31827-28-8

Upstream product

• 861322-19-2 2-hydroxyimino-2-p-tolyl-acetohydroxamic acid 
• 19227-13-5 p-toluamidoxime 
• 541-41-3 chloroformic acid ethyl ester 
• 19227-13-5 (Z)-N'-hydroxy-4-methylbenzimidamide 
• 2757-23-5 chloro(chlorosulfanyl)methanone 
• 31827-21-1 C₁₁H₁₄N₂O₃ 
• 530-62-1 1,1'-carbonyldiimidazole 
• 104-85-8 para-methylbenzonitrile 
• 616-38-6 carbonic acid dimethyl ester 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 81467-49-4 p-toluamide O-acetoacetyloxime 
• 110449-21-3 p-toluamide O-(α-ethoxycarbonylacetoacetyl)oxime 

Downstream Products

• 28180-28-1 4-methyl-3-(4-methylphenyl)-1,2,4-oxadiazol-5(4H)-one 
• 125772-50-1 4-methylbenzamidinium acetate 
• 23275-38-9 5-chloro-3-(p-tolyl)-1,2,4-oxadiazole 
• 18465-11-7 4-methylbenzamidine 
• 28425-88-9 N-Methyl-<4-methyl-benzoesaeure>-amid-oxim 
• 84940-58-9 4-phenyl-3-(p-tolyl)-1,2,4-oxadiazol-5(4H)-one 
• 58598-99-5 5-methoxy-3-(4-methylphenyl)-1,2,4-oxadiazole 

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.

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.

The first one-pot ambient-temperature synthesis of 1,2,4-oxadiazoles from amidoximes and carboxylic acid esters

The first one-pot room-temperature protocol for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles via the condensation between amidoximes and carboxylic acid esters in superbase medium MOH/DMSO is reported. A broad spectrum of alkyl, aryl and hetaryl amidoximes and esters was examined. This reaction route provides convenient access to 1,2,4-oxadiazoles, which is highly desirable because in the light of this privileged scaffold is recognized as an important core in the design of novel therapeutic agents and high-tech materials.

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.

NH-acidities and Hammett correlation of 3-para substituted phenyl-1,2,4-oxadiazol-5(4H)-ones and 1,2 λ43,5-oxathiadiazole 2-oxides in nonaqueous media

NH acidities of some 3-(p-substitutedphenyl)-1,2,4-oxadiazol-5(4H)-ones and 4-(p-substitutedphenyl)-1,2 λ43,5-oxathiadiazole 2-oxides were determined in methanol by means of potentiometric titration with sodium methoxide. pKa values of the titl

NOVEL BENSOPHENONE DERIVATIVES OR SALTS THEREOF

A benzophenone derivative represented by the following formula: whereinR1 represents, for example, an optionally substituted heterocyclic group, or a substituted phenyl group; Z represents, for example, an alkylene group; R2 represents, for example, a carboxyl group optionally protected with alkyl;R3 represents, for example, an optionally protected hydroxyl group; R4 represents, for example, an optionally substituted cycloalkyloxy group; and R5 represents, for example, a hydrogen atom, ???or a salt thereof has anti-arthritic activity, inhibits bone destruction caused by arthritis, and provides high safety and excellent pharmacokinetics and thus is useful as therapeutic agent for arthritis. These compounds have inhibitory effect on AP-1 activity and are useful as preventive or therapeutic agent for diseases in which excessive expression of AP-1 is involved.

Kinetics of base-catalysed hydrolysis and cyclisation of substituted acetamide and benzamide O-(phenoxycarbonyl)oximes

The reaction kinetics of acetamide O-(4-nitrophenoxycarbonyl)oxime have been studied in aqueous buffers at pH 2-11. At pH > 9, the pH dependence of kobs is linear with slope 1, the cyclisation to 3-methyl-1,2,4-oxadiazol-5(4H)-one and 4-nitrophenol being the only reaction. At pH obs on pH has been used to determine the rate equation and to propose the reaction mechanism. The cyclisation kinetics of substituted benzamide O-(phenoxycarbonyl)oximes have been studied in the pH range from 9.25 to 11. The reaction mechanism has been proposed based on the ρ constants found. In the first reaction step, the proton is split off from the NH2 group; the subsequent, rate-limiting step involves simultaneous N-C bond formation and C-O bond splitting.