* 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.
Reference：
[1] Chemistry of Heterocyclic Compounds, 2011, vol. 46, # 10, p. 1199 - 1207
2
[ 188290-36-0 ]
[ 543-20-4 ]
[ 13669-05-1 ]
[ 4653-08-1 ]
Reference：
[1] Chemistry of Heterocyclic Compounds, 2011, vol. 46, # 10, p. 1199 - 1207
3
[ 188290-36-0 ]
[ 543-20-4 ]
[ 13669-05-1 ]
Yield
Reaction Conditions
Operation in experiment
76%
With aluminum (III) chloride In dichloromethane at 40℃; for 4 h;
A solution of thiophene (9.6 mL, 0.12 mol) and succinychloride (5.4 mL,0.05 mol) were added dropwise to a suspension containing AlCl3 (16.2 g, 0.12 mol) in 100 mL of dichloromethane. After stirringfor 4 h at 40 °C, the mixture solution was poured into a mixture of 100 g ice and 10 mL hydrochloric acid and stirred for 30 min. The resulting solution was extracted with CHCl2 and washed with NaHCO3 solutions and water before desiccation with anhydrous MgSO4. The solvent was evaporated off, and the solid residues were purified by column chromatography to afford white product with ayield of 76percent. 1H NMR (500 MHz, CDCl3, 25 °C, TMS, d): 7.84 (dd,J = 3.8,1.1 Hz, 2H), 7.67 (dd, J = 5.0, 1.1 Hz, 2H), 7.17 (dd, J = 4.9, 3.8 Hz,2H), 3.42 (s, 4H). MALDI-TOF MS (mass m/z): 251.1 [M+ + H].
68%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 4 h;
A solution of thiophene (9.61 mL, 0.12 mol) and AlCl3 (16 g, 0.12 mol) in dry CH2Cl2 (50 mL) was added dropwise to a suspension of succinyl chloride (5.5 mL, 0.05 mol) in dry CH2Cl2 (50 mL) at 0 °C. The mixture was stirred for at 18-20 °C 4 h and poured into a mixture of 100 g ice and 10 mL hydrochloric acid and stirred for 1 h and the resulting dark green organic phase was washed with concentrated NaHCO3 (3 x 25 mL), and dried over Na2SO4. After the solvent was evaporated, a blue-green solid remained and was suspended in ethanol. Column chromatography (SiO2, CH2Cl2) and recrystallization from ethanol produced 8.98 g (68percent) of it in a white solid. 1H NMR: (400 MHz; CDCl3): 7.80 (dd, 2H), 7.63 (dd, 2H), 7.13 (dd, 2H), 3.38 (s, 4H).
58%
With aluminum (III) chloride In dichloromethane at 20℃; for 6 h;
To a suspension of AlCl3 (32 g, 0.24 mol) in 90 mL ofDCM, a solution of 11 mL (0.1 mol) succinyl chloride and19.2 mL (0.24 mol) of thiophene in 30 mL DCM was addeddropwise at room temperature. The suspension was stirredfor 6 h and poured into a mixture of 10 mL of hydrochloricacid and 400 g of ice. The color of the suspension turnedfrom red to dark green after further stirring for 30 min.The organic phase was collected and the aqueous phasewas extracted with DCM. The organic phases was combinedand washed with water and saturated aqueous NaHCO3,dried over NaSO4, concentrated in vacuo, and purified bycolumn chromatography (eluent:DCM:hexane = 1:1) toafford 14.5 g (58percent) of 1 as pale blue crystals. 1H NMR(500 MHz, CDCl3, d, ppm): 7.82 (dd, 2H), 7.65 (dd, 2H),7.15 (dd, 2H), 3.40 (s, 4H) (Fig. S1). MS (EI) (m/z): [M]+ calcdfor C12H10O2S2, 250.0; found, 250.1.
Reference：
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4
[ 10531-41-6 ]
[ 13669-05-1 ]
Yield
Reaction Conditions
Operation in experiment
51%
With titanium(IV) isopropylate; ethylmagnesium bromide In tetrahydrofuran; diethyl ether; water at 23℃; for 18 h; Inert atmosphere
General procedure: Ti(OiPr)4 (0.18 mL, 0.602 mmol) was added to a solution of 2-bromoacetophenone (4, 100. mg, 0.502 mmol) in THF (5 mL) atroom temperature. EtMgBr (0.47 mL, 1.41 mmol, 3 M in Et2O)was then added dropwise over 20 min during which the reactionmixture turned from clear to yellow to black. After 18 h,water (5 mL) was added, and the mixture was extracted EtOAc(3 × 5 mL). The combined organic layers were washed withbrine (1 × 10 mL), dried with MgSO4, and concentrated in vacuo.Purification by column chromatography (15percent EtOAc/hexanes)afforded 1,4-diketone 8 as a white powder (47 mg, 79percent).
