1456-22-0

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 30, p. 336, 1982 DOI: 10.1248/cpb.30.336

InChI:InChI=1/C8H6N2O2/c11-8-9-7(10-12-8)6-4-2-1-3-5-6/h1-5H,(H,9,10,11)

Upstream product

• 5421-95-4 (3-phenyl-[1,2,4]oxadiazol-5-yl)-urea 
• 32971-23-6 2-hydroxyimino-2-phenyl-acetohydroxamic acid 
• 75-36-5 acetyl chloride 
• 71-43-2 benzene 
• 32971-23-6 2-hydroxyimino-2-phenyl-acetohydroxamic acid 
• 613-92-3 N-hydroxyl-benzamidine 
• 2757-23-5 chloro(chlorosulfanyl)methanone 
• 118898-87-6 2-phenyl-2-hydroxyiminoacetonitrile oxide 
• 7647-01-0 hydrogenchloride 
• 3663-37-4 3-phenyl-1,2,4-oxadiazol-5-amine 
• 64-17-5 ethanol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 3201-46-5 4-methyl-3-phenyl-1,2,4-oxadiazol-5(4H)-one 
• 56493-57-3 4-(2-hydroxy-ethyl)-3-phenyl-4H-[1,2,4]oxadiazol-5-one 
• 10480-62-3 5-oxo-3-phenyl-[1,2,4]oxadiazole-4-carboxylic acid ethyl ester 
• 39741-07-6 3,3'-diphenyl-4H,4'H-4,4'-carbonyl-bis-[1,2,4]oxadiazol-5-one 
• 23129-57-9 4-(2-diethylamino-ethyl)-3-phenyl-4H-[1,2,4]oxadiazol-5-one 
• 10480-61-2 3-phenyl-4-propionyl-4H-[1,2,4]oxadiazol-5-one 
• 36891-91-5 4-acetyl-3-phenyl-4H-[1,2,4]oxadiazol-5-one 
• 10480-57-6 3-phenyl-4-(3,4,5-trimethoxy-benzoyl)-4H-[1,2,4]oxadiazol-5-one 
• 10480-58-7 4-Benzoyl-3-phenyl-4H-1,2,4-oxadiazol-5-on 
• 10480-59-8 4-but-2-enoyl-3-phenyl-4H-[1,2,4]oxadiazol-5-one 
• 56493-61-9 3,3'-diphenyl-4H,4'H-4,4'-ethane-1,2-diyl-bis-[1,2,4]oxadiazol-5-one 
• 10480-55-4 5-oxo-3-phenyl-[1,2,4]oxadiazole-4-carboxylic acid diethylamide 
• 10480-52-1 4-allyl-3-phenyl-4H-[1,2,4]oxadiazol-5-one 
• 10480-60-1 4-butyryl-3-phenyl-4H-[1,2,4]oxadiazol-5-one 

Relevant academic research and scientific papers

Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts

Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Tert-Butyl Nitrite Mediated Synthesis of 1,2,4-Oxadiazol-5(4 H)-ones from Terminal Aryl Alkenes

tert-Butyl nitrite (TBN) mediated synthesis of 3-aryl-1,2,4-oxadiazol-5(4H)-ones has been accomplished using terminal aryl alkenes via a biradical reaction intermediate. Three consecutive sp2 C-H bond functionalizations of styrenes afforded 3-phenyl-1,2,4-oxadiazol-5(4H)-ones via the formation of new C?N, C?O, C-O, and two C-N bonds. Both of the N atoms originate from TBN, while the carbonyl oxygen is from the water (moisture) the other oxygen from the N?O part of the TBN.

Development of the 99mTc-Hydroxamamide Complex as a Probe Targeting Carbonic Anhydrase IX

Carbonic anhydrase IX (CA-IX) is regarded as a favorable target for in vivo imaging because of its specific expression in hypoxic regions of tumors. Hypoxia assists tumor propagation and growth and is resistant to chemotherapy and radiotherapy. Here, we designed and synthesized [99mTc]hydroxamamide ([99mTc]Ham) and [99mTc]methyl-substituted-hydroxamamide ([99mTc]MHam) complexes including a bivalent CA-IX ligand, sulfonamide (SA), and ureidosulfonamide (UR). In a cell binding assay, [99mTc]Ham complexes with bivalent SA ([99mTc]SAB2A and [99mTc]SAB2B) and UR ([99mTc]URB2A and [99mTc]URB2B) showed significantly greater uptake into CA-IX high-expressing (HT-29) cells than that into CA-IX low-expressing cells. Since the binding affinity of [99mTc]URB2A and [99mTc]URB2B for CA-IX was significantly higher than that of [99mTc]SAB2A and [99mTc]SAB2B, we additionally synthesized [99mTc]MURB2 (a [99mTc]MHam complex with bivalent UR) and evaluated the CA-IX-specific binding affinity of [99mTc]URB2A, [99mTc]URB2B, and [99mTc]MURB2. Their uptake into HT-29 cells was reduced by the addition of a CA inhibitor, acetazolamide, suggesting their CA-IX-specific binding affinity. A biodistribution study in HT-29 tumor-bearing mice was carried out using [99mTc]URB2A and [99mTc]MURB2 with the highest specificity for HT-29 cells. [99mTc]URB2A showed moderate tumor uptake and reduction by coinjection with acetazolamide; however, the tumor/blood ratio was insufficient for in vivo imaging. These results provided key information for the design of novel Ham-based imaging probes targeting CA-IX.

