Direct synthesis of 4-benzo[][1,3]dioxin-4-one derivatives from salicylic acids and acetylenic esters (both mono- and disubstituted) has been described. The reaction is mediated by CuI and NaHCO in acetonitrile. Room temperature amidation of the synthesized 1,3-benzodioxinones with primary amines readily afforded the corresponding salicylamides in moderate to good yields.
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http://dx.doi.org/10.1039/d1ra05032j | DOI Listing |
Genes (Basel)
November 2024
College of Horticulture, Fujian Agriculture and Forestry University, Fuzhou 350002, China.
Background: Lipoxygenases (LOXs) are key enzymes in the unsaturated fatty acid oxidation reaction pathway and play an important regulatory role in the synthesis of fruit aroma volatiles.
Methods: gene family members were identified in the whole genome database of bitter gourd and analyzed bioinformatically. An RT-qPCR was used to analyze the expression differences in different tissues.
J Org Chem
January 2025
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Herein, we report a gold(I)-catalyzed cascade cyclization of azido-alkynes bearing an enol ester moiety, leading to indole-fused eight-membered rings. This method allows for the one-step construction of indole and tetrahydroazocin-4-one via an α-imino gold carbene intermediate. The resulting scaffold would be useful for accessing natural products with an eight-membered ring-fused indole moiety.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, University of Washington, Seattle, Washington 98195, United States.
Hydroalkylation of terminal alkynes is a powerful approach to the synthesis of disubstituted alkenes. However, its application is largely unexplored in the synthesis of α,β-unsaturated carbonyls, which are common among synthetic intermediates and biologically active molecules. The thermodynamically less stable -isomers of activated alkenes have been particularly challenging to access because of their propensity for isomerization and the paucity of reliable -selective hydroalkylation methods.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, China.
The direct enantioselective functionalization of C(sp)-H bonds in organic molecules could fundamentally transform the synthesis of chiral molecules. In particular, the enantioselective oxidation of these bonds would dramatically change the production methods of chiral alcohols and esters, which are prevalent in natural products, pharmaceuticals, and fine chemicals. Remarkable advances have been made in the enantioselective construction of carbon-carbon and carbon-nitrogen bonds through the C(sp)-H bond functionalization.
View Article and Find Full Text PDFChemistry
December 2024
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, China.
Pd-catalyzed alkoxycarbonylation of internal alkynes provides a straightforward access to α,β-disubstituted acrylic esters. Compared with the well-established regioselective alkoxycarbonylation of terminal alkynes, the regioselective hydrocarboxylation of non-functionalized unsymmetric internal alkynes was more challenging owing to the delicate differences of properties between the two substituents. Herein, by using either monophosphine ligand based on 2,3-dihydrobenzo[d][1,3]oxaphosphole motif or bidentate ligand Ph-Phox, the regioselective alkoxycarbonylations of aryl-aryl, aryl-alkyl and alkyl-alkyl disubstituted alkynes were achieved, giving a diversity of trisubstituted α,β-unsaturated carboxylic esters with moderate to excellent yields and high regioselectivity.
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