A novel photocatalytic protocol for effective and efficient synthesis of cyclic 1,5-diketones containing chroman-4-one skeletons in moderate to good yields radical cascade acylmethylation/cyclization of 2-(allyloxy)arylaldehydes with α-bromo ketones has been described. This reaction features a broad substrate scope, good functional group tolerance, and metal- and oxidant-free conditions. An acylmethyl radical-triggered cascade cyclization was involved.
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http://dx.doi.org/10.1039/d3ob01101a | DOI Listing |
ACS Cent Sci
January 2025
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.
Multicomponent reactions (MCRs), highly sought-after methods to produce atom-, step-, and energy-economic organic syntheses, have been developed extensively. However, catalytic asymmetric MCRs, especially those involving radical species, remain largely unexplored owing to the difficulty in stereoselectively regulating the extraordinarily high reactivity of open-shell radical species. Herein, we report a conceptually novel catalytic asymmetric three-component radical cascade reaction of readily accessible glycine esters, α-bromo carbonyl compounds and 2-vinylcyclopropyl ketones via synergistic photoredox/Brønsted acid catalysis, in which three sequential C-C (σ/π/σ) bond-forming events occurred through a radical addition/ring-opening/radical-radical coupling protocol, affording an array of valuable enantioenriched unnatural α-amino acid derivatives bearing two contiguous stereogenic centers and an alkene moiety in moderate to good yield with high diastereoselectivity, excellent enantioselectivity and good -dominated geometry under mild reaction conditions.
View Article and Find Full Text PDFChem Asian J
January 2025
Nanjing University, School of Chemistry and Chemical Engineering, CHINA.
A novel and efficient strategy for the direct synthesis of 3-arylthioquinoline derivatives via radical induced tandem cyclization of propargylamines with diaryl disulfides was developed. This protocol undergoes a cascade sulfuration/ cyclization/ oxidation/ aromatization pathway to afford the desired products in a broad substrate scope using readily available starting materials under mild conditions. Based on this strategy, we further modified 3-arylquinolines to obtain two novel deep blue fluorescent molecules, QLSCz and QLSTCz, with good optical properties through two-step synthesis by oxidation and electron donor modification.
View Article and Find Full Text PDFJ Colloid Interface Sci
January 2025
State Key Laboratory of Medicinal Chemical Biology, Tianjin Key Laboratory of Biosensing and Molecular Recognition, Research Center for Analytical Sciences, College of Chemistry, Nankai University, Tianjin 300071 China; National Chromatographic Research and Analysis Center, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 China.
Macrophages have emerged as promising cellular vehicles for the delivery of therapeutic agents to tumor sites. However, the cytotoxicity of therapeutic agents toward the cellular carriers and the effective release of therapeutic agents at the tumor site remain the main challenges faced by macrophage-mediated drug delivery systems. Herein, a near-infrared (NIR)-triggered release of self-accelerating cascade nanoreactor (HCFG) delivered by macrophages (HCFG@R) was developed for synergistic tumor photothermal therapy (PTT)/starvation therapy (ST)/chemodynamic therapy (CDT).
View Article and Find Full Text PDFMolecules
January 2025
Preclinical Department, Faculty of Medicine & Defence Health, Universiti Pertahanan Nasional Malaysia, Kuala Lumpur 57000, Malaysia.
2-phenylchromen-4-one, commonly known as flavone, plays multifaceted roles in biological response that can be abundantly present in natural sources. The methoxy group in naturally occurring flavones promotes cytotoxic activity in various cancer cell lines by targeting protein markers, in facilitating ligand-protein binding mechanisms and activating cascading downstream signaling pathways leading to cell death. However, the lipophilic nature of these analogs is a key concern as it impacts drug membrane transfer.
View Article and Find Full Text PDFJ Org Chem
January 2025
College of Chemistry and Chemical Engineering, Green Catalysis & Synthesis Key Laboratory of Xinyang City, Xinyang Normal University, Xinyang 464000, China.
A novel and efficient method for the intermolecular hydroxysulfonylation of vinylarenes using sodium sulfinates has been achieved through aerobic copper catalysis. This transformation proceeded smoothly with green air as the terminal oxidant in the presence of Cu (I)/1,10-phenanthroline as an efficient catalytic system, leading to an array of β-hydroxysulfones in moderate to high yields. The significant advantages of this protocol are the mild reaction conditions, readily available starting materials, good functional-group compatibility, synthetic convenience, and practicability.
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