14562-01-7

Upstream product

• 75-44-5 phosgene 
• 3488-57-1 N-phenylbenzamidoxime 
• 541-41-3 chloroformic acid ethyl ester 
• 14562-00-6 (3,4-diphenyl-4H-[1,2,4]oxadiazol-5-ylidene)-phenyl-amine 
• 1704-56-9 silver phenylcyanomethylenenitronate 
• 76-83-5 trityl chloride 
• 103-71-9 phenyl isocyanate 
• 186581-53-3 diazomethane 
• 495-18-1 Benzohydroxamic acid 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 591-50-4 iodobenzene 
• 1456-22-0 3-phenyl-4H-[1,2,4]oxadiazol-5-one 
• 66003-76-7 Diphenyliodonium triflate 
• 98-88-4 benzoyl chloride 

Downstream Products

• 716-79-0 2-phenyl-1H-benzoimidazole 
• 64671-56-3 3,4-diphenyl-1,2,4-oxadiazole-5(4H)-thione 
• 1527-91-9 N-phenylbenzamidine 

Relevant academic research and scientific papers

Synthesis of Oxadiazol-5-imines via the Cyclizative Capture of in Situ Generated Cyanamide Ions and Nitrile Oxides

An unprecedented intermolecular cyclizative capture of the cyanamide anion and several nitrile oxides enables the synthesis of oxadiazol-5-imines.

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.).

A convenient one-pot synthesis of: N -substituted amidoximes and their application toward 1,2,4-oxadiazol-5-ones

The first direct one-pot approach for the synthesis of N-substituted amidoximes from secondary amides or the intermediate amides has been developed. Through the Ph3P-I2-mediated dehydrative condensation, a variety of N-aryl and N-alkyl amidoximes (R1(CNOH)NHR2, where R1 or R2 = aryl, alkyl, or benzyl) were readily afforded under mild conditions and short reaction times. The synthetic application of the obtained amidoximes has also been demonstrated through the formation of 1,2,4-oxadiazolones via base-mediated carbonylative cyclization with 1,1′-carbonyldiimidazole.

Tuning chemoselectivity in: O -/ N -arylation of 3-aryl-1,2,4-oxadiazolones with ortho -(trimethylsilyl)phenyl triflates via aryne insertion

Herein, we first describe finely tunable chemoselectivity in arylation of 3-aryl-1,2,4-oxadiazolones with ortho-(trimethylsilyl)phenyl triflates, including O-arylation enabled by catalytic amount of silver nitrate and metal-free N-arylation. Both the arylation reactions can tolerate a series of functional groups, and afford the corresponding products in moderate to good yields.

13C NMR substituent-induced chemical shifts in 4-(substituted phenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-ones (thiones)

In the present, study mostly novel ten 4-(substituted phenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-ones and ten 4-(substituted phenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-thiones were synthesized. These oxadiazole derivatives were characterized by IR, 1H

Site selectivity in the synthesis of O-methylated hydroxamic acids with diazomethane

In this paper we report the results obtained by treating some selected hydroxamic acids with diazomethane in ethereal media. The multitask reagent diazomethane was used either as a base to induce deprotonation of the chosen hydroxamic acids or as conjugated acid which undergoes one-pot methylation processes of the generated anions. Product distributions clearly showed that a high site selectivity is expressed by the different deprotonated species in the alkylation processes. Under the adopted conditions, the prevalent site of methylation is in all the cases the oxygen of the hydroxamic acid. While in aliphatic hydroxamic acids only O-alkylation is observed, in the aromatic substrates, the NH group competes with the OH function as the nucleophilic site, although the OH reactivity still dominates.

Triphenylmethyl Phenylcyanomethylenenitronate: Formation and Thermolysis

The previously reported formation of carbon dioxide, α,α'-bis(tritylazo)stilbene (4), benzonitrile N-oxide (5), trityl isocyanate (6), and C33H25N3O (11) from a mixture ot trityl chloride and silver phenylcyanomethylenenitronate in toluene is now attributed to the initial formation at -20 deg C of trityl phenylcyanomethylenenitronate (3) and its dissociations at 5 deg C.The ester (3) was characterized by conversion into bromonitrophenylacetonitrile (7) by treatment with bromine, to p-nitrobenzoyl cyanide (8) by treatment with dinitrogen tetraoxide, to trityl alcohol by hydrolysis, and to a mixture of trityl alcohol and trityl peroxide by exposure to the atmosphere.The bisazostilbene (4) (18percent) and C33H25N3O, identified by X-ray crystallographic analysis to be 4,5-diphenyl-1-triphenylmethoxy-1,2,3-triazole (11) (24percent), were obtained from the nitronate ester (3) in toluene at 5 deg C; the nitrile oxide (5) and the isocyanate (6) were obtained in low yields from the ester (3) in dimethyl sulphoxide at 25 deg C.Hydrolysis converted the triazole (11) into 1-hydroxy-4,5-diphenyl-1,2,3-triazole (12) and trityl alcohol.Silver p-bromophenylcyanomethylenenitronate and trityl chloride afforded α,α'-bis-(tritylazo)-p,p'-dibromostilbene and its thermolysis product, p,p'-dibromodiphenylacetylene.Fragmentation of the ester (3) in presence of added phenyl isocyanate gave the bisazo compound (4) and 3,4-diphenyl-1,2,4-oxodiazol-5-one (18).A similar mixture stored at -20 deg C gave the triazole (11) and the oxadiazolone (18).Aroyl nitrile oxides as well as phenyl isocyanate suppressed the formation of the red bisazostilbene (4).The intermediacy of the N-trityl imine (14) of 4H-3-phenyl-1,2-oxazet-4-one-2-oxide in the thermolysis of the nitronate (3) was discussed.