AI Article Synopsis
- Alkynyl amides are important in organic synthesis for creating bioactive compounds and heterocycles, but their synthesis often requires harsh conditions and expensive reagents.
- The study introduces a one-pot method for synthesizing alkyne bonds without using transition metals, relying instead on easily accessible feedstock chemicals like methyl esters and acetamides.
- This new approach is efficient, cost-effective, and can accommodate various functional groups, making it a sustainable option for producing a diverse array of alkynyl amides.
Article Abstract
Alkynyl amides play crucial roles in organic synthesis in the production of bioactive compounds and valuable heterocycles. Despite numerous studies on their synthesis, challenges persist due to the necessity of harsh or hazardous conditions and the use of costly or unstable reagents. Herein, we present a one-pot method for the synthesis of all three bonds of the alkyne under transition-metal-free conditions. An important feature of this chemistry is the use of readily available feedstock chemicals, such as methyl esters and acetamides. This approach offers efficient access to a wide range of aryl and alkyl alkynyl amides and demonstrates excellent tolerance towards various functional groups in a sustainable and cost-effective manner.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.202415472 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Enrichable Protein Footprinting for Structural Proteomics.
J Am Soc Mass Spectrom
December 2024
Center for Genomic Science Innovation, University of Wisconsin Madison, Madison, Wisconsin 53706, United States.
Protein footprinting is a useful method for studying protein higher order structure and conformational changes induced by interactions with various ligands via addition of covalent modifications onto the protein. Compared to other methods that provide single amino acid-level structural resolution, such as cryo-EM, X-ray diffraction, and NMR, mass spectrometry (MS)-based methods can be advantageous as they require lower protein amounts and purity. As with other MS-based proteomic methods, such as post-translational modification analysis, enrichment techniques have proven necessary for both optimal sensitivity and sequence coverage when analyzing highly complex proteomes.
View Article and Find Full Text PDFOne-Pot Transition-Metal-Free Synthesis of Alkynyl Amides.
Angew Chem Int Ed Engl
September 2024
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34 Street, Philadelphia, Pennsylvania 19104-6323, USA.
Article Synopsis
- Alkynyl amides are important in organic synthesis for creating bioactive compounds and heterocycles, but their synthesis often requires harsh conditions and expensive reagents.
- The study introduces a one-pot method for synthesizing alkyne bonds without using transition metals, relying instead on easily accessible feedstock chemicals like methyl esters and acetamides.
- This new approach is efficient, cost-effective, and can accommodate various functional groups, making it a sustainable option for producing a diverse array of alkynyl amides.
Cascade Reactions of Alkynyl Ketones and Amides to Generate Unsaturated Oxacycles and Aromatic Carbocycles.
Chemistry
November 2024
Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor St., Chicago, Illinois, 60607, USA.
We describe novel amine-mediated transformation of alkynyl ketones and amides to generate 2-methylene-2H-pyrans, substituted 3-hydroxy-9H-fluoren-9-ones, and amine-incorporated arenes. These cascade processes are initiated by conjugate addition of secondary amine followed by hydrolysis of the enamine/vinylogous amide intermediates. The product distribution is highly sensitive to the steric and electronic effects of the substituents on both the alkyne moieties, the tether structure connecting them, and the nature of the amine.
View Article and Find Full Text PDFβ-Silyl alkynoates: Versatile reagents for biocompatible and selective amide bond formation.
Sci Adv
September 2024
College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, China.
The study introduces a previously unidentified method for amide bond formation that addresses several limitations of conventional approaches. It uses the β-silyl alkynoate molecule, where the alkynyl group activates the ester for efficient amide formation, while the bulky TIPS (triisopropylsilane) group prevents unwanted 1,4-addition reactions. This approach exhibits high chemoselectivity for amines, making the method compatible with a wide range of substrates, including secondary amines, and targets the specific ε-amino group of lysine among the native amino ester's derivatives.
View Article and Find Full Text PDFMetal-free photoinduced generation and alkynylation of carbamoyl radicals: a facile synthesis of alkynyl amides.
Chem Commun (Camb)
August 2024
Xi'an Key Laboratory of Functional Organic Porous Materials, School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi'an, 710129, China.
A metal-free photoinduced alkynylation of carbamoyl radicals with hypervalent iodine(III) reagents for a facile synthesis of alkynyl amides is described. This protocol features good functional group tolerance and a broad substrate scope for direct synthesis of alkynyl amide derivatives in good to excellent yields under mild and redox-neutral reaction conditions. The synthetic application is demonstrated by the late-stage installation of alkynyl amides into natural products and active pharmaceutical relevant molecules.
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!