1075-70-3

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 113, p. 4871, 1991 DOI: 10.1021/ja00013a024

InChI:InChI=1/C9H12N2/c1-11(2)10-8-9-6-4-3-5-7-9/h3-8H,1-2H3/b10-8+

Upstream product

• 100-52-7 benzaldehyde 
• 57-14-7 N,N-Dimethylhydrazine 
• 59359-10-3 ethyl 3-dimethylhydrazonopropanoate 
• 5877-58-7 N-benzylidene-3-methylaniline 
• 66064-57-1 (E)-1,1-dimethyl-2-(2-methylallylidene)hydrazine 
• 331-98-6 N-benzylidene-4-fluoroaniline 
• 889-38-3 N'-benzylidene-N,N-dimethyl-p-phenylenediamine 
• 91000-43-0 3,5-dimethyl-N-benzylideneaniline 
• 538-51-2 benzylidene phenylamine 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 106-47-8 4-chloro-aniline 
• 104-94-9 4-methoxy-aniline 
• 108-69-0 3,5-dimethylaminoaniline 
• 30862-08-9 N-benzylidene-2,4-dimethyl-aniline 

Downstream Products

• 5281-18-5 benzaldehyde, hydrazone 
• 38706-49-9 benzamide dimethylhydrazone 
• 61701-91-5 Phenyl-2,7-octadienylketon-dimethylhydrazon 
• 82453-68-7 N-[2-(Dimethyl-hydrazono)-2-phenyl-acetyl]-methanesulfonamide 
• 100-47-0 benzonitrile 
• 5770-97-8 3-Methyl-5-phenyl-1,3,4-thiadiazol-2(3H)-thion 
• 130799-78-9 benzaldehyde N,N-dimethyl-N-benzylhydrazonium bromide 
• 82453-70-1 phenylglyoxylic acid (4-methylphenyl-sulfonamide) N,N-dimethylhydrazone 
• 112080-67-8 5-Dimethylamino-6-phenyl-1,3-di(p-tolylsulfonyl)hexahydro-1,3,5-triazin-2,4-dion 
• 130799-79-0 benzaldehyde N,N-dimethyl-N-(p-bromobenzyl)hydrazonium bromide 
• 3533-63-9 dimethyl (2E)-2-(dimethylamino)but-2-enedioate 
• 130799-80-3 benzaldehyde N,N-dimethyl-N-(p-nitrobenzyl)hydrazonium bromide 
• 82453-69-8 N-[2-(Dimethyl-hydrazono)-2-phenyl-acetyl]-benzenesulfonamide 
• 111269-36-4 3-phenyl-1,1,1-trifluoropropane-2,3-dione 3-dimethylhydrazone 

Relevant academic research and scientific papers

Preparation and deprotection of aldehyde dimethylhydrazones

Aldehydes were conveniently protected as dimethylhydrazones by stirring a mixture of the aldehyde, N,N-dimethylhydrazine, anhydrous magnesium sulfate, and dichloromethane at room temperature. Azeotropic removal of water, formed during the course of the reaction, was not required because anhydrous magnesium sulfate functions as a water scavenger. Deprotection of aldehyde dimethylhydrazones was accomplished by stirring a mixture of the aldehyde dimethylhydrazone and aqueous glyoxylic acid at room temperature. The reaction time for the preparation and deprotection of aldehyde dimethylhydrazones varied with the structure of the aldehyde. Copyright Taylor & Francis Group, LLC.

Method development for the determination of 1,1-dimethylhydrazine by the high-performance liquid chromatography–mass spectrometry technique

Unsymmetrical dimethyl hydrazine is highly toxic, carcinogenic compound, widely used for organic synthesis and drug development. Therefore, due to its high reactivity, direct analysis is problematic. Current study proposes to use derivatization reaction t

An alternative channel of reductive condensation of trichloromethylarenes with hydrazines

The reductive condensation of trichloromethylarenes with hydrazines can proceed without intermediate formation of pyridinium salts and without participation of pyridine in the reduction act. Variants of reductive condensation using hydrazines as reducting agents and α-chlorobenzylhydrazines and hydrazonoyl chlorides, nitrite imines, or hydrazonoylpyridinium salts as intermediates are considered. α-Chlorobenzylhydrazines and hydrazonoyl chlorides are shown to be the most probable intermediates.

