940-48-7

Upstream product

• 5281-18-5 benzaldehyde, hydrazone 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 
• 1068-57-1 acetic acid hydrazide 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 110460-80-5 1-(5-methyl-2-phenyl-[1,3,4]oxadiazol-3-yl)ethanone 
• 55902-35-7 Z α-nitrobenzylidene acetone 
• 7151-53-3 1-acetyl-2-benzylhydrazine 
• 555-96-4 Benzylhydrazine 
• 100-44-7 benzyl chloride 
• 64-19-7 acetic acid 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 7732-18-5 water 

Downstream Products

• 1627-70-9 benzaldehyde (5-benzylidene-4-oxo-thiazolidin-2-ylidene)-hydrazone 
• 4046-03-1 2-methyl-5-phenyl-[1,3,4]oxadiazole 
• 928151-49-9 trans-[Ru(III)(C₆H₄CHNNC(CH₃)O)(PPh₃)2Cl] 

Relevant academic research and scientific papers

Mn(III)-mediated phosphinoylation of aldehyde hydrazones: Direct “one-pot” synthesis of α-iminophosphine oxides from aldehydes

A “one-pot” strategy for the straightforward Mn(III)-mediated phosphinoylation of aldehyde hydrazones with diphenylphosphine oxide to furnish α-iminophosphine oxides is described. This mild and practical method allows the direct use of aldehydes as substrates in one pot to generate the hydrazones, which are then engaged “in situ” by the phosphorus reagent in the presence of Mn(OAc)3 oxidant. Thus, the requisite isolation of the hydrazones is not needed in this operation. Conducted mechanistic experiments implicate a pathway involving phosphorus-centered radicals.

Harnessing Autoxidation of Aldehydes: In Situ Iodoarene Catalyzed Synthesis of Substituted 1,3,4-Oxadiazole, in the Presence of Molecular Oxygen

Isobutyraldehyde underwent auto-oxidation in the presence of molecular oxygen to generate an acyloxy radical under a "metal-free" environment. They were subsequently exploited in situ to afford hypervalent iodines with p-anisolyl iodide which generated substituted 1,3,4-oxadiazoles in moderate to excellent yields from N′-arylidene acetohydrazides. The reaction strategy tolerated diverse substitution on the hydrazide substrates. Control experiments and literature precedence supported the formation of an in situ iodosylarene complex that facilitates the formation of products.

Triazine-Substituted and Acyl Hydrazones: Experiment and Computation Reveal a Stability Inversion at Low pH

Condensation of a hydrazine-substituted s-triazine with an aldehyde or ketone yields an equivalent to the widely used, acid-labile acyl hydrazone. Hydrolysis of these hydrazones using a formaldehyde trap as monitored using HPLC reveals that triazine-subst

Multivalent DNA recognition by self-assembled clusters: deciphering structural effects by fragments screening and evaluation as siRNA vectors

The identification of low-molecular-weight clusters that effectively complex oligonucleotides of therapeutic interest is of great importance for applications in gene delivery. We recently reported the use of self-assembly processes based on chemoselective ligation in order to generate biomolecular clusters for the multivalent recognition of DNA. Herein, we exploit the modularity of this methodology to perform a one-pot fragments screening of scaffolds and binding groups. Structural parameters affecting DNA binding were observed and hits have been identified by fluorescence displacement and gel electrophoresis assays. Finally, we evaluated the potential of these systems for siRNA transfection. One biomolecular cluster was found to effectively complex and transport a 21-mer siRNA inside MCF7 human breast cancer cells, resulting in a significant knockdown of the target gene.

Synthesis of N-Acyl Triazolyl-Pyrazolines via Acylation Initiated by the Hydrazone Moiety with Carboxylic Acids

An efficient synthesis of N-acyl/N-substituted acyl pyrazolines and their triazole hybrids have been accomplished via acylation of pyrazolines and pyrazoline-triazole hybrids with carboxylic acids and/or substituted carboxylic acids in the absence of activating agents/catalysts. In the present study, a mechanism envisaging the in situ generation of a new transient acylating intermediate has been proposed to explain the acylation.

Metal-Free Synthesis of 1,3,4-Oxadiazoles from N′-(Arylmethyl)hydrazides or 1-(Arylmethyl)-2-(arylmethylene)hydrazines

An efficient and versatile metal-free synthesis of 1,3,4-oxadiazoles from N′-(arylmethyl)hydrazides or 1-(arylmethyl)-2-(arylmethylene)hydrazines through oxidative dehydrogenation is reported. A range of 2,5-disubstituted 1,3,4-oxadiazoles were prepared by treating N′-(arylmethyl)hydrazides with (diacetoxyiodo)benzene in acetonitrile or by treating 1-(arylmethyl)-2-(arylmethylene)hydrazines with [bis(trifluoroacetoxy)iodo]benzene in methyl tert-butyl ether. Aldehyde N-acylhydrazones and aldazines were initially generated in situ as intermediates.

ANTI-PROLIFERATIVE COMPOUNDS AND USES THEREOF

The present invention provides novel compounds of Formula (I), and pharmaceutically acceptable salts, tautomers, stereoisomers, solvates, hydrates, polymorphs, and compositions thereof. Also provided are methods and kits involving the inventive compounds

Unexpected synthesis of 1,3,5-triarly-1,5-diketones from aryl ketones via di-enamine mechanism

An unexpected reaction of aryl ketone with acetohydrazone of aromatic aldehyde via 1,2-di-enamine/di-iminium mechanism was discovered, leading to efficient synthesis of 1,3,5-triaryl-1,5-diketones in good to excellent yields.

Efficient oxidative cyclisation of acid hydrazides to 2,5-disubstituted 1,3,4-oxadiazoles catalysed by Bu4NI with t-BuOOH as oxidant

Acid hydrazides or araldehyde N-acylhydrazones can be converted in good yields to, respectively, symmetrical or unsymmetrical, 2,5-disubstituted 1,3,4-oxadiazoles at 60 °C by a Bu4NI-catalysed procedure which requires the presence of a base and 2.5 equiv. of t-butyl hydroperoxide.

Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: Proceeding through in situ directing group formation and removal

The Rh-catalyzed direct annulation of an aldehyde with an alkyne leading to indenone was achieved. The in situ temporal installation of acetylhydrazine enables the annulation of the ortho arene C-H bond with alkynes to form ketone hydrazone. Subsequently, the in situ directing group removal takes place since ketone hydrazone is more susceptible toward hydrolysis than aldehyde hydrazone. Notably, this procedure tolerates a series of functional groups, such as methoxyl, acetylamino, fluoro, trifluoromethyl, methoxycarbonyl, chloro, and bromo groups.