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Product Details of [ 721-04-0 ]

CAS No. :721-04-0 MDL No. :MFCD00156689
Formula : C14H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :KRSXGTAVHIDVPM-UHFFFAOYSA-N
M.W : 212.24 Pubchem ID :222171
Synonyms :

Calculated chemistry of [ 721-04-0 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 62.65
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.21
Log Po/w (XLOGP3) : 2.7
Log Po/w (WLOGP) : 2.95
Log Po/w (MLOGP) : 2.6
Log Po/w (SILICOS-IT) : 3.29
Consensus Log Po/w : 2.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.15
Solubility : 0.151 mg/ml ; 0.000711 mol/l
Class : Soluble
Log S (Ali) : -2.91
Solubility : 0.264 mg/ml ; 0.00124 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.01
Solubility : 0.00205 mg/ml ; 0.00000966 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.63

Safety of [ 721-04-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 721-04-0 ]

* 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.

  • Downstream synthetic route of [ 721-04-0 ]

[ 721-04-0 ] Synthesis Path-Downstream   1~59

  • 1
  • [ 721-04-0 ]
  • [ 4249-72-3 ]
YieldReaction ConditionsOperation in experiment
91% With sodium tetrahydroborate; In methanol; for 3h; 2-Phenoxy-1-phenylethanol: To a solution of 2-phenoxy-1-phenylethanone (7 g, 33 mmol) in methanol (200 mL) was addedNaBH4(2.5 g, 66 mmol) portion wise. The reaction was stirred for3 h, after which time the solvent was removed in vacuo. The residuewas redissolved in ethyl acetate (50 mL) and the reaction wasquenched by the addition of aqueous HCl (50 mL). The resultingsolution was filtered to remove insoluble salts and the productwas extracted into ethyl acetate (3× 20 mL), washed with brine(1× 30 mL), dried over MgSO4and the solvent removed in vacuo toafford a waxy, cream solid in 91% yield.1H NMR (CDCl3, 300 MHz): 4.02 (dd, J = 9.8, 9.0 Hz, 1H, CH2), 4.13 (dd, J = 9.8, 3.4 Hz, 1H,CH2), 5.15 (dd, J = 8.9, 3.2 Hz, 1H, CH), 6.91-7.02 (m, 3H, Ar-H),7.27-7.51 (m, 7H, Ar-H).13C{1H} NMR (CDCl3, 75 MHz): 72.6, 73.3,114.6, 126.3, 128.3, 128.6, 129.6, 144.5, 158.4. ESI-MS: m/z calcdfor [C14H14O2Na]+: 237.0891; found: 237.0894. Elemental Analy-sis: Anal. Calcd for C14H14O2: C, 78.48; H, 6.59. Found: C, 78.31; H,6.49.
80% With methanol; sodium tetrahydroborate; In methanol; at 20℃; for 2h; Step 2: 2-Phenoxy-1-phenylethanone (1.1089 g, 5.2 mmol) was dissolved in 35 mL of methanol. Sodium borohydride (0.3534 g, 10.4 mmol) was added portion-wise generating a gentle evolution of gas, after which the reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched with a saturated aqueous NH4Cl solution (30 mL). The resultant mixture was extracted with 20 mL diethyl ether three times. The combined organic extracts were dried with 50 mL saturated brine solution, dried over MgSO4, and filtered. The filtrate was evaporated to dryness to afford an off-white solid of 2-phenoxy-1-phenylethanol (80% yield). The solid was dried overnight in a vacuum desiccator.
Reference: [1]Chemistry - A European Journal,2020,vol. 26,p. 3641 - 3646
[2]Journal of the American Chemical Society,2020,vol. 142,p. 4037 - 4050
[3]Green Chemistry,2016,vol. 18,p. 6229 - 6235
[4]Dalton Transactions,2017,vol. 46,p. 11884 - 11889
[5]Green Chemistry,2019,vol. 21,p. 2005 - 2014
[6]Catalysis Today,2016,vol. 269,p. 40 - 47
[7]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 4637 - 4646
[8]Chemical Communications,2015,vol. 51,p. 4028 - 4031
[9]ACS Catalysis,2016,vol. 6,p. 1316 - 1328
[10]Journal of the American Chemical Society,2010,vol. 132,p. 12554 - 12555
[11]Tetrahedron Letters,2010,vol. 51,p. 6418 - 6421
[12]Chemical Communications,2019,vol. 55,p. 13144 - 13147
[13]Green Chemistry,2020,vol. 22,p. 248 - 255
[14]Patent: US2016/52949,2016,A1 .Location in patent: Paragraph 0101
[15]Green Chemistry,2014,vol. 16,p. 2432 - 2437
[16]Journal of the American Chemical Society,1958,vol. 80,p. 202
[17]Journal of the Chemical Society,1960,p. 3521 - 3527
[18]Journal of the Chemical Society. Perkin transactions II,1978,p. 1135 - 1144
[19]Zeitschrift fur Physikalische Chemie (Leipzig),1990,vol. 271,p. 927 - 930
[20]Journal of Organic Chemistry,2006,vol. 71,p. 7035 - 7044
[21]Journal of Organic Chemistry,2002,vol. 67,p. 7937 - 7945
[22]Tetrahedron,2008,vol. 64,p. 3867 - 3876
[23]Journal of Organic Chemistry,2011,vol. 76,p. 1883 - 1886
[24]Chemical Communications,2015,vol. 51,p. 12212 - 12215
[25]Green Chemistry,2015,vol. 17,p. 5009 - 5018
[26]Green Chemistry,2016,vol. 18,p. 2029 - 2036
[27]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[28]Green Chemistry,2019,vol. 21,p. 1974 - 1981
[29]Green Chemistry,2019,vol. 21,p. 6707 - 6716
  • 2
  • [ 3598-14-9 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 721-04-0 ]
  • 3
  • [ 70-11-1 ]
  • [ 108-95-2 ]
  • [ 721-04-0 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate; potassium iodide; In acetone; for 3h;Reflux; Step 1: 2-Phenoxy-1-phenylethanone was synthesized in the following manner: A round bottom flask equipped with a reflux condenser was charged with 2-bromoacetophenone (1.1942 g, 60 mmol), phenol (7.0582 g, 75 mmol), K2CO3 (12.3000 g, 89 mmol), KI (catalytic) and acetone (250 mL). The resulting mixture was heated to reflux and allowed to react for 3 hours, after which it was filtered and concentrated. 2-Phenoxy-1-phenylethanone was crystallised from cold ethanol (250 mL) (85% yield).
