An unprecedented protocol has been developed for the regioselective synthesis of structurally diverse indene derivatives from readily accessible N-benzylic sulfonamides and disubstituted alkynes through FeCl(3)-catalyzed cleavage of sp(3) carbon-nitrogen bonds to generate benzyl cation intermediates. In the presence of 10 mol % of FeCl(3), a broad range of N-benzylic sulfonamides smoothly react with internal alkynes, alkynylcarbonyl compounds, alkynyl chalcogenides, or alkynyl halides to afford various functionalized indene derivatives with extremely high regioselectivity.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol101524w | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
The Impact of Ligand Structure and Reaction Temperature on Ethenolysis of Fatty Acid Methyl Esters Catalyzed by Spirocyclic Alkyl Amino Carbene Ru Complexes.
ChemSusChem
January 2025
Lomonosov Moscow State University: Moskovskij gosudarstvennyj universitet imeni M V Lomonosova, Department of Chemistry, Leninskie Gory, 1-3, 119991, Moscow, RUSSIAN FEDERATION.
Spirocyclic alkyl amino carbene (SCAAC) Ru complexes demonstrate outstanding activity and selectivity in ethenolysis of methyl oleate (MO) or fatty acid methyl esters (FAMEs), and 5,6-dimethoxyindane derivative was the most active catalyst to date. For the further catalyst design, we proposed modifying the spirocyclic fragment by fusion of saturated carbo- or heterocycle, linked to the 5,6-positions of indane or 6,7- positions of tetralin. Another suggested way of the modification of SCAAC complex was the insertion of chromane fragment to the carbene ligand.
View Article and Find Full Text PDFBracken Fern Carcinogen, Ptaquiloside, Forms a Guanine -Adduct in DNA.
J Agric Food Chem
January 2025
Centre for Chemical Biology, Department of Chemistry, Institute for Nucleic Acids, University of Sheffield, Brook Hill, Sheffield S3 7HF, U.K.
Bracken fern ( sp.) is a viable and vigorous plant with invasive potential, ingestion of which causes chronic illness and cancers in farm animals. Bracken is a suspected human carcinogen, and exposure can result from ingestion of bracken-contaminated water, dairy products, or meat derived from livestock grazing on bracken fern.
View Article and Find Full Text PDFPhosphine Oxide Indenoquinoline Derivatives: Synthesis and Biological Evaluation as Topoisomerase I Inhibitors and Antiproliferative Agents.
Molecules
December 2024
Departamento de Química Orgánica I, Facultad de Farmacia and Centro de Investigación Lascaray (Lascaray Research Center), Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), Paseo de la Universidad 7, 01006 Vitoria-Gasteiz, Spain.
The synthesis of phosphorous indenoquinolines and their biological evaluation as topoisomerase 1 (TOP1) inhibitors and antiproliferative agents were performed. First, the preparation of new hybrid 5-indeno[2,1-]quinolines with a phosphine oxide group was performed by a two-step Povarov-type [4+2]-cycloaddition reaction between the corresponding phosphorated aldimines with indene in the presence of BF·EtO. Subsequent oxidation of the methylene present in the structure resulted in the corresponding indeno[2,1-]quinolin-7-one phosphine oxides .
View Article and Find Full Text PDFSelective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes.
ChemistryOpen
December 2024
MTA TTK Lendület Artificial Transporter Research Group, Institute of Materials and Environmental Chemistry, HUN-REN Research Center for Natural Sciences, H-1117, Budapest, Magyar tudósok krt. 2, Hungary.
Novel tetrahydroisoquinoline and piperidine derivatives were selectively synthesized from substituted indenes or cyclopentenes. The process starts with an oxidative cleavage of the ring olefin bond, which gives reactive diformyl intermediates. By a ring-closing step using chiral (R) or (S) α-methylbenzylamine under a reductive amination protocol facilitated ring formation with ring expansion of the corresponding nitrogen-containing heterocycles.
View Article and Find Full Text PDFNovel approach to alleviate lupus nephritis: targeting the NLRP3 inflammasome in CD8CD69CD103 T cells.
J Transl Med
December 2024
Department of Rheumatology, The First Affiliated Hospital, Sun Yat-sen University, 58 Zhongshan Second Road, Guangzhou, 510080, P. R. China.
Background: Renal CD8 tissue-resident memory T (T) cells display prolonged survival and activity in lupus nephritis (LN), exacerbating renal pathology. NLRP3 regulates the T cell response. This study explored the impact of NLRP3 inflammasome activity on the regulatory functions of T cells in LN.
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!