25688-22-6

Usage

Derivative of

1,2,4-triazole

Contains

a nitrophenyl group

Common use

building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds

Potential biological activities

antimicrobial, antifungal, and anticancer properties

Investigated for

development of new materials and coatings

Unique properties

due to its chemical structure

Upstream product

• 288-88-0 1,2,4-Triazole 
• 1493-27-2 ortho-nitrofluorobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 609-73-4 o-nitroiodobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 528-29-0 1,2-Dinitrobenzene 

Downstream Products

• 39876-84-1 2-(1H-1,2,4-triazol-1-yl)aniline 
• 13417-57-7 1-(2,4-dinitrophenyl)-1H-1,2,4-triazole 
• 124617-74-9 3-Ethyl-3H-1,2,4-triazolo<1,5-a>benzimidazole 

Relevant academic research and scientific papers

A post-synthetically modified metal-organic framework for copper catalyzed denitrative C-N coupling of nitroarenes under heterogeneous conditions

Here we report, for the first time, the Ullmann C-N coupling reaction of nitroarenes which is achieved by using a copper containing metal-organic framework (MOF) catalyst under heterogenous conditions. The ready availability of nitroarenes and their low cost have made them ideal replacements for haloarenes as electrophilic coupling partners. Notably, the reaction protocol suppresses the by-product formation in the catalytic reaction. The catalyst has been designed and synthesized by two step post-synthesis functionalization of a MOF,viz.dabco MOF-1 with a -NH2functional group (DMOF-NH2). In the post-synthetic treatment, salicylaldehyde has been used for organic modification first and then copper(ii) was successfully incorporated onto the inner surface of the porous material. The hybrid porous solid thus obtained has been employed in the catalytic C-N coupling reaction of nitroarenes with a wide variety of amines under heterogeneous conditions, which displayed very high turnover frequencies (TOF) in catalytic reactions attesting its efficacy towards theN-arylation reaction.

A catalytic intramolecular nitrene insertion into a copper(i)-N-heterocyclic carbene bond yielding fused nitrogen heterocycles

N-(2-Azidophenyl)azolium salts were easily prepared and reacted with copper(i) under conditions allowing the formation of NHC complexes. Under these conditions, the formation of benzimidazo-fused heterocycles occurred under catalytic, efficient and very mild conditions. This reaction is proposed to proceed via dinitrogen elimination and imido/nitrene-NHC cyclization.

Heterogeneous sequential N-arylation of N-heterocycles over copper anchored mesoporous silica catalyst

N-Arylation reaction of N-heterocyclic compounds has been carried out in excellent yield using copper anchored SBA-15 catalyst. Sequential N-arylation reactions employing single catalyst under heterogeneous condition provides a straightforward access to a

Triazole-substituted nitroarene derivatives: Synthesis, characterization, and energetic studies

A series of dense and energetic polynitroaryl-1,2,4-triazoles were synthesized through the nitration of aryl-1,2,4-triazoles. The Cu-catalyzed/base-mediated coupling reactions of haloarenes with 1,2,4-triazoles delivered N-aryl-1,2,4-triazoles. These new

A unified strategy towards N-aryl heterocycles by a one-pot copper-catalyzed oxidative C-H amination of azoles

An efficient one-pot synthesis of N-aryl-substituted heterocycles by a Cu-catalyzed two-fold C-N bond formation is reported. This strategy involves a CuI-catalyzed C-N bond-forming reaction between azoles and electron-deficient bromopyridines followed by an intramolecular sp2 C-H amination. One of the products thus formed has been successfully used as a ligand for the synthesis of a Pd complex. An efficient one-pot synthesis of N-aryl heterocycles by a Cu-catalysed double C-N bond formation is reported. This strategy involves a CuI-catalysed C-N bond-forming reaction between azoles and electron-deficient bromopyridines followed by an intramolecular sp2 C-H amination.

Aromatic N-arylations catalyzed by copper-anchored porous zinc-based metal-organic framework under heterogeneous conditions

A highly porous Zn-based metal-organic framework (MOF) IRMOF-3 was covalently decorated with pyridine-2-aldehyde. The free amine group of IRMOF-3 upon condensation with pyridine-2-aldehyde affords a bidentate Schiff-base moiety in the porous matrix. The Schiff base moieties are availed to anchor copper(II) ions to display the catalyst's utility towards catalytic reactions. The catalyst was characterized by UV/Vis and IR spectroscopy, powder XRD spectrometry, SEM energy-dispersive X-ray spectrometry, and nitrogen sorption measurements. The catalyst exhibits excellent activity in catalyzing the N-arylation reaction of nitrogen-containing heterocycles with aryl bromides in DMSO medium, under mild condition (90°C) in the presence of Cs 2CO3. The porous catalyst demonstrates size selectivity towards substrate as a result of the presence of active sites inside the pores of the MOF. The anchored complex seems to be not leached or decomposed during the catalytic reactions up to five successive catalytic cycles, demonstrating practical advantages over homogeneous catalysis.

Ligands for copper-catalyzed C-N bond forming reactions with 1 Mol% CuBr as catalyst

Several new ligands were designed to promote copper-catalyzed Ullman C-N coupling reactions. In this group, 8-hydroxyquinolin-N-oxide was found to serve as a superior ligand for CuBr-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-heterocycles under a low catalyst loading (1% [Cu] mol). Reactions with the inexpensive catalytic system display a high functional group tolerance as well as excellent chemoselectivity.

3-AZABICYCLO [3.1.0] HEXANE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The present invention relates to 3-azabicyclo[3.1.0]hexane derivatives, which are useful as vanilloid receptor (VR) ligands, methods of treating diseases, conditions and/or disorders modulated by vanilloid receptors with them, and processes for preparing them.

The Reaction of Some N-(Nitrophenyl)azoles with Alkali: Preparation of the Corresponding Azoxybenzenes. X-Ray Structure of 2,2'-Bis(1'',2'',4''-triazol-1''-yl)azoxybenzene

The reactions of some representative N-(nitrophenyl)azoles with boiling aqueous ethanolic potassium hydroxide solution gave the corresponding bis(azolyl)azoxybenzenes.It is deduced that, in these reactions, the N-attached azolyl groups concerned are acting as weak electron-withdrawing groups.The structure of 2,2'-bis(1'',2'',4''-triazol-1''-yl)azoxybenzene was determined in the solid state by X-ray crystallography.The monoclinic crystals belong to the space group P21/c with a 8.815(1), b 7.863(1), c 11.836(1) Angstroem, β 109.96(1) deg and Z 2.The structure was refined to an R index of 0.041 for 1172 observed terms.The midpoint of the exocyclic N=N bond lies on an inversion centre so that the azoxy oxygen is statistically distributed between two sites.The benzene ring atoms are coplanar to within experimental error, as are the triazole ring atoms, and the dihedral angle between the perpendiculars to the two rings is 35.3(3) deg.