83% With potassium carbonate; In N,N-dimethyl-formamide; 2-Phenoxy-1-phenylethanone: To a solution of 2-bromo-1-phenylethanone (9 g, 45 mmol) in dimethylformamide (150 mL)was added phenol (5 g, 53 mmol) and K2CO3(7.3 g, 53 mmol). Thesolution was stirred overnight and a colour change from yellowto orange was observed. The reaction mixture was then pouredinto warm water and left to recrystallize. The crystals were filteredand redissolved in toluene; this solution was dried over MgSO4,filtered and the solvent removed in vacuo to give the product as acream solid in 83% yield.1H NMR (CDCl3, 300 MHz): 5.29 (s, 2H,CH2), 6.92-7.06 (m, 3H, Ar-H), 7.28-7.35 (m, 2H, Ar-H), 7.48-7.56(m, 2H, Ar-H), 7.60-7.68 (m, 1H, Ar-H), 7.98-8.08 (m, 2H, Ar-H).13C{1H} NMR (CDCl3, 75 MHz): 70.8, 114.8, 121.7, 128.2, 128.9,129.6, 133.9, 158.0, 194.6. ESI-MS: m/z calcd for [C14H12O2Na]+:235.0735; found: 235.0792.
78% With potassium hydroxide; In acetone; for 5h;Reflux; A solution of phenol (4.72 g, 50.21 mmol) and potassium carbonate (6.93 g, 50.21 mmol) in acetone (103 mL) was stirred at ambient temperature. 2-bromoacetophenone (8 g, 40.2 mmol) was added and the reaction mixture was heated at reflux for 5 h. The mixture was concentrated in vacuum and the residue was dissolve in CH2Cl2. The organic layer was washed with aqueous 2N NaOH and H2O, dried (MgSO4) and the filtrate was concentrated to dryness. The crude product was purified by column chromatography on silica gel (EtOAc:hexane 0.5:9.5) to yield 2-phenoxy-1-phenylethan-1-one (6.67 g, 31.46 mmol, 78%) as white crystals.
71% Phenol (2.045 g, 21.8 mM) and 2.696 g (19.5 mM) potassium carbonate were dissolved in 40 ml acetone and the mixture was stirred for about 10 minutes. 3.532 g (17.7 mM) of phenacyl bromide was added to the mixture and the mixture was refluxed for 2 h. The reaction mixture was then quenched with 100 ml water and the phenacyl ether was extracted with (3×50 ml) diethyl ether. The organic extracts were washed with 2 M NaOH (3×50 ml), and water (3×50 ml), and dried over MgSO4. The solvent was evaporated under reduced pressure and a white solid was obtained. The crude product was crystallized with ethanol. Yield 2.659 g (71%) from 3.53 g phenacyl bromide, white crystalline solid: mp 70-72 C. (lit. mp 71-72 C. (Netto-Ferreira et al., J. Org. Chem.55:89-92 (1990)); 1H NMR (CDCl3) delta5.26 (s, 2H), 6.92-7.01 (m, 3H), 7.28 (t, J=7,2H), 7.45-7.65 (m, 3H), 7.99 (d, J=7,2H); 13C NMR (CDCl3) delta194.5, 158.0, 134.7, 133.8, 129.5, 128.8. 128.1, 121.6, 114.8, 70.8; EI-MS, m/z (rel. intensity) 213 (M+1, 5), 212 (M+, 29), 106 (16), 105 (100), 91 (13), 77 (90), 65 (15), 50 (45).
With potassium carbonate; In acetone; for 4h;Heating / reflux; A mixture of phenol (23.6 g, 0.25 M), 2-bromoacetophenone (50 g, 0.25 M) and K2CO3 (35 g, 0.25 M) in 150 mL of acetone was refluxed for 4 h, cooled, poured into 1.5L of water to give a suspension. The solid was collected by filtration, then crystallized in ethanol, dried under vacuum to give 33 g of compound 4 as a beige powder.
2-Phenoxy-1-phenylethanone was prepared by the literatureprocedures [38,39]. A 350 mL pressure bottle was charged withphenol (6.9 g, 73 mmol) and K2CO3 (10.4 g, 75 mmol) in acetone(150 mL) in Ar atmosphere and stirred at room temperature (RT)for 30 min. To this solution, 2-bromoacetophenone (14.0 g,70 mmol) was added, and the resulting suspension was stirred atRT for 16 h, after which the suspension was filtered and concentratedin cacuo. The solid was dissolved in ethyl acetate andwashed with NaOH aqueous (5%, 30 mL) and water (30 mL). Theorganic phase was dried over anhydrous Na2SO4. The crude productwas recrystallized from ethanol to give 2-phenoxy-1-phenylethanone as a white solid in 87% yield. Spectral data werein accordance with those previously reported. For the other methoxylsubstituted 2-phenoxy-1-phenylethanone, the preparationprocedure is the same as described above, except for using differentstating materials.
