15754-37-7

Upstream product

• 618-40-6 1-Methyl-1-phenylhydrazine 
• 98-86-2 acetophenone 
• 536-74-3 phenylacetylene 
• 6077-10-7 bis(phenylethynyl)mercury 
• 98-85-1 1-Phenylethanol 
• 100-63-0 phenylhydrazine 
• 583-11-9 N-(1-phenylethylidene)phenylhydrazine 
• 74-88-4 methyl iodide 

Downstream Products

• 3558-24-5 1-methyl-2-phenyl-1H-indole 
• 10604-22-5 3-phenylcinnoline 
• 109310-82-9 2-(N-methyl-N-phenylhydrazono)-2-phenylacetaldehyde 
• 200062-46-0 4-cyano-3-phenyl-1,2-diazanaphthalene 
• 167895-49-0 (C₆H₅C(CH₂)NN(CH₃)(C₆H₅))PdCl(P(C₆H₅)3) 
• 128737-90-6 2,4,7-Trinitro-fluoren-9-one; compound with N-methyl-N-phenyl-N'-[1-phenyl-eth-(E)-ylidene]-hydrazine 
• 106032-47-7 1-(Methyl-phenyl-amino)-6-phenyl-2,3-dihydro-1H-pyridin-4-one 

Relevant academic research and scientific papers

Zirconium complexes stabilized by amine-bridged bis(phenolato) ligands as precatalysts for intermolecular hydroamination reactions

A series of zirconium complexes bearing amine-bridged bis(phenolato) ligands of different steric and electronic properties have been synthesized, and their activities in catalyzing intermolecular hydroamination reactions have been studied and compared. In

Catalytic acceptorless dehydrogenative coupling of arylhydrazines and alcohols for the synthesis of arylhydrazones

The direct synthesis of arylhydrazones via catalytic acceptorless dehydrogenative coupling of arylhydrazines and alcohols has been accomplished. More importantly, complete selectivity for arylhydrazones and none of the N-alkylated byproducts were generated in this process, which exhibit new potential and provide a new horizon for the development of catalytic acceptorless dehydrogenative coupling reactions.

Adaptation in constitutional dynamic libraries and networks, switching between orthogonal metalloselection and photoselection processes

Constitutional dynamic libraries of hydrazones aAbB and acylhydrazones aAcC undergo reorganization and adaptation in response to a chemical effector (metal cations) or a physical stimulus (light). The set of hydrazones [1A1B, 1A2B, 2A1B, 2A 2B] undergoes metalloselection on addition of zinc cations which drive the amplification of Zn(1A2B)2 by selection of the fittest component 1A2B. The set of acylhydrazones [E-1A1C, 1A2C, 2A1C, 2A2C] undergoes photoselection by irradiation of the system, which causes photoisomerization of E- 1A1C into Z-1A1C with amplification of the latter. The set of acyl hydrazones [E-1A1C, 1A3C, 2A1C, 2A 3C] undergoes a dual adaptation via component exchange and selection in response to two orthogonal external agents: a chemical effector, metal cations, and a physical stimulus, light irradiation. Metalloselection takes place on addition of zinc cations which drive the amplification of Zn( 1A3C)2 by selection of the fittest constituent 1A3C. Photoselection is obtained on irradiation of the acylhydrazones that leads to photoisomerization from E-1A 1C to Z-1A1C configuration with amplification of the latter. These changes may be represented by square constitutional dynamic networks that display up-regulation of the pairs of agonists ( 1A2B, 2A1B), (Z-1A 1C, 2A2C), (1A3C, 2A1C), (Z-1A1C, 2A 3C) and the simultaneous down-regulation of the pairs of antagonists (1A1B, 2A2B), (1A 2C, 2A1C), (E-1A1C, 2A3C), (1A3C, 2A 1C). The orthogonal dual adaptation undergone by the set of acylhydrazones amounts to a network switching process.

