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CAS No. : | 36848-40-5 | MDL No. : | MFCD34178727 |
Formula : | C12H6Br2N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MILNCXRRKCVYAV-UHFFFAOYSA-N |
M.W : | 338.00 | Pubchem ID : | 12560083 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P313-P337+P313-P362-P403+P233-P405-P501 | 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 |
---|---|---|
With lead; iron(II) oxalate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 5% 2: 3% 3: 61% 4: 21% | With lead dioxide In benzene Ambient temperature; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 51% 2: 63% | With lead dioxide In acetonitrile Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 5% 2: 3% 3: 61% 4: 28% 5: 21% | With lead dioxide In benzene Ambient temperature; effect of substituents and solvents on the reactivity of 4'-substituted benzenesulphenanilides; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 1.5% 2: 17% 3: 2% 4: 90% | With silver(l) oxide In benzene Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
/BRN= 805551/ (3e), PbO2; | ||
p-Bromoanilin, p-Bromonitrobenzol, KOH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; tin(ll) chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: 5 percent / lead dioxide / benzene / Ambient temperature | ||
Multi-step reaction with 2 steps 2: 63 percent / lead dioxide / acetonitrile / Ambient temperature | ||
Multi-step reaction with 2 steps 2: 2 percent / silver(I) oxide / benzene / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: iron (II)-oxalate; lead |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In 1,4-dioxane at 100℃; for 4h; Inert atmosphere; | 13; 26.3 To a solution of 2,7-dibromophenazine (13-2) (1.52 g, 4.50 mmol) in dry dioxane (75 mL) under N2 was added tributyl(l-ethoxyvinyl)stannane (3.34 ml, 9.89 mmol) and Pd(dppf)Cl2 (0.316 g, 0.450 mmol). The resultant mixture was heated at 1000C for 4h in a sealed tube. The crude reaction mixture was filtered through CELITE545, and the volatiles were removed in vacuo. The crude brown solid was triturated with isohexanes and filtered to give 2,7-bis(l-ethoxyvinyl)phenazine as a brown solid (1.27 g, 88 % yield). 1H NMR (CDCl3) δ 8.55-8.53 (2H, m), 8.19-8.15 (2H, m), 8.11-8.07 (2H, m), 4.98 (2H, d, J = 3 Hz), 4.49 (2H, d, J = 3 Hz), 4.03 (4H, q, J = 7 Hz), 1.50 (6H, t, J = 7 Hz) ppm. LC-MS (ESI): m/z 322.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With acetic acid for 1.5h; Reflux; | 13; 26.2 5-bromo-N-(4-bromophenyl)-2-nitrosoaniline 513-1) (10 g, 28.1 mmol) in AcOH (300 mL) was heated under reflux for 1.5 h. Water (400 mL) was then added and the brown precipitate formed was collected by filtration after washing with water (2 x 200 mL). The product was purified by silica gel chromatography (SiO2, hexanes/DCM = 1/1 (v/v)) to afford a brown solid, 2,7-dibromophenazine 13-2 (1.52 g, 16 % yield).1H NMR (CDCl3) δ 8.43 (2H, dd, J2.2, 0.4 Hz), 8.10 (2H, dd, J9.2, 0.4 Hz), 7.91 (2H, dd, J 9.2, 2.2 Hz) ppm. LC-MS (ESI): m/z 338.6 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 15 h / 110 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; water / 15 h / Reflux 3: hydrogenchloride / water; methanol / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 15 h / 110 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; water / 15 h / Reflux 3: hydrogenchloride / water; methanol / 0.5 h 4: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 10 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 8 h / 110 °C / Inert atmosphere 2: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 15 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethyl sulfoxide / 8 h / 110 °C / Inert atmosphere 2: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 15 h / 110 °C / Inert atmosphere 3: sodium dithionite; potassium carbonate / acetonitrile; water / 10 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With potassium carbonate In dimethyl sulfoxide at 110℃; for 8h; Inert atmosphere; | 2 The example compound B-18 can be synthesized, for example, by the following procedure. First, a compound XX-3 is synthesized. In a 100-ml reaction chamber, 500 mg (1.48 mmol) of the compound XX-1 and 278 mg (2.96 mmol) of phenol were mixed