4969-62-4

Basic information

• Product Name: Pyridine, 4-(3-phenyl-1,2,4-oxadiazol-5-yl)-
• CAS NO: 4969-62-4
• Molecular Formula: C13H9N3O
• Molecular Weight: 223.234
• Mol File: 4969-62-4.mol

Chemical Properties

• CAS DataBase Reference: Pyridine, 4-(3-phenyl-1,2,4-oxadiazol-5-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 4-(3-phenyl-1,2,4-oxadiazol-5-yl)-(4969-62-4)
• EPA Substance Registry System: Pyridine, 4-(3-phenyl-1,2,4-oxadiazol-5-yl)-(4969-62-4)

Safety Data

• Hazardous Substances Data: 4969-62-4(Hazardous Substances Data)

Upstream product

• 100-48-1 pyridine-4-carbonitrile 
• 873-67-6 benzonitrile oxide 
• 6843-37-4 N-methylisonicotinamide 
• 613-92-3 (E)-N'-hydroxybenzimidamide 
• 55-22-1 pyridine-4-carboxylic acid 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 1448510-49-3 3-phenyl-5-(4-pyridyl)-1,2,4-oxadiazole-4-oxide 
• 1594-57-6 pyridine-4-carboxamidoxime 
• 698-16-8 benzohydroximoyl chloride 
• 3731-53-1 4-(aminomethyl)pyridine 
• 100-52-7 benzaldehyde 
• 1570-45-2 isonicotinic acid ethylester 
• 100-47-0 benzonitrile 
• 613-92-3 N-hydroxyl-benzamidine 

Relevant articles and documents

Copper-Catalyzed Three-Component Cascade Reaction of Benzaldehyde with Benzylamine and Hydroxylamine or Aniline: Synthesis of 1,2,4-Oxadiazoles and Quinazolines

The analogous three-component synthesis strategy for substituted 1,2,4-oxadiazole and quinazoline derivatives from readily available benzaldehyde, benzylamine and hydroxylamine or aniline has been developed. Both the cascade reaction sequences involves nucleophilic addition of C?N bond, introduction a halogen donor, nucleophilic substitution and Cu(II)-catalyzed aerobic oxidation. This synthesis methodology demonstrated good yields, broad substrate scope and oxygen as a green oxidant. Thus, this synthesis protocol provides strategies for the construction of substituted 1,2,4-oxadiazole and quinazolines from readily and simple starting materials. (Figure presented.).

Beyond direct Nrf2 activation; reinvestigating 1,2,4-oxadiazole scaffold as a master key unlocking the antioxidant cellular machinery for cancer therapy

Harnessing the antioxidant cellular machinery has sparked considerable interest as an efficient anticancer strategy. Activating Nrf2, the master switch of the cellular redox system, suppresses ROS, alleviates oxidative stress, and halts cancer progression

Convenient entry to N-pyridinylureas with pharmaceutically privileged oxadiazole substituents via the acid-catalyzed C[sbnd]H activation of N-oxides

Pyridine-N-oxides bearing a pharmacophoric oxadiazole moiety could be C[sbnd]H functionalized via the acid-catalyzed reaction with dialkylcyanamides, providing access to hitherto undescribed pyridine-2-yl substituted ureas, which have potential as “lead-l

One-pot synthesis of 3,5-diaryl substituted-1,2,4-oxadiazoles using gem -dibromomethylarenes

1,2,4-Oxadiazole is one of the most promising heterocyclic ring systems in medicinal chemistry. In the present paper, we report the method for an efficient one-pot synthesis of 3,5-diaryl substituted 1,2,4-oxadiazoles using a two-component reaction of gem-dibromomethylarenes with amidoximes in good yields. In this method, gem-dibromomethylarenes are used as benzoic acid equivalents for the efficient synthesis of aryl-substituted 1,2,4-oxadiazoles. It is anticipated that this methodology will have versatile applications in the practical syntheses of various molecules of both medicinal and material chemistry importance.

A convenient and mild method for 1,2,4-oxadiazole preparation: Cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO

Herein, we reported a general, convenient, and efficient synthesis of 3,5-disubstituted-1,2,4-oxadiazoles via cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO (M = Li, Na, K). Excellent isolated yields (up to 98%) were attained within

A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes

Various 3,5-disubstituted-1,2,4-oxadiazoles are smoothly formed via copper-catalyzed cascade annulation of amidines and methylarenes. This tandem oxidation-amination-cyclization transformation represents a straightforward protocol to prepare 1,2,4-oxadiazoles from easily available starting materials, with inexpensive copper catalysts and green oxidants. It has the advantages of atom- and step-economy, good functional group tolerance, as well as operational simplicity.

Construction of 3,5-substituted 1,2,4-oxadiazole rings triggered by tetrabutylammonium hydroxide: A highly efficient and fluoride-free ring closure reaction of O-acylamidoximes

Tetrabutylammonium hydroxide (TBAH) is an efficient and mild alternative to tetrabutylammonium fluoride (TBAF) for base catalyzed cyclizations of 1,2,4-oxadiazoles from O-acylamidoximes. For most 3,5-substituted 1,2,4-oxadiazoles the reactions were dramatically accelerated by addition of 0.1 equiv of TBAH at room temperature. This method was also more generally applicable allowing for a wider range of substrates. Additionally, due to the absence of fluoride, TBAH will not result in corrosion of reactor vessels and therefore is better suited for large-scale synthesis.

Construction of 3,5-substituted 1,2,4-oxadiazole rings triggered by tetrabutylammonium hydroxide: A highly efficient and fluoride-free ring closure reaction of O-acylamidoximes

Tetrabutylammonium hydroxide (TBAH) is an efficient and mild alternative to tetrabutylammonium fluoride (TBAF) for base catalyzed cyclizations of 1,2,4-oxadiazoles from O-acylamidoximes. For most 3,5-substituted 1,2,4-oxadiazoles the reactions were dramatically accelerated by addition of 0.1 equiv of TBAH at room temperature. This method was also more generally applicable allowing for a wider range of substrates. Additionally, due to the absence of fluoride, TBAH will not result in corrosion of reactor vessels and therefore is better suited for large-scale synthesis.

HNO made-easy from photochemical cycloreversion of novel 3,5-heterocyclic disubstituted 1,2,4-oxadiazole-4-oxides

A variety of symmetric and asymmetric 3,5-heterocyclic disubstituted 1,2,4-oxadiazole-4-oxides have been prepared through cycloaddition of aromatic and heteroaromatic nitrile oxides to heteroaromatic amidoximes. A library of novel, fully characterized, 1,

Synthesis and anticancer activities of novel 3,5-disubstituted-1,2,4-oxadiazoles

A series of 3,5-disubstituted-1,2,4-oxadiazoles were synthesized and evaluated for their in vitro anti-proliferative activities against various cancer cell lines. Formation of 1,2,4-oxadiazole ring was accomplished by the reaction of amidoxime with carbox