Bis(amidate)bis(amido) titanium complex: A regioselective intermolecular alkyne hydroamination catalyst

An efficient and selective bis(amidate)bis(amido) titanium precatalyst for the anti-Markovnikov hydroamination of alkynes is reported. Hydroamination of terminal and internal alkynes with primary alkylamines, arylamines, and hydrazines is promoted by 5-10 mol % of Ti catalyst. Various functional groups are tolerated including esters, protected alcohols, and imines. The in situ generated complex shows comparable catalytic activity, demonstrating its synthetic versatility for benchtop application. Applications of this catalyst for the synthesis of amino alcohols and a one-pot procedure for indole synthesis are described. A mechanistic proposal that invokes turnover-limiting protonolysis is presented to rationalize the observed regioselectivities.

Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones: Synthesis of cinnolines

O2 leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a C sp 3-H bond functionalization process (see scheme; DMF=N,N'-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives. Copyright

A general study of [(η5-Cp′)2Ti(η 2-Me3SiC2SiMe3)]-catalyzed hydroamination of terminal alkynes: Regioselective formation of Markovnikov and anti-Markovnikov products and mechanistic explanation (Cp′=C (5)H(5), C(5)H(4)Et, C(5)Me(5))

A general study of the regioselective hydroamination of terminal alkynes in the presence of [(η5-Cp)2Ti(η2-Me 3SiC2SiMe3)] (1), [(η5-CpEt) 2Ti(η2-Me3SiC2SiMe3)] (CpEt= ethylcyclopentadienyl) (2), and [(η5-Cp*) 2Ti(η2-Me3SiC2SiMe3)] (Cp=pentamethylcyclopentadienyl) (3) is presented. While aliphatic amines give mainly the anti-Markovnikov products, anilines and aryl hydrazines yield the Markovnikov isomer as main products. Interestingly, using aliphatic amines such as n-butylamine and benzylamine the different catalysts lead to a significant change in the observed regioselectivity. Here, for the first time a highly selective switch from the Markovnikov to the anti-Markovnikov product is observed simply by changing the catalyst. Detailed theoretical calculations for the reaction of propyne with different substituted anilines and tert-butylamine in the presence of [(η5-C5H5)Ti(= NR)(NHR)] (R=4-C6H4X; X=H, F, Cl, CH3, 2,6-dimethylphenyl) reveal that the experimentally observed regioselectivity is determined by the relative stability of the corresponding π-complexes 10. While electrostatic stabilization favors the Markovnikov performance for aniline, the steric repulsive destabilization disfavors the Markovnikov performance for tert-butylamine.

Hydrazinomercuriation of Terminal Alkynes and 3-Alken-1-ynes. Syntheses of Hydrazones and 1-Amino-1-aza-1,3-dienes

Although hydrazines cannot be directly added to non-activated, terminal acetylenes in the presence of mercury(II) salts, this difficulty was circumvented by treating hydrazines with 1-alkynylmercury trifluoroacetates (2); in this way, several hydrazones (4a-h) and 1-amino-1-aza-1,3-dienes (4i-m) were easily prepared.

Inhibiteurs mixtes des voies de la cyclooxygenase et des lipoxygenases: synthese et activite de derives hydrazoniques

Dual inhibitors of the cyclooxygenase and lipoxygenase pathways: synthesis and activity of hydrazone derivatives.Non-steroidal anti-inflammatory drugs (NSAIDs) act by preventing prostaglandin production.In recent years, research on non-steroid dual inhibitors of prostaglandin and leukotriene biosyntheses has been developed.These compounds should represent a new class of anti-inflammatory drugs, with a wider spectrum of activity than classical NSAIDs.The present paper reports the synthesis of hydrazone derivatives.The effect of various substitutions is studied on platelet cyclooxygenase (i.e. prostaglandin synthesis) and on leukocyte 5-lipoxygenase (i.e. leukotriene synthesis).Among the 50 tested compounds, 2 hydrazone derivatives were selected for their significant dual inhibitory potency: 2-acetylthiophene-2-thiazolylhydrazone 5g, and N-phenyl benzimidrazone 6c.Keywords - non-steroidal anti-inflammatory drugs / hydrazones / dual inhibitor / cyclooxygenase / lipoxygenase