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Product Details of [ 10349-57-2 ]

CAS No. :10349-57-2 MDL No. :MFCD00047613
Formula : C10H7NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VXGYRCVTBHVXMZ-UHFFFAOYSA-N
M.W : 173.17 Pubchem ID :82571
Synonyms :

Calculated chemistry of [ 10349-57-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.7
TPSA : 50.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.34
Log Po/w (XLOGP3) : 1.35
Log Po/w (WLOGP) : 1.93
Log Po/w (MLOGP) : 1.34
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 1.56

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.27
Solubility : 0.936 mg/ml ; 0.0054 mol/l
Class : Soluble
Log S (Ali) : -2.01
Solubility : 1.71 mg/ml ; 0.00986 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.07
Solubility : 0.147 mg/ml ; 0.000851 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.02

Safety of [ 10349-57-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10349-57-2 ]

* 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.

  • Upstream synthesis route of [ 10349-57-2 ]
  • Downstream synthetic route of [ 10349-57-2 ]

[ 10349-57-2 ] Synthesis Path-Upstream   1~29

  • 1
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Reference: [1] Tetrahedron, 2002, vol. 58, # 37, p. 7381 - 7389
  • 2
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  • [ 99071-54-2 ]
Reference: [1] Patent: US2011/281865, 2011, A1,
[2] Patent: WO2011/145035, 2011, A1,
[3] Patent: WO2013/144737, 2013, A2,
[4] Patent: US2015/57309, 2015, A1,
[5] Patent: JP2015/38095, 2015, A,
  • 3
  • [ 10349-57-2 ]
  • [ 100516-88-9 ]
YieldReaction ConditionsOperation in experiment
1.03 g With N-ethylmorpholine;; chloroformic acid ethyl ester In tetrahydrofuran for 0.25 h; Inert atmosphere Quinoline 6-carboxylic acid (1.73 g, 10.0suspended in 40 mnL of THF, under N2 at 0° C10.4,C3oH,mmol) wasand treated1.02 equiv)with N-ethyl morpholine (1.3 mL, 10.2 mmol, followed by the dropwise addition of ethyl chloroformate (1.1 mL, 11.5 mmmol, 1.15 equiv). After stirring for 15 min, the solution was filtered, and the resulting salts were rinsed with additional THF. The filtrate was then added to a rapidly stirring solution of NaBH4 (760 mg, 20 mmol) in H20 (50 mL). After stirring for 20 min, the reaction mixture was quenched with saturated NH4C1 solution and extracted with EtOAc (2x50 mL). The organic portion was washed with brine, dried over Na2S04, and concentrated under reduced pressure. Chromatography (Si02,1:3 Hexanes/EtOAc) gave the desired material (1.03 g) as a colorless oil.
Reference: [1] Patent: JP2015/38095, 2015, A, . Location in patent: Paragraph 0301; 0302
  • 4
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  • [ 541-41-3 ]
  • [ 100516-88-9 ]
Reference: [1] Patent: US5866549, 1999, A,
  • 5
  • [ 91-62-3 ]
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YieldReaction ConditionsOperation in experiment
70% With chromium(VI) oxide; sulfuric acid In water at 0℃; for 20 h; Heating / reflux To a solution of 6-methylquinoline (100.0 mg, 0.70 mmol) in H2O (1 .0 ml_) and H2SO4 (0.25 ml_) chromium trioxide (272.0 mg, 2.72 mmol) was added in portions at 00C and refluxing for twenty-four hours. The crystalline precipitate of the hydrosulphate which separated upon cooling was removed by filtration, dissolved in 10percent sodium hydroxide water solution and, after wash with hexane, was reprecipitated25 with acetic acid to give 85.0 mg of title compound (70percent yield) that was used in the following step without further purification.1H NMR, 300 MHz, (DMSO-^6) δ 7.61 (dd, 1 H, J1 = 8.3 Hz, J2 = 4.2 Hz), 8.08 (d, 1 H, J = 8.8 Hz), 8.20 (dd, 1 H, J1 = 8.8 Hz, J2 = 1 .7 Hz), 8.56 (d, 1 H, J = 8.2 Hz), 8.67 (m, 1 H), 9.00 (dd, 1 H, J1 = 4.1 Hz, J2 = 1 .5 Hz), 13.20 (br s, 1 H); 13C NMR, 300 MHz, (DMSO-d6) 122.9, 127.9, 129.2, 129.5, 130.0,30 131 .7, 138.2, 150.0, 153.4, 167.7; ESI-MS m/z 196 [M+Na]+, 174 [M+H]+. Anal. (C10H7NO2) C1 H1 N.
