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CAS No. : | 3128-77-6 | MDL No. : | MFCD04117579 |
Formula : | C13H9N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 179.22 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P337+P313-P361-P403+P233-P405-P501 | UN#: | 2811 |
Hazard Statements: | H301-H311-H315-H319-H331-H335 | Packing Group: | Ⅲ |
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 |
---|---|---|
37% | With sodium persulfate; silver carbonate In dimethyl sulfoxide at 100℃; for 6h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With manganese triacetate; In toluene; at 40℃;Inert atmosphere; | General procedure: General procedure for the synthesis of phenanthridin-6-yldiphenylphosphine oxides by oxidative cyclization of 2-isocyanobiphenyls with diarylphosphine oxides in the presence of manganous(III) acetate: Manganous(III) acetate (145.0mg, 0.6mmol) was added to a solution of 2-isocyanobiphenyl 1 (0.2mmol) and diarylphosphine oxide 2 (0.3mmol) in toluene (2.0mL) under N2 atmosphere. The mixture was stirred at 40C for 8-10h. After completion of the reaction as indicated by TLC, the reaction mixture was filtered through a thin layer of silica gel and washed by CH2Cl2 (3×5.0mL). The residue was concentrated in vacuo and purified by column chromatography on silica gel (eluted with PE/EA=4:1) to provide the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With manganese triacetate; In toluene; at 40℃;Inert atmosphere; | General procedure: General procedure for the synthesis of phenanthridin-6-yldiphenylphosphine oxides by oxidative cyclization of 2-isocyanobiphenyls with diarylphosphine oxides in the presence of manganous(III) acetate: Manganous(III) acetate (145.0mg, 0.6mmol) was added to a solution of 2-isocyanobiphenyl 1 (0.2mmol) and diarylphosphine oxide 2 (0.3mmol) in toluene (2.0mL) under N2 atmosphere. The mixture was stirred at 40C for 8-10h. After completion of the reaction as indicated by TLC, the reaction mixture was filtered through a thin layer of silica gel and washed by CH2Cl2 (3×5.0mL). The residue was concentrated in vacuo and purified by column chromatography on silica gel (eluted with PE/EA=4:1) to provide the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With tert.-butylhydroperoxide; caesium carbonate; p-benzoquinone In acetonitrile; benzene at 95℃; for 12h; Inert atmosphere; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With tert.-butylhydroperoxide; iron(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In decane; chlorobenzene at 100℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tert.-butylhydroperoxide; iron(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In decane; chlorobenzene at 100℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With tert.-butylhydroperoxide; iron(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In decane; chlorobenzene at 100℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With dipotassium peroxodisulfate; potassium carbonate In water; acetonitrile at 80℃; for 1h; Schlenk technique; Inert atmosphere; Green chemistry; | |
74% | With potassium pyrosulfate; silver(I) acetate; sodium acetate In dimethyl sulfoxide at 80℃; regioselective reaction; | Synthesis and Characterization of Phenanthridines 1 To a dry test tube was added isocyanide (0.3 mmol), carboxylic acid (0.45 mmol, 1.5 equiv), K2S2O8 (142.8 mg, 0.6 mmol, 2.0 equiv), NaOAc (49.2mg, 0.6 mmol, 2.0 equiv), AgOAc (10.0 mg, 0.06 mmol, 0.2 equiv), and DMSO (3.0mL). The mixture was stirred at 80 °C under air balloon. Upon completion as monitored by TLC (about 8 h), the reaction mixture was cooled down to room temperature and water (5 mL) was added to the reaction mixture. The reaction mixture was extracted with CH2Cl2 (3 × 10 mL). The combined organic layers were dried over anhydrous Na2SO4. The volatiles were removed under reduced pressure. The residue was purified by flash column chromatography on alkaline aluminum oxide (200-300 mesh) (eluent: petroleum ether/ CH2Cl2 = 50:1-20:1) to afford compound 1. 