13389-61-2

Basic information

• Product Name: Pyridine, 2-(5-phenyl-1,2,4-oxadiazol-3-yl)-
• CAS NO: 13389-61-2
• Molecular Formula: C13H9N3O
• Molecular Weight: 223.234
• Mol File: 13389-61-2.mol

Chemical Properties

• CAS DataBase Reference: Pyridine, 2-(5-phenyl-1,2,4-oxadiazol-3-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 2-(5-phenyl-1,2,4-oxadiazol-3-yl)-(13389-61-2)
• EPA Substance Registry System: Pyridine, 2-(5-phenyl-1,2,4-oxadiazol-3-yl)-(13389-61-2)

Safety Data

• Hazardous Substances Data: 13389-61-2(Hazardous Substances Data)

Upstream product

• 35854-46-7 3-phenylimidazo[1,5-a]pyridine 
• 425619-08-5 C₁₃H₁₁N₃O₂ 
• 1772-01-6 2-pyridylamidoxime 
• 98-88-4 benzoyl chloride 
• 51285-26-8 pyridine-2-carboxamidine hydrochloride 
• 108-88-3 toluene 
• 100-70-9 2-Cyanopyridine 
• 1121-60-4 pyridine-2-carbaldehyde 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 132353-23-2 2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazin 
• 65-85-0 benzoic acid 
• 873-69-8 2-pyridinealdoxime 
• 100-47-0 benzonitrile 

Downstream Products

• 1312793-00-2 [Cu(3-(2'-pyridyl)-5-phenyl-1,2,4-oxadiazole)2(ClO₄)2] 
• 1312793-02-4 [Ni(3-(2'-pyridyl)-5-phenyl-1,2,4-oxadiazole)2(ClO₄)2] 
• 1312793-01-3 [Zn(3-(2'-pyridyl)-5-phenyl-1,2,4-oxadiazole)2(ClO₄)2] 

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.).

Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles from Amidoximes and Aldehydes in the Superbasic System NaOH/DMSO

Abstract: A new procedure has been proposed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles by reaction of amidoximes with aldehydes in the superbasic system NaOH/DMSO at room temperature. The scope of the proposed procedure has been demonstrated by 15 syntheses from various amidoximes and aromatic aldehydes with 27–76% yields. The procedure is inapplicable to aliphatic aldehydes.

Potassium Poly(Heptazine Imide): Transition Metal-Free Solid-State Triplet Sensitizer in Cascade Energy Transfer and [3+2]-cycloadditions

Polymeric carbon nitride materials have been used in numerous light-to-energy conversion applications ranging from photocatalysis to optoelectronics. For a new application and modelling, we first refined the crystal structure of potassium poly(heptazine imide) (K-PHI)—a benchmark carbon nitride material in photocatalysis—by means of X-ray powder diffraction and transmission electron microscopy. Using the crystal structure of K-PHI, periodic DFT calculations were performed to calculate the density-of-states (DOS) and localize intra band states (IBS). IBS were found to be responsible for the enhanced K-PHI absorption in the near IR region, to serve as electron traps, and to be useful in energy transfer reactions. Once excited with visible light, carbon nitrides, in addition to the direct recombination, can also undergo singlet–triplet intersystem crossing. We utilized the K-PHI centered triplet excited states to trigger a cascade of energy transfer reactions and, in turn, to sensitize, for example, singlet oxygen (1O2) as a starting point to synthesis up to 25 different N-rich heterocycles.

Facile room-temperature assembly of the 1,2,4-oxadiazole core from readily available amidoximes and carboxylic acids

A one-pot ambient-temperature procedure for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles from amidoximes and carboxylic acids under superbase-promoted conditions is reported.

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.

Br?nsted acid-catalyzed simple and efficient synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles using 2,2,2-trichloroethyl imidates in PEG

A facile and highly efficient synthesis of 3,4,5-trisubstituted 1,2,4-triazoles and 3,5-disubstituted 1,2,4-oxadiazoles from 2,2,2-trichloroethyl imidates using PEG as a solvent and employing PTSA as the catalyst under mild conditions is described.

A simple and straightforward protocol to 3,5-disubstituted 1,2,4-oxadiazoles from carboxylic acids

A convenient one-pot synthesis of 1,2,4-oxadiazoles is described. The condensation of carboxylic acids and amidoximes in the presence of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N-methylmorpholine (NM1 B) has been employed to synthesize a variety of 3,5-disubstituted 1,2,4-oxadiazoles in good to excellent yields. The methodology has been applied for the synthesis of a metabotropic glutamate subtype 5 (mGlu5) receptor antagonist.

Synthesis and chemical characterization of CuII, NiII and ZnII complexes of 3,5-bis(2′-pyridyl)-1,2,4-oxadiazole and 3-(2′-pyridyl)5-(phenyl)-1,2,4-oxadiazole ligands

The synthesis and structural characterization of NiII, Cu II and ZnII complexes of two chelating 1,2,4-oxadiazole ligands, namely 3,5-bis(2′-pyridyl)-1,2,4-oxadiazole (bipyOXA) and 3-(2′-pyridyl)5-(phenyl)-1,2,4-oxadiazole (pyOXA), is here reported. The formed hexacoordinated metal complexes are [M(bipyOXA)2(H 2O)2](ClO4)2 and [M(pyOXA) 2(ClO4)2], respectively (M = Ni, Cu, Zn). X-ray crystallography, 1H and 13C NMR spectroscopy and C, N, H elemental analysis data concord in attributing them an octahedral coordination geometry. The two coordinated pyOXA ligands assume a trans coplanar disposition, while the two bipyOXA ligands are not. The latter result is a possible consequence of the formation of H-bonds between the coordinated water molecules and the nitrogen atom of the pyridine in position 5 of the oxadiazole ring. The expected splitting of the d metal orbitals in an octahedral ligand field explains the observed paramagnetism of the d8 and d9 electron configuration of the nickel(II) and copper(II) complexes, respectively, as determined by the broadening of their NMR spectra.

Rapid multistep synthesis of 1,2,4-oxadiazoles in a single continuous microreactor sequence

(Chemical Equation Presented) A general method for the synthesis of bis-substituted 1,2,4-oxadiazoles from readily available arylnitriles and activated carbonyls in a single continuous microreactor sequence is described. The synthesis incorporates three s

Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists

The present invention provides compounds and pharmaceutical compositions that act as antagonists at metabotropic glutamate receptors, and that are useful for treating neurological diseases and disorders. Methods of preparing the compounds also are disclosed.