23289-03-4

Upstream product

• 536-40-3 4-chlorobenzoic acid hydrazide 
• 104-88-1 4-chlorobenzaldehyde 
• 7335-27-5 ethyl 4-chlorobenzoate 

Downstream Products

• 2491-90-9 2,5-bis(4-chlorophenyl)-1,3,4-oxadiazole 
• 1328892-96-1 (2R)-(+)-2-(4-chlorophenyl)-3-acetyl-5-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole 
• 1328892-97-2 (2S)-(-)-2-(4-chlorophenyl)-3-acetyl-5-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole 
• 1185855-44-0 (+/-)-2-(4-chlorophenyl)-3-acetyl-5-(4-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole 

Relevant academic research and scientific papers

Electrochemical oxidation of aldehyde-N-arylhydrazones into symmetrical-2,5-disubstituted-1,3,4-oxadiazoles

A convenient, efficient and one-pot synthesis of chemically and pharmaceutically interesting symmetrical-2,5-disubstituted-1,3,4-oxadiazoles is reported. The protocol involves anodic oxidation of aldehyde-N-arylhydrazones in anhyd. MeCN-LiClO4. Constant potential electrolysis carried out in an undivided cell and platinum electrodes leads to the formation of the corresponding oxadiazoles under ambient condition and the mechanism was deduced from voltammetry studies. The reaction proceeded smoothly with high atom economy. Springer Science+Business Media Dordrecht 2013.

Acylhydrazide schiff bases: Synthesis and antiglycation activity

Acylhydrazide Schiff bases 1-27 were synthesized and their in vitro antiglycation potential was evaluated. Compounds 16 (IC50 = 199.82 ± 10.6 μM), 27 (IC50 = 234.83 ± 10.28 μM), 2 (IC50 = 240.99 ± 4.2 μM), and 14 (IC50 = 276.2 ± 2.3 μM) showed antiglycation potential comparable to the standard rutin (IC50 = 294.50 ± 1.5 μM). From this study we identified a new series of potent antiglycating agents. A structure-activity relationship has been described, while all compounds were characterized by using different spectroscopic techniques.

Efficient oxidative cyclization of N -acylhydrazones for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles using t-BuOI under neutral conditions

An efficient procedure for the oxidative cyclization of N -acylhydrazones was developed utilizing tert-butyl hypoiodite (t-BuOI), which is generated in situ from t -BuOCl and NaI. A variety of 2,5-disubstituted 1,3,4-oxadiazoles were synthesized in high yields within short reaction time. The method is also suitable for cyclization of N -acylhydrazones derived from heterocyclic aldehydes and aliphatic aldehydes. Mild reaction conditions and simple workup operations make the procedure a good alternative for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles.

Electrosynthesis and screening of novel 1,3,4-oxadiazoles as potent and selective antifungal agents

The electrochemical oxidation of aldehyde-N-aroylhydrazone has been studied in the presence of NaClO4 as supporting electrolyte in MeOH solution using cyclic voltammetry and controlled potential electrolysis. The results indicate that intramolecular cyclization of aldehyde-N-aroylhydrazone has been successfully performed at a platinum electrode in an undivided cell with good yields of the corresponding 1,3,4-oxadiazoles at ambient conditions. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetry studies. The antifungal activity of the synthesized compounds was evaluated on Fusarium oxysporum, Alternaria solani, Candida albicans and Aspergillus niger. The results revealed that all the synthesized compounds have significant antifungal activity against the tested fungi. Among the synthesized derivatives 7b, 7d, 7g, 7h, 7i, 7j and 7r were found to be the most effective antifungal compounds. The Royal Society of Chemistry 2013.

Acylhydrazide Schiff bases: DPPH radical and superoxide anion scavengers

Acylhydrazide Schiff bases 1-27 were evaluated for their in vitro DPPH radical and superoxide anion scavenging activity. They showed a varying degree of DPPH radical scavenging activity with IC50 values between 31.25-473.59 μM. Compounds 8, 2, and 10 have IC50 values 31.25 ± 1.32, 34.40 ± 0.66, and 37.24 ± 0.4 μM, respectively. Standard npropylgallate showed an IC50 value 30.12 ± 0.27 μM. Acylhydrazides 1-27 exhibited in vitro superoxide anion scavenging activities with IC50 values in the range of 175.6-450.89 μM. Results demonstrated that acylhyrazides 8, 2, and 10 have DPPH scavenging activity, comparable to standard n-propyl gallate while acylhyrazides 1-27 were found to be less superoxide anion scavenging active than the standard n-propyl gallate (IC50 = 106.34 ± 1.6 μM).

3-Acetyl-2,5-diaryl-2,3-dihydro-1,3,4-oxadiazoles: A new scaffold for the selective inhibition of monoamine oxidase B

3-Acetyl-2,5-diaryl-2,3-dihydro-1,3,4-oxadiazoles were designed, synthesized, and tested as inhibitors against human monoamine oxidase (MAO) A and B isoforms. Several compounds, obtained as racemates, were identified as selective MAO-B inhibitors. The enantiomers of some derivatives were separated by enantioselective HPLC and tested. The R-enantiomers always showed the highest activity. Docking study and molecular dynamic simulations demonstrated the putative binding mode. We conclude that these 1,3,4-oxadiazoles derivatives are promising reversible and selective MAO-B inhibitors.

Cu(II) catalyzed imine C-H functionalization leading to synthesis of 2,5-substituted 1,3,4-oxadiazoles

A direct access to symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C-H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)2. This is the first example of amidic oxygen functioning as a nucleophile in a Cu-catalyzed oxidative coupling of an imine C-H bond. These reactions can be performed in air atmosphere and moisture making it exceptionally practical for application in organic synthesis.

Lewis acid-mediated nucleophilic addition of dialkylphosphite to C=N double bond of hydrazones

The synthesis of new phenyl substituted derivatives (2) of -hydrazino-alkylphosphonic acids by Lewis acid-mediated addition of dialkylphosphite to hydrazones, derived from benzoylhydrazines and benzaldehydes, is described. Reactions were successfully prom

Kinetics and mechanism of oxidation of arylhydrazides by hexacyanoferrate(III) in alkaline medium

The kinetics of oxidation of a series of arylhydrazides, X-Ph*CO*NH*CH2 (X = H, p-Cl, p-CH3 and o-NO2) by alkaline hexacyanoferrate(III) have been investigated.The reactions are first order each in and and fractional order in OHsup