17537-15-4

Upstream product

• 496944-06-0 5-methyl-2-phthalimidophenyl azide 
• 132540-70-6 C₁₂H₁₇NO₂ 
• 106-49-0 p-toluidine 
• 160732-56-9 1-azido-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 1042161-63-6 C₁₄H₁₂N₄ 
• 1235454-79-1 8-methyl-3-phenyl-4-(trifluoromethyl)-[1,2,3]triazolo[1,5-a]quinoxaline 
• 7118-66-3 5-methyl-2-(4-methylphenyl)-1H-benzimidazole 

Relevant academic research and scientific papers

Copper-Mediated Diamination of Arylboronic Acids for the Synthesis of 2-Aryl Benzimidazoles Using Trimethylsilyl Azide as the Amino Sources with Aldehydes

A direct and versatile copper-mediated three-component reaction of arylboronic acids, trimethylsilyl azide and aldehydes for the synthesis of benzimidazoles is reported. The reaction is well tolerated by a wide range of substituted aromatic aldehydes and aromatic boronic acids to produce the corresponding benzimidazoles in moderate to high yields. Mechanism investigations demonstrated that copper-promoted Chan-Evans-Lam coupling, C?H amination, and oxidative cycloaddition are involved in the tandem processes. (Figure presented.).

Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion

Azides are building blocks of increasing importance in synthetic chemistry, chemical biology, and materials science. Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. Herein, we report a safety study of ABX, which shows its hazardous nature. We introduce two derivatives, tBu-ABX and ABZ (azidobenziodazolone), with a better safety profile, and use them in established photoredox- and metal-mediated azidations, and in a new ring-expansion of silylated cyclobutanols to give azidated cyclopentanones.

Method for preparing azide compound through azidation based on C-H activated anilines

The invention belongs to the technical field of organic chemistry, and particularly relates to a method for preparing an azide compound through azidation based on C-H activated anilines. The method comprises the following steps: by using anhydrous copper

A one-pot synthesis of [1,2,3]triazolo[1,5-a]quinoxalines from 1-azido-2-isocyanoarenes with high bond-forming efficiency

An efficient approach to prepare 1,2,3-triazolo[1,5-a]quinoxaline scaffolds, starting from 1-azido-2-isocyanoarenes and terminal acetylenes or substituted acetaldehydes, has been developed. In the case of trifluoromethylation triggered cyclization, four chemical bonds, including two C-C and two C-N bonds, were formed consecutively without isolating the triazole intermediate. In addition, these triazo-fused products were readily transformed into diversified quinoxaline derivatives via rhodium-catalyzed carbenoid insertion reactions.

New efficient synthesis of multisubstituted benzimidazoles and quinoxalin-2(1H)-ones by a Ugi 4CC/aza-Wittig sequence starting from aromatic amine precursors

An efficient preparation of multisubstituted benzimidazoles and quinoxalin-2(1H)-ones by Ugi 4CC/aza-Wittig sequence was developed. The 2-azidobenzenamines, obtained from [Formula presented] activation of aromatic amine precursors, reacted with aldehydes,

Room-temperature Cu(ii)-catalyzed aromatic C-H azidation for the synthesis of ortho-azido anilines with excellent regioselectivity

Cu(ii)-catalyzed aromatic C-H azidation with azido-benziodoxolone under mild conditions has been described. The primary amine exhibits an excellent ortho-directing effect, providing ortho-azidated anilines as the sole products. the Partner Organisations 2014.

Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides

(Chemical Equation Presented) The identity of the ortho-substituent of an aryl azide influences its reactivity toward transition metals. Substitution of a vinyl group with an imine disables rhodium(II)-mediated C-H amination and triggers a Lewis acid mechanism catalyzed by iron(II) bromide to facilitate benzimidazole formation.

Involvement of Free Nitrenium Ions, Ion Pairs, and Preassociation Trapping in the Reactions of Ester Derivatives of N-Arylhydroxylamines and N-Arylhydroxamic Acids in Aqueous Solution

Rate and product yield data for the decomposition of the ester derivatives of N-arylhydroxylamines and N-arylhydroxamic acids 1a-i in aqueous solution in the presence of N3- support a mechanistic scheme (Scheme 5) in which the trapping by N3- changes from trapping of the free ion, to trapping of an ion pair, to a preassociation process as the ion becomes more reactive.When the rate constant for trapping of the free ion by solvent, ks, 8 s-1, trapping by both N3- and solvent occurs almost exclusively at the free ion.When 108 s-1 s 10 s-1, a change in the mechanism occurs, and trapping of the ion pair by both solvent and N3- becomes important.In this range of reactivity there is also evidence, based on the apparent magnitude of kaz', the rate constant for N3- trapping of the ion pair, that some of the reaction with N3- occurs through a preassociation process.When ks > ca. 1010 s-1 essentially all of the observed N3- trapping occurs by a preassociation process because N3-, which cannot react with the ion pair faster than the diffusion limit, can no longer compete with solvent for the ion pair.This progression in trapping mechanisms as the ion becomes more reactive with solvent is apparently an important factor in determining the carcinogenic potential of aromatic amines and amides which are metabolized into sulfuric and carboxylic acid esters of N-arylhydroxylamines and N-arylhydroxamic acids.Nitrenium ions which undergo slow reactions with solvent are selectively trapped by biologically relevant nucleophiles such as 2'-deoxyguanosine.As the rate constant for reaction with solvent increases, the nitrenium ion is no longer capable of undergoing selective trapping by nonsolvent nucleophiles because these reactions are limited by diffusion, but solvent trapping is not.