together in dimethyl sulfoxide (DMSO) (5 ml), and dissolved oxygen was removed toy nitrogen. Next, 62.8 mg (0.074 mmol) of a CuI/Sparteine complex and 409 mg (2.96 mmol) of potassium carbonate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 110° C. for 8 hours.After the reaction solution was cooled to room temperature and was then condensed at a reduced pressure, separation and purification were performed by a silica gel chromatography (mobile phase: hexane/chloroform), so that a yellow solid compound XX-3 was obtained (160 mg, yield: 32%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; toluene at 100℃; for 6h; Inert atmosphere; | 6 The example compound A-3 can be synthesized, for example, by the following procedure. First, a compound XX-5 is synthesized. In a 50-ml reaction chamber, 507 mg (1.5 mmol) of the compound XX-1 and 638 mg (4.5 mmol) of 2-methoxyphenylboronic acid were mixed in a mixed solvent of toluene/1,4-dioxane (6 ml/6 ml), and dissolved oxygen was removed by nitrogen. Next, 13.5 mg (0.06 mmol) of Pd(OAc)2, 61.6 mg (0.15 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos), and 1.72 g (7.5 mmol) of tripotassium phosphate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 100° C. for 6 hours.After the reaction solution was cooled to room temperature, a powder precipitated by reduced-pressure condensation was purified by recrystallization, so that a yellow solid compound XX-5 was obtained (265 mg, yield: 45%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / acetonitrile / 9 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; toluene at 100℃; for 4h; Inert atmosphere; | 7 The example compound A-25 can be synthesized, for example, by the following procedure. First, a compound XX-6 is synthesized. In a 50-ml reaction chamber, 507 mg (1.5 mmol) of the compound XX-1 and 1.38 g (4.5 mmol) of 2,6-diphenoxyphenylboronic acid were mixed in a mixed solvent of toluene/1,4-dioxane (6 ml/6 ml), and dissolved oxygen was removed by nitrogen. Next, 13.5 mg (0.06 mmol) of Pd(OAc)2, 61.6 mg (0.15 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos), and 1.72 g (7.5 mmol) of tripotassium phosphate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 100° C. for 4 hours.After the reaction solution was cooled to room temperature, a powder precipitated by reduced-pressure condensation was purified by recrystallization, so that a yellow solid compound XX-6 was obtained (650 mg, yield: 62%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; toluene at 100℃; for 6h; Inert atmosphere; | 12 The example compound F-2 can be synthesized, for example, by the following procedure. First, a compound XX-9 is synthesized. In a 50-ml reaction chamber, 507 mg (1.50 mmol) of a compound XX-1 and 747 mg (4.5 mmol) of 4-metoxy-2-methylphenylboronic acid were mixed in a mixed solvent of toluene/1,4-dioxane (7 ml/7 ml), and dissolved oxygen was removed by nitrogen. Next, 13.5 mg (0.06 mmol) of Fd(OAc)2, 61.6 mg (0.15 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos), and 1.72 g (7.5 mmol) of tripotassium phosphate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 100° C. for 6 hours.After the reaction solution was cooled to room temperature and was then condensed at a reduce pressure, separation and purification were performed by a silica gel chromatography (mobile phase: hexane/chloroform), so that a yellow solid compound XX-9 was obtained (478 mg, yield: 76%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / acetonitrile; water / 9 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; toluene at 110℃; for 8h; Inert atmosphere; | 1 The example compound A-21 can be synthesized, for example, by the following procedure. First, a compound XX-2 is synthesized. In a 50-ml reaction chamber, 676 mg (2.0 mmol) of a compound XX-1 and 1.26 g (6.0 mmol) of 2-isopropoxy-6-methoxyphenylboronic acid were mixed together in a mixed solvent of toluene/1,4-dioxane (7 ml/7 ml), and dissolved oxygen was removed by nitrogen. In addition, the compound XX-1 was a compound synthesized in accordance with Tetrahedron Letters, 52, 6484 (2011).Next, 18.0 mg (0.08 mmol) of Pd(OAc)2, 82.1 mg (0.10 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos), and 2.30 g (10.0 mmol) of tripotassium