30152-33-1

Upstream product

• 6969-01-3 trans-2,3-epoxy-3-(4-chlorophenyl)-1-phenylpropan-1-one 
• 563-41-7 semicarbazide hydrochloride 
• 637-87-6 1-Chloro-4-iodobenzene 
• 98-88-4 benzoyl chloride 
• 4301-14-8 acetylenemagnesium bromide 
• 99-91-2 para-chloroacetophenone 
• 100-52-7 benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 98-86-2 acetophenone 
• 956-04-7 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one 
• 7400-27-3 tertbutylhydrazine hydrochloride 
• 89144-73-0 5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole 
• 536-74-3 phenylacetylene 
• 873-73-4 4-n-chlorophenylacetylene 

Relevant academic research and scientific papers

Copper-Promoted Oxidative Intramolecular C–H Amination of Hydrazones to Synthesize 1H-Indazoles and 1H-Pyrazoles Using a Cleavable Directing Group

A facile and efficient synthesis of 1H-indazoles and 1H-pyrazoles through a copper-promoted oxidative intramolecular C–H amination of hydrazones using a cleavable directing group was developed. This reaction is characterized by its mild conditions, operational simplicity, readily available reagents, and excellent yields. A tentative mechanism for Cu-mediated C–H oxidative amination was proposed.

One-Pot Coupling-Coupling-Cyclocondensation Synthesis of Fluorescent Pyrazoles

Consecutive four-component coupling-coupling-cyclocondensation syntheses of pyrazoles and pyrimidines were developed by taking advantage of the provisional, sequentially Pd-catalyzed one-pot generation of alkynones from aryl iodides, ethynylmagnesium bromide, and acid chlorides. This one-pot methodology allows the concise, diversity-oriented generation of a set of donor-, acceptor-, and donor-acceptor-substituted pyrazoles, which are interesting fluorophores. Most distinctly, donor-acceptor pyrazoles display remarkably red-shifted emission maxima and pronounced positive solvochromicity, spanning an overall range from 363 nm (cyclohexane) to 595 nm (acetonitrile). DFT and TD-DFT calculations elucidate the electronic structure and the photophysical behavior. Upon photonic excitation, considerable charge-transfer character becomes apparent, which rationalizes the origin of huge Stokes shifts and solvochromic behavior.

Iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate: Synthesis of 3,5-disubstituted 1H-pyrazoles

We have developed an iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate. Various 3,5-disubstituted 1H-pyrazoles were obtained in good to excellent yields. This method offers several advantages, including room-temperature conditions, short reaction time, high yields, simple work-up procedure, and use of air as an oxidant. The catalyst can be recovered and reused five times without loss of activity.

I2-mediated oxidative C-N bond formation for metal-free one-pot synthesis of di-, tri-, and tetrasubstituted pyrazoles from α,β-unsaturated aldehydes/ketones and hydrazines

An I2-mediated metal-free oxidative C-N bond formation methodology has been established for the regioselective pyrazole synthesis. This practical and eco-friendly one-pot protocol requires no isolation of the less stable intermediates hydrazone

One-pot synthesis of 3,5-diphenyl-1h-pyrazoles from chalcones and hydrazine under mechanochemical ball milling

A highly efficient and environmentally friendly method has been developed for facile synthesis of 3,5-diphenyl-1H-pyrazoles under mechanochemical ball-milling conditions. The advantages of short reaction time, high efficiency, no separation of in situ generated intermediate, using cheap sodium persulfate as the oxidant, together with very simple work-up procedure, make this one-pot and solvent-free protocol a green and powerful alternative to traditional methods for the synthesis of these kinds of compounds.

A facile and convenient approach to the synthesis of 3,5-diaryl-1H- pyrazoles

A simple and convenient one-pot synthesis route is described for the synthesis of 3,5-diaryl-1H-pyrazoles in short reaction times from the reaction of α-epoxyketones with semicarbazide hydrochloride under mild conditions.

One-pot four-component reaction for the generation of pyrazoles and pyrimidines

The palladium-catalysed four-component coupling of a halide, terminal alkyne, molybdenum hexacarbonyl and either a hydrazine or amidine has been shown to be an efficient method for the construction of highly substituted pyrazoles and pyrimidines, respectively, in a one-pot process. Georg Thieme Verlag Stuttgart.

Monoamine oxidase isoform-dependent tautomeric influence in the recognition of 3,5-diaryl pyrazole inhibitors

A series of 3,5-diaryl pyrazoles were prepared and assayed for their ability to inhibit reversibly monoamine oxidase-A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds show inhibitory activity with concentration values in the nanomolar range. A computational work was carried out on the two most selective inhibitors that have tautomeric pyrazole forms. The binding free energies of these compounds for each MAO isoform were influenced by the tautomeric equilibria.

Facile preparation of allyl amines and pyrazoles by hydrazinolysis of 2-ketoaziridines

Allyl amines and pyrazoles can be obtained by hydrazinolysis of 2-ketoaziridines. A variety of aziridines, including N-unprotected, N-substituted, as well as bicyclic enamine and aminal type, can be transformed into diversely substituted linear or cyclic products. The hydrazinolysis of homochiral aziridines proceeds without racemization.

A novel synthesis of 5-aryl-3-phenylpyrazole from 2-aryl-3-benzoyl-1,1- cyclopropanedicarbonitrile and hydrazine

A new process for synthesis of 5-aryl-3-phenylpyrazole is achieved. The regioselective ring-opening reaction of 2-aryl-3-benzoyl-1,1- cyclopropanedicarbonitrile with hydrazine plays a crucial role in the described process.