Intramolecular Copper(I)-Catalyzed Interrupted Click/Acylation Domino Reaction.

08:00 EDT 12th July 2019 | BioPortfolio

Summary of "Intramolecular Copper(I)-Catalyzed Interrupted Click/Acylation Domino Reaction."

Acyl substituted triazoles are valuable scaffolds, but the direct synthesis of these moieties from terminal alkynes via copper catalysis remains unexplored. We report a robust, general and efficient method using a simple CuI/2,2'-bipyridine catalytic system. This transformation involves a copper catalyzed azide-alkyne cycloaddition (CuAAC) followed by an intramolecular acylation onto a carbamoyl chloride. The reaction proceeds under mild conditions, tolerates several functional groups and is readily scalable. This method represents a novel strategy towards the synthesis of complex heterocycles via a CuAAC/acylation domino process.


Journal Details

This article was published in the following journal.

Name: Angewandte Chemie (International ed. in English)
ISSN: 1521-3773


DeepDyve research library

PubMed Articles [6750 Associated PubMed Articles listed on BioPortfolio]

Nanopore-Based Strategy for Sensing of Copper(II) Ion and Real-Time Monitoring of a Click Reaction.

A straightforward yet efficient, nanopore-based strategy that enables the sensitive detection of copper(II) ion (Cu2+) and real-time monitoring of a click reaction is provided. Two single-stranded DNA...

Desymmetrization by Asymmetric Copper-Catalyzed Intramolecular C-H Insertion Reactions of α-Diazo-β-oxosulfones.

Effective desymmetrization in copper catalyzed intramolecular C-H insertion reactions of α-diazo-β-oxosulfones in the formation of fused thiopyran dioxides is described for the first time. The use o...

Chemo- and Diastereoselective Synthesis of N-Propargyl Oxazolidines through a Copper-Catalyzed Domino A3 Reaction.

Herein we describe a highly chemoselective A3-coupling/annulation of amino alcohols, formaldehyde, two kinds of aldehydes and alkynes, catalyzed by a copper(II). This cascade reaction, employing readi...

Rapid Construction of Fused Heteropolycyclic Aromatics via Palladium-Catalyzed Domino Arylations of Imidazopyridine Derivatives.

By using diaryliodonium salts, a novel approach of a palladium-catalyzed cascade of diarylation/intramolecular dehydrogenative coupling reaction has been developed in the synthesis of phenanthro-imida...

Click Chemistry for Cyclic Peptide Drug Design.

Click chemistry is a powerful tool in constraining peptides into their active conformations. This chapter presents recent advancements involving the use of copper-catalyzed [3 + 2] azide-alkyne cycl...

Clinical Trials [1235 Associated Clinical Trials listed on BioPortfolio]

A Phase Ib Study of Intravenous Copper Loading With Oral Disulfiram in Metastatic, Castration Resistant Prostate Cancer

The purpose of this study is to determine the safety and optimal dosing of intravenous copper chloride and disulfiram in men with metastatic castrate-resistant prostate cancer (CRPC). Elig...

Immediate vs. Delayed Insertion of Copper T 380A IUD After Termination of Pregnancy Over 12-Weeks Gestation

The purpose of this study is to compare delayed vs. immediate insertion of the Copper T 380 IUD after termination of pregnancy after 12 weeks.

Human Biomarkers for Assessing Copper Deficiency

Copper is an essential nutrient for humans and is cofactor in enzymes that participate in critical body functions. Insufficient copper can lead to hematological and neurological abnormali...

IMPACT STUDY: Investigating Microbial Pathogen Activity of Copper Textiles

The purpose of this study is to assess the impact of copper linens on hospital acquired infections and drug resistant bacteria.

A Controlled Study of Potential Therapeutic Effect of Oral Zinc in Manifesting Carriers of Wilson Disease

The assumption is that in some of the carriers, the increase in enzymes reflects tissue damage due to excess copper. The reduction of the amount of copper absorbed will decrease excess cop...

Medical and Biotech [MESH] Definitions

A photoprotein isolated from the bioluminescent jellyfish Aequorea. It emits visible light by an intramolecular reaction when a trace amount of calcium ion is added. The light-emitting moiety in the bioluminescence reaction is believed to be 2-amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine (AF-350).

A reaction characterized by a violet color upon the addition of copper sulfate to all compounds with two amide or peptide bonds linked directly or through an intermediate carbon atom. Used in the detection and estimation of proteins and peptides having more than two amino acids.

Organic chemistry methodology that mimics the modular nature of various biosynthetic processes. It uses highly reliable and selective reactions designed to "click" i.e., rapidly join small modular units together in high yield, without offensive byproducts. In combination with COMBINATORIAL CHEMISTRY TECHNIQUES, it is used for the synthesis of new compounds and combinatorial libraries.

Unstable isotopes of copper that decay or disintegrate emitting radiation. Cu atoms with atomic weights 58-62, 64, and 66-68 are radioactive copper isotopes.

P-type ATPases which transport copper ions across membranes in prokaryotic and eukaryotic cells. They possess a conserved CYSTEINE-HISTIDINE-SERINE (CPx) amino acid motif within their transmembrane helices that functions in cation translocation and catalytic activation, and an N-terminal copper-binding CxxC motif that regulates enzyme activity. They play essential roles in intracellular copper homeostasis through regulating the uptake, efflux and storage of copper ions, and in cuproprotein biosynthesis.

Quick Search


DeepDyve research library

Searches Linking to this Article