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CAS No. : | 146581-82-0 | MDL No. : | MFCD11042459 |
Formula : | C11H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 184.19 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-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 |
---|---|---|
75% | With sodium acetate; acetic anhydride at 90℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With selenium(IV) oxide; water In 1,4-dioxane Heating; | |
Multi-step reaction with 2 steps 1: 94 percent / dimethylformamide / 18 h / 140 °C 2: 82 percent / NaIO4 / tetrahydrofuran; H2O / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: 2-acetylpyridine; 2,2'-bipyridine-4-carboxaldehyde With sodium hydroxide In methanol at 20℃; for 1h; Stage #2: With ammonium acetate In ethanol Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium periodate In tetrahydrofuran; water at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With sulfuric acid; acetic acid for 17h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 40 percent / ammonium acetate / methanol / 65 °C 2: 94 percent / dimethylformamide / 18 h / 140 °C 3: 82 percent / NaIO4 / tetrahydrofuran; H2O / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 75 percent / acetic anhydride, sodium acetate / 1 h / 90 °C 2: red phosphorous, 47percent aq. hydriodic acid, acetic anhydride / 3.5 h / Heating 3: HCl(g) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 75 percent / acetic anhydride, sodium acetate / 1 h / 90 °C 2: red phosphorous, 47percent aq. hydriodic acid, acetic anhydride / 3.5 h / Heating 3: HCl(g) 4: 0.2 M aq. NaHCO3 / 2 h / Ambient temperature; alkaline protease ( from Bacillus licheniformis) 5: 85 percent / 10percent aq. NaCO3 / dioxane / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 75 percent / acetic anhydride, sodium acetate / 1 h / 90 °C 2: red phosphorous, 47percent aq. hydriodic acid, acetic anhydride / 3.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 75 percent / acetic anhydride, sodium acetate / 1 h / 90 °C 2: red phosphorous, 47percent aq. hydriodic acid, acetic anhydride / 3.5 h / Heating 3: HCl(g) 4: 0.2 M aq. NaHCO3 / 2 h / Ambient temperature; alkaline protease ( from Bacillus licheniformis) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | Stage #1: di(pyrrol-2-yl)methane; 4-tert-Butylbenzaldehyde; 2,2'-bipyridine-4-carboxaldehyde With boron trifluoride diethyl etherate In methanol; dichloromethane for 96h; Inert atmosphere; Schlenk technique; Darkness; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In methanol; dichloromethane for 1h; Inert atmosphere; Schlenk technique; Darkness; Stage #3: With triethylamine In methanol; dichloromethane for 1.5h; Inert atmosphere; Schlenk technique; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With potassium carbonate In tetrahydrofuran at 20℃; for 0.583333h; Reflux; Stage #2: 2,2'-bipyridine-4-carboxaldehyde In tetrahydrofuran at 110℃; for 2h; Microwave irradiation; | E)-3-(2,20-Bipyridine-4-yl)-2-propenoic acid ethyl ester(7, C15H14N2O2) Dry potassium carbonate (1.3 g, 9.24 mmol) and 2.1 gtriethyl phosphonoacetate were suspended in 10 cm3 of anhydrous THF and stirred at room temperature for 15 minbefore the suspension was refluxed for 20 min (b) Microwave assisted synthesisAfter cooling the suspension to room temperature, it wastransferred into a microwave vessel and 1.1 g of 6(6.16 mmol) in 2.0 cm3 anhydrous THF were added. Thevessel was sealed and heated to 110 C in a way that duringa period of 10 min 110 C had to be reached using amaximum power of 1000 W. The reaction temperaturethen was maintained for 2 h after which the vessel wasallowed to cool down to room temperature. Purification procedure: After cooling 20.0 cm3 of a 10%potassium carbonate solution was added. The mixture wasextracted three times with 30 cm3 ethyl acetate. Theorganic phase was dried