29.28 g With potassium carbonate; In acetone; at 60℃; for 24h;Inert atmosphere; (1) Phenol (146 mmol) and potassium carbonate (150 mmol) were placed in a three-necked flask, and acetone (300 ml) was added. Then, it was placed under magnetic heating and stirred to dissolve and dissolve. (2) 2-bromoacetophenone (140 mmol) was dissolved in acetone (100 ml) in three batches, and each batch was added dropwise to the above solution. After the completion of the dropwise addition, the reaction was condensed and refluxed at 60 C for 24 hours, and the reaction was protected by an inert gas. (3) After completion of the reaction, filtration was carried out with a sand core funnel, and the organic phase was concentrated in vacuo using a rotary evaporator to give a crude product. (4) Dissolving the crude product in ethyl acetate, followed by washing with sodium hydroxide solution (5% by mass) and aqueous solution, respectively. This operation was performed twice and the organic phase was collected. (5) The collected organic phase was concentrated in a vacuum using a rotary evaporator, and the obtained product was dissolved in ethanol at 60 C. After that, it was cooled to room temperature for 8 hours to carry out recrystallization, and the recrystallization process was also protected by nitrogen. After 3 times of recrystallization, the product was filtered, and finally vacuum dried to obtain 2-phenoxy-1-acetophenone product. The quality and purity of the obtained product are shown in Table 2.

Reference: [1]Green Chemistry,2016,vol. 18,p. 6229 - 6235
[2]Green Chemistry,2017,vol. 19,p. 4538 - 4543
[3]Dalton Transactions,2017,vol. 46,p. 11884 - 11889
[4]Green Chemistry,2019,vol. 21,p. 2005 - 2014
[5]Journal of the American Chemical Society,2010,vol. 132,p. 12554 - 12555
[6]Chemical Communications,2019,vol. 55,p. 13144 - 13147
[7]Synthetic Communications,1996,vol. 26,p. 301 - 305
[8]Chemistry - A European Journal,2020,vol. 26,p. 10402 - 10405
[9]Journal of Organic Chemistry,2014,vol. 79,p. 6153 - 6163
[10]ACS Catalysis,2019,vol. 9,p. 11341 - 11349
[11]Synthetic Communications,2009,vol. 39,p. 4079 - 4087
[12]Green Chemistry,2017,vol. 19,p. 702 - 706
[13]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 825 - 832
[14]Green Chemistry,2013,vol. 15,p. 768 - 774
[15]ACS Catalysis,2016,vol. 6,p. 1316 - 1328
[16]Patent: US2016/52949,2016,A1 .Location in patent: Paragraph 0100
[17]Green Chemistry,2020,vol. 22,p. 248 - 255
[18]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 2773 - 2776
[19]Catalysis Today,2016,vol. 269,p. 40 - 47
[20]Organic Letters,2020,vol. 22,p. 6055 - 6060
[21]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 4637 - 4646
[22]Tetrahedron Letters,2016,vol. 57,p. 3024 - 3028
[23]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 7337 - 7343
[24]Tetrahedron,1999,vol. 55,p. 12699 - 12710
[25]Patent: US6392089,2002,B1 .Location in patent: Page column 26
[26]Tetrahedron Letters,2010,vol. 51,p. 6418 - 6421
[27]Chemistry - A European Journal,2020,vol. 26,p. 3641 - 3646
[28]Chemical Biology and Drug Design,2012,vol. 80,p. 591 - 597
[29]Green Chemistry,2014,vol. 16,p. 2432 - 2437
[30]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 1108 - 1110
[31]Tetrahedron,2008,vol. 64,p. 3867 - 3876
[32]Journal of Organic Chemistry,2005,vol. 70,p. 2720 - 2728
[33]Journal of the Chemical Society,1958,p. 822,824
[34]Chemische Berichte,1882,vol. 15,p. 2487
    Chemische Berichte,1885,vol. 18,p. 166
[35]Journal fur praktische Chemie (Leipzig 1954),1960,vol. 11,p. 239 - 248
[36]Berichte der Bunsen-Gesellschaft,1992,vol. 96,p. 50 - 61
[37]Journal of Physical Chemistry,1995,vol. 99,p. 8190 - 8195
[38]European Journal of Organic Chemistry,1999,p. 607 - 616
[39]Journal of the Chemical Society. Perkin transactions I,1999,p. 2421 - 2423
[40]Synthetic Communications,2007,vol. 37,p. 149 - 156
[41]Tetrahedron,2007,vol. 63,p. 6764 - 6773
[42]Patent: EP1589016,2005,A1 .Location in patent: Page/Page column 25
[43]Tetrahedron Letters,2008,vol. 49,p. 6579 - 6584
[44]Journal of Organic Chemistry,2011,vol. 76,p. 1883 - 1886
[45]Tetrahedron Letters,2013,vol. 54,p. 1428 - 1431
[46]ChemMedChem,2014,vol. 9,p. 177 - 188
[47]Chirality,2014,vol. 26,p. 272 - 278
[48]Chemical Communications,2015,vol. 51,p. 4028 - 4031
[49]Chemical Communications,2015,vol. 51,p. 12212 - 12215
[50]Green Chemistry,2015,vol. 17,p. 5009 - 5018
[51]Green Chemistry,2016,vol. 18,p. 2029 - 2036
[52]Journal of Catalysis,2017,vol. 346,p. 170 - 179
[53]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[54]Patent: CN109020792,2018,A .Location in patent: Page/Page column 5-7
[55]Green Chemistry,2019,vol. 21,p. 1974 - 1981
[56]Molecular Diversity,2019
[57]Green Chemistry,2019,vol. 21,p. 6707 - 6716
[58]Journal of the American Chemical Society,2020,vol. 142,p. 4037 - 4050
  • 4
  • [ 4249-72-3 ]
  • [ 721-04-0 ]
YieldReaction ConditionsOperation in experiment
5% With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(l) chloride; In acetonitrile; at 25℃; under 735.576 Torr; for 20h; 2-phenoxy-1-phenylethan-1-ol ((50 gm, 0.236 mmol), TEMPO (7.3 mg, 0.047 mmol), CuCl (4.6 mg, 0.047 mmol), NMI (7.7 mg, 0.94 mmol), bpy (7.3 mg, 0.047 mmol) and MeCN (.93 mL, 0.25 M of substrate) stirred under an air atmosphere (1 atm) at 25 C for 20 h. The reaction mixture was quenched with 1 N HCl and product were extracted with dichloromethane. The organic layer was washed with the water, dried over MgSO4 and concentrated under vacuum. The products were separated by silica-gel column chromatography (EtOAc:hexane 1:20) to produce 2-phenoxy-1-phenylethan-1-ol (48 mg, 0.224 mmol, 95%), 2-phenoxy-1-phenylethan-1-one (2.5 mg, 0.012 mmol, 5%).