Design, synthesis, and evaluation of analogues of 3,3,3-trifluoro-2-hydroxy-2-phenyl-propionamide as orally available general anesthetics

We have recently discovered a novel class of compounds that have oral general anesthetic activity, potent anticonvulsant activity, and minimal hemodynamic effects. The 3,3,3-trifluoro-2-hydroxy-2-phenyl-propionamide (1) demonstrated potent ability to reduce the minimum alveolar concentration (MAC) of isoflurane, with no effects on heart rate or blood pressure at therapeutic concentrations. Analogue 1 also had potent oral anticonvulsant activity against maximal electroshock (MES) and subcutaneous metrazol (scMET) models with a therapeutic index of 10 for MES activity. In this study, we further synthesized nine new racemic analogues and evaluated these compounds for effects on isoflurane MAC reduction and blood pressure. Preliminary data demonstrate potent reduction in the isoflurane MAC for two new compounds. Current mechanistic studies were unrevealing for effects on voltage-gated ion channels as a putative mechanism. Liposomal partitioning studies using 19F NMR reveal that the aromatic region partitions into the core of the lipid. This partitioning correlated with general anesthetic activity of this class of compounds. Further, compound 1 was used at a concentration of 1 mM and slightly enhanced GABAA current in hippocampal neurons at 10 μM. Altogether, 3,3,3-trifluoro-2-hydroxy-2-phenyl-propionamide exhibited excellent oral general anesthetic activity and appears devoid of significant side effects (i.e., alterations in blood pressure or heart rate).

Transient imine as a directing group for the metal-free o-C-H borylation of benzaldehydes

Organoboron reagents are important synthetic intermediates and have wide applications in synthetic organic chemistry. The selective borylation strategies that are currently in use largely rely on the use of transition-metal catalysts. Hence, identifying much milder conditions for transition-metal-free borylation would be highly desirable. We herein present a unified strategy for the selective C-H borylation of electron-deficient benzaldehyde derivatives using a simple metal-free approach, utilizing an imine transient directing group. The strategy covers a wide spectrum of reactions and (i) even highly sterically hindered C-H bonds can be borylated smoothly, (ii) despite the presence of other potential directing groups, the reaction selectively occurs at the o-C-H bond of the benzaldehyde moiety, and (iii) natural products appended to benzaldehyde derivatives can also give the appropriate borylated products. Moreover, the efficacy of the protocol was confirmed by the fact that the reaction proceeds even in the presence of a series of external impurities.

Efficient reductions of dimethylhydrazones using preformed primary amine boranes

A convenient method for the reduction of N,N-dimethylhydrazones using amine borane complexes generated in situ is described. It was found that primary amine borane complexes performed exceedingly well at reducing N,N-dimethylhydrazones in as little as 1.1 equivalents, furnishing the corresponding air-sensitive hydrazine products in excellent yields.

Perfluoroalkylation of Aryl-N,N-dimethyl Hydrazones Using Hypervalent Iodine(III) Reagents or Perfluoroalkyl Iodides

Radical trifluoromethylation of aryl N,N-dimethyl hydrazones using TBAI as an initiator and Togni's reagent as a trifluoromethyl radical source is described. Cascades proceed via electron-catalysis; this approach is generally more applicable to hydrazone perfluoroalkylation using perfluoroalkyl iodides as the radical precursors in combination with a base under visible-light initiation.

AROMATIC COMPOUNDS FROM FURANICS

Described are methods for preparing phenols, benzene carboxylic acids, esters and anhydrides thereof from furanic compounds by reaction with a dienophile, wherein the furanic compounds are reacted with a hydrazine and/or oxime and then reacted with a dienophile.

Modular construction of quaternary hemiaminal-based inhibitor candidates and their in cellulo assessment with HIV-1 protease

Non-peptidomimetic drug-like protease inhibitors have potential for circumventing drug resistance. We developed a much-improved synthetic route to our previously reported inhibitor candidate displaying an unusual quaternized hemi-aminal. This functional group forms from a linear precursor upon passage into physiological media. Seven variants were prepared and tested in cellulo with our HIV-1 fusion-protein technology that result in an eGFP-based fluorescent readout. Three candidates showed inhibition potency above 20 μM and toxicity at higher concentrations, making them attractive targets for further refinement. Importantly, our class of original inhibitor candidates is not recognized by two major multidrug resistance pumps, quite in contrast to most clinically applied HIV-1 protease inhibitors.

Hydrazone as the directing group for Ir-catalyzed arene diborylations and sequential functionalizations

The use of hemilabile pyridine-hydrazone N,N-ligands allows the highly selective Ir-catalyzed ortho,ortho'-directed diborylation of aromatic N,N-dimethylhydrazones in near-quantitative yields. One-pot sequential Suzuki-Miyaura cross-coupling with different aryl bromides provides a short entry to unsymmetrically substituted 2,6-diarylbenzaldehyde derivatives.