Rh(II)-Catalyzed Transannulation of 1,2,4-Oxadiazole Derivatives with 1-Sulfonyl-1,2,3-triazoles: Regioselective Synthesis of 5-Sulfonamidoimidazoles

An effective method for the synthesis of fully substituted 5-sulfonamidoimidazoles by Rh(II)-catalyzed transannulation of 1,2,4-oxadiazole derivatives with N-sulfonyl-1,2,3-triazoles is reported. The reaction works well with both aromatic 1,2,4-oxadiazoles and 1,2,4-oxadiazol-5-ones providing a flexible approach to N-(alkoxy/amino)carbonyl- and N-alkyl-substituted imidazoles. Both the disclosed reactions are completely regioselective and provide the first examples of a carbenoid-mediated transformation of N,N,O-heterocycles.

Green synthesis method of oxadiazole derivatives

The invention relates to the field of organic chemistry, overcomes disadvantages in the synthesis of oxadiazole derivatives in the prior art, and provides a green synthesis method of the oxadiazole derivatives. The method comprises the following specific steps: (1) adding a basic reagent, dropwise adding a carbonylation reagent, stirring evenly, and back-flowing at 100 DEG C, wherein water is usedas a solvent, N-hydroxybenzamidine or substituted N-hydroxybenzamidine is used as a raw material, the reaction time is 1-5 hours; and (2) after the reaction is finished, cooling, standing, adjustingpH to 3-4 with 1 mol/L diluted HCl acidification reaction solution, performing suction filtration, collecting filter cakes, washing the filter cakes with water, and performing vacuum drying to finallyobtain the oxadiazole derivative. N-hydroxybenzamidine or substituted N-hydroxybenzamidine and a carbonylation reagent are used as the raw materials, under the action of the basic reagent, the oxadiazole derivatives can be synthesized in one step in water, and the two steps of esterification and cyclization are simplified to one step, thus greatly shortening the reaction time and increasing the reaction yield. The method has the advantages of being mild in reaction conditions, convenient to separate and purify, green and environmentally friendly.

COMPOUNDS AND USES THEREOF

The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

Oxadiazolone-Enabled Synthesis of Primary Azaaromatic Amines

Despite their tremendous synthetic and pharmaceutical utility, primary azaaromatic amines remain elusive for access based on a generally applicable C-H functionalization strategy. An oxadiazolone-enabled approach is reported for convenient entry into N-unsubstituted 1-aminoisoquinolines through Co(III)-catalyzed redox-neutral, step-, atom-, and purification-economic C-H functionalization with alkynes. A 15N labeling experiment reveals the effectiveness of both oxadiazolone N atoms as directing sites. The installed primary amine can be harnessed as a synthetically useful handle for attachment of divergent appendages.

OXADIAZOLE COMPOUNDS

The present invention relates to a compound of formula (I) or (II) or a stereoisomer, enantiomer, racemic, or tautomer thereof, (I) (II) wherein R1,R2,R3,L1,L2,L3,L4,L5 and n, have the same meaning as that defined in the claims and the description. The present invention also relates to compositions, in particular pharmaceuticals, comprising such compounds, and to uses of such compounds and compositions for the prevention and/or treatment of metabolic disorders and/or neurodegenerative diseases, and/or protein misfolding disorders.

Synthesis of 2-(2-methyltetrazol-5-yl)-2,2-dinitroacetonitrile and its reaction with substituted nitrile N-oxides

A procedure of synthesis of 2-(2-methyltetrazol-5-yl)-2,2- dinitroacetonitrile has been developed and its reaction with substituted nitrile N-oxides has been investigated, proceeding by the mechanism of 1,3-dipolar cycloaddition and affording 2-methyl-5-[(1,2,4-oxadiazol-5-yl)(dinitro)methyl]- 2H-tetrazoles. The latter react with KOH in ethanol forming the potassium salt of 2-methyltetrazol-5-yldinitromethane and substituted 5-hydroxy-1,2,4- oxadiazoles.