59821-13-5

Basic information

• Product Name: 2-phenyl-5-(quinolin-2-yl)-1,3,4-oxadiazole
• Synonyms: 2-phenyl-5-(quinolin-2-yl)-1,3,4-oxadiazole
• CAS NO: 59821-13-5
• Molecular Weight: 273.294
• Mol File: 59821-13-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-phenyl-5-(quinolin-2-yl)-1,3,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-5-(quinolin-2-yl)-1,3,4-oxadiazole(59821-13-5)
• EPA Substance Registry System: 2-phenyl-5-(quinolin-2-yl)-1,3,4-oxadiazole(59821-13-5)

Safety Data

• Hazardous Substances Data: 59821-13-5(Hazardous Substances Data)

Upstream product

• 5382-44-5 quinoline-2-carboxylic acid hydrazide 
• 59821-08-8 β-Benzoyl-chinolincarbonsaeure-(2)-hydrazid 
• 93-10-7 quinoline-2-carboxylic acid 
• 106869-10-7 benzoic acid (quinolin-2-yl)methylenehydrazide 
• 5470-96-2 quinoline 2-carbaldehyde 
• 613-94-5 benzoic acid hydrazide 
• 4377-41-7 2-Chloromethylquinoline 
• 613-53-6 2-tribromomethyl-quinoline 

Relevant articles and documents

Design and Discovery of Novel Antifungal Quinoline Derivatives with Acylhydrazide as a Promising Pharmacophore

Inspired by natural 2-quinolinecarboxylic acid derivatives, a series of quinoline compounds containing acylhydrazine, acylhydrazone, sulfonylhydrazine, oxadiazole, thiadiazole, or triazole moieties were synthesized and evaluated for their fungicidal activity. Most of these compounds exhibited excellent fungicidal activity in vitro. Significantly, compound 2e displayed the superior in vitro antifungal activity against Sclerotinia sclerotiorum, Rhizoctonia solani, Botrytis cinerea, and Fusarium graminearum with the EC50 values of 0.39, 0.46, 0.19, and 0.18 μg/mL, respectively, and were more potent than those of carbendazim (EC50, 0.68, 0.14, >100, and 0.65 μg/mL, respectively). Moreover, compound 2e could inhibit spore germination of F. graminearum. Preliminary mechanistic studies showed that compound 2e could cause abnormal morphology of cell walls and vacuoles, loss of mitochondrion, increases in membrane permeability, and release of cellular contents. These results indicate that compound 2e displayed superior fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.

Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.

Novel method of synthesizing various five membered heterocycles from an aryl tribromomethyl group

Synthesis of five membered heterocycles from an aryl tribromomethyl functional group is discussed. Exposing a tribromomethyl group to subsequent nucleophilic attacks by a 1,2-di-nucleophilic species promotes the cyclization of five membered heterocycles. Such heterocycles as oxadiazoles, thiadiazole, benzimidazole, benzothioazole, and benzoxazole were synthesized in moderate to good yields. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.