226-47-1

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InChI:InChI=1/C20H12N2/c1-3-7-15-13(5-1)9-11-17-19(15)21-18-12-10-14-6-2-4-8-16(14)20(18)22-17/h1-12H

Upstream product

• 91-59-8 naphthalen-2-ylamine 
• 67-56-1 methanol 
• 20937-86-4 2-azidonaphthalene 
• 151-50-8 potassium cyanide 
• 6921-40-0 1-azidonaphthalene 

Related news

Oxidation of 1-amino-4,5-bis(dimethylamino)naphthalene as a route to the double “proton sponges” based on dibenzo[a,h]phenazine and 1,1′-azonaphthalene09/28/2019

Behavior of 4-amino-1-dimethylamino- and 1-amino-4,5-bis(dimethylamino)naphthalenes sharply differs on their treatment with tosyl chloride and oxidation with the ButOK/O2 system. While the former upon the action of tosyl chloride in protic media is transformed to sulfonamide, the latter unexpect...detailed

Relevant academic research and scientific papers

Prostaglandin H synthase-catalyzed ring oxygenation of 2-naphthylamine: Evidence for two distinct oxidation pathways

Previous studies showed that prostaglandin H synthase (PHS) cooxidizes 2- naphthylamine (2-NA) to ring-oxygenated products. These metabolites are atypical for a peroxidase-mediated reaction and are completely different from the polymeric nonoxygenated metabolites of 2-NA that are generated with the model peroxidase horseradish peroxidase (HRP). In this study, we investigated possible explanations for the PHS-catalyzed formation of ring-oxygenated 2- NA metabolites. We found that introduction of a peroxyl radical-generated cosubstrate into the HRP/2-NA system resulted in the formation of the same ring-oxygenated products observed in the PHS/2-NA system. 18O2 incorporation studies were utilized to further characterize the source of oxygen in the ring-oxygenated 2-NA metabolites. The data show that, in the case of PHS, ring oxygenation can occur both by peroxyl radical-mediated attack on 2-NA and by direct transfer of peroxide oxygen from PHS to 2-NA.

Oxidations of Aromatic Amines by Superoxide Ion

Superoxide ion acts as a mild and highly selective oxidizing agent for aromatic amines.Aniline and α-naphthylamine were not oxidized, but β-naphthylamine formed dibenzophenazine, dibenzophenazine and 2,2'-azonaphthalen-1-ol. o- and p-Diamines are oxidized to diaminoazobenzenes but m-diamines are unreactive.Similarly o- and p-aminophenols are oxidized to dihydroxyazobenzenes but m-aminophenols are unaffected, and o-mercaptoaniline forms the disulfide.The oxidations are considered to be free-radical processes, initiated by hydrogen abstraction by superoxide from the substrates.The biological significance of the results is discussed.

ORGANIC CHEMISTRY OF SUPEROXIDE. II OXIDATION OF β-NAPHTHYLAMINE - POSSIBLE INVOLVEMENT OF THE HYDROXYL RADICAL

Of a selection of aromatic monoamines examined only β-naphthylamine was oxidized by potassium superoxide and formed dibenzophenazine, dibenzophenazine and 1-hydroxy-2,2'-azonaphthalene, the latter product indicating that the hydroxyl radical may be involved in superoxide oxidations.

PHOTOCHEMICAL DECOMPOSITION OF 2-AZIDOPHENAZINE IN ALCOHOLS AND IN THE PRESENCE OF CYANIDE ION

The photochemical decomposition of 2-azidophenazine in alcoholic solvents has been investigated. 1-Amino-2-alkoxyphenazines are formed in neutral and (in higher yield and together with 2-amino-1-chlorophenazine) in acidic conditions, while the azepinoquinoxaline 7 is formed in basic conditions.With cyanide ion nucleophilic attack takes place giving 1-amino-2-phenazine carbonitrile.To allow comparison, 2-azidonaphthalene, 2-azidoanthracene and 2-azidoanthraquinone have also been photodecomposed in the conditions in which the most interesting results are obtained from 2-azidophenazine.The mechanism of these reactions is briefly discussed.

Thermal Decomposition of Aromatic Azides. Formation of Phenazines and Related Compounds

The decomposition of some aromatic azides yielding significant amounts of phenazines, and thereby constituting a potential synthetic procedure, is reported.