  • 5
  • [ 3598-16-1 ]
  • [ 23665-09-0 ]
  • [ 721-04-0 ]
  • 7
  • [ 70110-65-5 ]
  • [ 721-04-0 ]
  • [ 4249-72-3 ]
  • [ 100-52-7 ]
  • [ 98-86-2 ]
  • [ 93-55-0 ]
  • [ 100-51-6 ]
YieldReaction ConditionsOperation in experiment
1: 20 %Spectr. 2: 5 %Spectr. 3: 5 %Spectr. 4: 5 %Spectr. 5: 10 %Spectr. 6: 20 %Spectr. In toluene at 175℃; for 6h; vacuum-sealed tube; 5 In a vacuum- sealed tube (0.1-0.2 torr) and a final reaction volume of 0.50 ml in toluene, 2-phenoxy-l-phenylpropan-l,3-diol (0.225 mmol), was heated to 175 0C with carbonylhydridotrifluoroacetato-b/i'(triphenylphosphino)ruthenium(II) (0.0112 mmol) and (9,9- dimethylxanthene-4,5-diyl)Ms(diphenylphosphine) (0.0112 mmol). After 6 h, 90% consumption of the starting material yielded propiophenone (0.0450 mmol, 20%), acetophenone (0.0112 mmol, 5%), 2-phenoxyacetophenone (0.0112 mmol, 5%), benzaldehyde (0.0112 mmol, 5%), benzyl alcohol (0.0224 mmol, 10%), and 2-phenoxy-l-phenethanol (0.0450 mmol, 20%) as determined by 1H NMR integration relative to an external capillary standard.
  • 8
  • [ 721-04-0 ]
  • [ 599-94-0 ]
  • [ 1374846-72-6 ]
YieldReaction ConditionsOperation in experiment
65% With potassium <i>tert</i>-butylate In toluene at 120℃; for 36h; 1-Aryl-4-(phenylsulfonyl)butan-1-ones 3-20; General Procedure General procedure: To a Schlenk tube were added 1,2-bis(phenylsulfonyl)ethane (1a,0.2 mmol), ketone 2 (0.3 mmol), KOt-Bu (2.0 equiv), and toluene(2 mL). Then the tube was stirred at 120 °C (oil bath temperature)in air for the indicated time until complete consumption of startingmaterial (TLC and GC-MS monitoring). When the reaction wascomplete, the mixture was diluted with Et2O (5 mL), and washedwith brine (3 × 1 mL). The aqueous phase was re-extracted withEt2O (3 × 2 mL). The combined organic extracts were dried(Na2SO4) and concentrated in vacuo, and the resulting residue waspurified by column chromatography (silica gel, n-hexane-EtOAc,10:1) to afford the product.]]
  • 9
  • [ 50-00-0 ]
  • [ 721-04-0 ]
  • [ 70110-65-5 ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate In water; acetone at 20℃; for 20h;
  • 10
  • [ 6919-61-5 ]
  • [ 6707-01-3 ]
  • [ 721-04-0 ]
  • 11
  • [ 721-04-0 ]
  • [ 582-24-1 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
1: 95% 2: 85% With 1,10-Phenanthroline; oxygen; copper diacetate In methanol at 80℃; for 3h;
  • 12
  • [ 721-04-0 ]
  • [ 1864-94-4 ]
  • [ 65-85-0 ]
  • [ 108-95-2 ]
  • 13
  • [ 721-04-0 ]
  • [ 65-85-0 ]
YieldReaction ConditionsOperation in experiment
99% With oxygen; copper(II) nitrate; In acetonitrile; at 120℃; under 4500.45 Torr; for 10h; In a 15 mL PTFE-lined reactor, 0.1 mmol of <strong>[721-04-0]2-phenoxy-1-phenylethanone</strong> was added.Weigh 0.02mmol of copper nitrate as a catalyst,And adding 2mL solvent acetonitrile (<strong>[721-04-0]2-phenoxy-1-phenylethanone</strong> concentration is 0.05mol / L),The oxygen pressure is increased to 0.6 MPa, the temperature is raised to 120 C, and the reaction is stirred for 10 hours. After the reaction is completed,The product was detected by gas chromatography-mass spectrometry and the mass spectrum of the product benzoic acid and phenol was consistent with the standard mass spectrum.The gas chromatographic quantitative substrate conversion and the yield of the product benzoic acid are shown in Table 1.
With copper(II) nitrate trihydrate; oxygen; In acetonitrile; at 120℃; under 4500.45 Torr; for 10h;Autoclave; General procedure: The catalytic reactions were performed in a 15-mL autoclavereactor with an internal Teflon insert. Typically, 0.5 mmol ofketone, 0.1 mmol of copper salt and 2 mL of solvent were addedinto the reactor. Then, the reactor was charged with 0.6 MPa O2and heated to 120 C under magnetic stirring. After cooling to theroom temperature, the reaction mixture was diluted with 4 mLmethanol before analysis. The products were identified and quantifiedusing gas chromatography-mass spectrometry (GC-MS) andan Agilent 7890A/5975C instrument equipped with an HP-5 MScolumn (30 m in length, 0.25 mm in diameter). p-Xylene was usedas the internal standard.
