AI Article Synopsis
- The Passerini three-component reaction was modified to use alcohols instead of aldehydes.
- This reaction involved mixing alcohols, isocyanides, and carboxylic acids in toluene with a catalyst including cupric chloride, NaNO2, and TEMPO.
- Conducting the reaction under an oxygen atmosphere resulted in good yields of the P-3CR adducts.
Article Abstract
Alcohols instead of aldehydes were used in the Passerini three-component reaction under catalytic aerobic conditions. Mixing alcohols, isocyanides, and carboxylic acids in toluene in the presence of a catalytic amount of cupric chloride, NaNO(2), and TEMPO afforded, under an oxygen atmosphere, the P-3CR adducts in good yields.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol100012y | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Dual functionalization of carboxymethyl cellulose and alginate via Passerini three-component reaction to graft two hydrophobic moieties: Toward modular thin films.
Carbohydr Polym
March 2025
Université Claude Bernard Lyon 1, INSA Lyon, Université Jean Monnet, CNRS UMR 5223, Ingénierie des Matériaux Polymères, F-69621 Cédex, France. Electronic address:
Passerini reaction was advantageously exploited to hydrophobize carboxymethyl cellulose (CMC) and alginates (ALG) by employing various hydrophobic aldehydes and isocyanides. The Passerini reaction, carried out in ecofriendly conditions, allowed to design never described twofold hydrophobized polysaccharide derivatives via the covalent grafting of two hydrophobic moieties. The modified CMC and ALG products were in-depth characterized to guaranty the success of the modification and to calculate the degrees of substitution (DS).
View Article and Find Full Text PDFHigh Molecular Weight Uniform Polymers Encoding Octal Sequences by Passerini Iterative Exponential Growth.
J Am Chem Soc
January 2025
Department of Chemistry, Seoul National University, Seoul 08826, Korea.
Sequence-defined polymers composed of a large pool of chemically distinct monomers (SDPs) have been pursued to achieve the structural and functional precisions exhibited by biopolymers in nonbiological environments. In contrast to the incremental growth of SDPs by sequential addition of individual monomers, the iterative exponential growth (IEG) method allows the synthesis of high molecular-weight SDPs, but their sequences have been composed mostly of binary monomers. Consequently, achieving high molecular-weight SDPs built with a large pool of monomers remains a challenge.
View Article and Find Full Text PDFMystery of the Passerini Reaction for the Synthesis of the Antimicrobial Peptidomimetics against Nosocomial Pathogenic Bacteria.
Int J Mol Sci
July 2024
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
The first example of applying salicylaldehyde derivatives, as well as coumarin with the formyl group at the C8 position in its structure, as carbonyl partners in a three-component Passerini reaction, is presented. As a result of research on the conditions of the Passerini reaction, the important role of the hydroxyl group in the salicylaldehyde used in the course of the multicomponent reaction was revealed. When an aldehyde with an unprotected hydroxyl group is used, only two-component α-hydroxy amide products are obtained.
View Article and Find Full Text PDFInsight into the hydrophobic functionalization of cellulose microfibrils using the Passerini three-component reaction.
Carbohydr Polym
October 2024
Univ. Grenoble Alpes, CNRS, CERMAV, F-38000 Grenoble, France. Electronic address:
The aqueous catalyst-free one-pot Passerini 3-component reaction (P-3CR) was employed for the functionalization of dialdehyde cellulose (DAC) derived from the periodate oxidation of microfibrillated cellulose (MFC) with insights provided by C and N CP-MAS NMR and FTIR analyses. The kinetics of the P-3CR revealed rapid progress within the initial 2 h, reaching a plateau between 6 and 18 h. The reaction achieved a maximum degree of substitution (DS) with only 1 equivalent of carboxylic acid and isocyanide with respect to the number of aldehydes, therefore demonstrating the atom economy character of the P-3CR performed on MFC.
View Article and Find Full Text PDFInnovative synthesis of drug-like molecules using tetrazole as core building blocks.
Beilstein J Org Chem
April 2024
Department of Drug Design, University of Groningen, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands.
Tetrazole is widely utilized as a bioisostere for carboxylic acid in the field of medicinal chemistry and drug development, enhancing the drug-like characteristics of various molecules. Typically, tetrazoles are introduced from their nitrile precursors through late-stage functionalization. In this work, we propose a novel strategy involving the use of diversely protected, unprecedented tetrazole aldehydes as building blocks.
View Article and Find Full Text PDFWant 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!