6-(tert-butyl)phenanthridine (1a)[1]: colorless oil (52.2 mg, 74%). IR (KBr, cm-1): 2965, 2921, 1571, 1470, 1258, 1092, 1023, 802, 761, 726; 1H NMR (CDCl3, 500MHz): δ 8.69 (d, J = 8.3 Hz, 1H), 8.64 (d, J = 8.5 Hz, 1H), 8.53 (d, J = 8.2 Hz, 1H), 8.14 (d, J = 8.2 Hz, 1H), 7.79 (t, J = 7.6 Hz, 1H), 7.71 (t, J = 7.6 Hz, 1H), 7.67-7.60 (m, 2H), 1.75 (s, 9H); 13C NMR (CDCl3, 125 MHz): δ 166.65, 142.98, 134.03, 130.30, 129.25, 128.37, 128.26, 126.45, 125.94, 124.35, 123.43, 122.99, 121.62, 40.21, 31.22; ESI-MS (C17H17N): 235 [M]+; HRMS (ESI) [M]+ Calcd. for C17H17N: 235.1361; found: 235.1379. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With copper(I) oxide; dipotassium peroxodisulfate; potassium carbonate; N,N,N',N'-tetramethylguanidine; In water; acetonitrile; at 80℃; for 1h;Inert atmosphere; Green chemistry; | The starting material <strong>[59748-90-2]2-chloro-4-bromobenzoic acid</strong> (0.6 mmol, 3 equiv),Catalyst cuprous oxide (Cu2O, 0.02 mmol, 10percent), ligand tetramethylguanidine (TMG, 0.04 mmol, 20percent),An oxidizing agent potassium persulfate (K2S2O8, 0.6 mmol, 3 equiv) and an inorganic base potassium carbonate (K2CO3, 0.3 mmol, 1.5 equiv) were added to the reaction tube.Performing three pumping-nitrogen filling operations on the reaction tube continuously.Then, the reaction solvent acetonitrile (CH3CN) and water (H2O) (1:1 = 2 mL) and the starting material 2-isocyanobiphenyl (0.2 mmol, 1 equiv) were continuously added to the reaction tube.After that, the mixture is stirred at a reaction temperature of 80 ° C in an oil bath until the reaction is completed, and then the reaction solvent is directly spun off.After column chromatography (column packed with 300 mesh - 400 mesh silica gel eluting with petroleum ether and ethyl acetate 20:1), the product was obtained as a yellow solid, yield 71percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With tert.-butylhydroperoxide; iron(II) acetylacetonate; oxygen; In nonane; acetonitrile; at 100℃; for 24h;Molecular sieve; | General procedure: General procedure for the synthesis of phenanthridines 3: To a 25 mL tube containing a magnetic stir bar, was added 2-isocyanobiphenl 1 (0.2mmol, 1.0 equiv), Fe(acac)2 (20% mmol, 25.4mg), 4 AMS (100mg), TBHP (5.5M in nonane, 0.15ml, 0.8mmol, 4.0 equiv), benzyl alcohol 2 (0.8mmol, 4.0 equiv), and MeCN (2ml). The resulting mixture was heated under O2 at 100C for 24h. The solvent was removed under vacuum, and the residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate=1:10) to provide the desired products 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With N,N,N',N'-Tetraethylethylenediamine In tetrahydrofuran at 30℃; for 36h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With manganese(III) acetylacetonate; In tert-butyl alcohol; at 26℃; for 2.08333h;Inert atmosphere; | General procedure: An argon-degassed solution of cyclopropanol 1 (1 equiv) in t-BuOH (0.02 M) was added dropwise over 2 h to an argondegassed,stirred solution of 2-isocyano biphenyl 2 (2 equiv)and manganese(III) acetylacetonate (2.2 equiv) in t-BuOH(0.042 M) at 26 C. The resulting solution (0.01 M with respectto the cyclopropanol) was stirred for an additional 5 min beforethe solvent was removed under reduced pressure, and theresulting residue purified by flash chromatography to yield thedesired 2-substituted phenanthradine 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With copper(l) iodide; In 1,4-dioxane; at 80℃; for 2.0h; | Will be 0.5mmol2-phenylbenzene isonitrile (89.5 mg),(219.8 mg), 0.1 mmol of cuprous iodide (19.1 mg) and 5 mL of 1,4-dioxane were added to a 15 mL reaction tube. Subsequently, the mixture was magnetically stirred at 80 C for 2 hours. Then, two syrups of silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure. The residue