Herein, we report the synthesis of -sulfonyl formamidines from carbon tetrabromide and formamide under UVA irradiation without any additional catalysts. This approach represents a straightforward methodology for accessing this class of structural units and has been applied to a wide range of readily available sulfonamides and formamides, providing the corresponding products in moderate to excellent yields (30 examples, 16-99% yields). Mechanistic investigations associated with previous reports suggest the implication of an activated iminium intermediate (Vilsmeier-Haack reagent derivatives), obtained by the photoinduced reaction between carbon tetrabromide and formamides.
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http://dx.doi.org/10.1021/acs.joc.4c02160 | DOI Listing |
Org Biomol Chem
January 2025
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037, China.
Recent advancements in C-S bond formation electron donor-acceptor (EDA) complex photoactivation have been remarkable. EDA complexes, which are composed of electron donors and acceptors, facilitate C-S bond construction under mild conditions through single-electron transfer events upon visible light irradiation. This review highlights the utilization of various sulfur-containing substrates, including diacetoxybenzenesulfonyl (DABSO), sulfonic acids, sodium sulfinates, sulfonyl chlorides, and thiophenols, in EDA-promoted sulfonylation and thiolation reactions, covering the works published since 2017 to date.
View Article and Find Full Text PDFSci Rep
January 2025
Department of Pesticide Chemistry, National Research Centre, Dokki, 12622, Giza, Egypt.
Chemoprevention is one of the accessible strategies for preventing, delaying or reversing cancer processing utilizing chemical intervention of carcinogenesis. NAD(P)H quinone oxidoreductase 1 (NQO1) is a xenobiotic metabolizing cytosolic enzyme/protein with important functional properties towards oxidation stress, supporting its ability in detoxification/chemoprotective role. A set of 3,5-diylidene-4-piperidones (as curcumin mimics) bearing alkyl sulfonyl group were synthesized with potential NQO1 induction properties.
View Article and Find Full Text PDFArch Biochem Biophys
January 2025
Department of Biosciences Grand Asian University of Sialkot, Pakistan.
Acyl thiourea scaffolds are frequently employed in drug development to discern unique and essential therapies for the eradication of the most challenging diseases. Hence, we developed a library of novel cyclopropyl incorporating acyl thiourea derivatives (4a-j) and evaluated their antimicrobial, α-amylase, and proteinase K inhibition potential. Compound (4h) (4-methoxy) demonstrated the strongest α-amylase inhibition (IC = 1.
View Article and Find Full Text PDFMini Rev Med Chem
January 2025
Department of Physiology and Pharmacology Vittorio Erspamer, Sapienza University of Rome, 00161, Rome, Italy.
Currently, the synthesis of bioactive sulfonamides using amino acid as a starting reagent has become an area of research interest in organic chemistry. Over the years, an amine-sulfonyl chloride reaction has been adopted as a common step in traditional sulfonamide synthetic methods. However, recent developments have shown amino acids to be better precursors than amines in the synthesis of sulfonamides.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
A concise and convergent synthesis of the isosteroidal alkaloids veratramine and 20--veratramine has been accomplished. A Horner-Wadsworth-Emmons olefination joins two chiral building blocks of approximately equal complexity and a transition-metal catalyzed intramolecular Diels-Alder cycloaddition-aromatization cascade constructs the tetrasubstituted arene. Other key steps include a highly diastereoselective crotylation of an -sulfonyl iminium ion and an Eschenmoser fragmentation.
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