83725-77-3

Usage

Uses

Used in Pharmaceutical Development:
5-(2-chlorophenyl)-1,3,4-oxadiazol-2(3H)-one is used as a scaffold in pharmaceutical development for creating new drugs with diverse pharmacological activities. Its unique structure and properties make it a promising candidate for further investigation in drug discovery and development.
Used in Agrochemical Development:
In the agrochemical industry, 5-(2-chlorophenyl)-1,3,4-oxadiazol-2(3H)-one is utilized as a building block for the synthesis of biologically active compounds with potential applications in crop protection and pest control. Its chlorophenyl group may confer specific biological properties, making it a valuable component in the development of effective agrochemicals.

Upstream product

• 60014-17-7 6-chlorobenzoyleneurea 
• 503-38-8 trichloromethyl chloroformate 
• 5814-05-1 2-chlorobenzoylhydrazide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 50-00-0 formaldehyd 
• 609-66-5 2-chlorobenzamide 
• 201230-82-2 carbon monoxide 
• 609-65-4 o-chlorobenzoyl chloride 
• 124-38-9 carbon dioxide 
• 1422157-60-5 N′-[chloro-(2-chlorophenyl)methylene]-tert-butylcarbazate 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 129221-08-5 N-(4-Benzyl-2,5-dioxo-imidazolidin-1-yl)-2-chloro-benzamide 
• 90736-27-9 2-Chloro-5-(2-chloro-phenyl)-[1,3,4]oxadiazole 
• 40288-11-7 2-(2-chloro-phenyl)-[1,3,4]oxadiazolo[2,3-b]quinazolin-5-one 
• 75906-75-1 2-Chloro-N-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-benzamide 

Relevant academic research and scientific papers

5-Phenyl-1,3,4-oxadiazol-2(3 H)-ones Are Potent Inhibitors of Notum Carboxylesterase Activity Identified by the Optimization of a Crystallographic Fragment Screening Hit

Carboxylesterase Notum is a negative regulator of the Wnt signaling pathway. There is an emerging understanding of the role Notum plays in disease, supporting the need to discover new small-molecule inhibitors. A crystallographic X-ray fragment screen was performed, which identified fragment hit 1,2,3-Triazole 7 as an attractive starting point for a structure-based drug design hit-To-lead program. Optimization of 7 identified oxadiazol-2-one 23dd as a preferred example with properties consistent with drug-like chemical space. Screening 23dd in a cell-based TCF/LEF reporter gene assay restored the activation of Wnt signaling in the presence of Notum. Mouse pharmacokinetic studies with oral administration of 23dd demonstrated good plasma exposure and partial blood-brain barrier penetration. Significant progress was made in developing fragment hit 7 into lead 23dd (>600-fold increase in activity), making it suitable as a new chemical tool for exploring the role of Notum-mediated regulation of Wnt signaling.

Synthesizing method for medical intermediate oxazolone compound

The invention relates to a synthesizing method for a compound shown in a formula (III). The method comprises the steps that in organic solvent, a compound shown in a formula (I) reacts with formaldehyde shown in a formula (II) on the condition that a catalyst, an oxidizing agent, a nitrogen source compound and an activating agent exist, aftertreatment is performed after reacting is finished, and then the compound shown in the formula (III) is obtained, wherein R is selected from H or C1-C6 alkyl or C1-C6 alkoxy or halogen. According to the method, through comprehensive selection and cooperation of the catalyst, the oxidizing agent, the nitrogen source compound, the activating agent and the solvent, the target product can be obtained at a high yield, and the good application prospect and industrialized production potential are achieved in the field of medical intermediate synthesizing.