  • 14
  • [ 136-95-8 ]
  • [ 721-04-0 ]
  • 3-phenoxy-2-phenylbenzo[d] imidazo[2,1-b]thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With iodine; In 1,2-dichloro-ethane; at 100℃; for 0.5h; General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product.
97.5% With iodine; In chloroform; at 100℃; for 1.16667h;Inert atmosphere; Under an inert atmosphere, was added 2-phenoxy-acetophenone (0.5 mmol, 106 mg) was dried to a reactor, 2-amino benzothiazole (1.5 mmol, 226 mg), 15 mlof chloroform, and elemental iodine (0.5 mmol , 137 mg), followed by reaction in an oil bath at 100 C for 70 minutes.The reaction solution with saturated sodium thiosulfate, water and saturated brine, the organic layer was dried over anhydrous sodium sulfate, and column chromatography to give 3-phenoxy-2-phenyl-benzo [d] imidazo [2, 1-b] thiazole 167 mg, yield% 97.5;
85% With copper(l) iodide; oxygen; In 1,2-dichloro-ethane; at 100℃; for 16h; Take a clean 8mL sealed micro-reaction bottle, add a small magnet, dry, add2-aminobenzo [d] thiazole (90.1 mg, 0.6 mmol)2-phenoxyacetophenone (42.4 mg, 0.2 mmol),Cuprous iodide (0.01 mmol),1,2-dichloroethane (1.0 mL),After heating at 100 C for 16 hours under oxygen,The reaction product was isolated by direct column chromatography to give the desired product (58.0 mg, yield 85%).
70% With tert.-butylhydroperoxide; iodine; In water; 1,2-dichloro-ethane; at 110℃; under 760.051 Torr; for 16h; General procedure: An oven-dried screw-cap vial was charged with I2 (0.02 mmol, 10 mol%), 2-phenoxyacetophenone 2 (0.20 mmol, 1.0 equiv), 2-aminopyridine 1 or 2-aminobenzothiazole (4) (0.60 mmol, 3.0 equiv), and DCE (1.0 mL) in sequence. Then, tert-butyl hydroperoxide (70 wt% in H2O, 2.0 equiv) was added to the solution. The vial was sealed under air and heated to 110 C with stirring for 16 h. After cooling down to r.t., the mixture was filtered, and concentrated to give the crude product, which was purified by flash column chromatography.

  • 15
  • [ 721-04-0 ]
  • [ 42182-27-4 ]
  • 3-phenoxy-2-phenyl-7-cyanoimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With copper(l) iodide; oxygen; In 1,2-dichloro-ethane; at 100℃; for 16h; Take a clean 8mL sealed micro-reaction bottle, add a small magnet, dry, add<strong>[42182-27-4]2-aminoisonicotinonitrile</strong> (71.5 mg, 0.6 mmol),2-phenoxyacetophenone (42.5 mg, 0.2 mmol),Cuprous iodide (0.01 mmol),1,2-dichloroethane (1.0 mL),After heating at 100 ° C for 16 hours under oxygen,The reaction mixture was isolated by column chromatography to give the title compound (42.0 mg, yield 67percent).
  • 16
  • [ 695-34-1 ]
  • [ 721-04-0 ]
  • 3-phenoxy-2-phenyl-7-methylimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With iodine; In 1,2-dichloro-ethane; at 100℃; for 0.5h; General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product.
65% With copper(l) iodide; oxygen; In 1,2-dichloro-ethane; at 100℃; for 16h; Take a clean 8mL sealed micro-reaction bottle, add a small magnet, dry, add4-methyl-2-aminopyridine (64.9 mg, 0.6 mmol)2-phenoxyacetophenone (42.5 mg, 0.2 mmol),Cuprous iodide (0.01 mmol),1,2-dichloroethane (1.0 mL),Under the air100 CHeating reactionAfter 16 hours,The reaction solution was isolated by direct column chromatography to give the title product (39.0 mg, yield 65%).
56% With tert.-butylhydroperoxide; iodine; In water; 1,2-dichloro-ethane; at 110℃; under 760.051 Torr; for 16h; General procedure: An oven-dried screw-cap vial was charged with I2 (0.02 mmol, 10 mol%), 2-phenoxyacetophenone 2 (0.20 mmol, 1.0 equiv), 2-aminopyridine 1 or 2-aminobenzothiazole (4) (0.60 mmol, 3.0 equiv), and DCE (1.0 mL) in sequence. Then, tert-butyl hydroperoxide (70 wt% in H2O, 2.0 equiv) was added to the solution. The vial was sealed under air and heated to 110 C with stirring for 16 h. After cooling down to r.t., the mixture was filtered, and concentrated to give the crude product, which was purified by flash column chromatography.
  • 17
  • [ 6937-03-7 ]
  • [ 721-04-0 ]
  • 3-phenoxy-2-phenyl imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With iodine In 1,2-dichloro-ethane at 100℃; for 0.5h; General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product.
77% With copper(l) iodide; oxygen In 1,2-dichloro-ethane at 100℃; Sealed tube;
77% With copper(l) iodide; oxygen In 1,2-dichloro-ethane at 100℃; for 16h; 22 preparation of 3-phenoxy-2-phenylimidazo [1,2-a] pyridine-7-carboxylate Take a clean 8mL sealed micro-reaction bottle, add a small magnet, drying,Join2-Amino isonicotinic acid methyl ester(91.3 mg, 0.6 mmol),2-phenoxyacetophenone (42.5 mg, 0.2 mmol),Cuprous iodide (0.01 mmol),1,2-dichloroethane (1.0 mL),After heating at 100 ° C for 16 hours in air,The reaction solution was isolated by direct column chromatography to give the title product (53.0 mg, yield 77%).
