500891-76-9

Upstream product

• 536-74-3 phenylacetylene 
• 5021-43-2 2-phenylquinoxaline 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 2213-63-0 2,3-dichloroquinoxaline 
• 75163-15-4 2-chloro-3-(phenylethynyl)quinoxaline 
• 98-80-6 phenylboronic acid 
• 70-11-1 α-bromoacetophenone 
• 127388-13-0 1,4-diphenyl-3-butyne-1,2-dione 
• 95-54-5 1,2-diamino-benzene 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 582-24-1 1-phenyl-2-hydroxyethanone 

Downstream Products

• 113057-92-4 5-phenylbenzo[a]phenazine 

Relevant academic research and scientific papers

A alkynyl dione compound and its synthesis method

The invention discloses a synthetic method of an alkynyl diketone compound which is shown in a formula (II). The synthetic method comprises the following step: in methylbenzene, at 90 DEG C, carrying out a reaction to obtain the alkynyl diketone compound by using alpha hydroxy-ketone and terminal alkyne as reaction raw materials and oxygen as an oxidizing agent under the effect of a copper catalyst. The synthetic method provided by the invention has the advantages that the reaction is efficient and the yield is high; oxygen is used as the oxidizing agent; the reaction condition is mild and no strong acids or strong bases are needed; cheap metals are used for catalyzing; reaction substrates are easy to prepare; amplified reaction can be further achieved.

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.

Palladium-Catalyzed Intramolecular Fujiwara-Hydroarylation: Synthesis of Benzo[a]phenazines Derivatives

An atom-economical Pd-catalyzed approach for the synthesis of benzophenazine derivatives using substituted 2-aryl-3-(aryl/alkylethynyl) quinoxaline in the presence of trifluoroacetic acid at 65 °C has been described. The chemistry involves in situ generation of cationic Pd(II) species, which functionalized the aromatic C-H bonds via electrophilic metalation followed by concomitant intramolecular trans-insertion of C-C triple bond to aryl-Pd complex. The results were supported by various control experiments including with electron-deficient arenes and deuterium labeling studies. The deuterium labeling studies supports electrophilic palladation of aromatic C-H over activation of C-C triple bond of alkyne. The structure of synthesized compounds was further confirmed by X-ray crystallography studies. This catalytic protocol has been efficiently applied for novel synthesis of highly functionalized benzo fused phenazines.

Nucleophilic substitution on 2-monosubstituted quinoxalines giving 2,3-disubstituted quinoxalines: Investigating the effect of the 2-Substituent

An investigation on the effect of substituent at the 2-position of mono-substituted quinoxalines in the synthesis of di-substituted quinoxaline derivatives via nucleophilic substitution reactions, is reported. Di-substituted quinoxalines bearing aryl-Alky

Coordinated assembly of a new 3D mesoporous Fe3O4@Cu2O-graphene oxide framework as a highly efficient and reusable catalyst for the synthesis of quinoxalines

A new three-dimensional (3D) mesoporous hybrid framework was synthesized by coordinated layer-by-layer assembly between nanosheets of reduced graphene oxide and Fe3O4@Cu2O. This 3D mesoporous framework shows an excellent c

Lewis acid catalyzed C-N bond formation: Synthesis of quinoxalines via CuX (X = Cl, Br, I) catalyzed cyclotrimerization of alkynes with o-phenylendiamines

An efficient one-pot cycloisomerization reaction has been developed for the synthesis of quinoxaline derivatives from alkynes and o-phenylendiamines using CuX (X = Cl, Br, I) as a catalyst. This method provides a flexible and rapid route to synthesize qui

Oxidative coupling of terminal alkyne with α-hydroxy ketone: An expedient approach toward ynediones

An efficient and mild copper-catalyzed one-pot approach toward ynediones has been established. A variety of ynediones were constructed directly through oxidative coupling of alkyne with α-hydroxy ketone. Oxygen-oxidizing and neutral conditions in one-pot for a wide range of substrates including natural product derivatives make this transformation highly efficient and practical. On the basis of control experiments, in situ IR measurements, and isotopic labeling experiments, a plausible mechanism involving intermediate phenylglyoxal was drawn. Applications by synthesis of various heterocycles were also investigated.

Copper-catalyzed synthesis of quinoxalines with o-phenylenediamine and terminal alkyne in the presence of bases

A novel way of synthesizing quinoxalines efficiently through cyclization of o-phenylenediamine and terminal alkyne by Cu(II) and bases is developed. This reaction proceeds smoothly to give the products in moderate to good yields.