* 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] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2012, vol. 94, p. 340 - 345
[2] Inorganic Chemistry, 2013, vol. 52, # 21, p. 12492 - 12501
[3] Inorganic Chemistry, 2015, vol. 54, # 2, p. 460 - 469
2
[ 84175-10-0 ]
[ 17217-57-1 ]
Yield
Reaction Conditions
Operation in experiment
19%
Stage #1: With 5%-palladium/activated carbon In ethanol for 0.0833333 h; Inert atmosphere; Reflux Stage #2: With hydrazine hydrate In ethanol for 19 h; Inert atmosphere; Reflux
A mixture of 4,4′-dimethoxy-2,2′-bipyridine1,1′-dioxide (10) (2.50 g, 10.1 mmol), palladium on carbon (5percentPd, 5.16 g, 2.42 mmol, 0.24 equiv),and ethanol (290 mL) was refluxed for 5 min. To the mixture an ethanol solution (170 mL) ofhydrazine monohydrate (39.3 g, 0.785 mol) was added dropwise over 1 h. The reaction mixture wasrefluxed for 18 h and filtered through Celite®. The residue on the Celite was washed with hotethanol. Evaporation of the solvent from the combined filtrate and washings, and recrystallization ofthe residue from methanol gave 7f (0.412 g, 19percent). 7f: pale yellow crystals. 1H NMR (300 MHz,CDCl3) δ 8.48 (d, J = 5.4 Hz, 2H), 7.98 (d, J = 2.4 Hz, 2H), 6.86 (dd, J = 5.4 Hz, 2.4 Hz, 2H), 3.96(s, 6H).
Reference：
[1] Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 315 - 319
[2] Advanced Synthesis and Catalysis, 2003, vol. 345, # 4, p. 497 - 505
[3] Tetrahedron Letters, 2016, vol. 57, # 49, p. 5489 - 5492
[4] Journal of the American Chemical Society, 1958, vol. 80, p. 2745,2747
3
[ 620-08-6 ]
[ 17217-57-1 ]
Yield
Reaction Conditions
Operation in experiment
32 %Spectr.
at 140℃; for 18 h; Inert atmosphere
Under a nitrogen atmosphere, palladium acetate (11.2 mg, 0.05mmol), 1, 10 - phenanthroline (49.6 mg, 0.25mmol), silver acetate (250 mg, 1.5mmol), (1 ml) was suspended in pyridine (51.1 mg, 0.5mmol) pivalic acid, stirred at 140 °C 26 hours. After the reaction mixture was cooled to room temperature, the insoluble matter was removed by filtration over celite, methylene chloride (10 ml) was washed. The filtrate was concentrated under reduced pressure, 1, 1, 2, 2 - tetrachloroethane (15.8 μl, 0.15mmol) was added as an internal standard substance was obtained residue,1H NMR (88percent) yield was calculated based oxidizing agent. (Methylene chloride/hexane=5/95) to give a residue for a thin layer chromatography analysis, the subject compound (quantitative value NMR 89percent, 80percent isolated yield) was obtained as a white powder 93.1 mg.
Reference：
[1] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14830 - 14835
[2] Journal of the American Chemical Society, 2007, vol. 129, # 36, p. 11006 - 11007
[3] Organometallics, 2012, vol. 31, # 13, p. 4817 - 4831
[4] Organometallics, 2016, vol. 35, # 14, p. 2348 - 2360
[5] Patent: JP2017/132738, 2017, A, . Location in patent: Paragraph 0083; 0090; 0091; 0100-0102
4
[ 17228-69-2 ]
[ 17217-57-1 ]
Reference：
[1] Liebigs Annalen der Chemie, 1992, # 9, p. 953 - 960
Reference：
[1] Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 315 - 319
[2] Advanced Synthesis and Catalysis, 2003, vol. 345, # 4, p. 497 - 505
[3] Journal of the American Chemical Society, 1958, vol. 80, p. 2745,2747
7
[ 366-18-7 ]
[ 17217-57-1 ]
Reference：
[1] Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 315 - 319
[2] Advanced Synthesis and Catalysis, 2003, vol. 345, # 4, p. 497 - 505
8
[ 7275-43-6 ]
[ 17217-57-1 ]
Reference：
[1] Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 315 - 319
[2] Advanced Synthesis and Catalysis, 2003, vol. 345, # 4, p. 497 - 505
9
[ 17228-69-2 ]
[ 142929-23-5 ]
[ 17217-57-1 ]
[ 95881-80-4 ]
[ 142929-19-9 ]
Reference：
[1] Liebigs Annalen der Chemie, 1992, # 9, p. 953 - 960
A mixture of 4,4?-dimethoxy-2,2?-bipyridine1,1?-dioxide (10) (2.50 g, 10.1 mmol), palladium on carbon (5percentPd, 5.16 g, 2.42 mmol, 0.24 equiv),and ethanol (290 mL) was refluxed for 5 min. To the mixture an ethanol solution (170 mL) ofhydrazine monohydrate (39.3 g, 0.785 mol) was added dropwise over 1 h. The reaction mixture wasrefluxed for 18 h and filtered through Celite®. The residue on the Celite was washed with hotethanol. Evaporation of the solvent from the combined filtrate and washings, and recrystallization ofthe residue from methanol gave 7f (0.412 g, 19percent). 7f: pale yellow crystals. 1H NMR (300 MHz,CDCl3) delta 8.48 (d, J = 5.4 Hz, 2H), 7.98 (d, J = 2.4 Hz, 2H), 6.86 (dd, J = 5.4 Hz, 2.4 Hz, 2H), 3.96(s, 6H).
