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CAS No. : | 5565-72-0 | MDL No. : | MFCD00085145 |
Formula : | C8H5N3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NSIRBOSXFXTYQL-UHFFFAOYSA-N |
M.W : | 191.14 | Pubchem ID : | 2739389 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In methanol for 1h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sulfuric acid; silica gel at 20℃; | |
78.9% | at 100℃; for 3h; | 4.A Step A: 2-(3-nitrophenyl)-1,3,4-oxadiazole 2-(3-nitrophenyl)-l,3,4-oxadiazole. A mixture of 3-nitrobenzohydrazide (1.8 g, 10 mmol), triethoxymethane (5 mL) and 0.1 mL CH(OEt)3 was stirred at 100 °C for 3 hr. The mixture was concentrated to small volume and cooled down to give a colorless crystal. The solid was collected by filtration and dried under vacuum to afford the desired compound (1.5 g, 78.9% yield). MS: 192.2 (M+l)+. |
In xylene for 6.7h; Heating; |
4.A Step A: Step A: 2-(3-nitrophenyl)-1,3,4-oxadiazole A mixture of 3-nitrobenzohydrazide (1.8 g, 10 mmol), triethoxymethane (5 mL) and 0.1 mL CH(OEt)3 was stirred at 100° C. for 3 hr. The mixture was concentrated to small volume and cooled down to give a colorless crystal. The solid was collected by filtration and dried under vacuum to afford the desired compound (1.5 g, 78.9% yield). MS: 192.2 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In benzene for 0.0833333h; Ambient temperature; | |
85% | With Chloroacetic anhydride In toluene for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Hydrazid, RC(OEt)3; | ||
entspr. Benzhydrazid, RC(OEt)3; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With Al3+-K10 montmorillonite clay; In neat (no solvent); at 55℃; for 0.25h;Microwave irradiation; | General procedure: A 5 mL microwave vial was charged with acidhydrazide (100 mg, 1 eq), trimethyl orthoester (2 eq) and Al3+-K10 clay (75 mg). The resulting mixture was kept under microwave irradiation maintaining the temperature at 55 C for 15 min (Microwave irradiations were performed on CEM-discover model No. 908010). The reaction was monitored by TLC. After completion of the reaction, reaction mixture was diluted with ethyl acetate stirred well, filtered, washed well with ethyl acetate. Filtrate was evaporated under reduced pressure to obtain highly pure product. In some cases, products were purified by column chromatography using 60-120 mesh silica with 20-100 % ethyl acetate in pet ether as eluting solvents. The catalyst recovered by filtration was reused for another 5 more times. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / 0.33 h / Heating 2: 85 percent / chloroacetic anhydride / toluene / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: H2 / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: Py / 4 h / 95 °C 3: aq. NaOH / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: H2 / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: Py / 4 h / 95 °C 3: aq. NaOH / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: H2 / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: benzene / Ambient temperature 3: H2 / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2 / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: benzene / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2 / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: benzene / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2 / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: Py / 4 h / 95 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2 / Pd-C / methanol / 1 h / 760 Torr / Ambient temperature 2: Py / 4 h / 95 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / methanol / 16 h / 20 °C | ||
Multi-step reaction with 2 steps 1: methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 16h; | 4.B Step B: 3-(1,3,4-oxadiazol-2-yl)aniline. A mixture of 2-(3-nitrophenyl)-l ,3,4-oxadiazole (1 g, 5.2 mmol) and 10% palladium on carbon (0.1 g) in methanol (20 mL) was stirred at r.t. for 16 h under the atmosphere of hydrogen. The mixture was filtered through Celite and the filtrate was concentrated to give the desired compound (840 mg, quant.). MS: 162.2 (M+l)+. |
In methanol | 4.B Step B: Step B: 3-(1,3,4-oxadiazol-2-yl)aniline A mixture of 2-(3-nitrophenyl)-1,3,4-oxadiazole (1 g, 5.2 mmol) and 10% palladium on carbon (0.1 g) in methanol (20 mL) was stirred at r.t. for 16 h under the atmosphere of hydrogen. The mixture was filtered through Celite and the filtrate was concentrated to give the desired compound (840 mg, quant.). MS: 162.2 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With selenium; copper diacetate; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere; | 18 Synthesis of 2- (3-nitrobenzene) -5-phenylseleno-1,3,4-oxadiazole in room temperature,Iodobenzene (1.2 mmol, 3 equiv),Elemental selenium (1.2 mmol, 3 equiv),2- (3-nitrobenzene) -1,3,4-oxadiazole (0.4 mmol, 1 equiv)Cu (OAc) 2 (0.04 mmol),Potassium carbonate (1.2 mmol, 3 equiv) was added to the reaction tube,Then filled with nitrogen, and replaced three times, in the nitrogen reaction environment,Then, 2 mL of DMF was added to the reaction solvent and stirred at 140 ° C for 24 h.After the reaction was monitored by thin layer chromatography, the reaction mixture was cooled,Then diluted with ethyl acetate, and the diluted solution was transferred to a separatory funnel,Extracted with saturated brine, separated from the aqueous phase and organic phase, and then extracted with ethyl acetate 3 times,The organic phases were combined, 5 g of anhydrous sodium sulfate was added,Wash the filter cake with 5 mL of ethyl acetate each time 3 times, then spin off the solvent,The product was isolated by column chromatography (eluent: petroleum ether: ether = 98: 2)The product was a yellow solid in 95% yield and 131 mg of product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With trifluoroacetic acid In toluene at 130℃; for 12h; | 1,3,4-Oxadiazoles 2; General Procedure General procedure: A 25 mL pressure tube was charged with arylhydrazide 1 (0.5 mmol), TFBen (53 mg, 0.25 mmol, white solid, mp 57.2-58.5 °C), TFA (38 μL, 1.0 equiv), and toluene (4 mL). The tube was then heated by stirring the contents at 130 °C for 12 h. Afterwards, the mixture was cooled to r.t., quenched with sat. aq NaHCO3 (3 mL), and extracted with EtOAc (3 4 mL). The combined organic layers were dried (anhyd Na2SO4), filtered, and concentrated under reduced pressure. The pure product 2 was obtained after purification by column chromatography (EtOAc/ pentane 1:3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With titanium tetrachloride; at 110℃; for 1.5h; | General procedure: To a 10mL three-necked round bottle was charged with benzoylhydrazine (0.30 g,2.2 mmol), TiCl4 (0.83 g, 4.4 mmol) and DMA (3 mL, 32.1 mmol). The resulting solutionwas warmed to 110 C and stirred at this temperature for 1.5 h. When the reaction wascompleted, 50mL water was added and the resulting mixture was extracted with 50mLethyl acetate three times. The combined organic layer was successively washed withH2O (50 mL) and then brine (50 mL), then dried over anhydrous Na2SO4, filtered andconcentrated under reduced pressure. The residue was purified by column chromatographyon silica gel with petroleum ether and ethyl acetate to give the title products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37 mg | With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With potassium phosphate In acetonitrile at 100℃; for 1h; Sealed tube; Inert atmosphere; | 2. General procedure for the synthesis of 3 General procedure: CH3CN (2 mL) was added to a mixture of ClCF2COONa 2a (0.3 mmol, 1.5 equiv) and hydrazides 1 (0.2 mmol, 1 equiv) in the presence of K3PO4 (0.3 mmol, 1.5 equiv). Then the sealed tube was stirred at 100 °C under N2 for 1 h. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatograph (silica gel, petroleum ether:EtOAc = 2:1, v/v) to give the desired product 3. |
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