75163-16-5

Upstream product

• 2213-63-0 2,3-dichloroquinoxaline 
• 536-74-3 phenylacetylene 
• 95-54-5 1,2-diamino-benzene 
• 15804-19-0 quinoxaline-2,3-dione 
• 2579-22-8 Phenylpropargyl aldehyde 
• 75163-23-4 2-(2-phenylethynyl)quinoxaline 
• 91-19-0 2,3-diethynylquinoxaline 
• 6142-95-6 phenylpropargyl aldehyde diethyl acetal 
• 180967-67-3 1,6-diphenyl-hexa-1,5-diyne-3,4-dione 

Downstream Products

• 75163-40-5 2,3-Bis-((E)-2-phenyl-2-piperidin-1-yl-vinyl)-quinoxaline 
• 75163-39-2 2,3-Bis-((E)-2-morpholin-4-yl-2-phenyl-vinyl)-quinoxaline 
• 75163-41-6 2,3-Bis-[(E)-2-(4-methyl-piperazin-1-yl)-2-phenyl-vinyl]-quinoxaline 
• 75163-69-8 2,13-Diphenyl-dipyrido[1,2-a;2',1'-c]quinoxaline-4,11-dione 
• 75163-76-7 2,3-bis(2-hydroxy-2-phenylvinyl)-3-methylquinoxaline 
• 75163-36-9 Ethyl-{(E)-2-[3-((E)-2-ethylamino-2-phenyl-vinyl)-quinoxalin-2-yl]-1-phenyl-vinyl}-amine 
• 75163-37-0 Methyl-{(E)-2-[3-((E)-2-methylamino-2-phenyl-vinyl)-quinoxalin-2-yl]-1-phenyl-vinyl}-amine 
• 1416917-53-7 (Z)-3-iodo-1-(iodo(phenyl)methylene)-2-phenyl-1H-cyclopenta[b]quinoxaline 
• 1416917-51-5 (Z)-3-bromo-1-(bromo(phenyl)methylene)-2-phenyl-1H-cyclopenta[b]quinoxaline 
• 1416917-59-3 2,3-bis((Z)-2-bromo-2-phenylvinyl)quinoxaline 
• 1416917-58-2 (1,1-dibromo-2-phenyl-1H-cyclopenta[b]quinoxalin-3-yl)(phenyl)methanone 
• 1416917-54-8 (Z)-1-(chloro(phenyl)methylene)-3-iodo-2-phenyl-1H-cyclopenta[b]quinoxaline 
• 1416917-55-9 (E)-1-(chloro(phenyl)methylene)-3-iodo-2-phenyl-1H-cyclopenta[b]quinoxaline 
• 1352810-12-8 (Z)-2-(1-phenyl-2-(3-(phenylethynyl)quinoxalin-2(1H)-ylidene)ethylidene)malononitrile 

Relevant academic research and scientific papers

An unconventional route to an ambipolar azaheterocycle and itsin situgenerated radical anion

Herein we report the synthesis, characterization and application of an azaheterocycle4obtainedviaan unprecedented C-N coupling. The neutral azaheterocycle undergoes one-electron reduction to form an air-stable radical anionin situ, which provides added benefit towards operational stability of the device during n-type charge transport. The unusual stability of this radical anion is due to the fact that the fused cyclopentane ring upon reduction forms aromatic cyclopentadienyl anion, and the negative charge delocalizes over the nearly planar azaheterocycle core. The present azaheterocycle can be considered as a mimic of a fullerene fragment, which shows balanced ambipolar charge transport in space charge limited current (SCLC) devices with moderate hole (μh) and electron (μe) mobilities (μh= 2.96 × 10?3cm2V?1s?1andμe= 1.11 × 10?4cm2V?1s?1). Theoretical studies such as nucleus independent chemical shifts (NICS) calculations, anisotropy of the induced current density (ACID) plots, spin density mapping and anisotropic mobility calculations were performed to corroborate the experimental findings.

