40353-41-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
2-(2-Thienyl)quinoxaline is utilized as a building block in the synthesis of pharmaceuticals and agrochemicals due to its unique structural features and potential to contribute to the development of novel therapeutic agents and crop protection products.
Used in Optoelectronic Devices:
Leveraging its intriguing photophysical properties, 2-(2-Thienyl)quinoxaline is employed in the development of organic light-emitting diodes (OLEDs) and other optoelectronic devices, where its ability to emit light upon electrical stimulation is harnessed for various applications, including displays and lighting.
Used in Anticancer Applications:
2-(2-Thienyl)quinoxaline has been investigated for its potential as an anticancer agent, showing promise in targeting and inhibiting the growth of cancer cells. Its specific mechanisms of action and efficacy against various types of cancer are areas of ongoing research.
Used in Antimicrobial Applications:
As an antimicrobial agent, 2-(2-Thienyl)quinoxaline is studied for its ability to combat microbial infections, including bacteria and fungi, offering a potential alternative or supplement to existing antimicrobial treatments.

InChI:InChI=1/C12H8N2S/c1-2-5-10-9(4-1)13-8-11(14-10)12-6-3-7-15-12/h1-8H

Upstream product

• 128694-37-1 2-oxo-2-(thiophen-2-yl)acetaldehyde oxime 
• 95-54-5 1,2-diamino-benzene 
• 81321-96-2 1,2-Dihydro-2-(2-thienyl)chinoxalin 
• 81322-00-1 1,2,3,4-Tetrahydro-2,3-di(3-thienyl)chinoxalin 
• 1448-87-9 2-chloroquinoxaline 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 98-03-3 thiophene-2-carbaldehyde 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 1074-12-0 phenylglyoxal hydrate 
• 872-55-9 2-ethylthiophene 
• 15690-25-2 3-(2-thienyl)acrylic acid 
• 188290-36-0 thiophene 
• 91-19-0 2,3-diethynylquinoxaline 
• 4298-52-6 2-ethynyl-thiophene 

Downstream Products

• 175135-75-8 2-(5-bromothiophen-2-yl)quinoxaline 

Relevant academic research and scientific papers

Transition Metal-Free Heteroarylation of Quinoxaline: Construction of Heteroaryl-Fused Phenazines by Oxidative Coupling

A concise method for the construction of heteroaryl-fused phenazines was developed via PIFA-BF3·Et2O-mediated oxidative coupling of di-heteroarylated quinoxalines for the first time. Synthesis of mono- and di-heteroarylation of quinoxaline was performed effectively using only LiTMP reagent under transition metal-free conditions and without the use of halogen-containing starting compounds. In addition, nonsymmetrical di-heteroarylated quinoxalines were synthesized through reheteroarylation of mono-heteroarylated quinoxalines in the same way. Oxidation of the saturated compounds formed after heteroarylation was easily accomplished with iodine. The UV-vis absorption and fluorescence features of some compounds were examined.

Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water

Sulfoxonium ylides as safe carbene precursors are described for iridium-catalyzed carbene insertions and annulation, providing a facile and green approach to access a variety of quinoxaline derivatives in water. This water-mediated method also allows the preparation of β-keto thioethers under mild condition.

Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls

2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.

Iridium-Catalyzed [4+2] Annulations of β-Keto Sulfoxonium Ylides and o-Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives

A synthetic method for quinoxaline derivatives from the [4+2] annulation of β-keto sulfoxonium ylides and o-phenylenediamine by using (Cp*IrCl2)2 catalyst is described. This novel protocol features mild reaction conditions, moderate to excellent yields, wide substrate scope, and high functional-group compatibility. Moreover, this cyclization strategy was successfully applied in late-stage modification for structurally complex bioactive compounds.

Synthesis and characterization of linear 1,4-diazine-triphenylamine–based selective chemosensors for recognition of nitroaromatic compounds and aliphatic amines

Novel 1,4-diazine-based dyes of the D–π–A type, possessing triphenylamine as an electron-donating group, have been developed. Fluorescence studies have demonstrated that emission of these fluorophores is sensitive towards different nitroaromatic compounds and aliphatic amines, both in solutions and in a vapor phase. Moreover, these compounds can be considered as “naked-eye” fluorescent probes for solution polarity because they possess pronounced solvatochromic properties. Therefore, these compounds have to be regarded as potential multifunctional chemosensors for monitoring hazardous organic substances.

(DPEPhos)Ni(mesityl)Br: An Air-Stable Pre-Catalyst for Challenging Suzuki-Miyaura Cross-Couplings Leading to Unsymmetrical Biheteroaryls

The successful application of (DPEPhos)Ni(mesityl)Br (C1) as a pre-catalyst in the Suzuki-Miyaura cross-coupling of heteroaryl chlorides or bromides and heteroaryl boronic acids is reported. The use of C1 in this context allows for such reactions to be conducted under mild conditions (2 mol% Ni, 25 °C), including cross-couplings leading to unsymmetrical biheteroaryls. Successful transformations of this type involving problematic pyridinyl boronic acid substrates (10 mol% Ni, 60 °C) are also described.

Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones

Valuable and direct aerobic oxidation reactions of 2-hydroxyacetophenones were explored. The concept was based on the in situ treatment of small quantities of aerobically formed α-keto aldehydes that drove the reactions to the corresponding products. This new strategy was applied for a variety of oxidative reactions of 2-hydroxyacetophenones, and valuable products such as phthalides, quinoxalines, and α-keto amides were obtained in good to high yields.

Copper-catalyzed aerobic oxidative coupling of o-phenylenediamines with 2-aryl/heteroarylethylamines: direct access to construct quinoxalines

A copper-catalyzed oxidative coupling reaction of o-phenylenediamines with 2-aryl/heteroarylethylamines using molecular oxygen as an oxidant has been developed. This approach provides a practical and direct access to construct quinoxalines in excellent yields at room temperature. The reaction has a broad substrate scope and exhibits excellent functional-group tolerance. This method could be easily scaled up and applied to the synthesis of biologically active molecules bearing a quinoxaline structural scaffold.

Copper-Catalyzed Cascade Cycloamination of α-Csp3-H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines

A copper-catalyzed cycloamination of α-Csp3-H bond of N-aryl ketimines with sodium azide has been developed. This methodology provides an efficient access to quinoxalines and features mild reaction conditions and readily available ketimines with diverse functional group tolerance.

Elemental sulfur mediated synthesis of benzoxazoles, benzothiazoles and quinoxalines: Via decarboxylative coupling of 2-hydroxy/mercapto/amino-anilines with cinnamic acids

An easy and practical method has been developed for the synthesis of 2-benzylbenzoxazoles and 2-benzylbenzothiazoles using sulfur mediated decarboxylative coupling of cinnamic acids with 2-hydroxyanilines and 2-mercaptoanilines respectively under metal- and solvent-free conditions. However, the reaction of 2-aminoanilines with cinnamic acids leads to the formation of 2-arylquinoxalines under the same set of reaction conditions. The transformation is versatile and compatible with a number of functional groups.