With aluminum (III) chloride; In dichloromethane; at 40℃; for 4h;
A solution of thiophene (9.6 mL, 0.12 mol) and succinychloride (5.4 mL,0.05 mol) were added dropwise to a suspension containing AlCl3 (16.2 g, 0.12 mol) in 100 mL of dichloromethane. After stirringfor 4 h at 40 C, the mixture solution was poured into a mixture of 100 g ice and 10 mL hydrochloric acid and stirred for 30 min. The resulting solution was extracted with CHCl2 and washed with NaHCO3 solutions and water before desiccation with anhydrous MgSO4. The solvent was evaporated off, and the solid residues were purified by column chromatography to afford white product with ayield of 76%. 1H NMR (500 MHz, CDCl3, 25 C, TMS, d): 7.84 (dd,J = 3.8,1.1 Hz, 2H), 7.67 (dd, J = 5.0, 1.1 Hz, 2H), 7.17 (dd, J = 4.9, 3.8 Hz,2H), 3.42 (s, 4H). MALDI-TOF MS (mass m/z): 251.1 [M+ + H].
68%
With aluminum (III) chloride; In dichloromethane; at 0 - 20℃; for 4h;
A solution of thiophene (9.61 mL, 0.12 mol) and AlCl3 (16 g, 0.12 mol) in dry CH2Cl2 (50 mL) was added dropwise to a suspension of succinyl chloride (5.5 mL, 0.05 mol) in dry CH2Cl2 (50 mL) at 0 C. The mixture was stirred for at 18-20 C 4 h and poured into a mixture of 100 g ice and 10 mL hydrochloric acid and stirred for 1 h and the resulting dark green organic phase was washed with concentrated NaHCO3 (3 x 25 mL), and dried over Na2SO4. After the solvent was evaporated, a blue-green solid remained and was suspended in ethanol. Column chromatography (SiO2, CH2Cl2) and recrystallization from ethanol produced 8.98 g (68%) of it in a white solid. 1H NMR: (400 MHz; CDCl3): 7.80 (dd, 2H), 7.63 (dd, 2H), 7.13 (dd, 2H), 3.38 (s, 4H).
58%
With aluminum (III) chloride; In dichloromethane; at 20℃; for 6h;
To a suspension of AlCl3 (32 g, 0.24 mol) in 90 mL ofDCM, a solution of 11 mL (0.1 mol) succinyl chloride and19.2 mL (0.24 mol) of thiophene in 30 mL DCM was addeddropwise at room temperature. The suspension was stirredfor 6 h and poured into a mixture of 10 mL of hydrochloricacid and 400 g of ice. The color of the suspension turnedfrom red to dark green after further stirring for 30 min.The organic phase was collected and the aqueous phasewas extracted with DCM. The organic phases was combinedand washed with water and saturated aqueous NaHCO3,dried over NaSO4, concentrated in vacuo, and purified bycolumn chromatography (eluent:DCM:hexane = 1:1) toafford 14.5 g (58%) of 1 as pale blue crystals. 1H NMR(500 MHz, CDCl3, d, ppm): 7.82 (dd, 2H), 7.65 (dd, 2H),7.15 (dd, 2H), 3.40 (s, 4H) (Fig. S1). MS (EI) (m/z): [M]+ calcdfor C12H10O2S2, 250.0; found, 250.1.
With aluminum (III) chloride; In dichloromethane; at 0 - 5℃; for 5h;
Step 1. Synthesis of 1 ,4-dithienylbutane-l ,4-dione [0106] Succinyl chloride was dissolved in dichloromethane, and anhydrous aluminium trichloride was added to the solution as the mixed solution is stirred. The mixed solution is cooled to about 0-5 C. Thiophene solution was slowly added dropwise into the cooled solution. The solution was continuously stirred for 5 hours, and poured into ice-cold water. [0107] Concentrated hydrochloric acid was added to the solution and the organic phase was collected. The organic phase was washed with deionized water. The steps of washing with acid and water are repeated until no aluminium ions could be detected from the water phase. The organic phase was dried over anhydrous MgS04. The organic solvent was removed by reduced pressure distillation at room temperature. The obtained solid, 1,4- dithienylbutane-l,4-dione, was washed with anhydrous ethanol to remove the residual thiophene.