  • 18
  • [ 1072-97-5 ]
  • [ 721-04-0 ]
  • 3-(2-methoxyphenoxy)-2-(4-methoxyphenyl)-6-bromoimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With copper(l) iodide; oxygen; In 1,2-dichloro-ethane; at 100℃; for 16h; Take a clean 8mL sealed micro-reaction bottle, add a small magnet, dry, add2-amino-5-bromopyridine (103.8 mg, 0.6 mmol)2-phenoxyacetophenone (42.5 mg, 0.2 mmol),Cuprous iodide (0.01 mmol), 1,2-dichloroethane (1.0 mL),After heating at 100 C for 16 hours in air,The reaction solution was isolated by column chromatography to give the title compound (41.0 mg, yield 57%).
57% With tert.-butylhydroperoxide; iodine; In water; 1,2-dichloro-ethane; at 110℃; under 760.051 Torr; for 16h; General procedure: An oven-dried screw-cap vial was charged with I2 (0.02 mmol, 10 mol%), 2-phenoxyacetophenone 2 (0.20 mmol, 1.0 equiv), 2-aminopyridine 1 or 2-aminobenzothiazole (4) (0.60 mmol, 3.0 equiv), and DCE (1.0 mL) in sequence. Then, tert-butyl hydroperoxide (70 wt% in H2O, 2.0 equiv) was added to the solution. The vial was sealed under air and heated to 110 C with stirring for 16 h. After cooling down to r.t., the mixture was filtered, and concentrated to give the crude product, which was purified by flash column chromatography.
  • 19
  • [ 71-23-8 ]
  • [ 721-04-0 ]
  • [ 2315-68-6 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
1: 88 %Chromat. 2: 40 %Chromat. With boron trifluoride diethyl etherate; oxygen; copper diacetate at 100℃; for 6h; Autoclave; Green chemistry;
  • 20
  • [ 111-87-5 ]
  • [ 721-04-0 ]
  • [ 94-50-8 ]
  • [ 108-95-2 ]
  • 21
  • [ 78-83-1 ]
  • [ 721-04-0 ]
  • [ 120-50-3 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
1: 82 %Chromat. 2: 52 %Chromat. With boron trifluoride diethyl etherate; oxygen; copper diacetate at 100℃; for 6h; Autoclave; Green chemistry;
  • 22
  • [ 721-04-0 ]
  • [ 1678-91-7 ]
  • [ 100-41-4 ]
  • [ 40515-89-7 ]
  • [ 108-93-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogen; In hexane; at 190℃; under 15001.5 Torr; for 2h; General procedure: All the experiments were carried out in a 300 mL batch stainlessautoclave equipped with a mechanical stirrer. In a typical reaction,0.25 g of fresh catalyst, 1.0 g of lignin model compound and 50 mL of nhexanewere added into the reactor. Prior to the reaction, the reactorwas purged with H2 for three times to exclude the residue air and thenpressurized with H2 to 2 MPa at ambient temperature. After that, thereaction system was heated to reaction temperature and maintained fora designated time with a stirring rate of 500 rpm. Finally, the reactionsystem was cooled to ambient temperature, and the liquid productswere collected for subsequent analysis. The products were analyzedusing GC-MS (Agilent 7890A-5975C) equipped with a flame ionizationdetector (FID) and a HP-5MS columnv
  • 23
  • [ 721-04-0 ]
  • [ 4249-72-3 ]
  • [ 108-93-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogen; In hexane; at 120℃; under 15001.5 Torr; for 2h; General procedure: All the experiments were carried out in a 300 mL batch stainlessautoclave equipped with a mechanical stirrer. In a typical reaction,0.25 g of fresh catalyst, 1.0 g of lignin model compound and 50 mL of nhexanewere added into the reactor. Prior to the reaction, the reactorwas purged with H2 for three times to exclude the residue air and thenpressurized with H2 to 2 MPa at ambient temperature. After that, thereaction system was heated to reaction temperature and maintained fora designated time with a stirring rate of 500 rpm. Finally, the reactionsystem was cooled to ambient temperature, and the liquid productswere collected for subsequent analysis. The products were analyzedusing GC-MS (Agilent 7890A-5975C) equipped with a flame ionizationdetector (FID) and a HP-5MS columnv
  • 24
  • [ 721-04-0 ]
  • [ 29509-35-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / methanol / 4 h / 25 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 °C 2.2: 0 - 20 °C
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / methanol / 12 h / 30 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 °C 2.2: 12 h / 0 - 30 °C
Multi-step reaction with 2 steps 1.1: MnMoS; hydrogen / methanol / 6 h / 180 °C / 7500.75 Torr 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 °C 2.2: 12 h / 0 - 30 °C
Multi-step reaction with 2 steps 1: MnMoS; hydrogen / methanol / 6 h / 180 °C / 7500.75 Torr 2: nickel(II) sulfide; hydrogen / 4 h / 180 °C / 7500.75 Torr
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 12 h / 30 °C 2: nickel(II) sulfide; hydrogen / 4 h / 180 °C / 7500.75 Torr
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; methanol / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere

  • 25
  • [ 721-04-0 ]
  • [ 292638-84-7 ]
  • [ 3299-05-6 ]
  • [ 93-89-0 ]
  • [ 574-09-4 ]
  • [ 4249-72-3 ]
  • (2,4-dimethylphenyl)-2-(4-methoxyphenyl) diazene [ No CAS ]
  • [ 80463-21-4 ]
  • [ 98-86-2 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With nitrogen; water; In ethanol; at 280.0℃; for 4.0h;Autoclave; General procedure: The decomposition reactions were performed in a T316stainless-steel autoclave equipped with a controller, a thermocouple,and a mechanical agitator (Model 4598, Parr InstrumentCompany, Moline, USA). The reactions were typicallyperformed by first introducing 0.100 g of 2-PAP and 0.010 g ofthe catalyst (or no catalyst) into the dry autoclave, and then 50mL of AE was introduced. The autoclave was quickly closed toprevent adsorption of water and then purged with N2 severaltimes. The reaction was performed at 280 C for 4 h with a stirringspeed of 300 r/min. After a predetermined time, the reactorwas cooled to room temperature and the products werethen collected for further analysis [53].
