17359-82-9

Usage

InChI:InChI=1/C13H10Cl2N2/c14-11-6-8-12(9-7-11)16-17-13(15)10-4-2-1-3-5-10/h1-9,16H/b17-13-

Upstream product

• 2833-68-3 benzaldehyde-p-chlorophenylhydrazone 
• 100-52-7 benzaldehyde 
• 17473-76-6 N'-(4-chlorophenyl)benzohydrazide 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 588-64-7 benzaldehyde phenylhydrazone 
• 88267-39-4 <(p-chlorophenyl)azo>stilbene 

Downstream Products

• 54249-05-7 1-(4-chloro-phenyl)-3-phenyl-(3ar,8bc)-3a,8b-dihydro-1H-benzo[4,5]thieno[3,2-c]pyrazole 4,4-dioxide 
• 63637-57-0 1-(4-chlorophenyl)-3-phenyl-1H-pyrazole 
• 17647-24-4 C₁₃H₉ClN₂ 
• 1111748-01-6 methyl 1-(4-chlorophenyl)-5-(2-nitrobenzyl)-3-phenyl-4,5-dihydro-1H-pyrazole-5-carboxylate 
• 78830-52-1 (1-(4-chlorophenyl)-3-phenyl-1H-pyrazol-4-yl)phenylmethanone 
• 78830-53-2 [1-(4-Chloro-phenyl)-3-phenyl-1H-pyrazol-4-yl]-p-tolyl-methanone 
• 78830-41-8 [(3R,4S)-2-(4-Chloro-phenyl)-4-(4-methyl-benzoyl)-5-phenyl-3,4-dihydro-2H-pyrazol-3-yl]-p-tolyl-methanone 

Relevant academic research and scientific papers

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

[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.

Spirotriazoline oxindoles: A novel chemical scaffold with in vitro anticancer properties

The design and synthesis of a library of twenty-six spirotriazoline oxindoles and their in vitro evaluation as potential anticancer agents is reported. The antiproliferative activity of the synthesized compounds was assessed against four different cancer cell lines (HCT-116 p53 (+/+), HCT-116 p53 (?/?), MCF-7, and MDA-MB-231). Four spirotriazoline oxindoles showed selectivity against the four cancer cell lines tested over the non-cancer derived HEK 293T cell line. To characterize the molecular mechanisms involved in compound antitumoral activity, two spirotriazoline oxindoles were selected for further studies. Both compounds were able to induce apoptosis and cell cycle arrest at G0/G1 phase and upregulated p53 steady-state levels, while decreasing its main inhibitor MDM2, in HCT-116 cells. Importantly, cytotoxic effects induced by spirotriazoline oxindoles occurred in cancer cells without eliciting cell death in non-malignant CCD-18Co human colon fibroblasts. In addition, four spirotriazoline oxindoles showed selectivity against the triple-negative breast cancer cell line MDA-MB-231 with IC50 values of 3.5–6.7 μM. These results highlight the anticancer potential of spirotriazoline oxindoles, especially when dealing with aggressive and challenging triple-negative breast cancer.

Exploiting the Electrophilic and Nucleophilic Dual Role of Nitrile Imines: One-Pot, Three-Component Synthesis of Furo[2,3-d]pyridazin-4(5H)-ones

An expeditious multicomponent reaction to synthesize tetrasubstituted furo[2,3-d]pyridazin-4(5H)-ones is reported. In brief, hydrazonoyl chlorides react with isocyanoacetamides, in the presence of TEA, to give 1,3-oxazol-2-hydrazones which, without being isolated, can react with dimethylacetylene dicarboxylate to afford furo[2,3-d]pyridazin-4(5H)-ones with an unprecedented level of complexity in a triple domino Diels-Alder/retro-Diels-Alder/lactamization reaction sequence.

Synthesis of aminocarbonyl N-Acylhydrazones by a three-component reaction of isocyanides, hydrazonoyl chlorides, and carboxylic acids

A novel one-pot multicomponent synthesis of α-aminocarbonyl N-acylhydrazones starting from readily available hydrazonoyl chlorides, isocyanides, and carboxylic acids is reported. The strategy exploits the ability of the carboxylic acid as a third component to suppress all competing reactions between nitrile imines and isocyanides, channeling the course of the reaction toward the formation of this novel class of compounds. (Chemical Equation Presented).

Straightforward strategy for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from Baylis-Hillman adducts by 1,3-dipolar cycloaddition and reductive cyclization

A straightforward and general approach for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from the adducts offorded from the Baylis-Hillman reaction of 2-nitrobenzaldehyde and ethyl acrylate by sequential 1,3-dipolar cycloaddition and reductive cyclization is presented. It was found that the reductive cyclization of the isoxazoline derivatives proceeded efficiently in the presence of In/HCl, whereas similar reductions of pyrazolines gave better yields when carried out in the presence of an Fe/AcOH mixture. However, similar attempts employing the Baylis-Hillman adduct of 2-nitrobenzaldehyde and methyl vinyl ketone did not yield the desired compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

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(

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

Synthesis and reactions of 1H-4,1,2-benzothiadiazines, and observations on the structure of hydrazonoyl sulphides

Syntheses of 1-acetyl-7- and -8-bromo- and -6,8-dibromo-3-phenyl-4,1,2-benzothiadiazines establish, in conjunction with previous data, the generality of 1H-4,1,2-benzothiadiazine synthesis from appropriately substituted N′-acetyl-N′-arylbenzothiohydrazides. The corresponding 6-nitrobenzothiadiazine is also available by this route, and such cyclizations can proceed by expulsion of a nitro-group, presumably as nitrite ion. These 1H-4,1,2-benzothiadiazines undergo electrophilic substitution at positions 6 and 8, are nucleophilic at position 1, and are oxidizable at position 4 to the corresponding sulphone. X-Ray crystallographic studies of bis-[α-(2,6-dibromophenylhydrazono)benzyl] sulphide confirm the symmetrical structure of hydrazonoyl sulphides.