With hydrogen bromide; acetic acid; In water; at 140℃;Inert atmosphere;
To a solution of 4,4?-dimethoxy-2,2?-bipyridine (3.055 g, 14.13 mmol) in 180 ml of glacial acetic acid was added 48 wt percent HBr solution in water (25 ml, 146 mmol). The mixture was refluxed overnight at 140° C. under N2 (g). The mixture was allowed to cool and the solvent was removed in vacuo to render a white solid. The residue was dissolved in 100 ml of water and neutralised by adding aqueous ammonium hydroxide. The white solid (2.425 g, 12.89 mmol, 91percent yield) was filtered and dried, and used in the next step without further purification. 1H NMR (300 MHz, NaOD/D2O): deltaH=7.74 (s, 1H, OH), 7.38 (d, 2H, 3JH5=5.9 Hz, H6), 6.34 (d, 2H, 4JH5=2.4 Hz, H3), 5.85 (dd, 2H, 3JH6=5.9 Hz, 4JH3=2.4 Hz, H5). EI-MS(+): m/z 188.1 [M]+., 160.1 [M?N2)+., 94.0 [c-C5H3N?OH]+. IR (cm?1): 3209.17, 3059.21, 2760.30, 1594.48, 1523.34, 1475.20, 1393.46, 1218.35.
64%
With hydrogen bromide; acetic acid;Reflux;
The ligand was synthesized according to the literature with slight modifications. [2] HBr solution (41 wtpercent, 0.554 mL,2.77 mmol) was added to a mixture of glacial acetic acid (13.85 mL) and 4,4?-dimethoxy-2,2?-bipyridine (60 mg, 0.277 mmol); the resulting mixture was subsequently refluxed overnight. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in distilled water and neutralized to pH 6?7 by addition of aqueous ammonium hydroxide to provide a white precipitate with 64percent (33 mg) yield.
With hydrogen bromide; acetic acid; for 8h;Reflux;
Specifically, 4,4'-Dimethoxy-2,2'-Bipyridine and HBr were refluxed with glacial acetic acid solvent for 6-10 hours. After completion of the reaction, neutralization was performed using ammonia water.
With silver(I) acetate; palladium diacetate; Trimethylacetic acid; at 140℃; for 18h;Inert atmosphere;
Under a nitrogen atmosphere, palladium acetate (11.2 mg, 0.05mmol), 1, 10 - phenanthroline (49.6 mg, 0.25mmol), silver acetate (250 mg, 1.5mmol), (1 ml) was suspended in pyridine (51.1 mg, 0.5mmol) pivalic acid, stirred at 140 °C 26 hours. After the reaction mixture was cooled to room temperature, the insoluble matter was removed by filtration over celite, methylene chloride (10 ml) was washed. The filtrate was concentrated under reduced pressure, 1, 1, 2, 2 - tetrachloroethane (15.8 mul, 0.15mmol) was added as an internal standard substance was obtained residue,1H NMR (88percent) yield was calculated based oxidizing agent. (Methylene chloride/hexane=5/95) to give a residue for a thin layer chromatography analysis, the subject compound (quantitative value NMR 89percent, 80percent isolated yield) was obtained as a white powder 93.1 mg.
General procedure: All the solvents used in this work were of reagent quality and usedwithout further purification. Lapachol was obtained according to theprocedure described in [24]. The precursors cis-[RuCl2(PPh3)2(X-bipy)](X = H, methyl (Me) and methoxy (MeO)) and cis-[RuCl2(PPh3)2(phen)] were prepared according to literature [26,27]. Typically[100.0 mg; 0.1 mmol] of the [RuCl2(PPh3)3] was dissolved in degassed20 mL of dichloromethane (Merck) and N-heterocyclic (X-bipy or phen) [22.0 mg; 0.11 mmol] ligand was added. The reaction mixturewas stirred for 30 min at room temperature and the volume of theresulting blue solution was reduced, under vacuum, to ca. 2 mL anddiethyl ether (Merck) was then added to precipitate a red solid, whichwas filtered off, washed several times with diethyl ether, and driedunder vacuum. Yield: ~78 mg (80?90percent).
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