Tq[10]CPPs) via a post-lateral annulation using Diels-Alder reactions of oxTh[10]CPP. X-ray analysis reveals that Nq[10]CPP displays a side by side packing via naphthoquione stacking while Aq[10]CPP adopts an intercalated conformation through anthraquinone interaction.
View Article and Find Full Text PDFACS Omega
December 2024
Department of Chemistry, Humboldt Universität zu Berlin, Brook-Taylor-Str. 2, Berlin 12489, Germany.
In this study, we extended a previously developed one-pot double derivatization reaction to establish the first routine isotope-coded multiplex derivatization for vitamin D and its metabolites for application in clinical environments, using commercial reagents, without the need for specialized reagents and advanced synthesis requirements. The original derivatization process consisted of using both a Cookson-type reagent and derivatization of hydroxyl groups. Initially, the analytes are derivatized by a Diels-Alder reaction using 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), followed by acetylation using acetic anhydride, catalyzed by 4-dimethylaminopyridine at room temperature.
View Article and Find Full Text PDFBeilstein J Org Chem
December 2024
Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Universidad de Alcalá (IRYCIS), 28805 Madrid, Spain.
Asymmetric cycloaddition is a straightforward strategy which enables the synthesis of structurally distinct cyclic derivatives which are difficult to access by other methodologies, using an efficient and atom-economical path from simple precursors. In recent years several asymmetric catalytic cyclization strategies have been accomplished for the construction of -heterocycles using various catalytic systems such as chiral metal catalysts, chiral Lewis acids or chiral organocatalysts. This review presents an overview of the recent advances in enantioselective cyclization reactions of 1-azadienes catalyzed by non-covalent organocatalysts.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, and Chemical Biology Center, Peking University, 38 Xueyuan Road, Beijing 100191, China.
Molecules
November 2024
Catalyse Organométallique, Synthèse Organique et Santé (COSyS), Institut de Chimie (UMR-CNRS 7177), Université de Strasbourg, 67000 Strasbourg, France.
Due to the importance of biaryls as natural products, drugs, agrochemicals, dyes, or organic electronic materials, a green alternative biaryl synthesis has been developed based on easy-to-prepare and cheap copper(I)-exchanged zeolite catalysts. Cu-USY proved to efficiently catalyze the direct homocoupling of either phenols or aryl boronic acids under simple and practical conditions. The Cu-USY-catalyzed oxidative homocoupling of phenols could conveniently be performed under air either in warm methanol or water with good to high yields.
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