was packed in column and separated by column chromatography using petroleum ether, 10: 1 as the eluent, the eluate containing the product was collected and the solvent was distilled off to give the pure product 2,2'-diphenyl oxalanilide. The material was a pale yellow solid in 64% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With silver(l) oxide; In dichloromethane; water; at 20℃; for 0.166667h;Sealed tube; Schlenk technique; Inert atmosphere; | General procedure: In air, the potassium alkyltrifluoroborate (0.2 mmol, 1.0 eq.), Ag2O (0.2 mmol, 1.0 eq.) and 2-isocyano-1,1'-biphenyl (0.2 mmol, 1.0 eq.) were sequentially weighed andadded to a screw-capped Schenk tube containing a magnetic stir bar. The vessel was evacuated and refilled with nitrogen for three times. DCM (2.0 mL) and distilled water(40 muL) were added in turn under N2 atmosphere using syringes through a septum which was temporarily used to replace the screw cap. The reaction mixture was thenvigorously stirred at room temperature for the indicated time. The resulting mixture was filtered through a pad of Celite, and the filter cake was washed with ethyl acetate (3mL x 2). The combined filtrate was evaporated under vacuum to dryness and the residue was purified by column chromatography to yield the desired product. |
88% | With silver(l) oxide; In water; toluene; at 25℃; for 0.166667h;Schlenk technique; Inert atmosphere; | In air, the potassium alkyltrifluoroborate (0.10 mmol, 1.0 eq.), Ag2O (0.1 mmol, 1.0 eq.) and 2-isocyano-1,1'-biphenyl (0.1 mmol, 1.0 eq.) were sequentially weighed and added to a screw-capped Schenk tube containing a magnetic stir bar. The vessel was evacuated and refilled with nitrogen for three times. Toluene (1.0 mL) and distilled water (20 muL) were added in turn under N2 atmosphere using syringes through a septum which was temporarily used to replace the screw cap. The reaction mixture was then vigorously stirred at room temperature for 10 min. The resulting mixture was filtered through a pad of Celite, and the filter cake was washed with ethyl acetate (3 mL x 2). The combined filtrate was evaporated under vacuum to dryness and the residue was purified by column chromatography to yield the desired product 4f (20.7mg, yield 88%). IR (thin film): 3901, 3853, 3801, 3689, 2956, 1869, 1772, 1651, 1522, 1338, 825, 730 cm-1 1H NMR (400 MHz, CDCl3) delta 8.65 (d, J = 8.3 Hz, 1H), 8.54 (d, J = 8.2 Hz, 1H), 8.26 (d, J = 8.2 Hz, 1H), 8.08 (d, J = 8.1 Hz, 1H), 7.84 (t, J = 7.6 Hz, 1H), 7.70 (t, J = 7.8 Hz, 2H), 7.62 (t, J = 7.5 Hz, 1H), 3.40 (t, J = 8.0 Hz, 2H), 1.91 (m, 2H), 1.56 (m, 2H), 1.01 (t, J = 7.4 Hz, 3H); 13C NMR (100 MHz, CDCl3) delta 162.4, 133.0, 130.4, 129.4, 128.7, 127.3, 126.5, 126.4, 125.2, 123.7, 122.5, 121.9, 35.6, 31.5, 22.9, 13.8; HRMS (ESI+): Calculated for C17H17N [M+H] 236.1434, found 236.1429. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With silver(l) oxide; In dichloromethane; water; at 20℃; for 0.166667h;Sealed tube; Schlenk technique; Inert atmosphere; | General procedure: In air, the potassium alkyltrifluoroborate (0.2 mmol, 1.0 eq.), Ag2O (0.2 mmol, 1.0 eq.) and 2-isocyano-1,1'-biphenyl (0.2 mmol, 1.0 eq.) were sequentially weighed andadded to a screw-capped Schenk tube containing a magnetic stir bar. The vessel was evacuated and refilled with nitrogen for three times. DCM (2.0 mL) and distilled water(40 muL) were added in turn under N2 atmosphere using syringes through a septum which was temporarily used to replace the screw cap. The reaction mixture was thenvigorously stirred at room temperature for the indicated time. The resulting mixture was filtered through a pad of Celite, and the filter cake was washed with ethyl acetate (3mL x 2). The combined filtrate was evaporated under vacuum to dryness and the residue was purified by column chromatography to yield the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With silver(l) oxide; In