25938-97-0

Upstream product

• 60-29-7 diethyl ether 
• 6048-21-1 4-bromobenzoyl cyanide 
• 100-63-0 phenylhydrazine 
• 586-75-4 4-chlorobenzoyl chloride 
• 586-76-5 4-Bromobenzoic acid 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 79071-43-5 5-(4-Bromo-phenyl)-2,3-diphenyl-2,3-dihydro-[1,3,4]oxadiazole 
• 83844-92-2 (4-Bromo-phenyl)-phenylazo-methyl-hydroperoxide 

Downstream Products

• 859078-11-8 N'-(4-bromo-benzoyl)-N-chloroacetyl-N-phenyl-hydrazine 
• 79071-43-5 5-(4-Bromo-phenyl)-2,3-diphenyl-2,3-dihydro-[1,3,4]oxadiazole 
• 25939-12-2 4-bromo-N-phenylbenzohydrazonoyl chloride 
• 33064-18-5 3-(4-bromophenyl)-1-phenyl-1H-pyrazole 

Relevant academic research and scientific papers

Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs

Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.

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.

[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 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.

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

Oxidation of Sulfides by Acyclic α-Azohydroperoxides

The oxidation of sulfides with a series of substituted benzylazobenzene α-hydroperoxides (2a-f) produced the corresponding sulfoxides in good yield (ca. 90 percent) in C6D6 at 34 deg C.The reaction was found to be of the first order with respect to α-azohydroperoxide and to sulfide in aprotic medium.The reaction of BzSPh with acyclic α-azohydroperoxide 2a in C6D6 was found to be slower than the corresponding oxidation with 3-bromo -4,5-dihydro-5-hydroperoxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole in CDCl3.The relative reactivity series of sulfides with α-azohydroperoxide 2a was found to be Me2S (25)> BzSMe (14)> PhSMe (2.5)> BzSPh (1.0).This is similar to that observed for the reaction of the sulfides with hydrogen peroxide in protic solvent and reflects the relative nucleophilicities of the sulfides.The second-order rate constants for the reaction of a series of substituted benzylazobenzene α-hydroperoxides with PhSMe and BzSMe exhibited an excellent correlation with ? values.Both LFERs had ρ values of approximately 1.0.The results were interpreted to be consistent with nucleophilic attack of the sulfide on oxygen.Concomitant transfer of the hydroperoxy proton to the azo nitrogen would account for the lack of the requirement of general acid catalysis in aprotic medium.

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