15089-03-9

Usage

Uses

Agricultural chemical.

Hazard

Moderately toxic by ingestion.

InChI:InChI=1/C14H14N2O2/c1-18-13-9-7-11(8-10-13)14(17)16-15-12-5-3-2-4-6-12/h2-10,15H,1H3,(H,16,17)

Upstream product

• 64-17-5 ethanol 
• 30410-44-7 (4-methoxy-benzoyl)-phenyl-diazene 
• 2829-34-7 1-(hydroperoxy(4-methoxyphenyl)methyl)-2-phenyldiazene 
• 7732-18-5 water 
• 100-09-4 4-methoxybenzoic acid 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 65-85-0 benzoic acid 
• 56180-44-0 C₁₁H₁₂O₅ 
• 20433-10-7 5-(4-methoxyphenyl)-2-phenyl-2H-tetrazole 
• 34885-34-2 phenyldiazonium acetate 
• 871899-67-1 4-methoxy-benzoic acid-(N-nitro-N'-nitroso-N'-phenyl-hydrazide) 
• 4231-69-0 1-(4-methoxybenzoyl)-1H-1,2,3-benzotriazole 
• 64-19-7 acetic acid 

Downstream Products

• 79202-02-1 4-methoxy-N′-methyl-N′-phenylbenzohydrazide 
• 30410-44-7 (4-methoxy-benzoyl)-phenyl-diazene 
• 40277-63-2 4-methoxy-N'-phenylbenzohydrazonoyl chloride 
• 1146143-84-1 dimethyl 5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3,4-dicarboxylate 
• 1196908-53-8 3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-amine 
• 304668-43-7 4-methoxy-N',N'-diphenylbenzohydrazide 
• 59812-31-6 3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5(4H)-one 
• 33064-21-0 3-(4-methoxy-phenyl)-1-phenyl-1H-pyrazole 
• 588-59-0 stilbene 

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.

A formal [3+2] cycloaddition reaction of: N -methylimidazole as a masked hydrogen cyanide: Access to 1,3-disubstitued-1 H -1,2,4-triazoles

N-Methylimidazole (NMI) can act as a masked HCN in the synthesis of 1,3-disubstitued-1H-1,2,4-triazoles via a formal cycloaddition reaction of hydrazonoyl chloride with NMI. The product was proved to be formed via an initial nucleophilic substitution of hydrazonoyl chloride with NMI following cyclization and two sequential C-N bond cleavages. This journal is

[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.

KOt-Bu promoted homocoupling and decomposition of N'-aryl acylhydrazines: synthesis of unsymmetric N',N'-diaryl acylhydrazines

The KOt-Bu promoted homocoupling and decomposition of N'-aryl acylhydrazines has been achieved. The method allows for a novel and efficient synthesis of unsymmetric N',N'-diaryl acylhydrazines under mild reaction conditions. The reaction probably proceeds via the generation of N'-centered acylhydrazine radicals and the subsequent homolytic aromatic substitution.

1,2,4-Triazolo[1,5-a]quinoxaline derivatives and their simplified analogues as adenosine A3 receptor antagonists. Synthesis, structure-affinity relationships and molecular modeling studies

The 1,2,4-triazolo[1,5-a]quinoxaline (TQX) scaffold was extensively investigated in our previously reported studies and recently, our attention was focused at position 5 of the tricyclic nucleus where different acyl and carboxylate moieties were introduced (compounds 2-15). This study produced some interesting compounds endowed with good hA3 receptor affinity and selectivity. In addition, to find new insights about the structural requirements for hA3 receptor-ligand interaction, the tricyclic TQX ring was destroyed yielding some 1,2,4-triazole derivatives (compounds 16-23). These simplified compounds, though maintaining the crucial structural requirements for adenosine receptor-ligand interaction, have a very low hA3 adenosine receptor affinity, the only exception being compound 23 (1-[3-(4-methoxyphenyl)-1-phenyl-1H-1,2,4-triazol-5-yl]-3-phenylurea) endowed with a Ki value in the micro-molar range and high hA3 selectivity versus both hA1 and hA2A AR subtypes. Evaluation of the side products obtained in the herein reported synthetic pathways led to the identification of some new triazolo[1,5-a]quinoxalines as hA3AR antagonists (compounds 24-27). These derivatives, though lacking the classical structural requirements for the anchoring at the hA3 receptor site, show high hA3 affinity and in some case selectivity versus hA1 and hA2A subtypes. Molecular docking of the herein reported tricyclic and simplified derivatives was carried out to depict their hypothetical binding mode to our model of hA3 receptor.

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

An approach to pyrazoline-fused chlorins by dipolar [3 + 2]-cycloaddition of iminonitriles to Meso-Tetrakis(pentafluorophenyl)porphyrin: Synthesis of new PDT photosensitizers

Meso-Tetrakis(pentafluorophenyl)porphyrin reacts at higher temperature with unstable iminonitriles (RC≡N+-N--Ar), affording pyrazoline-fused chlorins, according to dipolar [3 + 2]-cycloaddition pathway. The respective iminonitriles were in situ generated from the corresponding functionalized α-halogenohydrazine derivatives by 1,3-elimination of HX in the presence of base (NEt3, DABCO). This method allows synthesis of very attractive moieties which may be of potential use as sensitizers in photodynamic therapy (PDT).

Synthesis and antifungal activities of New pyrazole derivatives via 1,3-dipolar cycloaddition reaction

A series of cycloadducts - pyrazoles via 1,3-dipolar cycloaddition reactions of generated nitrilimines with N-(4-chloro-2-fluorophenyl)maleimide were described. The novel compounds synthesized were characterized by 1H NMR, MS, and elemental analysis. The fungicidal tests showed that most of the title compounds exhibit significant fungicidal activities against Corynespora cassiicola.