Regioselective facile one-pot synthesis of 16 different sugar-based quinoline, naphthyridine, and xanthone derivatives is reported. The compounds are characterized by NMR spectroscopy and elemental analysis. The beta-Anomeric form of the sugar moiety was identified from (1)H NMR studies. Antimicrobial studies of these sugar-heterocyclic derivatives, 3a, 3b, 3f, 5c, 7a, 7b, and 7c show excellent activity against different microbes.
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http://dx.doi.org/10.1016/j.carres.2010.07.016 | DOI Listing |
Chem Commun (Camb)
January 2025
School of Chemistry & Material Science, Northwest University, 1st Xuefu Avenue, Xi'an, Shaanxi 710127, China.
C(sp)-H bond nitration provides facile access to nitro compounds that are inaccessible through traditional nitration pathways. This work describes a C(sp)-H bond nitration of aryl alkenes using DNDMH, a nitration reagent developed previously in our lab. Notably, this novel nitration process presents excellent regioselectivity and chemoselectivity between C(sp)-H nitration and C(sp)-H nitration.
View Article and Find Full Text PDFOrg Lett
January 2025
Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou, Guangdong 511436, China.
Presented herein is a nickel-catalyzed chemo- and regioselective three-component tandem carboamination and cyclization of terminal alkynes with organoboronic acids and anthranils for facile and modular access to 2,3-substituted quinolines. In this process, anthranil has dual roles: serving as an electrophilic aminating reagent and a redox buffer to suppress the generation of an off-cycle Ni(0) complex. Moreover, the anionic acetylacetonate (acac) ligand was found to be vital to ensure a productive Ni(I)-Ni(III)-Ni(I) catalytic cycle.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, Uttarakhand, India.
Ni(II)-hydrazineylpyridine (Ni(II)-PyH)-catalyzed regioselective synthesis of α-benzyl substituted β-hydroxy ketones from α,β-unsaturated ketones and alcohols is reported a Fenton free-radical reaction. This protocol enables facile access to desired products in good to excellent yields in 12 h using toluene solvent at room temperature to 100 °C. The structural analysis of the products was confirmed by H, C-NMR, GC-MS, and HRMS data.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.
The direct synthesis of C(sp)-rich architectures is a driving force for innovation in synthetic organic chemistry. Such scaffolds impart beneficial properties onto drug molecules that correlate with greater clinical success. Consequently, there is a strong impetus to develop new methods by which to access sp-rich molecules from commercial feedstocks, such as alkenes.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.
By leveraging the fast oxidative addition of arylthianthrenium salts (aryl-TT) to palladium(0), a regioselective diazoester installation has been developed. This approach enables the introduction of a diazo moiety to densely functionalized arenes at a late stage. The installed diazo group is amenable to facile further derivatization.
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