Herein, we describe acridine-based SNS-Ru pincer-catalysed unprecedented dehydrogenative annulation of alcohols with 2'-aminoacetophenone to synthesize 2,3-disubstituted-4-quinolones. The developed protocol was utilized with a wide range of alcohols with various aminoacetophenones. To expand the synthetic utility, 4-quinolones with antibiotic properties were synthesized and various important post-synthetic modifications of the synthesized scaffolds were performed. Various control experiments were performed to understand the mechanism, which showed that -alkylation has the edge over -alkylation and referred to the possibility of alkenylation to branched ketones.
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http://dx.doi.org/10.1039/d3cc02426a | DOI Listing |
Dalton Trans
December 2024
Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, c/Maria Aurèlia Capmany 69, 17003 Girona, Catalonia, Spain.
The oxalamide skeleton is a common structural motif in many biologically active molecules. These scaffolds can be synthesized ruthenium pincer complex-catalyzed acceptorless dehydrogenative coupling of ethylene glycol and amines. In this study, we elucidate the mechanism of this oxalamide synthesis using density functional theory calculations.
View Article and Find Full Text PDFOrg Lett
November 2024
Key Laboratory of Green Chemistry & Technology, Ministry of Education College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.
Described herein is the synthesis of 2-pyrazolines via acceptorless dehydrogenative coupling of allylic alcohols with hydrazines based on a Ru(CO)/NHC-phosphine-phosphine ligand catalytic system. The reaction not only exhibits low catalyst loading (only 0.3 mol %), wide substrate scope, good to excellent yields, and high selectivity but also omits the use of sacrificial hydrogen acceptor with only H and HO as byproducts, making the reaction green and atom-economical.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
Developing plastics that fill the need of polyolefins yet are more easily recyclable is a critical need to address the plastic waste crisis. However, most efforts in this vein have focused on high-density polyethylene (PE), while many different types of PE exist. To create broadly sustainable PE with modular properties, we present the synthesis, characterization, and demonstration of materials applications for chemically recyclable PE-like multiblock polymers prepared from distinct hard and soft blocks using ruthenium-catalyzed dehydrogenative polymerization.
View Article and Find Full Text PDFOrg Lett
July 2024
School of Environmental and Chemical Engineering, Wuyi University, Jiangmen, Guangdong 529020, People's Republic of China.
Selective dehydrogenative C-H silylation is one of the most powerful tools to synthesize silacycles. Herein, we developed Ru-catalyzed sequential hydrosilylation/C-H silylation of allyl-indoles and dehydrogenative O-H/C-H silylation of pyrrole phenols. Both six-membered indole silacycles and pyrrole silyl ether cycles were successfully synthesized with good functional group tolerance.
View Article and Find Full Text PDFJ Org Chem
December 2023
School of Chemical Sciences, National Institute of Science Education and Research (NISER), An OCC of Homi Bhabha National Institute, Bhubaneswar 752050, India.
A simple catalytic method for self-coupling of secondary alcohols leading to the synthesis of β-branched ketones under mild conditions is reported. Well-defined ruthenium pincer complex catalyzed the reactions. Optimization studies revealed that sodium -butoxide is an appropriate base for this transformation.
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