78593-40-5

Usage

Uses

Used in Organic Synthesis:
3-Ethynylquinoline is used as a precursor for the synthesis of functionalized organic molecules. Its unique structure allows for the creation of a variety of complex organic compounds, making it a valuable component in the development of new materials and chemical processes.
Used in Pharmaceutical Compounds:
In the pharmaceutical industry, 3-Ethynylquinoline is utilized as a starting material for the development of new drugs. Its ability to be modified and functionalized makes it a promising candidate for the creation of novel therapeutic agents.
Used in Medicinal Chemistry:
3-Ethynylquinoline has been studied for its potential biological activities, such as its role as an inhibitor of acetylcholinesterase, an enzyme involved in the breakdown of the neurotransmitter acetylcholine. This makes it a candidate for use in the development of treatments for neurological disorders and other conditions related to neurotransmitter imbalances.

Upstream product

• 5332-24-1 3-bromoquinoline 
• 4301-14-8 acetylenemagnesium bromide 
• 86521-08-6 3-((trimethylsilyl)ethynyl)-quinoline 
• 78625-06-6 2-methyl-4-(quinolin-3-yl)but-3-yn-2-ol 

Downstream Products

• 34846-64-5 3-cyanoquinoline 
• 1873-54-7 3-ethyl quinoline 
• 856412-57-2 [Pt(4'-(4-methylphenyl)-2,2':6',2''-terpyridine)(C_.ident.CC₉H₆N)]PF₆ 

Relevant academic research and scientific papers

Synthesis, characterization and palladium complex formation of pyridinium- and quinolinium-3-acetylides: Mesomeric betaines or betaine-stabilized carbenes?

3-Ethynyl-1-methylpyridinium- and 3-ethynyl-1-methyl-quinolinium triflates were prepared by methylation of 3-ethynylpyridine and 3-ethynylquinoline with methyl triflate, respectively. Whereas deprotonation of the former mentioned salt gave no stable produ

Dipolar Bent and Linear Acetylenes Substituted by Cationic Quinolinium and Anionic Benzoates. Formation of Mesomeric Betaines

3-Ethynylquinoline was subjected to a Sonogashira-Hagihara reaction with methyl 2-, 3-, and 4-bromobenzoates, respectively, and then N-methylated to give 3-[((methoxycarbonyl)phenyl)ethynyl]-1-methylquinolinium salts (two X-ray analyses). On saponification of the 3- and 4-substituted benzoates, the mesomeric betaines 3- and 4-[(1-methylquinolinium-3-yl)ethynyl]benzoates were formed. By contrast, the 2-benzoate derivative gave either the corresponding (1-oxo-1H-isochromen-3-yl)quinolinium derivative or the mesomeric betaine 2-(1-methylquinolinium-3-yl)-1,3-dioxo-2,3-dihydro-1H-inden-2-ide depending on the reaction conditions. A DFT calculation predicts a transoid conformation of the acetylene bond in the intermediate 2-[(1-methylquinolinium-3-yl)ethynyl]benzoate which is due to a strong hydrogen bond between the carboxylate group and 2H of the quinolinium ring, in addition to a 1,5-interaction between the carboxylate group and the CC triple bond. The bond angles of the transoid CC triple bond were calculated to be 211.6° and 175.1° in vacuo. The corresponding linear triple bond is 50.4 kJ/mol less stable in vacuo according to the calculation, and the N-heterocyclic carbene quinoline-2-ylidene is not formed as a tautomer.

Aryl Nitriles from Alkynes Using tert -Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage

Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. (Figure Presented).

Direct synthesis of α-trifluoromethyl ketone from (hetero)arylacetylene: Design, intermediate trapping, and mechanistic investigations

Regioselective addition across the alkynes has been achieved in a silver-catalyzed protocol utilizing Langlois reagent (CF3SO2Na) and molecular O2 to access medicinally active α-trifluoromethyl ketone compounds. This metho

Aerobic oxynitration of alkynes with tBuONO and TEMPO

An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.

Visible-light-induced synthesis of a variety of trifluoromethylated alkenes from potassium vinyltrifluoroborates by photoredox catalysis

A facile synthesis of trifluoromethylated alkenes by the radical-mediated trifluoromethylation of vinyltrifluoroborates has been developed. Togni's reagent serves as a CF3 radical precursor in the presence of the photoredox catalyst [Ru(bpy)3](PF6)2 under visible light irradiation. This new photocatalytic protocol can be applicable to a wide variety of vinylborates containing electronically diverse substituents and hetero-aromatics. The Royal Society of Chemistry 2013.

Gold-catalyzed oxazoles synthesis and their relevant antiproliferative activities

Nine 5-aryl-2-methyloxazole derivatives were synthesized via gold-catalyzed alkyne oxidation. All of the compounds have been screened for their antiproliferative activities against MCF-7 cell (human breast carcinoma), A549 cell (human lung carcinoma) and

K3PO4-KOH mixture as efficient reagent for the deprotection of 4-aryl-2-methyl-3-butyn-2-ols to terminal acetylenes

A mixture of potassium hydroxide and potassium phosphate was found to be an active reagent mixture for the cleavage of 2-hydroxypropyl-protected acetylenes. The reaction was performed in toluene at reflux temperature and gave terminal acetylenes in good to excellent yields within very short periods of time. Numerous other functional groups are tolerated. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for full experimental and spectral details.

Design and synthesis of O-GlcNAcase inhibitors via 'click chemistry' and biological evaluations

Protein O-GlcNAcylation has been shown to play an important role in a number of biological processes, including regulation of the cell cycle, DNA transcription and translation, signal transduction, and protein degradation. O-GlcNAcase (OGA) is responsible for the removal of O-linked β-N-acetylglucosamine (O-GlcNAc) from serine or threonine residues, and thus plays a key role in O-GlcNAc metabolism. Potent OGA inhibitors are useful tools for studying the cellular processes of O-GlcNAc, and may be developed as drugs for the treatment neurodegenerative diseases. In this study, Cu(I)-catalyzed 'Click' cycloaddition reactions between glycosyl azides and alkynes were exploited to generate inhibitory candidates of OGA. Enzymatic kinetic screening revealed that compound 7 was a potent competitive inhibitor of human O-GlcNAcase (Ki = 185.6 μM). Molecular docking simulations of compound 7 into CpOGA (Clostridium perfringens OGA) suggested that strong π-π stacking interaction between the compound and W490 considerably contributed to improving the inhibitory activity. Crown Copyright

Synthesis of 1-hetarylethylphosphonates

Previously unknown potentially biologically active diethyl 1-(pyridin-3-yl)-, 1-(quinolin-3-yl)-, and 1-(quinolin-6-yl)ethylphosphonates were synthesized by palladium-catalyzed reduction of the corresponding α,β-unsaturated precursors with ammonium formate. The reduction of diethyl 1-(quinolin-6-yl)ethenylphosphonate was accompanied by formation of diethyl 1-(1,2,3,4-tetrahydroquinolin-6-yl)ethylphosphonate as by-product.