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CAS No. : | 49669-26-3 | MDL No. : | MFCD06771787 |
Formula : | C12H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NHWCJRHPJLHJPL-UHFFFAOYSA-N |
M.W : | 212.20 | Pubchem ID : | 4975903 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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 |
---|---|---|
77% | With hydrogenchloride | |
63% | With toluene-4-sulfonic acid In acetone for 4h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With selenium(IV) oxide In glacial acetic acid for 24h; Heating; | |
48% | With iodine; oxygen In dimethyl sulfoxide at 160℃; for 0.75h; Microwave irradiation; | 4. Experimental section General procedure: A 2-5 mL microwave compatible, disposable vial was charged with the requisite methyl heteroarene (0.308 mmol, 1.00 equiv) in reagent grade dimethylsulfoxide (2.0 mL, 0.15 M) at ambient temperature. Subsequently, I2 (82.0 mg,0.32 mmol, 1.05 equiv) was charged in one portion followed by purging of the vial head space with O2. The resulting dark-brown solution was capped with an appropriately sized microwave vialcap and placed in a microwave reactor (high power level) for 0.75 hat 160 °C. The resulting dark brown mixture was cooled to ambient temperature, diluted with minimal ethyl acetate, and transferred toa separatory funnel. The combined organics were treated with a 3 mL of a saturated, aqueous solution of sodium thiosulfate and then separated. The aqueous layer was back-extracted with ethyl acetate (3 10 mL). The combined organics were washed with water (10 mL) to remove residual dimethylsulfoxide and then a saturated aqueous sodium chloride solution (10 mL). The mixture was dried over anhydrous sodium sulfate, filtered through a cotton plug, and subsequently evaporated under reduced pressure at ambient temperature to afford the crude material which was purified using automated flash column chromatography as described below. |
45% | With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 4h; Reflux; |
30% | With selenium(IV) dioxide; glacial acetic acid for 48h; Reflux; | |
With selenium(IV) oxide In glacial acetic acid | ||
Multi-step reaction with 2 steps 1: 25 percent / NBS, AIBN, 62percent HBr, Br2 / CCl4 / 4 h / Heating 2: 20 percent / DMSO / 8 h / 150 °C | ||
With selenium(IV) dioxide In 1,4-dioxane Heating; Inert atmosphere; | ||
Multi-step reaction with 4 steps 1: sulfuric acid; chromium(VI) oxide / 22 h / 0 - 75 °C / Inert atmosphere 2: sulfuric acid / 16 h / Reflux; Inert atmosphere 3: sodium tetrahydridoborate / ethanol / 4 h / Reflux; Inert atmosphere 4: SIBX / ethyl acetate / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 6,6'-Dibromo-2,2'-bipyridine With n-butyllithium In tetrahydrofuran at -90℃; for 0.75h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -80 - -30℃; Further stages.; | |
55% | With n-butyllithium In tetrahydrofuran; hexane at -90℃; | |
41% | Stage #1: 6,6'-Dibromo-2,2'-bipyridine With n-butyllithium In tetrahydrofuran at -78℃; for 0.75h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 3h; |
With n-butyllithium In tetrahydrofuran at -100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With dimethyl sulfoxide at 150℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With toluene-4-sulfonic acid In toluene for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With selenium(IV) oxide In methanol Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium periodate In dichloromethane; water at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In methanol at 20℃; for 72h; | |
In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
220 mg | With lithium ethoxide In ethanol; N,N-dimethyl-formamide at -40℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium tetrahydroborate | |
99% | With sodium tetrahydroborate In methanol | |
