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The synthesis of neopetrosins A and C, two 2-indolyl -α-d-mannopyranosides, and their congeners has been realized via a direct Ni/photoredox-catalyzed reductive coupling of 3-methoxycarbonyl-2-iodo-1-indoles with pyranosyl bromides.
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http://dx.doi.org/10.1021/acs.orglett.3c02601 | DOI Listing |
J Org Chem
August 2025
CNRS, Institut des Sciences Chimiques de Rennes (ISCR), University of Rennes, UMR 6226, F-35000 Rennes, France.
Herein, a novel synthesis of different indolopyrido-quinazolinones by the reaction of easily accessible 2-indolyl quinazolinone with propargylic alcohols has been developed. This [4 + 2] annulation proceeds through sequential acid-catalyzed C-propargylation and base-promoted -annulation by forming C-C and C-N bonds in a one-pot operation. Interestingly, the reagent-controlled regiodivergent annulations were observed leading to diversely fused N1-C2 or C2-N3 indolopyrido-quinazolinones.
View Article and Find Full Text PDFOrg Biomol Chem
June 2025
College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, P. R. China.
A base-promoted synthesis of α-(2-indolyl) ketones (or 2-(α-aryl benzyl ketone) indoles) is developed 5- cyclization of 2-alkynylanilines, followed by aroylation of the resulting carbanion. This transition metal-free reaction proceeded with high regioselectivity and a wide substrate scope (46 examples, up to 93% yield). Among the syntheses of 2-substituted indoles, this tandem process is straightforward and convenient.
View Article and Find Full Text PDFChem Biol Interact
July 2025
Laboratory of Chemical Biology, Department of Studies in Organic Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, India. Electronic address:
While 2-Indolyl-1,3,4-oxadiazole derivatives are recognized for their antibacterial properties, their potential as anticancer agents remains underexplored. This study investigates the anti-breast cancer properties of a novel 2-Indolyl-1,3,4-oxadiazole compound, 5l, focusing on its ability to induce apoptosis, paraptosis, and autophagy, and targeting poly (ADP-ribose) polymerase (PARP1), a critical enzyme in DNA repair. A series of 1,3,4-oxadiazole derivatives (compounds 5a-5m) were synthesized using an optimized multi-step process, enhancing reaction efficiency and yield.
View Article and Find Full Text PDFRSC Adv
March 2025
College of Chemical Engineering, Qingdao University of Science and Technology Qingdao 266042 China.
Nickel complexes of chiral spiroBox ligand catalyzed Friedel-Crafts alkylation reaction of indoles with nitroalkenes. Excellent yields (up to 99%) and enantiomeric excess (ee) values (up to 97%) were obtained with a broad scope of substrates. This catalytic system provides a facile synthesis of optically active 2-indolyl-1-nitro derivatives with high yield and enantioselectivity.
View Article and Find Full Text PDFMolecules
December 2024
Institut für Pharmazeutische und Medizinische Chemie, Universität Münster, Corrensstraße 48, D-48149 Münster, Germany.