49829-54-1

Upstream product

• 539-44-6 N-4-methylphenylhydrazine 
• 65763-66-8 1-Benzoyl-2-(4-methylphenyl)hydrazine 
• 98-88-4 benzoyl chloride 
• 100-52-7 benzaldehyde 
• 1858-99-7 (E)-1-benzylidene-2-(p-tolyl)hydrazine 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 65-85-0 benzoic acid 
• 1858-99-7 benzaldehyde p-tolylhydrazone 
• 344891-06-1 (p-tolylazo)stilbene 

Downstream Products

• 117600-59-6 3-Phenyl-1-p-tolyl-1,8a-dihydro-[1,2,4]triazolo[4,3-a]pyridine 
• 104057-98-9 N-[1-Benzoimidazol-1-yl-1-phenyl-meth-(E)-ylidene]-N'-p-tolyl-hydrazine 
• 104057-93-4 N-[1-(4,5-Diphenyl-imidazol-1-yl)-1-phenyl-meth-(E)-ylidene]-N'-p-tolyl-hydrazine 
• 123149-92-8 1-Cyclohexyl-4-phenyl-2-p-tolyl-2H-[1,2,3]triazol-1-ium; chloride 
• 131286-52-7 diethyl N-(p-nitrophenyl)-P-phosphonimidate 
• 123150-06-1 4-Cyclohexyl-1,3-diphenyl-5-[phenyl-(p-tolyl-hydrazono)-methyl]-1H-[1,2,4]triazol-4-ium; chloride 
• 98321-12-1 C₁₄H₁₂N₂ 

Relevant academic research and scientific papers

Synthesis of 3 H-1,2,4-Triazol-3-ones via NiCl2-Promoted Cascade Annulation of Hydrazonoyl Chlorides and Sodium Cyanate

A nickel-promoted cascade annulation reaction for the facile synthesis of 3H-1,2,4-triazol-3-ones from readily available hydrazonoyl chlorides and sodium cyanate has been developed. The transformation occurs through a cascade nickel-promoted intermolecular nucleophilic addition-elimination process, intramolecular nucleophilic addition, and a hydrogen-transfer sequence. The method has been successfully applied for the construction of the core skeleton of the angiotensin II antagonist.

Sequential [3+2] annulation reaction of prop-2-ynylsulfonium salts and hydrazonyl chlorides: Synthesis of pyrazoles containing functional motifs

A novel sequential [3+2] annulation reaction has been developed using prop-2-ynylsulfonium salts and hydrazonyl chlorides, affording a series of pyrazoles with functional motifs that can be post modified in the preparation of various drugs or drug candidates. Further transformation and gram-scale operations could also be achieved efficiently. This journal is

Palladium-Catalyzed cascade carbonylative synthesis of 1,2,4-triazol-3-ones from hydrazonoyl chlorides and NaN3

A palladium-catalyzed three-component carbonylative reaction for the synthesis of 3H-1,2,4-triazol-3-ones from hydrazonoyl chlorides and NaN3 has been achieved. The reaction presumably proceeds through a cascade carbonylation, acyl azide format

[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.

A [4 + 3] Annulation Reaction of aza- o-Quinone Methides with Arylcarbohydrazonoyl Chlorides for Synthesis of 2,3-Dihydro-1 H-benzo[ e][1,2,4]triazepines

An unprecedented [4 + 3] annulation reaction of aza-ortho-quinone methides with arylcarbohydrazonoyl chlorides has been achieved under mild conditions. The annulation underwent a sequential conjugate addition/intramolecular annulation/rearrangement, providing a useful method for the synthesis of biologically interesting 2,3-dihydro-1H-benzo[e][1,2,4]triazepine.

Synthesis of Spirobidihydropyrazole through Double 1,3-Dipolar Cycloaddition of Nitrilimines with Allenoates

The double 1,3-dipolar cycloaddition of allenoates with nitrilimines has been achieved under mild reaction conditions, affording a variety of spirobidihydropyrazoles in moderate to excellent yields with excellent diastereoselectivities. The reaction diastereoselectively constructs double dihydropyrazole moieties and two chiral centers including a spiro carbon center.

[3+3]-cycloaddition of donor-acceptor cyclopropanes with nitrile imines generated in situ: Access to tetrahydropyridazines

Donor-acceptor cyclopropanes are reacted under the influence of a Lewis acid with hydrazonyl chlorides to afford tetrahydropyridazines. Formally, this transformation can be regarded as a [3 + 3]-cycloaddition of three-membered rings and nitrile imines generated in situ. This efficient method provides fast access to a variety of structurally diverse pyridazine derivatives. The structure of a typical product was confirmed by X-ray crystallography.

Regiospecific Synthesis of N 2-Aryl 1,2,3-Triazoles from 2,5-Disubstituted Tetrazoles via Photochemically Generated Nitrile Imine Intermediates

The synthesis of N2-aryl 1,2,3-triazoles from 2,5-disubstituted tetrazoles was achieved under photochemical conditions. This simple and mild one-step reaction provides regiospecific access to 2,4,5-substituted 1,2,3-triazoles via a nitrile imine intermediate. Syntheses of alkyl and heterocylic derivatives were also investigated.

Asymmetric catalytic 1,3-dipolar cycloaddition reaction of nitrile imines for the synthesis of chiral spiro-pyrazoline-oxindoles

A new 1,3-dipolar cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a new chiral Mg(ClO4)2 complex of an N,N'-dioxide ligand. The reaction is so far the sole catalytic synthesis of spiro-pyrazoline-oxindole derivatives. A wide variety of substrates were explored to obtain good yields (up to 98%) and excellent enantioselectivities (up to 99%). This cycloaddition expands the scope of propargyl anion type 1,3-dipole in the construction of 2-pyrazoline subunit.

Effect of metal ions in organic synthesis. Part XV. Reaction of (arylazo) alkenes and copper(II) chloride in dienophiles or acetone. Synthesis of some N-(α-chlorobenzylidene)-N'-arylhydrazines

The reaction of (phenylazo) stilbene and copper(II) chloride with some dienophiles produced benzaldehyde and N-(α-chlorobenzylidene)-N'-phenylhydrazine, instead of the expected (4+2)-cycloaddition products.By reaction of some (arylazo) alkenes and copper(