  • 26
  • [ 721-04-0 ]
  • [ 100-42-5 ]
  • 2,3-diphenyloxirane [ No CAS ]
  • [ 41497-31-8 ]
  • [ 3299-05-6 ]
  • [ 588-59-0 ]
  • [ 93-89-0 ]
  • [ 6314-97-2 ]
  • [ 4249-72-3 ]
  • (2,4-dimethylphenyl)-2-(4-methoxyphenyl) diazene [ No CAS ]
  • [ 98-86-2 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With nitrogen; water In ethanol at 280℃; for 4h; Autoclave; 2.4. Decomposition of the lignin model compound General procedure: The decomposition reactions were performed in a T316stainless-steel autoclave equipped with a controller, a thermocouple,and a mechanical agitator (Model 4598, Parr InstrumentCompany, Moline, USA). The reactions were typicallyperformed by first introducing 0.100 g of 2-PAP and 0.010 g ofthe catalyst (or no catalyst) into the dry autoclave, and then 50mL of AE was introduced. The autoclave was quickly closed toprevent adsorption of water and then purged with N2 severaltimes. The reaction was performed at 280 °C for 4 h with a stirringspeed of 300 r/min. After a predetermined time, the reactorwas cooled to room temperature and the products werethen collected for further analysis [53].
  • 27
  • [ 721-04-0 ]
  • [ 292638-84-7 ]
  • [ 29909-72-6 ]
  • [ 1689-71-0 ]
  • [ 3299-05-6 ]
  • [ 588-59-0 ]
  • [ 60-12-8 ]
  • [ 93-89-0 ]
  • [ 6314-97-2 ]
  • [ 574-09-4 ]
  • [ 4249-72-3 ]
  • [ 1817-90-9 ]
  • (2,4-dimethylphenyl)-2-(4-methoxyphenyl) diazene [ No CAS ]
  • [ 98-86-2 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With nitrogen; water; In ethanol; at 280.0℃; for 4.0h;Autoclave; General procedure: The decomposition reactions were performed in a T316stainless-steel autoclave equipped with a controller, a thermocouple,and a mechanical agitator (Model 4598, Parr InstrumentCompany, Moline, USA). The reactions were typicallyperformed by first introducing 0.100 g of 2-PAP and 0.010 g ofthe catalyst (or no catalyst) into the dry autoclave, and then 50mL of AE was introduced. The autoclave was quickly closed toprevent adsorption of water and then purged with N2 severaltimes. The reaction was performed at 280 C for 4 h with a stirringspeed of 300 r/min. After a predetermined time, the reactorwas cooled to room temperature and the products werethen collected for further analysis [53].
  • 28
  • [ 4249-72-3 ]
  • [ 721-04-0 ]
  • [ 100-52-7 ]
  • [ 1864-94-4 ]
  • 29
  • [ 4249-72-3 ]
  • [ 721-04-0 ]
  • [ 100-52-7 ]
  • [ 1864-94-4 ]
  • [ 65-85-0 ]
  • 30
  • 2-Phenoxy-1-phenylethanol-1-d(1) [ No CAS ]
  • [ 3592-47-0 ]
  • [ 721-04-0 ]
  • [ 1864-94-4 ]
  • 31
  • [ 721-04-0 ]
  • [ 1864-94-4 ]
  • [ 65-85-0 ]
  • 32
  • [ 721-04-0 ]
  • [ 6669-13-2 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: MnMoS; hydrogen / methanol / 6 h / 180 °C / 7500.75 Torr 2: nickel-molybdenum sulfide; hydrogen / 180 °C / 7500.75 Torr
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 12 h / 30 °C 2: nickel-molybdenum sulfide; hydrogen / 180 °C / 7500.75 Torr
  • 33
  • [ 721-04-0 ]
  • [ 3299-05-6 ]
  • [ 6314-97-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: MnMoS; hydrogen / methanol / 6 h / 180 °C / 7500.75 Torr 2: nickel-molybdenum sulfide; hydrogen / 180 °C / 7500.75 Torr
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 12 h / 30 °C 2: nickel-molybdenum sulfide; hydrogen / 180 °C / 7500.75 Torr
  • 34
  • [ 721-04-0 ]
  • [ 40515-89-7 ]
Reference: [1]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[2]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[3]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[4]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[5]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[6]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[7]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[8]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[9]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[10]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[11]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[12]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[13]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[14]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[15]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[16]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[17]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[18]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[19]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[20]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[21]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[22]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[23]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[24]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[25]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[26]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[27]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[28]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[29]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[30]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[31]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[32]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[33]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[34]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[35]Green Chemistry,2016,vol. 18,p. 6545 - 6555
[36]Journal of the American Chemical Society,2020,vol. 142,p. 4037 - 4050
[37]Journal of the American Chemical Society,2020,vol. 142,p. 4037 - 4050
[38]Journal of the American Chemical Society,2020,vol. 142,p. 4037 - 4050
[39]Journal of the American Chemical Society,2020,vol. 142,p. 4037 - 4050
[40]Journal of the American Chemical Society,2020,vol. 142,p. 4037 - 4050
[41]Journal of the American Chemical Society,2020,vol. 142,p. 4037 - 4050
[42]Green Chemistry,2020,vol. 22,p. 3802 - 3808
  • 35
  • [ 20511-12-0 ]
  • [ 721-04-0 ]
  • 3-phenoxy-2-phenyl-6-iodoimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tert.-butylhydroperoxide; iodine; In water; 1,2-dichloro-ethane; at 110℃; under 760.051 Torr; for 16h; General procedure: An oven-dried screw-cap vial was charged with I2 (0.02 mmol, 10 mol%), 2-phenoxyacetophenone 2 (0.20 mmol, 1.0 equiv), 2-aminopyridine 1 or 2-aminobenzothiazole (4) (0.60 mmol, 3.0 equiv), and DCE (1.0 mL) in sequence. Then, tert-butyl hydroperoxide (70 wt% in H2O, 2.0 equiv) was added to the solution. The vial was sealed under air and heated to 110 C with stirring for 16 h. After cooling down to r.t., the mixture was filtered, and concentrated to give the crude product, which was purified by flash column chromatography.
