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Although the transition-metal-catalyzed [3+2] cycloadditions to access isoxazoles have been described well, organocatalytic methods remain underdeveloped. Herein, we report the use of an organophosphine catalyst for the preparation of a series of isoxazoles with exceptional regioselectivity via the [3+2] cycloaddition of -hydroxyamides and alkynes. The scope of this organocatalytic transformation is broad, tolerating numerous functional groups and proceeding uniformly in an environmentally friendly, simple, and efficient manner.
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http://dx.doi.org/10.1021/acs.orglett.4c02852 | DOI Listing |
Eur J Pharm Sci
September 2025
Department of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary. Electronic address:
Platinum-group metal half-sandwich complexes are considered to be potential replacements of the clinically widely used platins which have several side effects and tend to cause resistance to develop. In our previous works, we used a range of 2-pyridyl-substituted N- and C-glycosyl heterocycles as N,N-chelating ligands to prepare ruthenium(II), osmium(II), iridium(III) and rhodium(III) polyhapto arene/arenyl half-sandwich complexes. Some of these complexes, particularly with the C-glucopyranosyl isoxazole derived ligand in its O-perbenzoylated form, exhibited greater anticancer efficiency than cisplatin and had minimal or negligible effects on non-transformed fibroblasts.
View Article and Find Full Text PDFJ Colloid Interface Sci
September 2025
School of Chemistry and Chemical Engineering, Guangdong Provincial Key Lab of Green Chemical Product Technology, South China University of Technology, Guangzhou 510640, China. Electronic address:
Fluorine (F)-doped carbon materials (FCMs) were one-pot synthesized and applied as the catalysts for the cycloaddition of carbon dioxide (CO) towards the cyclic carbonate for the first time. In this process, F dopants and oxygen (O)-containing groups on the carbon surface played a key role in enhancing the activity. The FCM synthesized at 500 °C (FCM-500) with 5.
View Article and Find Full Text PDFChem Biodivers
September 2025
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University Sub Campus, Dharashiv, India.
The present study aims to develop novel antimalarial and antimicrobial agents by synthesizing a series of 25 triazolyl quinoline carboxylate derivatives via azide-alkyne 1,3-dipolar cycloaddition, starting from isatin and p-fluoroacetophenone. Structural characterization was performed using IR, H NMR, C NMR, and mass spectrometry. The synthesized hybrids were evaluated for their in vitro antimalarial activity against the chloroquine-sensitive Plasmodium falciparum 3D7 strain.
View Article and Find Full Text PDFJ Org Chem
September 2025
Institute of Integrated Science and Technology, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan.
An efficient method for the enantio- and diastereoselective synthesis of tricyclic γ-butyrolactones bearing three quaternary stereocenters has been developed through transformations of achiral alkenoic acid substrates. The target optically active tricyclic lactones were obtained as single diastereomers with good enantioselectivities through a sequence of catalytic asymmetric bromolactonization, azidation, and subsequent 1,3-dipolar cycloaddition. The origin of the complete diastereoselectivity observed in the formation of the tricyclic γ-butyrolactone products was elucidated in this study.
View Article and Find Full Text PDFInorg Chem
September 2025
Institute of Inorganic Chemistry of Czech Academy of Sciences, Husinec-Řež 1001, 250 68, Czech Republic.
We report the synthesis and reactivity of phenylpyridine-based boron azides readily accessible via nucleophilic substitution from generated borenium-type precursors. Three azides were obtained: a hydridic species (L)BHN (L = 2-phenylpyridine), a cyclopentyl-substituted analogue (L)B(cyclopentyl)N, and a boron diazide (L)B(N) obtained as a byproduct from the synthesis of (L)BHN. The prepared borane azides exhibit notable thermal and photochemical robustness, with decomposition temperatures around 140 °C in mesitylene solution and above 170 °C in the solid state, as evidenced by DSC/TGA analysis.
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