over sodium sulfate and the solventwas evaporated under reduced pressure. Theremaining triethyl phosphonoacetate was removed by distillationin vacuo. The crude product was purified bycolumn chromatography on silica gel using a diethyl ether:light petroleum (40-60) 1: 1 mixture as the eluent. Thewhite crystalline product was then recrystallized fromethanol/water by first dissolving the crude product inethanol and then adding water until the solution misted.For crystallization the solution was placed in the refrigerator.Yield: 50% (0.78 g, 3.08 mmol, for both syntheticprocedures); m.p.: 51-52 C; IR: v = 1711 vs, 1645 m,1582 m, 1547 m, 1458 w, 1400 w, 1365 w, 1323 w,1306 s, 1271 m, 1242 w, 1189 s, 1177vs, 1034 m, 997 s,845 s, 789 vs, 743 s, 600 m, 571 m, 492 m cm-1; MS(EI): m/z (%) = 254.1 (30) [M?], 225.2 (10) [M?-C2H5 ],210.2 (60) [M?-C2H4O], 182.4 (100) [M?-CO2C2H5 ,?H?]; 1H NMR (CDCl3, 600 MHz, 298 K): d = 1.34(CH3, 3H, t, J = 7.1 Hz), 4.28 (CH2, 2H, q, J = 7.1 Hz),6.72 (=CH, 1H, d, J = 15.9 Hz), 7.33 (=CHar, 1H, ddd,J = 1.1 Hz, 4.7 Hz, 7.7 Hz), 7.36 (=CHar, 1H, dd,J = 1.6 Hz, 4.9 Hz), 7.68 (=CH, 1H, d, J = 15.9 Hz),7.81 (=CHar, 1H, ddd, J = 1.9 Hz, 7.7 Hz, 8.1 Hz), 8.40(=CHar, 1H, d, J = 8.1 Hz), 8.53 (=CHar, 1H, s), 8.66-8.70(=CHar, 2H, m) ppm; 13C NMR (CDCl3, 150.92 MHz,298 K): d = 14.2 (CH3), 60.8 (CH2), 119.1 (=CHar), 121.1(=CHar), 121.7 (=CHar), 123.0 (=CH), 124.0 (=CHar),136.9 (=CHar), 141.8 (=CH), 142.6 (=Car), 149.2 (=CHar),149.8 (=CHar), 155.5 (=CH), 157.0 (=CH), 166.1 (C=O)ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Compound 4 (1.8 g, 7.7 mmol) was dissolved in 20 cm3anhydrous diethyl ether and 20 cm3 anhydrous tolueneunder a nitrogen atmosphere at -78 C. Butyl lithium inhexane (4.0 cm3, 2.5 M) was added dropwise. The solutionwas stirred at -78 C for 90 min before 8.0 cm3 anhydrousdimethyl formamide were added. The resulting solutionwas then stirred for another 90 min at the same temperature.To stop the reaction 50 cm3 of 2 N hydrochloric acidwere added at -78 C and the solution was allowed toreach room temperature. The organic phase was separatedand the aqueous phase was neutralized with diluted sodiumhydroxide solution. A smooth white precipitate wasformed. The aqueous phase was extracted three times withCH2Cl2. The solvent was evaporated under reducedpressure and a light brown oil that solidified to a lightbrown solid was obtained. Yield: 80% (1.1 g, 6.16 mmol);m.p.: 85-56 C [18]; MS (EI): m/z (%) = 184.1 (80) [M?],185.0 (10) [M??H?], 156.2 (100) [M?-CO?]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sulfuric acid; potassium nitrate / 2 h / 130 °C / Microwave irradiation; Cooling 2.1: acetic acid; Acetyl bromide / 2 h / 130 °C / Microwave irradiation 3.1: n-butyllithium / diethyl ether; toluene; hexane / 1.5 h / -78 °C / Inert atmosphere 3.2: 1.5 h / -78 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; Acetyl bromide / 2 h / 130 °C / Microwave irradiation 2.1: n-butyllithium / diethyl ether; toluene; hexane / 1.5 h / -78 °C / Inert atmosphere 2.2: 1.5 h / -78 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / 24 h / 20 °C / Cooling with ice 2.1: sulfuric acid; potassium nitrate / 2 h / 130 °C / Microwave irradiation; Cooling 3.1: acetic acid; Acetyl bromide / 2 h / 130 °C / Microwave irradiation 4.1: n-butyllithium / diethyl ether; toluene; hexane / 1.5 h / -78 °C / Inert atmosphere 4.2: 1.5 h / -78 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With piperidine; acetic acid In n-heptane for 17h; Reflux; | 2.2 Synthesis of diethyl 2-(2,2'-bipyridin-4-ylmethylene)malonate (3) 0.5 cm3 (2.5 mmol) diethyl malonate, one drop of piperidine,one drop of acetic acid and 0.46 g (2.5 mmol) 2,2'-bipyridine-4-carbaldehyde17 were dissolved in 10 cm3 n-heptane. Thereaction mixture was heated to reflux for 17 h. After coolingto room temperature 10 cm3 distilled water and 10 cm3methyl