N-Heterocycle-Fused Pentalenes by a Gold-Catalyzed Annulation of Diethynyl-Quinoxalines and -Phenazines

The gold-catalyzed annulation of diethynyl N-heterocycles for the synthesis of quinoxaline-/phenazine-based pentalenes and the study of their optoelectronic properties are described. The inhibition of the gold catalyst by the nitrogen centers in the subst

Regioselective 6-endo-dig iodocyclization: An accessible approach for iodo-benzo [a] phenazines

A facile approach for the synthesis of substituted iodo-benzo[a]phenazines from 2-aryl-3-(aryl/alkylethynyl)quinoxalines via 6-endo-dig ring closure has been described under mild reaction conditions. Iodocyclization proceeds through the iodonium ion intermediate followed by nucleophilic cyclization with the C-H bond of the arene. Furthermore, the resulting 6-iodo-5-aryl/alkyl benzo[a]phenazine derivatives allowed for structural diversification by employing various coupling reactions. The structure of iodo-benzo[a]phenazine was confirmed by X-ray crystallographic studies of the compound.

Regioselective 5-endo-dig Electrophilic Iodocyclization of Enediynes: A Convenient Route to Iodo-substituted Indenes and Cyclopenta-Fused Arenes

An efficient iodine-mediated regioselective tandem approach for the synthesis of symmetric and asymmetric iodo-substituted indenes and stereoselective cyclopenta [b]pyridine/thiophenes from easily accessible enediynes that proceeds by in situ formation of an iodonium intermediate followed by a regioselective 5-endo-dig cyclization has been described. The intramolecular electrophilic iodocyclization was selectively triggered by a distribution of electronic density along the alkyne bond. Subsequently, the iodo-substituted indenes were diversified by employing palladium-catalyzed cross-coupling reactions and the coupled products were further confirmed by X-ray crystallographic studies.

Pyrrolo[2,3-b]quinoxalines as inhibitors of firefly luciferase: Their Cu-mediated synthesis and evaluation as false positives in a reporter gene assay

2-Substituted pyrrolo[2,3-b]quinoxalines having free NH were prepared directly from 3-alkynyl-2-chloroquinoxalines in a single pot by using readily available and inexpensive methane sulfonamide (or p-toluene sulfonamide) as an ammonia surrogate. The reaction proceeded in the presence of Cu(OAc)2 affording the desired product in moderate yield. The crystal structure analysis of a representative compound and its supramolecular interactions are presented. Some of the compounds synthesized exhibited inhibitory activities against luciferase that was supported by the predictive binding mode of these compounds with luciferase enzyme through molecular docking studies. The key observations disclosed here can alert users of luciferase reporter gene assays for possible false positive results due to the direct inhibition of luciferase.

A novel tandem cyclization of condensed 2,3-dialkynylpyrazines into [1,2,3]triazolo[1′,5′;1,2]pyrido[3,4-b]pyrazines promoted by sodium azide

6,7-Dialkynyl-1,3-dimethylpteridine-2,4(1H,3H)-diones and 2,3-dialkynylquinoxalines have been shown to react with sodium azide in DMF at room temperature giving rise 9,11-dimethyl-[1,2,3]triazolo[1′,5′;1,2]pyrido[4,3-g]pteridine-8,10(9H,11H)-diones and [1

Direct introduction of acetylene moieties into azines by SNH methodology

The N-oxides of azines 1a-g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a-g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place.

One-step synthesis of dialkynyl-1,2-diones and their conversion to fused pyrazines bearing enediyne units

A convenient procedure for the preparation of symmetrically end-protected dialkynyl-1,2-diones 3 from lithium acetylides and oxalyl chloride in the presence of CuBr and LiBr is described. The condensation of 3 with various aromatic and heteroaromatic 1,2-diamines leads to pyrazine-based α-dialkynylated heterocycles. The enediyne substructure of diethynylquinoxaline can be thermally rearranged in a Bergman cyclization reaction.

Alkynyl- and Dialkynyl-quinoxalines. Synthesis of Condensed Quinoxalines

Condensation of 2-chloro- and 2,3-dichloroquinoxalines with alk-1-ynes in the presence of bis(triphenylphosphine)palladium(II) dichloride and copper(I) iodide gives mono- and di-alkynylquinoxalines.Addition of amines to these products gives stable enamines; hydration gives 2'-oxoalkyl compounds which exist predominantly in the intramolecularly hydrogen-bonded enol form.Condensation of the alkynylquinoxalines with diethyl sodiomalonate, and related compounds, yields pyridoquinoxalin-4-one derivatives. 2-Alkynyl-3-chloroquinoxalines are intermediates for convenient syntheses of pyrroloquinoxalines.