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Keywords = photoacylation

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11 pages, 2298 KB  
Article
Photochemical Acylation of 1,4-Naphthoquinone with Aldehydes Under Continuous-Flow Conditions
by Madyan A. Yaseen and Michael Oelgemöller
Organics 2025, 6(1), 9; https://doi.org/10.3390/org6010009 - 14 Feb 2025
Cited by 3 | Viewed by 2785
Abstract
A series of photoacylations of 1,4-naphthoquinone with various aldehydes and using Pyrex-filtered UVB light was conducted under continuous-flow conditions. Acetone served as a triplet photosensitizer and convenient solvent that kept all materials in solution and could be easily removed. The corresponding acylated 1,4-naphthohydroquinone [...] Read more.
A series of photoacylations of 1,4-naphthoquinone with various aldehydes and using Pyrex-filtered UVB light was conducted under continuous-flow conditions. Acetone served as a triplet photosensitizer and convenient solvent that kept all materials in solution and could be easily removed. The corresponding acylated 1,4-naphthohydroquinone photoproducts were obtained in acceptable to excellent yields of 30–90% with residence times of just 70 min. The photoacylation process was successfully coupled with in-line oxidation to obtain acylated 1,4-naphthoquinones. Full article
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10 pages, 333 KB  
Article
Synthesis of Acylated Naphthohydroquinones Through Photo-Friedel–Crafts Acylation and Evaluation of Their Antibiotic Potential
by Alexis Mercier, Alizée Monet, Madyan A. Yaseen, M. Iris Hermanns and Michael Oelgemöller
Photochem 2024, 4(4), 501-510; https://doi.org/10.3390/photochem4040031 - 5 Dec 2024
Cited by 1 | Viewed by 2246
Abstract
A variety of 1-(1,4-dihydroxynaphtalen-2-yl) ketones was synthesized using the photo-Friedel–Crafts acylation of 1,4-naphthoquinone with aldehydes. Subsequent oxidation using silver oxide readily furnished the corresponding 2-acylated 1,4 naphthoquinones. Notably, these naphthoquinone derivatives underwent spontaneous partial reduction upon storage. The synthesized compounds were subjected to [...] Read more.
A variety of 1-(1,4-dihydroxynaphtalen-2-yl) ketones was synthesized using the photo-Friedel–Crafts acylation of 1,4-naphthoquinone with aldehydes. Subsequent oxidation using silver oxide readily furnished the corresponding 2-acylated 1,4 naphthoquinones. Notably, these naphthoquinone derivatives underwent spontaneous partial reduction upon storage. The synthesized compounds were subjected to antimicrobial screening. High inhibition effects on Staphylococcus aureus were found for the majority of compounds, which makes them interesting for potential future medicinal applications. Full article
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5 pages, 63 KB  
Article
Quinones as Key Intermediates in Natural Products Synthesis. Syntheses of Bioactive Xanthones from Hypericum perforatum
by George A. Kraus and John Mengwasser
Molecules 2009, 14(8), 2857-2861; https://doi.org/10.3390/molecules14082857 - 3 Aug 2009
Cited by 17 | Viewed by 12054
Abstract
Two bioactive xanthones from Hypericum perforatum have been synthesized by direct routes. Benzo[c]xanthone 5 can be prepared from intermediate 4. Full article
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