1. 0.006 mol of aluminum trichloride was dispersed in 30 mL of anhydrous dichloromethane to obtain aluminum trichloride and anhydrous dichloromethane A boiled pond solution; 2. A mixed solution of 4.8 mL of thiophene and 2.7 mL of succinyl chloride / dichloromethane was added dropwise to 30 mL of a dropwise addition of 30 drops / min to 30 mL of the suspension of aluminum trichloride and anhydrous dichloromethane obtained in step And then stirred at a rate of 700 r / min for 7 h, then 50 g of ice and 5 mL of hydrochloric acid at a mass fraction of 37% were added and stirred at a stirring speed of 850 r / min for 1.5 h and separated using a separatory funnel Out of the organic layer and water layer, discard the water layer, followed by Extraction with hydrochloric acid and NaHCO3 with a mass fraction of 37% and drying with magnesium sulfate followed by Rotating the evaporator to obtain a solid material A; the solid A substance was washed 4 times with anhydrous ethanol and ether, and the solid matter A was dissolved in methylene chloride, and then the residue was purified by column chromatography A was purified and recrystallized from anhydrous ethanol to give 1,4-bis (2-thiophene) -1,4-butanedione monomer. in a step of the succinyl chloride / methylene chloride mixed solution of succinyl chloride and the mixture of methylene chloride, succinyl chloride and a volume ratio of 3:30 and methylene chloride. A column chromatography method step according to in dichloromethane and petroleum ether mixture as eluent; dichloromethane and the mixture petroleum ether and petroleum ether in a volume ratio of methylene chloride 1: 1
With aluminum (III) chloride; In dichloromethane; for 8.5h;
1. Disperse 0.006 mol of aluminum trichloride in 30 mL of anhydrous methylene chloride to obtain a suspension of aluminum trichloride and anhydrous methylene chloride;2, 4.8mL thiophene,2.7 mL of a mixed solution of succinyl chloride/dichloromethane was added dropwise to 30 mL of a suspension of aluminum trichloride and anhydrous methylene chloride obtained in Step 1 at a dropping rate of 30 drops/min.The reaction is then stirred for 7 h at a stirring speed of 700 r/min, 50 g of ice and 5 mL of hydrochloric acid with a mass fraction of 37% are added.After stirring for 1.5 hours at a stirring speed of 850 r/min, the organic layer and the water layer were separated using a separatory funnel, and the water layer was discarded.The use of 37% by mass of dilute HCl and NaHCO3 extraction, and then dried using magnesium sulfate, and then rotary evaporation using a rotary evaporator to obtain a solid substance A;The solid substance A was washed four times with absolute ethanol and ether, and the solid substance A was dissolved in methylene chloride.Further purification of the solid substance A by column chromatography purification method, followed by recrystallization using anhydrous ethanol gives 1,4-di(2-thiophene)-1,4-butanedione monomers; The mixed solution of succinyl chloride/dichloromethane described in Step 2 is prepared by mixing succinyl chloride with dichloromethane, and the volume ratio of succinyl chloride and dichloromethane is 3:30;The column chromatography purification method described in step one 2 uses a mixture of dichloromethane and petroleum ether as an eluent;The volume ratio of dichloromethane and petroleum ether in the mixture of dichloromethane and petroleum ether is 1:1;
1-(4-Methoxy-phenyl)-2-{5-[(E)-2-methylsulfanyl-2-(toluene-4-sulfonyl)-vinyl]-thiophen-2-yl}-5-{5-[(Z)-2-methylsulfanyl-2-(toluene-4-sulfonyl)-vinyl]-thiophen-2-yl}-1H-pyrrole[ No CAS ]
1-(4-(furan-2-yl)phenyl)-2,5-di(thiophen-2-yl)-pyrrole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
63%
With toluene-4-sulfonic acid; In toluene; at 110℃; for 18h;
A 100 mL round-bottomed flask equipped with a magnetic mixerwas charged with 1,4-di(2-thienyl)-1,4-butanedione (2.1 mmol, 0.53 g),<strong>[59147-02-3]4-(furan-2-yl)aniline</strong> (6.3 mmol, 1 g), 22 mL toluene, and 12 mg p-TSA,and the solution was stirred for 18 h at 110 C. After evaporating offtoluene using a rotavapor, the remaining product was purified using acolumn chromatography on silica with an eluent (dichloromethane/hexane=1/2). Yield: 63%. 1H NMR (700 MHz, DMSO-d6):delta 7.82 (d,3H, Fu-H and phenyl-H), 7.39 (d, 2H, phenyl-H), 7.29 (d, 2H, Th-H),7.11 (d, 1H, Fu-H), 6.88 (dd, 2H, Th-H), 6.72 (d, 2H, Th-H), 6.65 (dd,1H, Fu-H), 6.58 (d, 2H, Py-H). 13C NMR (125 MHz, DMSO-d6): delta 107.4,109.7, 112.4, 124.2, 124.4, 125.0, 127.2, 129.8, 130.7, 131.3, 134.0,136.6, 143.7, 152.0. Elem. anal. calcd. for C22H15NOS2: C, 70.75%; H,4.05%; N, 3.75%. Found: C, 70.58%; H, 3.97%; N, 3.62%.
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