Reference: [1] Chemical Communications, 2002, # 2, p. 180 - 181
[2] Patent: WO2008/43839, 2008, A1, . Location in patent: Page/Page column 10; 11
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 22, p. 9578 - 9597
[4] Heterocycles, 2011, vol. 83, # 7, p. 1649 - 1658
[5] Monatshefte fuer Chemie, 1891, vol. 12, p. 309
[6] Proceedings of the National Institute of Sciences of India, 1941, vol. 7, p. 215,219
[7] Monatshefte fuer Chemie, 1891, vol. 12, p. 309
  • 6
  • [ 150-13-0 ]
  • [ 56-81-5 ]
  • [ 10349-57-2 ]
YieldReaction ConditionsOperation in experiment
95% at 140℃; Step 1.
Quinoline-6-carboxylic acid
Into a 500-mL 3-necked round-bottom flask, was placed 4-aminobenzoic acid (13.7 g, 100.00 mmol, 1.00 equiv), 4-nitrobenzoic acid (10.7 g, 64.07 mmol, 0.64 equiv), boric acid (5.9 g), FeSO4.7H2O (6.4 g), glycerol (38 mL), and concentrated sulfuric acid (18 mL).
The resulting solution was stirred overnight at 140° C.
The reaction mixture was cooled.
The pH value of the solution was adjusted to 10 with sodium hydroxide (10percent).
The resulting solution was extracted with 2*100 mL of ethyl acetate and the aqueous layers were combined.
The pH value of the aqueous layers was adjusted to pH 6 with conc. hydrochloric acid.
The solids were collected by filtration.
The resulting solution was diluted with 200 mL of methanol and the resulting solids were collected by filtration.
The solid was dried to afford 17.3 g (95percent) of quinoline-6-carboxylic acid as a dark-grey solid.
LC-MS: (ES, m/z):174 [M+H]+
56%
Stage #1: at 135℃; for 48 h;
Stage #2: at 0℃;
Step 1:
Quinoline-6-carboxylic acid
To a mixture of 4-aminobenzoic acid (175 g, 1.28 mol), 4-nitrophenol (88.75 g, 0.64 mol) and sulphuric acid (1.2 lit.), glycerol (234.8 g, 2.55 mol) was added dropwise at 135° C.
After 48 h, the reaction mixture was cooled to 0° C. and the pH adjusted to 3-5 with 10percent sodium hydroxide solution.
The resulting precipitate was collected by filtration and washed with water and dried under vacuum to afford the title compound as a black solid (125 g, 56percent).
56% at 135℃; for 48 h; To a mixture of 4-aminobenzoic acid (175 g, 1.28 mol), 4-nitrophenol (88.75 g, 0.64 mol) and sulphuric acid (1.2 lit.), glycerol (234.8 g, 2.55 mol) was added dropwise at 135°C. After 48h, the reaction mixture was cooled to 0°C and the pH adjusted to 3-5 with 10percent sodium hydroxide solution. The resulting precipitate was collected by filtration and washed with water and dried under vacuum to afford the title compound as a black solid (125 g, 56percent).
56% at 135℃; for 48 h; [252] Intermediates Intermediate 1: Quinolin-6-ylmethanamine: Stepl : Quinoline-6-carboxylic acid: To a mixture of 4-aminobenzoic acid: (175 g, 1.28 mol), 4-nitrophenol (88.75 g, 0.64 mol) and sulphuric acid (1.2 lit.), glycerol (234.8 g, 2.55 mol) was added drop wise at 135°C. After 48h, the reaction mixture was cooled to 0°C and the pH adjusted to 3-5 with 10percent sodium hydroxide solution. The resulting precipitate was collected by filtration and washed with water and dried under vacuum to afford the title compound as a black solid (125 g, 56percent).
56%
Stage #1: at 135℃; for 48 h;
Stage #2: With sodium hydroxide In water at 0℃;
Step 1:
Quinoline-6-carboxylic acid
To a mixture of 4-aminobenzoic acid: (175 g, 1.28 mol), 4-nitrophenol (88.75 g, 0.64 mol) and sulphuric acid (1.2 lit.), glycerol (234.8 g, 2.55 mol) was added drop wise at 135° C.
After 48 h, the reaction mixture was cooled to 0° C. and the pH adjusted to 3-5 with 10percent sodium hydroxide solution.
The resulting precipitate was collected by filtration and washed with water and dried under vacuum to afford the title compound as a black solid (125 g, 56percent).

