This study aimed to develop a novel protocol for the synthesis of 2-pyrrolo[1,2-]imidazol-7(3)-ones (PIDOs) from heterocyclic ketene aminals (HKAs) through an unprecedented cascade reaction by refluxing. Consequently, a series of PIDOs was produced through an amazing oxidative dimerization, followed by sequential cleavage of the C-N and C-C bonds in dimeric HKAs. This formation of PIDOs was accompanied by the formation and cleavage of many bonds. This method is suitable for the parallel construction of bicyclic pyrrolidone-like products.
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http://dx.doi.org/10.1021/acs.orglett.0c02689 | DOI Listing |
ACS Omega
January 2025
Departamento de Física - Instituto de Ciências Exatas - ICEx, Universidade Federal Fluminense, Volta Redonda, Rio de janeiro 27213-145,Brazil.
Ketene dithioacetals have significant applications in various fields, including natural products, pharmaceuticals, agrochemicals, and corrosion inhibitors. These compounds are highly valued for their reactivity and ability to participate in a wide range of organic syntheses. In this context, the reaction between 1,3-diaminopropan-2-ol and 1,1-bismethylsulfanyl-2-nitroethylene has been studied experimentally and theoretically by using density functional theory (DFT) calculations.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Department of Colloid Chemistry, Max Planck Institute of Colloids and Interfaces, 14476, Potsdam, Germany.
The development of versatile strategies for preparing functional carbon materials is essential for advancing a wide range of applications in materials science. Precursor design plays a pivotal role in governing the chemistry and structure of carbon materials for target applications. In this work, we report the synthesis of Meldrum's acid derivatives through Knoevenagel condensation with aromatic heterocycles such as pyrrole, furan, and thiophene, which serve as precursors for carbonaceous materials with tailored chemical and electronic properties.
View Article and Find Full Text PDFJ Org Chem
September 2024
Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. China.
Herein, a visible-light-promoted radical cascade cyclization of heterocyclic ketene aminals (HKAs) and thiocyanates was developed to access functionalized fused 2-iminothiazolines. This novel cascade reaction can be realized under only visible-light irradiation without the help of external photocatalysts, oxidants, and additives. These multicomponent cascade reactions demonstrate excellent selectivity for the -isomers and ensure the formation of the products only in their isomeric form.
View Article and Find Full Text PDFOrg Lett
August 2024
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China.
We developed a protocol for the synthesis of highly functionalized 5,6-dihydro-imidazo[1,2-][1,2,3]triazole derivatives - (DHITs) from 1-diazonaphthalen-2(1)-one derivatives with heterocyclic ketene aminals (HKAs). This strategy involved cycloaddition and skeletal rearrangement entailing the heating of a mixture of substrates with HKAs - and THF without any catalyst. As a result, a series of DHITs - were produced by cleaving one bond (1 C═N bond) and forming three bonds (1 N-N and 2 C-N bonds) in a single step.
View Article and Find Full Text PDFChem Biol Drug Des
July 2024
Departamento de Química, Instituto de Ciências Exatas, Universidade Federal Fluminense, Rio de Janeiro, Brazil.
N-heterocyclic compounds are important molecular scaffolds in the search for new drugs, since most drugs contain heterocyclic moieties in their molecular structure, and some of these classes of heterocycles are able to provide ligands for two or more biological targets. Ketene dithioacetals are important building blocks in organic synthesis and are widely used in the synthesis of N-heterocyclic compounds. In this work, we used double vinylic substitution reactions on ketene dithioacetals to synthesize a small library of heterocyclic derivatives and evaluated their cytotoxic activity in breast and ovarian cancer cells, identifying two benzoxazoles with good potency and selectivity.
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