14850-86-3

Upstream product

• 91099-00-2 2'-(4-methoxybenzyl)benzohydrazide 
• 93-89-0 benzoic acid ethyl ester 
• 93-58-3 benzoic acid methyl ester 
• 65-85-0 benzoic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 613-94-5 benzoic acid hydrazide 

Downstream Products

• 85759-88-2 (C₅H₅)TiCl₂(CH₃OC₆H₄)CHNNC(O)C₆H₅ 
• 85767-98-2 (C₅H₅)TiCl((CH₃OC₆H₄)CHNNC(O)C₆H₅)2 
• 32983-58-7 Ni(p-MeOC₆H₄CHNNCOPh)2 
• 1124127-49-6 dimethyl 2-[N-benzoyl-N'-(4-methoxy-benzylidene)-hydrazino]-3-(cyclohexyliminomethylene)succinate 
• 554447-15-3 (S)-benzoic acid N'-[1-(4-methoxyphenyl)but-3-enyl]hydrazide 
• 1259388-07-2 N'-(2,2-difluoro-1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl)benzohydrazide 
• 134022-07-4 2-(4-methoxyphenyl)-3-acetyl-5-phenyl-2,3-dihydro-1,3,4-oxadiazole 
• 77420-69-0 N-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-N'-[1-phenyl-1-thiocyanato-meth-(Z)-ylidene]-hydrazine 
• 92311-70-1 N-[3-Chloro-2-(4-methoxy-phenyl)-4-oxo-azetidin-1-yl]-benzamide 
• 69341-73-7 1-chloro-4-(4-methoxyphenyl)-1-phenyl-2,3-diazabutadiene 
• 2299-73-2 N,N-bis(4-methoxybenzylidene)hydrazine 

Relevant academic research and scientific papers

Planar AIEgens with Enhanced Solid-State Luminescence and ROS Generation for Multidrug-Resistant Bacteria Treatment

Planar luminogens have encountered difficulties in overcoming intrinsic aggregation-caused emission quenching by intermolecular π-π stacking interactions. Although excited-state double-bond reorganization (ESDBR) can guide us on designing planar aggregati

Synthesis and biological evaluation in vitro and in silico of N-propionyl-N′-benzeneacylhydrazone derivatives as cruzain inhibitors of Trypanosoma cruzi

Abstract: An N-acylhydrazone scaffold has been used to develop new drugs with diverse biological activities, including trypanocidal activity against different strains of Trypanosoma cruzi. However, their mechanism of action is not clear, although in T. cr

Sodium hypochlorite-mediated synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from hydrazides and aldehydes

[Figure not available: see fulltext.] A simple and convenient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed. Structurally divergent symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles can be obtained in moderate to high yields via NaOCl-mediated oxidative cyclization of N-acylhydrazones, generated in situ from aliphatic and aromatic hydrazides and aldehydes.

Experimental and Theoretical Studies on the Mechanism of DDQ-Mediated Oxidative Cyclization of N-Aroylhydrazones

The controversial single-electron-transfer process, frequently proposed in many 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated reactions, was investigated experimentally and theoretically using the oxidative cyclization of aroylhydrazone with DDQ. DDQ-mediated oxadiazole formation involves several processes, including cyclization to form an oxadiazole ring and N-H bond cleavage, either by proton, hydride, or hydrogen atom transfer. The detailed mechanistic study using the M06-2X density functional theory, and the 6-31+G(d,p) basis set, suggests that the pathways involving radical ion pair (RIP) intermediates, which resulted from single-electron transfer (SET), were found to be energetically nearly identical to the pathway without the SET. The substituent-dependent reactivity of oxadiazole formation was consistent with the free energy profiles of both pathways, with or without the SET. This result indicates that in addition to the electron-transfer pathway, the nucleophilic addition/elimination pathway for DDQ should be considered as a possible mechanism of the oxidative transformation reaction using DDQ.

Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions

Acylhydrazones formation has been widely applied in materials science and biolabeling. However, their sluggish condensation rate under neutral conditions limits its application. Herein, indolines with electron-donating groups are reported as a new catalyst scaffold, which can catalyze acylhydrazone, hydrazone, and oxime formation via an iminium ion intermediate. This new type of catalyst showed up to 15-fold rate enhancement over the traditional anilinecatalyzed reaction at neutral conditions. The identified indoline catalyst was successfully applied in hydrogel formation.

Mixed Ligand Complexes of Copper(II) and Cobalt(II) with Hydrazones Derivatives and ortho-Vanillin: Syntheses, characterizations and antimicrobial activity

The purpose of this paper was to synthesis new mixed-ligand Cu(II) and Co(II) metal complexes utilizing bidentate and tridentate donor hydrazones derivatives as primary ligands and ortho-Vanillin as co-ligand. The obtained compounds were characterized by

An efficient one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles from aldehydes and hydrazides using Lawesson’s reagent

Five-membered heterocyclic-ring systems, such as thiadiazoles, remain an important and prevalent scaffold in the development of novel leads in medicinal chemistry for a variety of therapeutic targets. A two-step, one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from aryl hydrazides and aryl aldehydes using Lawesson’s reagent is described, yielding 2,5-disubstituted-1,3,4-thiadiazoles in moderate-to-high yields. Based on preliminary biological experiments, some of the newly synthesized thiadiazoles show antioxidant activity.

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.

IBX/KI promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles

Background: Oxadiazoles are privileged scaffolds in different areas of medicinal, pesticidal, polymer and material science. They act as anticancer, benzodiazepine receptor agonists, antimicrobial, analgesic, diuretic and tyrosinase inhibitors etc. A number of compounds containing an oxadiazole moiety are in late stage clinical trials including zibotentan and furamizole. Despite numerous methods are reported, the majority of them suffer from major drawbacks such as the use of strong alkaline or acidic conditions, highly toxic and corrosive reagents and also involve the use of costly reagents, elevated temperatures and longer reaction times. Inspired by the potential application of hypervalent iodonium reagents in organic synthesis, we would like to explore the readily available IBX and KI reagents for the facile synthesis of 1, 3, 4-oxadiazoles. Method: Oxidative cyclization has successfully been developed for the synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles. Results: An efficient process for the one-pot synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles has been developed using IBX/KI system at 25°C. The reaction was successful with a wide range of substrates such as aromatic and heterocyclic aldehyde and arylhydrazides to afford the corresponding unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles. The mild reaction conditions, cost-effective reagents and short reaction time are noteworthy advantages of this methodology. Conclusion: We have developed a one-pot strategy for the synthesis of 1, 3, 4-oxadiazioles using a combination of IBX/KI at ambient temperature. This one-pot procedure proved to be quite general and worked well with a wide variety of aryl and heterocyclic aldehydes and variety of acylhydrazides. The advantage of this method lies in the simplicity of experimental procedure and the ready accessibility of the reagents, which render this, an experimentally attractive method for the preparation of unsymmetrical 1, 3, 4-oxadiazoles.

Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions

A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O 2.