Reference: [1] Patent: US2012/277224, 2012, A1, . Location in patent: Page/Page column 82
[2] Patent: US2011/281865, 2011, A1, . Location in patent: Page/Page column 83
[3] Patent: WO2011/145035, 2011, A1, . Location in patent: Page/Page column 107-108
[4] Patent: WO2013/144737, 2013, A2, . Location in patent: Paragraph 252
[5] Patent: US2015/57309, 2015, A1, . Location in patent: Paragraph 0504
[6] Journal of the American Chemical Society, 1946, vol. 68, p. 2721
  • 7
  • [ 5382-49-0 ]
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Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10652 - 10658
[2] ChemCatChem, 2013, vol. 5, # 8, p. 2183 - 2186
  • 8
  • [ 5332-25-2 ]
  • [ 124-38-9 ]
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Reference: [1] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 82, p. 11574 - 11577
  • 9
  • [ 161685-42-3 ]
  • [ 10349-57-2 ]
Reference: [1] Patent: WO2009/95438, 2009, A1, . Location in patent: Page/Page column 11
  • 10
  • [ 7664-93-9 ]
  • [ 150-13-0 ]
  • [ 62-23-7 ]
  • [ 10349-57-2 ]
Reference: [1] Patent: US5134148, 1992, A,
[2] Patent: EP381375, 1990, A1,
  • 11
  • [ 15226-74-1 ]
  • [ 10349-57-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 419 - 425
  • 12
  • [ 15226-74-1 ]
  • [ 173089-80-0 ]
  • [ 10349-57-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 419 - 425
  • 13
  • [ 7664-93-9 ]
  • [ 118-92-3 ]
  • [ 62-23-7 ]
  • [ 10349-57-2 ]
Reference: [1] Patent: US5089495, 1992, A,
  • 14
  • [ 100516-88-9 ]
  • [ 10349-57-2 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 13, p. 3038 - 3043
  • 15
  • [ 150-13-0 ]
  • [ 56-81-5 ]
  • [ 62-23-7 ]
  • [ 10349-57-2 ]
Reference: [1] Monatshefte fuer Chemie, 1891, vol. 12, p. 309
[2] Monatshefte fuer Chemie, 1881, vol. 2, p. 519
  • 16
  • [ 4113-04-6 ]
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Reference: [1] Pharmaceutical Chemistry Journal, 1987, vol. 21, # 3, p. 182 - 184[2] Khimiko-Farmatsevticheskii Zhurnal, 1987, vol. 21, # 3, p. 295 - 297
  • 17
  • [ 7647-01-0 ]
  • [ 23395-72-4 ]
  • [ 10349-57-2 ]
Reference: [1] Chemische Berichte, 1884, vol. 17, p. 441
  • 18
  • [ 103796-41-4 ]
  • [ 10349-57-2 ]
Reference: [1] Monatshefte fuer Chemie, 1921, vol. 42, p. 425,436
  • 19
  • [ 7664-93-9 ]
  • [ 150-13-0 ]
  • [ 56-81-5 ]
  • [ 62-23-7 ]
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Reference: [1] Monatshefte fuer Chemie, 1881, vol. 2, p. 519
  • 20
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  • [ 38896-30-9 ]
YieldReaction ConditionsOperation in experiment
98% at 0 - 50℃; for 12 h; 6.0 mmol of thionyl chloride was slowly added to 2.0 mmol of 6-quinolinecarboxylic acid dissolved in 5 mL of methanol at 0 and the reaction mixture was stirred at 50 for 12 hours. 30 mL of saturated aqueous NaHCO3solution was added thereto, and the reaction was allowed to be completed. The reaction mixture was extracted with 30 mL of dichloromethane three times. The reaction mixture was dried over MgSO4, then a solid was filtered off, and an organic solvent was removed under reduced pressure 6-(methoxycarbonyl)quinoline as a white solid in 98 percent yield.
89% at 50℃; Quinoline-6-carboxylic acid (510 mg, 2.95 mmol, 1.0 eq.)Dissolved in 20 ml of methanol,Add 1 ml concentrated sulfuric acid,The reaction was stirred overnight at 50 °C.Cool to room temperature, add saturated aqueous sodium bicarbonate, with ethyl acetateExtraction, liquid separation, drying of the organic phase over anhydrous sodium sulfate, filtration, and concentration under reduced pressure gave the methyl ester of quinolin-6-carboxylic acid as a white solid (540 mg, yield: 89percent).
75% at 0 - 65℃; for 12 h; Step 2:
Methyl quinoline-6-carboxylate
To a solution of quinoline-6-carboxylic acid (183 g, 1.06 mol) in methanol (1 lit.), thionyl chloride (150.7 g, 1.2 mol) was added dropwise at 0° C. and then stirred at 65° C. for 12 h.
The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added.
The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (150 g, 75percent).
75% at 0 - 65℃; for 12 h; To a solution of quinoline-6- carboxylic acid (183 g, 1.06 mol) in methanol (1 lit.), thionyl chloride (150.7 g, 1.2 mol) was added dropwise at 0°C and then stirred at 65°C for 12h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (150 g, 75percent).
75% at 0 - 65℃; for 12 h; Step 2: Methyl quinoline-6-carboxylate: To a solution of quinoline-6-carboxylic acid (183 g, 1.06 mol) in methanol (1 lit.), thionyl chloride (150.7 g, 1.2 mol) was added drop wise at 0°C and then stirred at 65°C for 12h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (150 g, 75percent).
75% at 0 - 65℃; for 12 h; Step 2:
Methyl quinoline-6-carboxylate
To a solution of quinoline-6-carboxylic acid (183 g, 1.06 mol) in methanol (1 lit.), thionyl chloride (150.7 g, 1.2 mol) was added drop wise at 0° C. and then stirred at 65° C. for 12 h.
The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added.
The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (150 g, 75percent).

