An efficient cascade reaction involving sulfonylation and [2 + 3]-cycloaddition reactions of -dibromoalkenes with arylsulfonyl methyl isocyanides was described for the synthesis of 3-aryl-2,4-disulfonyl-1-pyrroles. The main highlight of this study is the introduction of a new dual-functional reactivity of arylsulfonyl methyl isocyanides as the sulfonyl source as well as a 1,3-dipolar reagent in the same reaction. This system is facilitated by CsCO mediation in DMSO and 100 °C conditions.
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http://dx.doi.org/10.1039/d0ra10451e | DOI Listing |
J Org Chem
October 2024
Department of Chemistry, School of Natural Sciences, Shiv Nadar Institution of Eminence Deemed to be University, Dadri, Chithera, Gautam Buddha Nagar, UP 201314, India.
Herein, we report an expedient synthesis of aryl sulfonyl ureas and from -amino pyridinium ylides and aryl isocyanates. -Aminopyridinium ylides are synthesized via blue light-emitting diode irradiation of pyridine/isoquinoline and appropriate iminoiodinanes. The strategy involved a hitherto unknown carboamination of imine moieties (of aryl isocyanates) via a three-component reaction of pyridine derivatives/isoquinoline , -aryl sulfonyl iminoiodinanes , and numerous aryl isocyanates at room temperature in 2-methyl tetrahydrofuran to afford the target compounds in moderate to excellent yields.
View Article and Find Full Text PDFACS Omega
September 2022
Department of Agricultural, Food and Nutritional Science, Faculty of Agricultural, Life and Environmental Sciences, University of Alberta, Edmonton, Alberta T6G 2R3, Canada.
Herein, a series of -1-sulfonyl substituted derivatives of 2-substituted benzimidazoles (-) were designed and synthesized via structural tailoring of the acceptor part of donor-π-acceptor schemes, and their nonlinear optic (NLO) characteristics were reported. The structures of - were investigated and their characterization was accomplished by employing spectroscopic procedures, ., UV-vis, FT-IR, and H and C NMR.
View Article and Find Full Text PDFChem Sci
June 2022
Department of Cellular and Molecular Pharmacology, University of California San Francisco San Francisco CA 94158 USA
Chemical probes for chromatin reader proteins are valuable tools for investigating epigenetic regulatory mechanisms and evaluating whether the target of interest holds therapeutic potential. Developing potent inhibitors for the plant homeodomain (PHD) family of methylation readers remains a difficult task due to the charged, shallow and extended nature of the histone binding site that precludes effective engagement of conventional small molecules. Herein, we describe the development of novel proximity-reactive cyclopeptide inhibitors for PHD3-a trimethyllysine reader domain of histone demethylase KDM5A.
View Article and Find Full Text PDFRSC Adv
April 2021
Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University Chandigarh - 160014 India
A series of 2,4-aryl-4-((arylsulfonyl)methyl)-4-benzo[][1,3]oxazines in good to excellent yields have directly been obtained from -(2-vinylphenyl)amides and thiols by employing a mixture of KSO-activated charcoal in aqueous acetonitrile solution at 50 °C. A plausible mechanism for the reaction is reported. It reveals that the reaction follows a radical pathway and the persulfate has been the oxygen source for formation of the sulfone group in the products.
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April 2021
Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University Vanak Tehran 1993893973 Iran
An efficient cascade reaction involving sulfonylation and [2 + 3]-cycloaddition reactions of -dibromoalkenes with arylsulfonyl methyl isocyanides was described for the synthesis of 3-aryl-2,4-disulfonyl-1-pyrroles. The main highlight of this study is the introduction of a new dual-functional reactivity of arylsulfonyl methyl isocyanides as the sulfonyl source as well as a 1,3-dipolar reagent in the same reaction. This system is facilitated by CsCO mediation in DMSO and 100 °C conditions.
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