87829-01-4

Upstream product

• 72358-76-0 phenylhydrazine acetate 
• 1571-08-0 methyl 4-formylbenzoate 
• 6908-41-4 4-(methoxycarbonyl)benzyl alcohol 
• 62-53-3 aniline 
• 100-63-0 phenylhydrazine 
• 619-66-9 4-Carboxybenzaldehyde 
• 623-24-5 1,4-bis(bromomethyl)benzene 

Downstream Products

• 123560-44-1 C₁₆H₁₃ClN₂O₃ 
• 1014625-49-0 4-(1-phenyl-5-p-tolyl-1H-pyrazol-3-yl)-benzoic acid methyl ester 
• 1016169-25-7 4-(1-phenyl-4-p-tolyl-1H-pyrazol-3-yl)-benzoic acid methyl ester 
• 1016169-26-8 4-(5-amino-1-phenyl-4-p-tolyl-1H-pyrazol-3-yl)-benzoic acid methyl ester 
• 1016169-27-9 4-(3-nitro-1-phenylazo-2-p-tolyl-propyl)-benzoic acid methyl ester 
• 1310486-83-9 methyl 4-(1-benzyl-1H-benzo[d]imidazole-2-yl)benzoate 
• 50802-11-4 C₁₅H₁₃ClN₂O₂ 
• 1608493-96-4 methyl 4-(4-nitro-1,5-diphenyl-1H-pyrazol-3-yl)benzoate 
• 1608493-97-5 methyl 4-(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)benzoate 
• 1447058-85-6 1-p-iodophenyl-3-(p-methoxycarbonylphenyl)-5-phenylformazan 
• 1447058-81-2 1-m-iodophenyl-3-(p-methoxycarbonylphenyl)-5-phenylformazan 
• 1447058-77-6 1-o-iodophenyl-3-(p-methoxycarbonylphenyl)-5-phenylformazan 

Relevant academic research and scientific papers

Synthesis, spectral analysis, structural elucidation and quantum chemical studies of (E)-methyl-4-[(2-phenylhydrazono)methyl]benzoate

The title compound, (E)-methyl-4-[(2-phenylhydrazono)methyl]benzoate, (I), (C15H14N2O2), has been synthesized by condensation reaction of methyl-4-formylbenzoate and phenylhydrazine. The compound has been charac

Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles

Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.

Experimental and quantum chemical studies of the structural and spectral properties of novel diazenyl formazans

A new series of 3-(p-substitutedphenyl)-5-phenyl-1-(4-phenyldiazenyl)phenylformazans were synthesized by coupling p-substituted phenyl or pyridinylhydrazones with p-aminoazobenzene diazonium chloride. All compounds were characterized by FT-IR, UV–Vis, 1H NMR, and 13C NMR spectroscopic techniques, and HR-MS. DFT was used to calculate the molecular structures and 1H and 13C chemical shift values of the synthesized compounds with PBE1PBE functional and 6-311G(2d,2p)basis set combination. The IR spectra of the novel formazans were calculated using DFT at PBE1PBE/6-311G(d,p)level of theory. The electronic absorption spectra of the optimized structures were evaluated by TD-DFT method at PBE1PBE/6-311G(2d,2p)level of theory. The absorption spectra of the synthesized diazenyl formazans were investigated in three different solvents. A good correlation was established between the experimental data and calculated results.

Synthesis of hybrid polycycles containing fused hydroxy benzofuran and 1H-indazoles via a domino cyclization reaction

A stoichiometry controlled domino cyclization reaction of hydrazone and p-benzoquinone to an angularly fused 3H-benzofuro[3,2-e]indazole core with an embedded oxygenated dibenzofuran framework under mild reaction conditions is disclosed. The reaction involves palladium catalyzed 5-hydroxy-1H-indazole formation followed by TFA mediated [3+2] annulation between the in situ formed 5-hydroxy-1H-indazole and p-benzoquinone. The developed method is attractive because of the concomitant formation of two heterocyclic rings with consecutive multiple bond forming events that include two C-C, one C-N and one C-O bonds. Spectroscopic and theoretical studies of the blue emissive benzofuroindazole derivatives have also been described.

Ion-pairing catalysis in the enantioselective addition of hydrazones to N-acyldihydropyrrole derivatives

We have demonstrated that dihydropyrrole-based enamide derivatives can act as efficient precursors of chiral quaternary N-acyliminium salts under Br?nsted acid catalysis that undergo reactions with hydrazones, the latter participating as masked nucleophilic carbonyl group equivalents. The optimized methodology provides a variety of enantiopure α-substituted proline derivatives in excellent yields, being even compatible with disubstituted β-enamides that generate two contiguous stereocentres.

Co-opting a Bioorthogonal Reaction for Oncometabolite Detection

Dysregulated metabolism is a hallmark of many diseases, including cancer. Methods to fluorescently detect metabolites have the potential to enable new approaches to cancer detection and imaging. However, fluorescent sensing methods for naturally occurring cellular metabolites are relatively unexplored. Here we report the development of a chemical approach to detect the oncometabolite fumarate. Our strategy exploits a known bioorthogonal reaction, the 1,3-dipolar cycloaddition of nitrileimines and electron-poor olefins, to detect fumarate via fluorescent pyrazoline cycloadduct formation. We demonstrate hydrazonyl chlorides serve as readily accessible nitrileimine precursors, whose reactivity and spectral properties can be tuned to enable detection of fumarate and other dipolarophile metabolites. Finally, we show this reaction can be used to detect enzyme activity changes caused by mutations in fumarate hydratase, which underlie the familial cancer predisposition syndrome hereditary leiomyomatosis and renal cell cancer. Our studies define a novel intersection of bioorthogonal chemistry and metabolite reactivity that may be harnessed to enable biological profiling, imaging, and diagnostic applications.

Divergent construction of pyrazoles via Michael addition of n -arylhydrazones to 1,2-diaza-1,3-dienes

The base (NaH)-promoted Michael addition of N-arylhydrazones (AHs) with 1,2-diaza-1,3-dienes (DDs) produces unprecedented β-azohydrazone adducts. Strategically, the use of AHs as acyl anion equivalents (d1 synthon) and DDs as α-electrophiles (a

Synthesis, spectral properties of 1-substituted phenyl-3-(p- methoxycarbonyl)phenyl-5-phenylformazans

Formazans 1-14 were prepared by the coupling reaction of phenylhydrazones and diazonium salts of aniline or -NO2, -CH3, -OCH3, -I, substituted anilines. The phenylhydrazones were synthesized by condensation of benzaldehyde or methyl-4-formylbenzoate with phenylhydrazine. The structures of the compounds were confirmed by IR, 1H NMR and 13C NMR. The dependence of ?max upon the type of substituents and their positions on the phenyl ring was investigated using UV-visible spectra.

Copper-mediated synthesis of substituted 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles via C-H functionalization/C-N/C-O bond formation

An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.

Base-mediated reaction of hydrazones and nitroolefins with a reversed regioselectivity: A novel synthesis of 1,3,4-Trisubstituted pyrazoles

A regioselective synthesis of 1,3,4-tri- or 1,3,4,5-tetrasubstituted pyrazoles by the reaction of hydrazones with nitroolefins is described. Mediated with strong bases such as t-Bu OK, the reaction exhibits a reversed, exclusive 1,3,4-regioselectivity. Su