Reference: [1] Heterocycles, 2011, vol. 83, # 7, p. 1649 - 1658
[2] Journal of the American Chemical Society, 2014, vol. 136, # 30, p. 10770 - 10776
[3] Patent: WO2015/160125, 2015, A1, . Location in patent: Paragraph 143-145
[4] Chemistry - A European Journal, 2015, vol. 21, # 48, p. 17200 - 17204
[5] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6570 - 6580
[6] Patent: CN107383024, 2017, A, . Location in patent: Paragraph 0357
[7] Patent: US2011/281865, 2011, A1, . Location in patent: Page/Page column 83
[8] Patent: WO2011/145035, 2011, A1, . Location in patent: Page/Page column 108
[9] Patent: WO2013/144737, 2013, A2, . Location in patent: Paragraph 252
[10] Patent: US2015/57309, 2015, A1, . Location in patent: Paragraph 0505
[11] Suomen Kemistilehti B, 1959, vol. 32, p. 157,159
[12] Patent: EP1466912, 2004, A1, . Location in patent: Page 21
[13] Patent: WO2012/177893, 2012, A2, . Location in patent: Page/Page column 139
[14] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 24 - 30
[15] Medicinal Chemistry, 2013, vol. 9, # 4, p. 596 - 607
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  • [ 38896-30-9 ]
Reference: [1] Patent: US2004/122001, 2004, A1,
  • 22
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  • [ 10349-57-2 ]
  • [ 38896-30-9 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 5622,5627
  • 23
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Reference: [1] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 24 - 30
[2] Medicinal Chemistry, 2013, vol. 9, # 4, p. 596 - 607
  • 24
  • [ 10349-57-2 ]
  • [ 64-17-5 ]
  • [ 73987-38-9 ]
YieldReaction ConditionsOperation in experiment
89% for 8 h; Heating / reflux [0345] A solution of 6-quinolinecarboxylic acid (9.50 g, 54.9 mmol) and 2 ml of concentrated sulfuric acid in ethanol (250 ml) was refluxed for 8 h. The solvent was evaporated and the residue was taken up in water. After adjustment of the pH to 8 by the addition of potassium hydroxide the product was collected by filtration and dried in vacuum. Yield 9.85 g (89percent) of ethyl 6-quinolinecarboxylate as a pale brown solid. M.p.: 66-67° C., TLC (CH2Cl2/MeOH/AcOH 9:0.5:0.1): Rf 0.52 [0346] A solution of ethyl 6-quinolinecarboxylate (9.80 g, 48.7 mmol) was acidified to pH 2 by the addition of 1N aqueous HCl. After addition of 20percent Pd-Mohr catalyst (1.96 g) the solution was hydrogenated at 60° C. under 3 bar of hydrogen pressure for 17 h. The reaction mixture was filtered through celite. The filtrate was evaporated and the residue was taken up in ethyl acetate and water. The pH was adjusted to 16 by the additon of 1 N aqueous potassium hydroxide. The phases were separated and the organic phase was washed with brine, dried over Na2SO4 and evaporated. Yield 8.72 g (87percent) of ethyl 1,2,3,4-tetrahydro-6-quinolinecarboxylate as a pale brown solid. M.p.: 68-70° C., GC-MS: [M+]=205.
81% Reflux To a solution of quinoline-6-carboxylic acid (2.8 g, 16 mmol) in ethanol (100 mL) was added concentrated sulfuric acid (2 mL). The reaction was heated to reflux overnight. The solvent was evaporated to give a brown residue that was taken up in ethyl acetate (150 mL). The mixture was washed with water (2.x.30 mL), saturated aqueous sodium bicarbonate (2.x.30 mL), and brine (2.x.30 mL). The organic layer was dried over sodium sulphate, filtered, and concentrated to an oil. Purification by flash column chromatography gave the title compound (2.0 g, 81percent) as a brown solid.
