25957-94-2

Upstream product

• 98-88-4 benzoyl chloride 
• 529-27-1 2-methylphenylhydrazine 
• 112341-96-5 (2-methylphenyl)azocarbonylbenzene 
• 65-85-0 benzoic acid 
• 635-26-7 o-tolylhydrazine hydrochloride 
• 615-37-2 ortho-methylphenyl iodide 
• 613-94-5 benzoic acid hydrazide 

Downstream Products

• 1426854-89-8 1-o-tolyl-1H-indazol-3-amine 
• 112341-96-5 (2-methylphenyl)azocarbonylbenzene 
• 143490-41-9 N',N'-di-o-tolylbenzohydrazide 

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.

[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.

Copper(ii)-catalyzed coupling reaction: An efficient and regioselective approach to N′,N′-diaryl acylhydrazines

Using N′-aryl acylhydrazines as aryl donors, a novel copper(ii)-catalyzed homo-coupling reaction of N′-aryl acylhydrazines has been developed for the synthesis of N′,N′-diaryl acylhydrazines. We also provided a complementary procedure for the preparation of unsymmetrical diaryl acylhydrazines via cross-coupling reaction. These protocols featured mild reaction conditions, wide functional group tolerance and highly regioselective products. Control experiments indicated that this kind of coupling reaction might undergo a transient acyl diazene intermediate. This journal is

Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides.

[reaction--see text] A convenient method for intermolecular N-arylation of hydrazides with substituted aryl iodides in the presence of a copper catalyst and Cs(2)CO(3) is reported. The C-N coupling of N-Boc hydrazine with para- and meta-substituted aryl iodides afforded the N-arylated products A, regioselectively. A reversal in regioselectivity is observed for the arylation of benzoic hydrazide with ortho-substituted aryl iodides, providing the N'-arylated products B.

Non Conventional Syntheses of Heterocyclic Compounds. 3. Synthesis of Indazole Derivatives

The thermal cyclization of a few 2,6-dimethylphenylazo compounds to indazole derivatives is described.

Method of use, composition, and compounds

Certain benzoyl chloride phenylhydrazones have been found to be active against insects and mites. The benzoyl ring and the phenylhydrazone ring can be substituted with a halogen atom, a nitro group, or an alkyl group of from 1 to 6 carbon atoms, inclusive