dichloromethane; water; at 20℃; for 0.166667h;Sealed tube; Schlenk technique; Inert atmosphere; | General procedure: In air, the potassium alkyltrifluoroborate (0.2 mmol, 1.0 eq.), Ag2O (0.2 mmol, 1.0 eq.) and 2-isocyano-1,1'-biphenyl (0.2 mmol, 1.0 eq.) were sequentially weighed andadded to a screw-capped Schenk tube containing a magnetic stir bar. The vessel was evacuated and refilled with nitrogen for three times. DCM (2.0 mL) and distilled water(40 muL) were added in turn under N2 atmosphere using syringes through a septum which was temporarily used to replace the screw cap. The reaction mixture was thenvigorously stirred at room temperature for the indicated time. The resulting mixture was filtered through a pad of Celite, and the filter cake was washed with ethyl acetate (3mL x 2). The combined filtrate was evaporated under vacuum to dryness and the residue was purified by column chromatography to yield the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With dipotassium peroxodisulfate; silver nitrate; In N,N-dimethyl-formamide; at 20℃; for 2h;Inert atmosphere; | General procedure: A mixture of 2-isocyanobiphenyl 1 (0.25 mmol), sodium sulfinate 2 (0.25mmol), AgNO3 (15 mol%), K2S2O8 (0.50 mmol), and DMF (3 mL) was taken in a flask and stirred at rt for 2 h under N2 (Table 2). After completion of the reaction (monitored by TLC), water (5 mL) was added and the mixture was extracted with ethyl acetate (3 × 5 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography using a mixture of hexane/ethyl acetate (4:1) as eluent to afford an analytically pure sample of product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With dipotassium peroxodisulfate; silver nitrate; In N,N-dimethyl-formamide; at 20℃; for 2h;Inert atmosphere; | General procedure: A mixture of 2-isocyanobiphenyl 1 (0.25 mmol), sodium sulfinate 2 (0.25mmol), AgNO3 (15 mol%), K2S2O8 (0.50 mmol), and DMF (3 mL) was taken in a flask and stirred at rt for 2 h under N2 (Table 2). After completion of the reaction (monitored by TLC), water (5 mL) was added and the mixture was extracted with ethyl acetate (3 × 5 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography using a mixture of hexane/ethyl acetate (4:1) as eluent to afford an analytically pure sample of product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With bis(acetylacetonate)nickel(II) In acetone at 50℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With di-tert-butyl peroxide In benzene at 20℃; for 2h; | 18 Example 18 2-Phenylbenzonitrile 1a (2mmol),Adamantane 2h (4mmol) and free radical initiator di-tert-butyl peroxide(2 mmol) was mixed, and 10 mL of benzene was added as a solvent, and the reaction was carried out at room temperature under air.The reaction was carried out for 2 hours.The conversion rate of 2-phenylbenzonitrile is 100%.The yield of 3ag was 48%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With lithium hemisulfide In N,N-dimethyl acetamide for 12h; Schlenk technique; Inert atmosphere; Irradiation; | 1; 38-70 General procedure: Into a 10mL Schlenk reaction tube (Beijing Xinweier Glass Instrument Co., Ltd., F891410 reaction tube, capacity 10mL, grinding mouth 14/20), add redox alkyl active carboxylate (0.3mmol) and lithium sulfide (0.04mmol). The air in the tube was completely replaced with argon three times, and then 2 mL of N,N-dimethylacetamide (DMA) and radical acceptor isocyanide (0.2 mmol) were added under an argon atmosphere. The reaction system was continuously stirred at room temperature for 12 hours under the irradiation of a 40W purple LED (427 nm) lamp (IKA magnetic stirrer, RCT basic type, stirring speed 500 rpm). After the completion of the reaction, the reaction was quenched with saturated NaCl solution, and the reaction solution was repeatedly extracted 3 times with 10 mL of ethyl acetate, and the combined organic phase was concentrated by rotary evaporation (Swiss Buchi Co., Ltd., BUCHI rotary evaporator R-3 ). The concentrated residue was chromatographed on a column (Beijing Xinweier Glass Instrument Co., Ltd., C383040C spherical column with sand plate storage, 35/20, effective length: 500ml) to obtain the product. (The product was a colorless viscous liquid, totaling 43.3 mg, yield 92%, eluent ethyl acetate:petroleum ether=1:50), |
