20147-55-1

Usage

InChI:InChI=1/C13H10ClN3O2/c14-13(16-15-11-4-2-1-3-5-11)10-6-8-12(9-7-10)17(18)19/h1-9,15H/b16-13-

Upstream product

• 39718-99-5 N-anilino-4-nitrobenzamide 
• 122-04-3 4-nitro-benzoyl chloride 
• 149833-51-2 (E)-1-(4-nitrobenzylidene)-2-phenylhydrazine 
• 555-16-8 4-nitrobenzaldehdye 
• 62-23-7 4-nitro-benzoic acid 
• 2829-27-8 4-nitro-benzaldehyde phenylhydrazone 

Downstream Products

• 20147-68-6 3-(4-nitro-phenyl)-1-phenyl-(3ar,6ac)-3a,4,5,6a-tetrahydro-1H-furo[2,3-c]pyrazole 
• 37628-06-1 4-ethoxy-3-(4-nitro-phenyl)-1-phenyl-1,4,5,6-tetrahydro-[1,2,4]diazaphosphinine 4-oxide 
• 37628-11-8 4-ethoxy-5-methyl-3-(4-nitro-phenyl)-1-phenyl-1,4,5,6-tetrahydro-[1,2,4]diazaphosphinine 4-oxide 
• 37758-19-3 4-ethoxy-3-(4-nitro-phenyl)-1,5-diphenyl-1,4,5,6-tetrahydro-[1,2,4]diazaphosphinine 4-oxide 
• 62436-60-6 6-methyl-3-(4-nitro-phenyl)-1,4,4-triphenyl-1,4,5,6-tetrahydro-[1,2,4]diazaphosphininium; chloride 
• 39143-30-1 3-(4-nitro-phenyl)-1,4,4-triphenyl-1,4-dihydro-[1,2,4]diazaphosphininium; chloride 
• 39143-34-5 3-(4-nitro-phenyl)-1,4,4,6-tetraphenyl-1,4-dihydro-[1,2,4]diazaphosphininium; chloride 
• 51104-63-3 4-ethoxy-1,4-dihydro-3-p-nitrophenyl-1-phenyl-1,2,4-diazaphosphorine 4-oxide 
• 51104-66-6 4-ethoxy-6-methyl-3-(4-nitro-phenyl)-1-phenyl-1,4-dihydro-[1,2,4]diazaphosphinine 4-oxide 
• 39222-23-6 4-butoxy-3-(4-nitro-phenyl)-1-phenyl-1,4-dihydro-[1,2,4]diazaphosphinine 4-oxide 
• 51128-69-9 6-(4-nitro-phenyl)-2,5,5-triphenyl-2H-5λ⁵-[1,2,4,5]triazaphosphinin-3-one 
• 51104-74-6 4-ethoxy-3-(4-nitro-phenyl)-1,6-diphenyl-1,4-dihydro-[1,2,4]diazaphosphinine 4-oxide 
• 37518-40-4 5-methyl-3-(4-nitro-phenyl)-1,4,4-triphenyl-1,4,5,6-tetrahydro-[1,2,4]diazaphosphininium; chloride 
• 37518-47-1 3-(4-nitro-phenyl)-1,4,4,6-tetraphenyl-1,4,5,6-tetrahydro-[1,2,4]diazaphosphininium; chloride 

Relevant academic research and scientific papers

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

Transition-Metal-Free Coupling of 1,3-Dipoles and Boronic Acids as a Sustainable Approach to C?C Bond Formation

The need for alternative, complementary approaches to enable C?C bond formation within organic chemistry is an on-going challenge in the area. Of particular relevance are transformations that proceed in the absence of transition-metal reagents. In the current study, we report a comprehensive investigation of the coupling of nitrile imines and aryl boronic acids as an approach towards sustainable C?C bond formation. In situ generation of the highly reactive 1,3-dipole facilitates a Petasis–Mannich-type coupling via a nucleophilic boronate complex. The introduction of hydrazonyl chlorides as a complementary nitrile imine source to the 2,5-tetrazoles previously reported by our laboratory further broadens the scope of the approach. Additionally, we exemplify for the first time the extension of this protocol into another 1,3-dipole, through the synthesis of aryl ketone oximes from aryl boronic acids and nitrile N-oxides.

Intramolecular Diels-Alder and [3+2] Cycloaddition Reactions in the One-Pot Synthesis of Epoxypyrrolo[3,4-g]indazoles

A one-pot approach for the synthesis of epoxypyrrolo[3,4- g ]indazoles is presented. The first step was initiated by a three-component reaction of an isocyanide, a dialkyl acetylenedicarboxylate, and 2-furancarboxylic acid, and led to 1,3-dioxoepoxyisoindole, followed by the addition of hydrazonoyl chloride through a [3+2]-cycloaddition reaction in the second step. The key step in the formation of final compound involves a bicyclization strategy through intramolecular Diels-Alder (IMDA) reaction.

[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.

Synthesis, UV-Vis spectra, and Hammett correlation of some novel bis(dihydropyrrolo[3,4-c]pyrazoles)

Twenty-nine novel bis(dihydropyrrolo[3,4-c]pyrazole) derivatives were obtained by reacting C, N-phenyl-substituted nitrilimines generated in situ from corresponding hydrazonyl chlorides with bismaleimides. The structures were elucidated by physical and spectroscopic methods [m.p., Rf, infrared (IR),1H nuclear magnetic resonance (NMR), 13C NMR, correlation spectroscopy (COSY), heteronuclear correlation (HETCOR), nuclear Overhauser effect (NOE), and high-resolution mass spectrometry (HRMS)]. Also, Hammett correlation graphs were obtained between Hammett constants σp and λmax values of bis(pyrrolopyrazoles) carrying p-substituted phenyl-ring-bearing electron-withdrawing and electrondonating groups and discussed in terms of substituent effects. Springer-Verlag 2010.

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.

Heterocyclic derivatives of fullerene C60. 1. Synthesis of new fulleropyrazolines by the 1,3-dipolar cycloaddition of nitrile imines

New stable [6,6]-closed cycloadducts, fulleropyrazolines containing aryl, hetaryl, trifluoromethyl, and other substituents in the five-membered ring, have been obtained by the 1,3-dipolar cycloaddition of nitrile imines to C 60. Two methods of generating nitrile imines in situ have been used, the dehydrohalogenation of the corresponding hydrazonoyl halides by the action of triethylamine and the thermal decomposition of 2,5-diaryltetrazoles.

Facile synthesis of hydrazonyl halides by reaction of hydrazones with N-halosuccinimide-dimethyl sulfide complex

A new and convenient method is described for the synthesis of hydrazonyl halides. Hydrazones on treatment with N-chlorosuccinimide-dimethyl sulfide complex result in the formation of the corresponding hydrazonyl chlorides in good yields. Similarly, treatment of hydrazones with N-bromosuccinimide-dimethyl sulfide complex gives the corresponding hydrazonyl bromide under extremely mild conditions.

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

Anthelmintic methods employing benzoyl chloride phenylhydrazones

Certain benzoyl chloride phenylhydrazones have been found to be active against insects and mites, and they have also been found to be effective, broad-spectrum anthelmintics for suppressing parasitic worms in animals, particularly sheep. The benzoyl ring