4492-01-7

Usage

InChI:InChI=1/C15H12N2/c1-3-7-13(8-4-1)15-11-12-17(16-15)14-9-5-2-6-10-14/h1-12H

Upstream product

• 64-17-5 ethanol 
• 57623-18-4 1-phenyl-3-(N-phenyl-hydrazino)-propenone 
• 6372-54-9 1-cyclohexyl-2-benzoylaziridine 
• 64-19-7 acetic acid 
• 100-63-0 phenylhydrazine 
• 15724-86-4 E-2-chlorovinyl phenyl ketone 
• 59-88-1 phenylhydrazine hydrochloride 
• 77169-12-1 1,3-diphenyl-1H-pyrazole-4-carboxylic acid 
• 165676-63-1 1,3-diphenyl-1H-pyrazole-4,5-dicarboxylic acid 
• 57623-20-8 3-benzoyloxy-1-phenyl-propenone 
• 40414-70-8 3-ethoxy-1-phenylprop-2-en-1-one 
• 30091-50-0 bis-(3-oxo-3-phenyl-propenyl)-amine 
• 60-29-7 diethyl ether 
• 15397-33-8 3-Oxo-3-phenylpropanal 

Downstream Products

• 2538-52-5 1,3-diphenyl-4,5-dihydro-1H-pyrazole 
• 92438-75-0 1,3-bis-(4-nitro-phenyl)-1H-pyrazole 
• 17647-21-1 1,3-diphenyl-1H-pyrazole-4-carbonitrile 
• 21487-45-6 1,3-diphenyl-4-formylpyrazole 
• 4847-47-6 β-(phenylamino)-cinnamic acid nitrile 

Relevant academic research and scientific papers

Primary Vinyl Ethers as Acetylene Surrogate: A Flexible Tool for Deuterium-Labeled Pyrazole Synthesis

A novel synthetic path to 1,3-disubstituted pyrazoles and their deuterated derivatives was developed. It is based on the reaction of vinyl ethers with hydrazonoyl chlorides in the presence of triethylamine. The reaction mechanism, clarified by the joint experimental and computational study, involves 1,3-dipolar cycloaddition of the in situ generated nitrile imines to vinyl ethers and subsequent cleavage of alcohol from the formed alkoxypyrazoline. The results highlight the possibility of using vinyl ethers as acetylene surrogate and provide a novel access to pyrazoles, 4,5-dideuteropyrazoles and their regioselectively labeled derivatives, 5-deuteropyrazoles.

Copper-Promoted Coupling of Propiophenones and Arylhydrazines for the Synthesis of 1,3-Diarylpyrazoles

Synthesis of 1,3-diarylpyrazoles from commercial substrates and/or simple transformations is still underrated. In this report, we have developed a method for copper-promoted coupling of propiophenones and arylhydrazines. The reactions afforded substituted pyrazoles in the presence of TEMPO oxidant, acetic acid additive, and DMF solvent. A number of functionalities were compatible with reaction conditions, including halogens, methoxy, trifluoromethyl, and nitro groups. An indazole could be obtained if an electron-poor propiophenone was used.

COMPOUNDS AND METHODS FOR HEMATOPOIETIC REGENERATION

The invention relates to compounds that promote hematopoietic regeneration. The invention further relates to methods of promoting hematopoietic regeneration using the novel compounds of the invention.

Ruthenium-catalyzed formation of pyrazoles or 3-hydroxynitriles from propargyl alcohols and hydrazines

Functionalized pyrazoles are generated from secondary propragyl alcohols and hydrazines in a ruthenium-catalyzed cascade process, consisting of redox isomerization, Michael addition, cyclocondensation and dehydrogenation steps. The same bifunctional catalyst mediates the conversion of tertiary propargyl alcohols with hydrazine to 3-hydroxynitriles via anti-Markovnikov hydroamination followed by elimination of ammonia.

Facile synthesis of pyrazoles by iron-catalyzed regioselective cyclization of hydrazone and 1,2-diol under ligand-free conditions

A facile synthesis of pyrazoles by the cyclization of hydrazones and 1,2-diols was described. In the presence of ferric nitrate, the reaction occurs under neat conditions and makes the use of potassium persulfate to oxidize the diol to α-hydroxy carbaldehyde for the reaction with hydrazones to produce 1,3- and 1,3,5-substituted pyrazoles selectively. The overall regioselective transformation occurs in one-pot under ligand-free, mild conditions even in the presence of air.

[3+2]-cycloaddition of in situ generated nitrile imines and acetylene for assembling of 1,3-disubstituted pyrazoles with quantitative deuterium labeling

A novel synthetic methodology for the preparation of 1,3-disubstituted pyrazoles from in situ generated nitrile imines and acetylene is reported. The reactions are performed in a simple two-chamber reactor. One part of the reactor is loaded with hydrazonoyl chloride precursors of active nitrile imine species and a base. The other part is used to generate acetylene from CaC2 and water. Partitioning of the reactants improves the yields of desired pyrazoles up to 99% and simplifies their isolation to a simple procedure of solvent evaporation. The approach requires no complex equipment and utilizes inexpensive, safe, and easy to handle calcium carbide as a starting material. A model deuterium incorporation is carried out according to the developed methodology, producing a series of novel 4,5-dideuteropyrazoles with excellent deuterium enrichment. Theoretical calculations on reaction mechanism and characterization of possible intermediate structures were performed.

COMPOUNDS AND METHODS FOR HEMATOPOIETIC REGENERATION

The invention relates to compounds that promote hematopoietic regeneration. The invention further relates to methods of promoting hematopoietic regeneration using the novel compounds of the invention.

Solvent-dependent copper-catalyzed synthesis of pyrazoles under aerobic conditions

We present a copper-catalyzed oxidative cyclization of β,γ-unsaturated hydrazones, utilizing molecular oxygen as a stoichiometric oxidant. The methodology provides distinct classes of pyrazoles simply by changing the reaction solvent. Tris-substituted pyr

Catalytic Chan-Lam coupling using a 'tube-in-tube' reactor to deliver molecular oxygen as an oxidant

A flow system to perform Chan-Lam coupling reactions of various amines and arylboronic acids has been realised employing molecular oxygen as an oxidant for the re-oxidation of the copper catalyst enabling a catalytic process. A tube-in-tube gas reactor has been used to simplify the delivery of the oxygen accelerating the optimisation phase and allowing easy access to elevated pressures. A small exemplification library of heteroaromatic products has been prepared and the process has been shown to be robust over extended reaction times.

Cu-promoted sydnone cycloadditions of alkynes: Scope and mechanism studies

Cu salts have been found to promote the cycloaddition reaction of sydnones and terminal alkynes, providing significant reduction in reaction times. Specifically, the use of Cu(OTf)2 is found to provide 1,3-disubstituted pyrazoles, whereas simpl