13788-77-7

Upstream product

• 5535-48-8 PVS 
• 25939-13-3 N-(p-nitrophenyl)benzohydrazonoyl chloride 
• 52866-26-9 ((E)-Buta-1,3-dienyl)-diethyl-amine 
• 636-98-6 p-nitrobenzene iodide 
• 2458-26-6 3-phenylpyrazole 
• 74327-12-1 propiophenone 4-nitrophenylhydrazone 
• 5920-39-8 1-(4-nitro-phenyl)-3-phenyl-4,5-dihydro-1H-pyrazole 
• 100-16-3 4-nitrophenylhydrazone 
• 93-55-0 1-phenyl-propan-1-one 
• 100-25-4 para-dinitrobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 6299-51-0 3-(4-nitrophenyl)sydnone 

Downstream Products

• 92438-75-0 1,3-bis-(4-nitro-phenyl)-1H-pyrazole 

Relevant academic research and scientific papers

Regioselective microwave-assisted synthesis of substituted pyrazoles from ethynyl ketones

Reaction of α,β-ethynyl ketones and hydrazine derivatives gives 1,3- and 1,5-disubstituted pyrazoles in good yield. Microwave irradiation in concentrated hydrochloric acid-methanol (1.5% v/v), with concurrent cooling at sub-ambient temperatures or at 120°

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.

Divergent Synthesis of 1H-Indazoles and 1H-Pyrazoles from Hydrazones via Iodine-Mediated Intramolecular Aryl and sp3 C–H Amination

A divergent intramolecular C–H amination of hydrazones has been developed employing molecular iodine (I2) as the sole oxidant. The required hydrazone substrates were readily obtained by condensation of hydrazines with the corresponding ketones.

Regioselective Synthesis, NMR, and Crystallographic Analysis of N1-Substituted Pyrazoles

A systematic study of the N-substitution reactions of 3-substituted pyrazoles under basic conditions has been undertaken. Regioselective N1-alkylation, -arylation, and -heteroarylation of 3-substituted pyrazoles have been achieved using K2CO3-DMSO. The regioselectivity is justified by the DFT calculations at the B3LYP/6-31G??(d) level. A consistent steric effect on chemical shift has been observed for N-alkyl pyrazole analogues. Twenty-five X-ray crystallographic structures have been obtained to confirm the regiochemistry of the major products.

In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides

A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is

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.

An efficient regioselective copper catalyzed multi-component synthesis of 1,3-disubstituted pyrazoles

An efficient synthesis of unsymmetrically substituted 1,3-pyrazole derivatives has been developed via three-component coupling reaction involving 3-(dimethylamino)-1-phenylprop-2-en-1-one, hydrazine, and aryl halides in one pot process exhibiting high regioselectivity. The pyrazole synthesis proceeds via a sequential series of reactions such as Michael addition, heterocyclization, dehydration, and Ullmann cross-coupling.

Alkyne [3 + 2] cycloadditions of iodosydnones toward functionalized 1,3,5-trisubstituted pyrazoles

(Chemical Equation Presented) The cycloaddition of 4-iodosydnones with terminal alkynes proceeds with excellent regiocontrol to provide 5-iodo pyrazoles. These products participate smoothly in subsequent C-C and C-heteroatom bond forming processes.

The Cycloaddition of N,N-Diethyl-1,3-butadienylamine with Some Diarylnitrilimines

The cycloaddition of N,N-diethyl-1,3-butadienylamine with some diarylnitrilimines was investigated. 1,3-diaryl-4-vinylpyrazoles, (1,3-diaryl-2-pyrazolin-5-yl)acetaldehydes, 1,3-diaryl-4-(1,3-diaryl-2-pyrazolin-5-yl)pyrazoles, and 1,3-diarylpyrazoles were obtained.