87% | With tripotassium phosphate tribasic; salicylic aldehyde; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 40℃; for 6h; Schlenk technique; Inert atmosphere; UV-irradiation; | |
77% | With triphenylphosphine; sodium iodide In acetonitrile at 25℃; Irradiation; Green chemistry; |
75% | With Sodium hydrogenocarbonate; N-ethyl-N,N-diisopropylamine; Eosin In dimethyl sulfoxide for 24h; Irradiation; | 6 Example 6: Isonitrile 1a (0.30mmol), N-(acyloxy)phthalimide 2f (0.60mmol), Eosin Y (5mol%), sodium bicarbonate (0.36mmol), N,N-di Isopropylethylamine (0.60 mmol) was dissolved in dimethyl sulfoxide (3.0 mL) and placed under an 18W white lamp for 24 hours. After the reaction was completed, the reaction system was diluted with water, the aqueous phase was extracted three times with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure on a water pump to obtain a crude product. The crude product was subjected to chromatography on a silica gel column ( Ethyl acetate: petroleum ether = 1:80 ~ 1:60) purification to obtain 52.9mg white solid product 3af, the yield was 75%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; eosin y In dimethyl sulfoxide for 4h; Irradiation; | 4 Example 4: Isonitrile 1a (0.30mmol), N-(acyloxy)phthalimide 2d (0.60mmol), Eosin Y (5mol%), sodium bicarbonate (0.36mmol), N,N-di Isopropylethylamine (0.60 mmol) was dissolved in dimethyl sulfoxide (3.0 mL) and placed under an 18W white lamp for 4 hours. After the reaction was completed, the reaction system was diluted with water, the aqueous phase was extracted three times with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation on a water pump under reduced pressure to obtain a crude product, which was passed through a chromatography silica gel column (Ethyl acetate: petroleum ether=1:40) Purification gave 61.6 mg of yellow oil product 3ad with a yield of 93%. |
71% | With triphenylphosphine; sodium iodide In acetonitrile at 25℃; Irradiation; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triphenylphosphine; sodium iodide In acetonitrile at 25℃; Irradiation; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; eosin y; In dimethyl sulfoxide; for 24.0h;Irradiation; | Isonitrile 1a (0.30mmol), N-(acyloxy)phthalimide 2a (0.60mmol), Eosin Y (5mol%), sodium bicarbonate (0.36mmol), N,N-di Isopropylethylamine (0.60 mmol) was dissolved in dimethyl sulfoxide (3.0 mL) and placed under an 18W white lamp for 24 hours. After the reaction was completed, the reaction system was diluted with water, the aqueous phase was extracted three times with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation on a water pump under reduced pressure to obtain a crude product, which was passed through a chromatography silica gel column (Ethyl acetate: petroleum ether=1:40) Purification gave 48.1 mg of yellow solid product 3aa in 83% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; eosin y In dimethyl sulfoxide for 24h; Irradiation; | 8 Example 8: Isonitrile 1a (0.30mmol), N-(acyloxy)phthalimide 2h (0.60mmol), Eosin Y (5mol%), sodium bicarbonate (0.36mmol), N,N-di Isopropylethylamine (0.60 mmol) was dissolved in dimethyl sulfoxide (3.0 mL) and placed under an 18W white lamp for 24 hours. After the reaction was completed, the reaction system was diluted with water, the aqueous phase was extracted three times with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure on a water pump to obtain a crude product, which was passed through a chromatography silica gel column ( (Petroleum ether) purification gave 88.1 mg