With sodium tetrahydroborate In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With SIBX In ethyl acetate Reflux; Inert atmosphere; | |
99% | With oxygen; nitrosonium tetrafluoroborate In dichloromethane at 20℃; for 16h; | |
57% | Stage #1: 6,6′-bis(hydroxymethyl)-2,2′-bipyridine With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; for 0.25h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at 20℃; for 5h; Cooling; Inert atmosphere; |
With oxalyl dichloride; dimethyl sulfoxide; triethylamine 1.) CH2Cl2, -30 deg C, 3 h; 2.) triethylamine, -> r.t.; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With sodium hydride In tetrahydrofuran for 12h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With sodium hydride In tetrahydrofuran 1) 60 deg C, 60 min, 2) reflux, 15 min; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With toluene-4-sulfonic acid In toluene for 25h; Heating; | |
In toluene Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With acetic acid In ethanol at 80℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In methanol for 21h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / methanol / 21 h / Heating 2: 91 percent / K3Fe(CN)6; Na2CO3 / dimethylformamide; H2O / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 72 percent / methanol / 72 h / 20 °C 2: 70 percent / aq. sodium periodate / CH2Cl2 / 1 h | ||
Multi-step reaction with 2 steps 1: methanol 2: 70 percent / aq. sodium periodate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 54 percent / n-BuLi / diethyl ether 2: 72 percent / benzene 3: 30 percent / NiCl2(PPh3)2, Zn, NEt4I / tetrahydrofuran 4: 77 percent / aq. HCl | ||
Multi-step reaction with 2 steps 1.1: n-butyllithium / diethyl ether; hexane / 1 h / -78 °C 1.2: 1 h / -78 °C 2.1: n-butyllithium / tetrahydrofuran / 0.75 h / -78 °C 2.2: 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 72 percent / benzene 2: 30 percent / NiCl2(PPh3)2, Zn, NEt4I / tetrahydrofuran 3: 77 percent / aq. HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 30 percent / NiCl2(PPh3)2, Zn, NEt4I / tetrahydrofuran 2: 77 percent / aq. HCl | ||
Multi-step reaction with 2 steps 1: 65 percent / NiCl2(PPh3)2 / Zn-powder / Et4NI / tetrahydrofuran / 24 h / 50 °C 2: 63 percent / p-TsOH / acetone / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 50 percent / sodium hydride / tetrahydrofuran / 12 h / Heating 2: 70 percent / conc. HCl, H2 / Pd-C / ethanol / 24 h / 760 Torr / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SeO2 / methanol / Ambient temperature 2: 50 percent / NaIO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / NaBH4 / methanol 2: 73 percent / SOCl2 3: 21 percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / NaBH4 / methanol 2: 73 percent / SOCl2 3: 10 percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 99 percent / NaBH4 / methanol 2: 73 percent / SOCl2 3: 3 percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 99 percent / NaBH4 / methanol 2: 73 percent / SOCl2 | ||
Multi-step reaction with 2 steps 1: sodium borohydride / methanol 2: thionyl chloride | ||
Multi-step reaction with 2 steps 1: 100 percent / NaBH4 2: 73 percent / thionyl chloride / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 59 percent / p-TsOH / toluene / 5 h / Heating 2: n-BuLi / tetrahydrofuran / 72 h / -45 °C 3: NBS / tetrahydrofuran; methanol / 0 °C 4: H2NOH*HCl / acetic acid / 24 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 59 percent / p-TsOH / toluene / 5 h / Heating 2: n-BuLi / tetrahydrofuran / 72 h / -45 °C 3: NBS / tetrahydrofuran; methanol / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 59 percent / p-TsOH / toluene / 5 h / Heating 2: n-BuLi / tetrahydrofuran / 72 h / -45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium borohydride / methanol 2: thionyl chloride 3: 1.3 percent / potassium carbonate / dimethylformamide / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium borohydride / methanol 2: thionyl chloride 3: 35 percent / potassium carbonate / dimethylformamide / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1) 48percent HBr, Br2 2) NaNO2 / 1) -15 to -10 deg C, 30 min 2) water, 90 min 2: 1) Raney Nickel 2) water / 1) toluene, 22 h, reflux 2) 2 h, 40 deg C 3: 25 percent / NBS, AIBN, 62percent HBr, Br2 / CCl4 / 4 h / Heating 4: 20 percent / DMSO / 8 h / 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1) Raney Nickel 2) water / 1) toluene, 22 h, reflux 2) 2 h, 40 deg C 2: 25 percent / NBS, AIBN, 62percent HBr, Br2 / CCl4 / 4 h / Heating 3: 20 percent / DMSO / 8 h / 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 220 mg / LiOEt / dimethylformamide; ethanol / -40 °C 2: 5 mg / H2 / 5percent Pd/C / toluene / 96 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With acetic acid In ethanol at 50℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 3,6-dioxa-1,8-diaminooctane; 2,2'-bipyridine-6,6'-dicarbaldehyde With magnesium chloride In methanol for 1h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: 1-amino-2-propene; 2,2'-bipyridine-6,6'-dicarbaldehyde In dichloromethane for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: With sodium cyanoborohydride; acetic acid In dichloromethane at 20℃; for 12h; Inert atmosphere; Schlenk technique; Stage #3: di-<i>tert</i>-butyl dicarbonate With triethylamine In methanol for 4h; Reflux; Inert atmosphere; Schlenk technique; | |
79% | Stage #1: 1-amino-2-propene; 2,2'-bipyridine-6,6'-dicarbaldehyde With sodium cyanoborohydride; acetic acid In dichloromethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; Stage #2: di-<i>tert</i>-butyl dicarbonate With triethylamine In methanol for 4h; Reflux; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: dichloromethane / 0.5 h / Inert atmosphere; Schlenk technique 1.2: 12 h / 20 °C / Inert atmosphere; Schlenk technique 1.3: 4 h / Reflux; Inert atmosphere; Schlenk technique 2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 4,6-Dichlororesorcinol / 1,2-dichloro-ethane / 2 h / 760.05 Torr / Inert atmosphere; Schlenk technique 2.2: 24 h / 50 - 70 °C / 760.05 Torr / Schlenk technique 3.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In methanol for 5h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In methanol Reflux; | Macrocyclic Schiff base complexes 2,2’-Bipyridine-6,6’-dicarboxaldehyde or 1,10-phenanthroline-2,9-dicarboxaldehyde(1.0 mmol) was dissolved in MeOH (25 mL)containing Pb(ClO4)2·H2O or Pb(NO3)2 (1.0 mmol). The solution was stirred vigorously and heated while a methanolic solution of 6,6’-bis(2-aminophenoxymethyl)-2,2’-bipyridine(0.40 g, 1.0 mmol) was added slowly. The resultant solution was refluxed for 4-5 h and filtered hot. The solvent of the reaction mixture was reduced to half its original volume andthen the mixture was placed in a refrigerator to induce precipitation.The yellow powder products were filtered and dried.Yields 70 and 50 % respectively.[PbL1](ClO4)2 (νmax, cm-1):1632m (C=N), 1586m, 1490m,1441m, 1373w, 1262m, 1213m, 1183w, 1080vs (ClO4-),1005m, 911w, 795s, 756m, 743s, 622s (ClO4-), 582w, 524w.1HNMR (300 MHz; acetone-d6): δ5.80 (4H, s, CH2), 6.93 (2H,d, J = 7.9 Hz), 7.16 (2H, t, J = 7.1 Hz), 7.28-7.49 (4H, m),7.68 (2H, t, J = 7.8 Hz), 7.81 (2H, d, J = 7.9 Hz), 7.87 (2H, d,J = 7.5 Hz), 8.36 (2H, d, J = 7.6 Hz), 8.68 (2H, t, J = 7.9 Hz),8.93 (2H, d, J = 8.3 Hz), 9.40 (2H, s, HC=N). ΛM (μS/cm),(acetone, 10-3 M): 160, 25.4 °C. μeff (BM), 24 °C: 0.88 BM.UV-visible (DMSO): 305 nm π→π* (C=N), 292 nm π→π*(aromatik ring). MALDI-TOF (m/z): Found: 781.788, calc.:781.828 for [Pb(L1)]+. Found: C, 44.67; H, 3.14; N, 8.53.Calcd. for C36H26N6O10Cl2Pb: C, 44.09; H, 2.67; N, 8.57. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | In acetonitrile Reflux; | General procedure for the synthesis of Schiff bases and hemiaminals: (Schemes 1-4) General procedure: General procedure for the synthesis of Schiff bases and hemiaminals: (Schemes 1-4) Each dicarboxaldehydes (1, 4, 7 & 10) were dissolved in refluxing solvent (EtOH, MeOH or CH3CN). 4-Amino-3,5-dimethyl-1,2,4-triazole was then added to the hot solutions of dicarboxaldehydes and refluxing was continued. After 2-4 h the reaction mixtures were cooled to room temperature to isolate the products as solid precipitate. The products were collected by vacuum filtration and washed with cold methanol followed by hot acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In ethanol Reflux; | General procedure for the synthesis of Schiff bases and hemiaminals: (Schemes 1-4) General procedure: General procedure for the synthesis of Schiff bases and hemiaminals: (Schemes 1-4) Each dicarboxaldehydes (1, 4, 7 & 10) were dissolved in refluxing solvent (EtOH, MeOH or CH3CN). 4-Amino-3,5-dimethyl-1,2,4-triazole was then added to the hot solutions of dicarboxaldehydes and refluxing was continued. After 2-4 h the reaction mixtures were cooled to room temperature to isolate the products as solid precipitate. The products were collected by vacuum filtration and washed with cold methanol followed by hot acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 4 h / Reflux; Inert atmosphere 2: SIBX / ethyl acetate / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid In tetrahydrofuran at 20℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With hydrogenchloride; potassium hydroxide In water; N,N-dimethyl-formamide at -75 - -40℃; | 1.i (i) Synthesis of 6,6’-diformyl-2,2’-bipyridine Add dehydrated THF (150 mL) to a 300 mL three-necked flask equipped with an isostatic dropping funnel and thermometer.Cool to -78 Add 2.6M n-BuLi (11mL, 28.8mmol)And stir.Combine 6,6’-dibromo-2,2’-bipyridine (13.6g, 71.5mmol)Dehydrated THF (150mL) dissolved at about 50 ° CAfter allowing to cool to room temperature,Transfer to an isostatic dropping funnel.While being careful to prevent the temperature in the system from exceeding -60 ° C, add this solution dropwise,A dark red solution was obtained.After stirring at -75 ° C for 1 hour,DMF (2.7 mL, 28.8 mmol) was added to quench the reaction.Then heat up to -40 ,4M hydrochloric acid (60 mL) was added for hydrolysis.Warm the reaction solution to room temperature,Using a saturated potassium hydroxide aqueous solution, the aqueous layer was extracted with chloroform (100 mL × 3) under alkaline conditions,Dehydrate with anhydrous magnesium sulfate,The solvent was distilled off using an evaporator.The obtained reddish brown solid was dispersed and washed with 10 mL of methanol to obtain 6,6'-diformyl-2,2'-bipyridine (1.36 g, 67%) as a pale gray white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | Stage #1: methyl-3-pyridylketone; 2,2'-bipyridine-6,6'-dicarbaldehyde With potassium hydroxide In ethanol Stage #2: With ammonia at 0℃; for 2h; Inert atmosphere; | 1.ii (ii) 6,6’-BPy3TPy In 6,6’-diformyl-2,2’-bipyridine (1.10g, 5.18mmol)Ethanol (55 mL) was added and stirred.Add 3-acetylpyridine to the suspension solution(3.4mL, 31.1mmol),Potassium hydroxide (1.75g, 31.1mmol),As a result, the solid dissolves,A yellow transparent solution was obtained.then,Add ammonia (25%, 55mL, 0.735mol)And heat and stir all night under a nitrogen atmosphere,An orange solution is obtained.After cooling,Cool at 0 ° C for 2 hours.After performing ultrasonic dispersion washing with 50 mL of distilled water,filter,The obtained solid was washed with ethanol,6,6’-BPy3TPy is obtained as a yellow-white solid(0.99g, 31%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Isophthalaldehyde In chloroform-d1 at 25℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In acetonitrile at 20℃; |