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Selenium dioxide-mediated one-pot oxidative annulation of sulfonyl -hydroxyacetophenones with acetophenones generates good yields of aurone analogs in refluxing dioxane under dry air atmosphere conditions. A plausible mechanism is proposed and discussed here. In the overall reaction process, selenium-containing compounds were generated as byproducts. Various oxidant-promoted conditions were also investigated for one-pot annulation.
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http://dx.doi.org/10.1039/d5ob00989h | DOI Listing |
Org Biomol Chem
July 2025
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Selenium dioxide-mediated one-pot oxidative annulation of sulfonyl -hydroxyacetophenones with acetophenones generates good yields of aurone analogs in refluxing dioxane under dry air atmosphere conditions. A plausible mechanism is proposed and discussed here. In the overall reaction process, selenium-containing compounds were generated as byproducts.
View Article and Find Full Text PDFACS Omega
October 2021
Department of Chemistry, North-Eastern Hill University, Shillong, Meghalaya 793022, India.
An efficient method for the synthesis of α,β-unsaturated α'-bromoketones and α,β-unsaturated α',α'-dibromoketones is described using -bromosuccinimide (NBS) as the brominating agent mediated by selenium dioxide (SeO) in the presence of -toluenesulfonic acid (PTSA) monohydrate in toluene. The method is simple, employing easily available shelf reagents to afford a wide range of products in good yields. The method highlighted that simple fine-tuning of the reaction conditions and molar equivalents of the reactants easily affords either mono- or dibrominated products in excellent yields.
View Article and Find Full Text PDFTetrahedron Lett
August 2012
Department of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA.
A facile and expeditious synthetic approach to α-ketoamides 3 is described. A series of α-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation.
View Article and Find Full Text PDFJ Am Chem Soc
June 2002
Division of Medicinal and Natural Products Chemistry, College of Pharmacy, The University of Iowa, Iowa City, Iowa 52242, USA.
The highly potent anticancer natural saponin OSW-1 has been successfully synthesized from commercially available 5-androsten-3beta-ol-17-one 79 in 10 operations with 28% overall yield. The key steps in the total synthesis included a highly regio- and stereoselective selenium dioxide-mediated allylic oxidation of 80 and a highly stereoselective 1,4-addition of alpha-alkoxy vinyl cuprates 68 to steroid 17(20)-en-16-one 12E to introduce the steroid side chain. This total synthesis demonstrated once again the versatile synthetic applications of alpha-halo vinyl ether chemistry developed in our laboratories.
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