phosphate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 110° C. for 8 hours.After the reaction solution was cooled to room temperature and was then condensed at a reduced pressure, separation and purification were performed by a silica gel chromatography (mobile phase: hexane/chloroform), so that a yellow solid compound XX-2 was obtained (770 mg, yield: 75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 8 h / 110 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / acetonitrile; water / 9 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid In ethanol at 65℃; for 4h; Overall yield = 82.4 %; Overall yield = 5.82 g; | 1 Example 1 Synthesis of dibromophenazine To 250 ml three-necked flask was added 4-bromo o-phenylenediamine 3.91 g (molecular weight 186, 0.021 mol)4-bromo-o-benzoquinone 3.91 g (molecular weight 186,0.021mol),Ethanol (40 ml),Under stirring,3 minutes 0.2 g concentrated sulfuric acid (concentration 98%),The reaction was carried out at 65 ° C for 4 hours,After the reaction,Cool to room temperature,filter,Washed,drying,Column chromatography,Ethyl acetate / petroleum ether rinse,Almost equal amounts of 2,7-dibromophenazine and 2,8-dibromophenazine were obtained,Total 5.82 grams (molecular weight 336),The total yield of 82.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With BSA In acetonitrile at 100℃; for 16h; Sealed tube; | 1 Embodiment 1, the synthetic process of phenazine base compound Put 1mmol of p-bromonitrobenzene and 1mmol of p-bromoaniline into a single-necked bottle, add an appropriate amount of potassium tert-butoxide and tetrahydrofuran, and react at -78 degrees Celsius for 1 hour to obtain a tan intermediate product. After filtering, the tan intermediate is obtained. Put it into a high-pressure reaction cylinder, add 15 mL of acetonitrile as a solvent, add 6 mL of BSA as a ring-closing agent, seal the cylinder, react at 100 degrees Celsius for 16 hours, filter out bright yellow fractions, and obtain 2,6-dibromophenazine with a yield of about 90%. |
68% | With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 100℃; for 12h; Inert atmosphere; Sealed tube; | |
3.4 g | With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 100℃; for 16h; Inert atmosphere; Sealed tube; |
With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 100℃; for 12h; Sealed tube; | In the second step, N-aryl-2-nitrosoanilines is cyclized as follows. N, O bis(trimethylsilypacetamide (BSA) (1.2 mL, 5 mmol) was added to a solution of nitrosoaniline (1 mmol) in MeCN (4 mL) to form a reaction mixture. The reaction mixture was added into a sealed tube. The sealed tube was then heated to 100° C. for 12 hours. The reaction mixture was filtered to obtain a precipitate, and the precipitate was washed with cold MeOH, then dried under vacuum to obtain the main body of the phenazine group of the organic electroluminescent compound represented by Formula (I). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 12 h / 100 °C / Inert atmosphere; Sealed tube | ||
Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / -78 °C / Inert atmosphere 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 16 h / 100 °C / Inert atmosphere; Sealed tube | ||
Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 12 h / 100 °C / Sealed tube |
Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C 2: BSA / acetonitrile / 16 h / 100 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 12 h / 100 °C / Inert atmosphere; Sealed tube | ||
Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / -78 °C / Inert atmosphere 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 16 h / 100 °C / Inert atmosphere; Sealed tube | ||
Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C 2: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 12 h / 100 °C / Sealed tube |