75%
Stage #1: at 80℃; for 48 h;
Stage #2: With sodium hydroxide; ammonia In water
Example 66: Synthesis of 6-f3-(2.4-dimethoχybenzylidene)-3A5,6- tetrahydropyridin-2-yl)quinoline hydrochloride.; The preparation of 6-(3-(2,4-dimethoxybenzylidene)-3,4,5,6- tetrahydropyridin-2-yl)quinoline hydrochloride is described below.; A. Step 1: Preparation of Intermediate 14; Intermediate 14 was prepared as described in EP 0381375 Bl, page 21. 6- quinolinecarboxylic acid (12.2 g, 70.4 mmol) was suspended into ethanol (70 mL) in a reaction vessel. Concentrated sulfuric acid (12 mL) was added, the reaction vessel was sealed and the reaction was heated to 800C for 48 hours. The reaction was then cooled to room temperature, partially concentrated under reduced pressure and treated with concentrated ammonium hydroxide and 1 NNaOH(aq) until pH = 9. This produced an oil that separated from solution. This mixture was extracted three times with EtOAc. The EtOAc extracts were then washed with brine, combined, iσ dried over Na2SO4, filtered, concentrated under reduced pressure giving a green oil. This oil was filtered through a 9.5 cm x 3.0 cm plug of silica gel with 50percent EtOAc : hexane. The filtrate was concentrated under reduced pressure and dried under vacuum giving 10.66g (75percent) of a light green oil. 1H NMR (DMSO-rf6) δ 9.03 (dd, IH, J = 4.27, 1.70 Hz), 8.70 (d, IH, J= 1.71 Hz), 8.60 (broad d, IH5 J= 8.12 Hz),15 8.22 (dd, IH, J= 8.54, 1.71 Hz), 8.11 (d, IH, J= 8.97 Hz)3 7.64 (dd, 1H, J= 8.12, 4.27 Hz), 4.40 (q, 2H, J= 7.26 Hz), 1.38 (t, 3H, J= 7.26 Hz).
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[2] Patent: US2012/108619, 2012, A1, . Location in patent: Page/Page column 36
[3] Patent: WO2007/89626, 2007, A2, . Location in patent: Page/Page column 75-76
[4] Chemische Berichte, 1909, vol. 42, p. 4854
[5] Journal of the Chemical Society, 1948, p. 2008,2010
[6] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 5, p. 1487 - 1496
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Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2721
[2] Patent: US2003/109547, 2003, A1,
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[2] ChemCatChem, 2013, vol. 5, # 8, p. 2183 - 2186
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[5] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 1981 - 1985
[6] ACS Catalysis, 2018, vol. 8, # 5, p. 4545 - 4557
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[11] Patent: US5385909, 1995, A,
[12] Patent: US2004/122001, 2004, A1,
[13] ACS Catalysis, 2018, vol. 8, # 1, p. 17 - 21
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[2] Organic Letters, 2017, vol. 19, # 16, p. 4291 - 4294
  • 28
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  • [ 177478-49-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 670 - 676
  • 29
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  • [ 849807-09-6 ]
Reference: [1] Heterocycles, 2011, vol. 83, # 7, p. 1649 - 1658
[2] Patent: WO2012/177893, 2012, A2,
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