3933-77-5

Upstream product

• 67661-49-8 2-Azido-4'-chloroazobenzene 
• 99137-16-3 5-(4-chlorophenyl)-1-(2-nitrophenyl)tetrazole 
• 637-87-6 1-Chloro-4-iodobenzene 
• 273-02-9 2H-benzo[d][1,2,3]triazole 
• 95-14-7 1,2,3-Benzotriazole 
• 6141-95-3 trans-(4-chloro-phenyl)-phenyl-diazene 
• 100-00-5 4-chlorobenzonitrile 
• 95-54-5 1,2-diamino-benzene 
• 88-74-4 2-nitro-aniline 
• 106-47-8 4-chloro-aniline 
• 612-29-3 o-nitronitrosobenzene 
• 35527-26-5 4’-chloro-2-nitroazobenzene 

Relevant academic research and scientific papers

Cu(I)/KOH-Promoted Condensation between o-Arylenediamines and Nitroarenes to Access 2-Aryl-2H-Benzotriazoles

Reported is the condensation between o-arylenediamines and nitroarenes enabled by a cooperative action of acid and base, providing a direct entry to 2-aryl-2H-benzotriazoles. The potential practicability of this methodology was demonstrated by 100 mmol-scale reactions and the synthesis of serotonin/dopamine receptor ligand and human growth hormone. (Figure presented.).

Preparation method of 2-aryl benzotriazole compound

The invention relates to a synthesis method of a 2-aryl benzotriazole compound. In an organic solvent, under a nitrogen condition, an o-phenylenediamine compound with a structure shown as a formula (I) in the structural formula and an aryl nitrogen source with a structure shown as a formula (II) in the structural formula are used as reaction substrates to be successively subjected to intermolecular N-N coupling and intramolecular N-N bond coupling condensation by using a cheap copper-containing catalyst in a strong alkali environment so as to obtain a 2-aryl benzotriazole compound. According to the method, o-phenylenediamine and nitrobenzene raw materials are commercialized, cheap and easily available, the reaction substrate range is wide, the functional group tolerance is good, the reaction conditions are simple, the yield and purity of the product are high, a new synthesis route and a method are developed for the 2-aryl benzotriazole compound, and the method has good application potential and research value.

Selective and Scalable Electrosynthesis of 2H-2-(Aryl)-benzo[d]-1,2,3-triazoles and Their N-Oxides by Using Leaded Bronze Cathodes

Electrosynthesis of 2H-2-(aryl)benzo[d]-1,2,3-triazoles and their N-oxides from 2-nitroazobenzene derivatives is reported. The electrolysis is conducted in a very simple undivided cell under constant current conditions with a leaded bronze cathode and a g

AgNO3 as nitrogen source for rhodium(III)-catalyzed synthesis of 2-aryl-2H -benzotriazoles from azobenzenes

A new approach has been established for Rh(iii)-catalyzed direct aza oxidative cyclization of non-prefunctionalized azobenzenes to provide 2-aryl-2H-benzotriazoles in good yields, in which AgNO3 instead of conventional azide reagents for the first time functions as the nitrogen source for the nitrogenation reaction. Preliminary mechanistic studies suggest that the Rh(iii)-catalyst could account for the nitration reaction, and subsequently cationic silver species might both play a vital role in the fission of the nitrogen-oxygen bonds in nitro groups and promote aza oxidative cyclization.

Metal-free N-arylation of indolines with diaryliodonium salts

The N-arylation of indolines using diaryliodonium salts as electrophilic arylating reagents is described. Without the use of any additional additives, the desired N-aryl indolines could be obtained in up to 85% yield.

Deproto-metallation using a mixed lithium-zinc base and computed CH acidity of 1-aryl 1H-benzotriazoles and 1-aryl 1H-indazoles

1-Aryl-1H-benzotriazoles and -1H-indazoles were synthesized, and their deproto-metallation using the base prepared by mixing LiTMP with ZnCl 2·TMEDA (1/3 equiv.) was studied. In the indazole series, reactions occurring at the 3 position were fo

Cross-coupling reactions of aryl halides with amines, phenols, and thiols catalyzed by an N,N′-dioxide-copper(I) catalytic system

The coupling reactions of various N, O, and S nucleophilic reagents with aryl halides have been successfully carried out under mild conditions by using a novel chiral N,N′-dioxide-copper(I) catalytic system as the catalyst. This versatile and efficient catalyst system has been demonstrated to facilitate the cross-coupling reactions of aryl halides with amines, phenols, and thiols to afford the corresponding desired products in good to excellent yields.

THE REACTION OF ORTHO-SUBSTITUTED AROMATIC AZIDES WITH BORON TRICHLORIDE OR TRIFLUORIDE

The reactiont of boron trichloride or trifluoride with ortho-aryl, -diazoaryl, and -arylazoaryl phenyl azides in benzene at room temperature generally gives fused azoles in high yields.Treatment of 2-nitrophenyl azide with boron trichloride mainly affords chlorinated nitroanilines, whereas with boron trifluoride it gives N-o-nitrophenylaniline.In aromatic solvents at 60 deg C in the presence of boron trifluoride-diethyl ether, 2-azidobiphenyl forms carbazole and 2-(arylamino)biphenyls, the formation of which depends greatly upon the nucleophilicity of the solvent used; however, its pseudo-first-order decomposition rate is slightly greater in benzene than in toluene or m-xylene.Under the same conditions, phenyl azide forms diarylamines.The results suggest that singlet nitrenium ions, arising from the corresponding azidetrihalogenoborane complexes by loss of molecular nitrogen, are generally the reactive intermediates.

Intramolecular Reaction Between Nitro and Carbodi-imide Groups; A New Synthesis of 2-Arylbenzotriazoles

1-(2-Nitrophenyl)-5-phenyltetrazole (5b) decomposes when heated to give nitrogen, carbon dioxide, and 2-phenylbenzotriazole (6) in high yield.This new molecular rearrangement proceeds via 2-nitrophenyl(phenyl)carbodi-imide (8).Other precursors of this carbodi-imide, i.e. oxadiazolone (10), oxadiazolethione (11), oxathiadiazole 2-oxide (12), and the aminimide (16), and carbodi-imide itself, all give 2-phenylbenzotriazole (6) on thermolysis, the last three in high yield.This reaction is general for diarylcarbodi-imides with an ortho nitro group, and their precursors, and it provides a useful new route to 2-arylbenzotriazoles.A sequence of electrocyclic ring closing and opening reactions (Scheme 5) is proposed as the mechanism of this process.The key intermediate, 2-phenyl-1,2,4-benzotriazin-3-one 1-oxide (19) has been isolated from a careful thermolysis of (12) in toluene; in solution it is in reversible equlibrium with the ring-opened form (20).This new nitro-carbodi-imide group interaction has been extended to the more stable nitrobiphenyl(phenyl)carbodi-imide (25) and nitronaphthyl(phenyl)carbodi-imide (24) which, on flash vacuum pyrolysis, give benzimidazophenanthridine (29) and benzindazole 1-oxide (32) respectively, in new rearrangements.

The reaction of Organic Azides with Boron Trichloride: A New Simple Route for the Production of Fused Heterocycles Containing Nitrogen

The reaction of boron trichloride with an ortho-aryl and ortho-diazoaryl phenyl azides at room temperature yielded fused azoles via 1,5-cyclization of a probable singlet nitrenium ion intermediate, arising from displacement of molecular nitrogen from the azido group.