The -functionalized indole is a privileged structural framework in a wide range of bioactive molecules. The nucleophilic addition between indoles with vinylene carbonate proceeded smoothly in the presence of KCO as the catalyst to produce novel indolyl-containing skeletons and 4-indolyl-1,3-dioxolanones in satisfactory to excellent yields (up to >97% yield). Various synthetically useful functional groups, such as halogen atoms, cyano, nitro, and methoxycarbonyl groups, remained intact during the regioselective -H addition reactions. The developed catalytic system also could accommodate 2-naphthalenol to achieve the target O-H additive product in good yield.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10649246PMC
http://dx.doi.org/10.3390/molecules28217450DOI Listing

Publication Analysis

Top Keywords

nucleophilic addition
8
indoles vinylene
8
vinylene carbonate
8
base-catalyzed nucleophilic
4
addition reaction
4
reaction indoles
4
carbonate approach
4
approach synthesize
4
synthesize 4-indolyl-13-dioxolanones
4
4-indolyl-13-dioxolanones -functionalized
4

Similar Publications

In this study, CO reacted with a curing agent through nucleophilic addition to form ammonium salts, enabling the stable capture and internal release of CO, which achieved gas-phase nucleation and foaming. Additionally, the introduction of wave-absorbing agents improved the absorption mechanism and promoted uniform foaming. This nucleation-free foaming process relies on the induced growth of gas nuclei and the synergistic effect of the wave-absorbing agents, effectively preventing the uneven foaming issues caused by traditional nucleating agents.

View Article and Find Full Text PDF
Article Synopsis
  • A new method for C-H functionalization of heteroaryl compounds is introduced, which involves a process called dearomative addition followed by hydrogen autotransfer.
  • This process starts with the hydroruthenation of dienes to create allylruthenium nucleophiles, leading to branched C-C coupling products through addition and β-hydride elimination.
  • The study also details the formation of enantiomerically enriched heteroarylethyl alcohols and amines through oxidative cleavage and dynamic kinetic asymmetric reduction, supported by density functional theory calculations linking regioselectivities to molecular factors.
View Article and Find Full Text PDF

Aim: There is an urgent need for new antimicrobial compounds with alternative modes of action for the treatment of drug-resistant bacterial and fungal pathogens.

Background: Carbohydrates and their derivatives are essential for biochemical and medicinal research because of their efficacy in the synthesis of biologically active drugs.

Objective: In the present study, a series of methyl α-D-mannopyranoside (MMP) derivatives (2-6) were prepared via direct acylation, and their biological properties were characterized.

View Article and Find Full Text PDF

Reactivity of Imidazole- and Pyridine-Carboxaldehydes for Gem-Diol and Hemiacetal Generation: Theoretical and Experimental Insights.

ChemistryOpen

January 2025

Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Department of Chemistry, Ciudad Autónoma de Buenos Aires, 1113, Argentina.

Gem-diols are defined as organic molecules carrying two hydroxyl groups at the same carbon atom, which is the result of the nucleophilic addition of water to a carbonyl group. In this work, the generation of the hydrated or hemiacetal forms using pyridine- and imidazole-carboxaldehyde isomers in different chemical environments was studied by Nuclear Magnetic Resonance (NMR) recorded in different media and combined with theoretical calculations. The change in the position of aldehyde group in either the pyridine or the imidazole ring had a clear effect in the course of the hydration/hemiacetal generation reaction, which was favored in protic solvents mainly in the presence of methanol.

View Article and Find Full Text PDF

A Stable Solid-Electrolyte Interphase Constructed by a Nucleophilic Molecule Additive for the Zn Anode with High Utilization and Efficiency.

ACS Appl Mater Interfaces

January 2025

College of Energy, Soochow Institute for Energy and Materials Innovations, Light Industry Institute of Electrochemical Power Sources, Key Laboratory of Advanced Carbon Materials and Wearable Energy Technologies of Jiangsu Province, Soochow University, Suzhou, Jiangsu 215006, China.

The solid-electrolyte interphase (SEI) strongly determines the stability and reversibility of aqueous Zn-ion batteries (AZIBs). In traditional electrolytes, the nonuniform SEI layer induced by severe parasitic reactions, such as the hydrogen evolution reaction (HER), will exacerbate the side reactions on Zn anodes, thus leading to low zinc utilization ratios (ZURs). Herein, we propose to use methoxy ethylamine (MOEA) as a nucleophilic additive, which has a stronger nucleophilic characteristic than water, with the advantage of an abundance of nucleophilic atoms.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!