tert-butyl ether were added. The organic layer wasseparated and washed with 10 cm3 water and 10 cm3 brine.The organic layer was dried over sodium sulfate and thesolvent was evaporated. The crude product was purified bycolumn chromatography using alumina as stationary phaseand a mixture of diethyl ether and toluene (1:2) as eluent. Theproduct was recrystallized from an ethanol water mixture bydissolving the product first in ethanol and adding water untilthe solution turned cloudy. Yield: 14% (0.12 g, 0.35 mmol).IR (298 K) [cm-1]: 2995w, 2970w, 2936w, 1715vs, 1697s,1643m, 1589m, 1547m, 1450m, 1364s, 1317s, 1206s, 1177vs,1028m, 982m, 839s; MS (EI), m/z (%): 327 (1) [MH+], 297(65) [M+- C2H5], 282 (62) [MH+- C2H5O], 269 (65) [M+-2 C2H5], 253 (80) [MH+- C2H5O - C2H5], 235 (30) [MH+-2 C2H5OH], 225 (100) [MH+- C3H5O2 - C2H5], 210 (100)[C13H10N2O+], 182 (95) [C10H9N+2 ], 156 (15) [C10H8N+2 ];1H-NMR (CDCl3): δ [ppm] = 1.32 (t, J= 7.07 Hz, 3 H), 1.36(t, J= 7.20 Hz, 3 H), 4.34 (q, J= 1.00 Hz, 2 H), 4.39 (q, J=1.00 Hz, 2 H), 7.31-7.36 (m, 2 H), 7.76 (s, 1 H), 7.83 (td, J=7.77, 1.89 Hz, 1 H), 8.40 (dt, J= 7.89, 0.98 Hz, 1 H), 8.48-8.51 (m, 1 H), 8.66-8.69 (m, 1 H), 8.71 (d, J= 5.31 Hz, 1H); 13C-NMR (CDCl3):δ [ppm] = 13.8, 14.1, 62.0, 120.6,121.0, 122.4, 124.0, 130.5, 136.9, 139.3, 141.3, 149.2, 149.7,155.3, 157.0, 163.4, 165.6; M.p.: 65-67 °C; elemental analysis:calc. (%) for C18H18N2O4: C 66.25, H 5.56, N 8.58;found: C 67.94, H 5.65, N 8.85. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In dichloromethane at 20℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.31% | With piperidine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: ethanol / 3 h / Reflux; Inert atmosphere 1.2: 3 h / 20 °C / Cooling with ice 2.1: toluene / 4 h / Inert atmosphere; Reflux 3.1: 12 h / Inert atmosphere; Darkness; High pressure 4.1: tetrahydrofuran / 12 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: ethanol / 3 h / Reflux; Inert atmosphere 1.2: 3 h / 20 °C / Cooling with ice 2.1: toluene / 4 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: ethanol / 3 h / Reflux; Inert atmosphere 1.2: 3 h / 20 °C / Cooling with ice 2.1: toluene / 4 h / Inert atmosphere; Reflux 3.1: 12 h / Inert atmosphere; Darkness; High pressure |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: ethanol / 3 h / Reflux; Inert atmosphere 1.2: 3 h / 20 °C / Cooling with ice 2.1: toluene / 4 h / Inert atmosphere; Reflux 3.1: 12 h / Inert atmosphere; Darkness; High pressure 4.1: tetrahydrofuran / 12 h / Reflux; Inert atmosphere 5.1: GLUTATHIONE / aq. phosphate buffer / 12 h / 24.84 °C / pH 7.4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: ethanol / 3 h / Reflux; Inert atmosphere 1.2: 3 h / 20 °C / Cooling with ice 2.1: toluene / 4 h / Inert atmosphere; Reflux 3.1: 12 h / Inert atmosphere; Darkness; High pressure 4.1: tetrahydrofuran / 12 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: N-tosylethylenediamine; 2,2'-bipyridine-4-carboxaldehyde In ethanol for 3h; Reflux; Inert atmosphere; Stage #2: With sodium tetrahydroborate at 20℃; for 3h; Cooling with ice; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In methanol at 20℃; for 72h; | |
73% | In methanol at 20℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triphenylphosphine In toluene for 72h; Schlenk technique; Inert atmosphere; Further stages; | |
40% | With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triphenylphosphine In toluene for 72h; Schlenk technique; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol / 72 h / 20 °C 2: dichloromethane / 2.5 h / 20 °C | ||
Multi-step reaction with 2 steps 1: methanol / 72 h / 20 °C 2: dichloromethane / 2.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: methanol / 72 h / 20 °C 2: dichloromethane / 2.5 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 72 h / 0 - 20 °C |
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