40594-88-5

Upstream product

• 119-61-9 benzophenone 
• 539-44-6 N-4-methylphenylhydrazine 
• 106-43-4 para-chlorotoluene 
• 5350-57-2 benzophenone hydrazone 
• 62-53-3 aniline 
• 624-31-7 4-tolyl iodide 
• 1665-83-4 2-(diphenylmethylene)-1-methyl-1-phenylhydrazine 
• 106-38-7 para-bromotoluene 

Downstream Products

• 1419611-76-9 3-phenyl-1-(p-tolyl)-1H-indazole 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 1220278-84-1 2-(4-chlorophenyl)-N'-(diphenylmethylene)-N-p-tolylacetohydrazide 
• 1220278-79-4 2-(diphenylmethylene)-1-phenethyl-1-p-tolylhydrazine 
• 18820-82-1 Pyridine hydrobromide 

Relevant academic research and scientific papers

Biarylhydrazine compounds and their adducts and applications in the preparation of antitumor drugs

The present invention discloses a biarylhydrazine compound and its application in the preparation of antitumor drugs, the structure of the arylhydrazine compound as shown in formula I, the adduct is a biarylhydrazine compound on the hydrazine group plus benzyloxycarbonyl glycyl prolyl. The anticancer activity of the biarylhydrazine compounds of the present invention is superior to that of the existing positive control drug procarbazine; its Z-GP adduct can significantly reduce in vitro toxicity and in vivo toxicity to normal cells, and can be excised by FΑP-α enzyme specific hydrolysis in vivo (Z-GP) to release hydrolysate products; its Z-GP adduct can significantly inhibit tumor growth in tumor-bearing nude mice and reduce toxicity to non-target organs.

Synthesis of 1: H -indazoles by an electrochemical radical Csp2-H/N-H cyclization of arylhydrazones

The development of efficient and sustainable C-N bond-forming reactions to N-heterocyclic frameworks has been a long-standing interest in organic synthesis. In this work, we develop an electrochemical radical Csp2-H/N-H cyclization of arylhydrazones to 1H-indazoles. The electrochemical anodic oxidation approach was adopted to synthesize a variety of 1H-indazole derivatives in moderate to good yields. HFIP was not only employed as a solvent or the proton donor, but also can promote the formation of N free radicals. This synthetic methodology is operationally simple, and less expensive electrodes would be suitable for this chemistry. This journal is

Divergent Synthesis of 1H-Indazoles and 1H-Pyrazoles from Hydrazones via Iodine-Mediated Intramolecular Aryl and sp3 C–H Amination

A divergent intramolecular C–H amination of hydrazones has been developed employing molecular iodine (I2) as the sole oxidant. The required hydrazone substrates were readily obtained by condensation of hydrazines with the corresponding ketones.

An efficient transition-metal-free synthesis of 1H-indazoles from arylhydrazones with montmorillonite K-10 under O2 atmosphere

An efficient transition-metal-free synthetic method of 1H-indazoles has been developed. The reaction of arylhydrazones in the presence of montmorillonite K-10 in 1,2-dichlorobenzene at 130 °C afforded 1H-indazoles in good yields most likely via a sequenti

Nickel-catalyzed N-arylation of benzophenone hydrazone with bromoarenes

A nickel-catalyzed method for the cross-coupling of benzophenone hydrazone with aryl bromides is described. The use of a simple Ni(ii)/NHC catalyst leads to the arylated hydrazones in good or acceptable yields. This protocol provides a simple, convenient alternative to the synthesis of arylhydrazines.

Rational and predictable chemoselective synthesis of oligoamines via Buchwald-Hartwig amination of (hetero)aryl chlorides employing Mor-Dalphos

We report a diverse demonstration of synthetically useful chemoselectivity in the synthesis of di-, tri-, and tetraamines (62 examples) by use of Buchwald-Hartwig amination employing a single catalyst system ([Pd(cinnamyl)Cl]2/L1; L1 = N-(2-(di(1-adamantyl)phosphino)phenyl) morpholine, Mor-DalPhos). Competition reactions established the following relative preference of this catalyst system for amine coupling partners: linear primary alkylamines and imines > unhindered electron-rich primary anilines, primary hydrazones, N,N-dialkylhydrazines, and cyclic primary alkylamines > unhindered electron-deficient primary anilines, α-branched acyclic primary alkylamines, hindered electron-rich primary anilines ? cyclic and acyclic secondary dialkylamines, secondary alkyl/aryl and diarylamines, α,α-branched primary alkylamines, and primary amides. The new isomeric ligand N-(4-(di(1-adamantyl)phosphino)phenyl)morpholine (p-Mor-DalPhos, L2) was prepared in 63% yield and was crystallographically characterized; the [Pd(cinnamyl)Cl]2/L2 catalyst system exhibited divergent reactivity. Application of the reactivity trends established for [Pd(cinnamyl)Cl] 2/L1 toward the chemoselective synthesis of di-, tri-, and tetraamines was achieved. Preferential arylation was observed at the primary alkylamine position within 2-(4-aminophenyl)ethylamine with [Pd(cinnamyl)Cl] 2/L1 and 4-chlorotoluene (affording 5a); the alternative regioisomer (5a′) was obtained when using [Pd(cinnamyl)Cl]2/L2. These observations are in keeping with coordination chemistry studies, whereby binding of 2-(4-aminophenyl)ethylamine to the in situ generated [(L1)Pd(p-tolyl)] + fragment occurred via the primary amine moiety, affording the crystallographically characterized adduct [(L1)Pd(p-tolyl)(NH2CH 2CH2(4-C6H4NH2)] +OTf- (7) in 72% yield.

INDOLE AND INDOLINE DERIVATIVES AND METHODS OF USE THEREOF

The present application relates to indole and indoline derivatives of formula (I), (II), (III), (IV), (V), or (VI) wherein a, R1, R2, R3, R4, R5, U, V, W, X, Y, and Z are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating disease conditions using such compounds and compositions, and methods for identifying such compounds.

Method of forming a carbon-heteroatom bond

The present invention relates to a method of creating a carbon-heteroatom bond, and preferably a carbon-nitrogen bond, by reacting a leaving group-bearing unsaturated compound and a nucleophilic compound. In particular, the invention relates to the creation of a carbon-nitrogen bond, using a method involving the arylation of nitrogenous organic derivatives; the inventive method consists in creating a carbon-heteroatom bond by reacting a leaving group-bearing unsaturated compound and a nucleophilic compound introducing a heteroatom which can be substituted for the leaving group, thereby creating a carbon-heteroatom bond, in the presence of a palladium-based catalyst, optionally a ligand. The invention is characterized in that the reaction takes place in the presence of an effective quantity of a metal hydroxide or ammonium hydroxide which is associated with an alcohol-type solvent.

Efficient and convenient method for the synthesis of N-arylhydrazones using a palladium-catalyzed bond-forming reaction

A highly effective, convenient, and reproducible industrial process for palladium-catalyzed carbon-nitrogen cross coupling has been developed and applied on a large scale. Thus various functionalized N-arylhydrazones have been easily prepared and well cha

Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account

The palladium-catalyzed coupling of amines and aryl halides or aryl alcohol derivatives has matured from an exotic small-scale transformation into a very general, efficient and robust reaction during the last ten years. This article reports several applications of this method from an industrial vantage point, including ligand synthesis, synthesis of arylpiperazines, arylhydrazines and diarylamines. Much emphasis in placed on issues of scale-up and safety to underline the potential of C-N couplings as solutions for industrial-scale synthetic problems.