of white solid product 3ah in 81% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium pyrosulfate; silver(I) acetate In water; acetone at 70℃; regioselective reaction; | One-Pot Synthesis of Multi-Substituted Phenanthridines 3j-l from Biphenyl Isocyanides General procedure: To a dry test tube was added the respective biphenyl isocyanide (0.2mmol), carboxylic acid 2 (1.0 mmol, 5.0 equiv), K2S2O8 (162 mg, 0.6mmol, 3.0 equiv), AgOAc (10.0 mg, 0.06 mmol, 0.3 equiv), acetone (1.0mL), and H2O (1.0 mL). The reaction mixture was stirred at 70 °C under air balloon. Upon completion as monitored by TLC (about 22 h), the mixture was cooled down to r.t. and H2O (5 mL) was added to the mixture. The mixture was extracted with CH2Cl2 (3 × 10 mL). The combined organic layers were dried (anhyd Na2SO4), and the volatiles were removed under reduced pressure. The residue was purified by flash column chromatography on alkaline aluminum oxide (200-300 mesh) (eluent: PE/CH2Cl2 50:1 to 20:1) to afford product 3. |
Multi-step reaction with 2 steps 1: potassium pyrosulfate; sodium acetate; silver(I) acetate / dimethyl sulfoxide / 80 °C 2: potassium pyrosulfate; silver(I) acetate / acetone; water / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With potassium pyrosulfate; silver(I) acetate; sodium acetate In dimethyl sulfoxide at 80℃; regioselective reaction; | Synthesis and Characterization of Phenanthridines 1 General procedure: To a dry test tube was added isocyanide (0.3 mmol), carboxylic acid (0.45 mmol, 1.5 equiv), K2S2O8 (142.8 mg, 0.6 mmol, 2.0 equiv), NaOAc (49.2mg, 0.6 mmol, 2.0 equiv), AgOAc (10.0 mg, 0.06 mmol, 0.2 equiv), and DMSO (3.0mL). The mixture was stirred at 80 °C under air balloon. Upon completion as monitored by TLC (about 8 h), the reaction mixture was cooled down to room temperature and water (5 mL) was added to the reaction mixture. The reaction mixture was extracted with CH2Cl2 (3 × 10 mL). The combined organic layers were dried over anhydrous Na2SO4. The volatiles were removed under reduced pressure. The residue was purified by flash column chromatography on alkaline aluminum oxide (200-300 mesh) (eluent: petroleum ether/ CH2Cl2 = 50:1-20:1) to afford compound 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; trifluoroacetic acid In dichloromethane | 7.1.8 General procedure for the preparation of 35 and 46 General procedure: To a solution of 7a or 12a (1.0 equiv) and 14 (1.5 equiv) in dry CH2Cl2 (2mL), trifluoroacetic acid (2.0 equiv) was added dropwise at-5°C. The reaction mixture was allowed to stir for 2hat 0°C. Then pyridine (4.0 equiv) was added at 0°C. The resulting solution was stirred at 0°C for 1h CH2Cl2 was added, the pH value of the reaction was adjusted to 5-6 with 1N HCl in ice bath. The aqueous layer was separated, the organic layer was washed with water (30mL) and brine (30mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 5) to get product as white solid. To a solution of compound 8a or 13a (1.0 equiv) in DMSO was added IBX (2.0 equiv). The resulting solution was stirred at room temperature for 5h. Saturated NaHCO3 solution was added and extracted with ethyl acetate (3×30mL). The combined organic layer was washed with saturated NaHCO3 solution, water, brine, dried over anhydrous sodium sulfate, filtered, concentrated under vacuum. The crude product was precipitated from ethyl acetate to give final product 35 or 46. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tributyl-amine; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In ethyl acetate at 30℃; for 12h; Sealed tube; Inert atmosphere; Irradiation; |
Tags: 3128-77-6 synthesis path| 3128-77-6 SDS| 3128-77-6 COA| 3128-77-6 purity| 3128-77-6 application| 3128-77-6 NMR| 3128-77-6 COA| 3128-77-6 structure
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P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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