Palladium-catalyzed oxidative O-H/N-H carbonylation of hydrazides: Access to substituted 1,3,4-oxadiazole-2(3 H)-ones

A novel palladium-catalyzed oxidative annulation reaction for the C-O, C-N bond formations is developed. The intramolecular cyclocarbonylation provides an efficient and direct approach for the construction of valuable 1,3,4-oxadiazole-2(3H)-ones and their

Synthesis of 5-substituted-3H-[1,3,4]-oxadiazol-2-one derivatives: A carbon dioxide route (CDR)

A carbon dioxide route (CDR) for making biologically important 5-substituted-3H-[1,3,4]-oxadiazol-2-ones (SHOs) has been accomplished through synthesis and cyclization of a variety of hydrazides as the key intermediates. All of these hydrazides were prepared readily in 89-97% yields by reacting acid chlorides with a hydrazine monohydrate in the initial step. Then, SHOs were obtained in high yields from hydrazides by reacting them with carbon dioxide under basic conditions. More notable than the high yields, is that the present CDR process for the first time has succeeded in providing a straightforward cyclization reaction leading to SHO formation with simple reagents in ethanol solution.

Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N′-(chloro-aryl- methylene)-tert-butylcarbazates using basic alumina as an efficient and recyclable surface under solvent-free condition

The synthesis of biologically important 5-aryl-3H-[1,3,4]oxadiazol-2-ones has been carried out by heating the easily synthesized N′-(chloro-aryl- methylene)-tert-butylcarbazates on basic alumina surface under solvent-free condition. The dual characteristic of basic alumina as a solid support as well as a nucleophile is successfully exploited in these reactions. The method provides special attributions such as reduced reaction times, easier work-up procedures, and good to excellent yields as well as increased purity of products and most importantly environmentally friendly protocols. The basic alumina is easily recovered and utilized for further reactions several times without serious loss of activity.

Some 1-Aroyl-4,4-dialkylsemicarbazides and Their Cyclization to Afford 5-Aryl-1,3,4-oxadiazol-2(3H)-ones

Some 1-aroyl-4,4-dialkylsemicarbazides have been prepared by reacting aroyl-hydrazides with dimethyl- or diethyl-carbamoyl chloride.In boiling DMF they lose dimethylamine or diethylamine to give 5-aryl-1,3,4-oxadiazol-2(3H)-ones. - Keywords: 1-Aroyl-4,4-d

1,3,4-Oxadiazolin-2-ones from Carbo-t-butoxyhydrazones

5-Substituted-1,3,4-oxadiazolin-2-ones 2 were synthesized by the oxidation of carbo-t-butoxyhydrazones 1 of aromatic aldehydes with lead tetraacetate or, preferably, iodosobenzene diacetate.In some instances 5-acetoxy-1,3,4-oxadiazoles 3 were obtained along with 2.The oxidation of carboethoxyhydrazones 4 gave 2-ethoxy-1,3,4-oxadiazoles 5.

Synthesis of Some New 5-Aryl/Aryloxymethyl-2-Chloro-1,3,4-Oxadiazoles and their Oxadiazoloquinazolone Derivatives as Potential Pesticides

Several 5-aryl/aryloxymethyl-2-chloro-1,3,4-oxadiazoles (III) have been prepared by treating 2-aryl/aryloxymethyl-Δ2-1,3,4-oxadizolin-5-ones (IIa) with POCl3/PCl5.The latter were prepared by cyclisation of their corresponding N-aroylaryloxyacet

Synthesis of Substituted N-(2,4-Dioxo-1,2,3,4-tetrahydroquinazolinyl)benzamides and N-(2-Thiono-4-oxo-1,2,3,4-tetrahydroquinazolinyl)benzamides

Substuted N-(2,3-dioxo-1,2,3,4-tetrahydroquinazolinyl)benzamides (3a-g) and substituted N-(2-thiono-4-oxo-1,2,3,4-tetrahydroquinazolinyl)benzamides (4a-g) were synthetized in one step from the reaction of methyl anthranilate with 2-aryl-1,3,4-oxadiazolin-5-ones (1a-g) and 2-aryl-1,3,4-oxadiazoline-5-thiones (2a-g), respectively, in m-cresol at 150-160 deg C.Alternative routes leading to the formation of 3a and 4a are also reported.