Multi-step reaction with 2 steps 1: potassium-t-butoxide / tetrahydrofuran / 1 h / -78 °C 2: BSA / acetonitrile / 16 h / 100 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: johnphos; caesium carbonate; palladium diacetate / 1,4-dioxane / 24.08 h / 20 - 150 °C / Inert atmosphere; Sealed tube 2: hydrogenchloride / chloroform; isopropyl alcohol; water / 24 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With palladium diacetate; caesium carbonate; johnphos In 1,4-dioxane at 20 - 150℃; for 24.0833h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 16h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper; potassium carbonate In 1,2-dichloro-benzene at 190℃; for 24h; Inert atmosphere; | Dibromophenazine (1 mmol), nitrogen donor (2 mmol), copper powder (4 mmol) and K2CO3 (5 mmol) were added in a flask. Dichlorobenzene (5 mL) was further added into the flask under nitrogen atmosphere and the flask was heated to 190° C. in an oil bath for 24 hours to obtain a reaction mixture. The reaction mixture was filtered to obtain a solution. The organic solvent of the solution was removed under vacuum to obtain a residue. The residue was purified by silica gel chromatography to obtain the organic electroluminescent compound represented by Formula (II). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl(2′,4′,6′-tri-isopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane; potassium-t-butoxide In <i>tert</i>-butyl alcohol at 100℃; for 16h; Sealed tube; | |
92% | With tris-(dibenzylideneacetone)dipalladium(0); potassium-t-butoxide; BrettPhos In <i>tert</i>-butyl alcohol at 100℃; for 12h; Inert atmosphere; Sealed tube; | 1 Example 1-9 Synthesis of phenazine amino acid derivatives Under nitrogen atmosphere,Weigh 2,7-dibromophenazine (3mmol, 1.014g), glycine (7.2mmol, 0.54g), Pd2(dba)3 (5mol%, 137.4mg),BrettPhos (10mol%, 161mg), potassium tert-butoxide (15mmol, 1.68g),30 mL of tert-butanol was placed in a thick-walled pressure-resistant reaction tube.Stir well and raise the temperature to 100°C,After 12 h of reaction, it was cooled to room temperature.filter and collect the filter cake,The filter cake was dissolved in deionized water and filtered again to remove water-insoluble impurities.Collect the filtrate,The filtrate was acidified with HCl to pH=34,After the solid is separated out, filter, collect the filter cake,The filter cake was washed with deionized water (2×5 mL), and the target compound 3 was obtained after drying.further,Purified by reversed-phase column (C18) (MeOH:H2O=15:85), the yield was 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 100℃; for 16h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 100℃; for 16h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 100℃; for 16h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.9% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 85℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59.9% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 85℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); BrettPhos; Cs2CO3 In <i>tert</i>-butyl alcohol at 100℃; for 12h; Inert atmosphere; | 10 Under nitrogen atmosphere,Weigh 2,7-dibromophenazine (3mmol, 1.014g),3,3'-iminodipropionitrile (12mmol, 1.48g),Pd2(dba)3 (5mol%, 137.4mg),BrettPhos (10mol%, 161mg),Cesium carbonate (21mmol, 6.842g), tert-butanol 10mL,in the reaction tube.Fully stirred and heated to 100 , reacted for 12h and filtered while hot.The solid was washed with deionized water and EtOH successively and then dried in a vacuum drying oven.Compound 18 was obtained.Weigh compound 18 (1 mmol, 422 mg) into a thick-walled pressure bottle, add NaOH (4 mmol, 160 mg), 4 mL of deionized water, fully stir and heat up to 150 ° C, react for 12 h after cooling and filtration,Collect solids.further,Purified by reverse phase column (C18) (MeOH:H2O=5:95),Compound 19 was obtained.Yield 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); BrettPhos; Cs2CO3 / <i>tert</i>-butyl alcohol / 12 h / 100 °C / Inert atmosphere 2: water monomer / 12 h / 150 °C / Sealed tube; Alkaline conditions |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper oxide (I); potassium carbonate In N,N-dimethyl-formamide at 135℃; for 24h; | 1 Put 1 g (3 mmol) of 2,6-dibromophenazine into a three-necked flask, add 0.1 g of cuprous oxide, add 6 mmol of a donor group (the donor group is carbazole, tert-butylcarbazole, diphenylamine) , triphenylamine, phenoxazine, tert-butyl diphenylamine, phenylcarbazole), 3 g of potassium carbonate and 20 mL of DMF were used as solvents. The reaction was carried out at 135 degrees Celsius for 24 hours to obtain the final product. The NMR of the final product was |