  • 36
  • [ 721-04-0 ]
  • [ 106447-97-6 ]
  • 3-phenoxy-2-phenyl-7-trifluoromethylimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tert.-butylhydroperoxide; iodine; In water; 1,2-dichloro-ethane; at 110℃; under 760.051 Torr; for 16h; General procedure: An oven-dried screw-cap vial was charged with I2 (0.02 mmol, 10 mol%), 2-phenoxyacetophenone 2 (0.20 mmol, 1.0 equiv), 2-aminopyridine 1 or 2-aminobenzothiazole (4) (0.60 mmol, 3.0 equiv), and DCE (1.0 mL) in sequence. Then, tert-butyl hydroperoxide (70 wt% in H2O, 2.0 equiv) was added to the solution. The vial was sealed under air and heated to 110 C with stirring for 16 h. After cooling down to r.t., the mixture was filtered, and concentrated to give the crude product, which was purified by flash column chromatography.
  • 37
  • [ 721-04-0 ]
  • [ 3483-12-3 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In N,N-dimethyl-formamide;Inert atmosphere; Reflux; 2-phenoxyacetophenone 6 (8 mg, 0.038 mmol) was added to excess sodium carbonate and dithiothreitol (0.058 g, 0.38 mmol) and purged under nitrogen. A 10 mL aliquot of dried and/or oxygen free solvent either THF, DMF, ACN, water, or dioxane was added through a septum. The reaction was refluxed under nitrogen overnight. It was then filtered, quenched with equal volumes of water, and extracted with equal volumes of dichloromethane. The organic layer was extracted again with equal volumes of water and evaporated to form the product 2, 7, 8. 1 H NMR (500 MHz, DMSO-d6) delta 7.97 (d, J = 8.0 Hz, 2H),7.65 (t, J = 7.95 Hz, 1 H), 7.54 (t, J = 7.8 Hz, 2H), 7.16 (t, J = 7.9 Hz, 2H), 6.80- 6.72 (m, 3H).
  • 38
  • [ 721-04-0 ]
  • [ 3483-12-3 ]
  • [ 98-86-2 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In neat (no solvent); at 130℃;Inert atmosphere; 2-phenoxyacetophenone 6 (8 mg, 0.038 mmol) was added to excess sodium carbonate and dithiothreitol (0.058 g, 0.38 mmol) and purged under nitrogen. A 10 mL aliquot of dried and/or oxygen free solvent either THF, DMF, ACN, water, or dioxane was added through a septum. The reaction was refluxed under nitrogen overnight. It was then filtered, quenched with equal volumes of water, and extracted with equal volumes of dichloromethane. The organic layer was extracted again with equal volumes of water and evaporated to form the product 2, 7, 8. 1 H NMR (500 MHz, DMSO-d6) delta 7.97 (d, J = 8.0 Hz, 2H),7.65 (t, J = 7.95 Hz, 1 H), 7.54 (t, J = 7.8 Hz, 2H), 7.16 (t, J = 7.9 Hz, 2H), 6.80- 6.72 (m, 3H).
  • 39
  • [ 721-04-0 ]
  • [ 3483-12-3 ]
  • 2-((2,3-dihydroxy-4-mercaptobutyl)thio)-1-phenylethan-1-one [ No CAS ]
  • [ 98-86-2 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;Inert atmosphere; Reflux; 2-phenoxyacetophenone 6 (8 mg, 0.038 mmol) was added to excess sodium carbonate and dithiothreitol (0.058 g, 0.38 mmol) and purged under nitrogen. A 10 mL aliquot of dried and/or oxygen free solvent either THF, DMF, ACN, water, or dioxane was added through a septum. The reaction was refluxed under nitrogen overnight. It was then filtered, quenched with equal volumes of water, and extracted with equal volumes of dichloromethane. The organic layer was extracted again with equal volumes of water and evaporated to form the product 2, 7, 8. 1 H NMR (500 MHz, DMSO-d6) delta 7.97 (d, J = 8.0 Hz, 2H),7.65 (t, J = 7.95 Hz, 1 H), 7.54 (t, J = 7.8 Hz, 2H), 7.16 (t, J = 7.9 Hz, 2H), 6.80- 6.72 (m, 3H).
  • 40
  • [ 721-04-0 ]
  • [ 1597-32-6 ]
  • 5-fluoro-3-phenoxy-2-phenylimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With iodine; In 1,2-dichloro-ethane; at 100℃; for 0.5h; General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product.
  • 41
  • [ 721-04-0 ]
  • [ 1597-32-6 ]
  • 6-fluoro-3-phenoxy-2-phenylimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With iodine; In 1,2-dichloro-ethane; at 100℃; for 0.5h; General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product.
  • 42
  • [ 1072-98-6 ]
  • [ 721-04-0 ]
  • 6-chloro-3-phenoxy-2-phenylimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With iodine In 1,2-dichloro-ethane at 100℃; for 0.5h; General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product.
  • 43
  • [ 1072-98-6 ]
  • [ 721-04-0 ]
  • 3-(2-methoxyphenoxy)-2-(4-methoxyphenyl)-6-bromoimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With iodine In 1,2-dichloro-ethane at 100℃; for 0.5h; General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product.
  • 44
  • [ 721-04-0 ]
  • [ 124-40-3 ]
  • [ 611-74-5 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
1: 55% 2: 63% With copper diacetate In water; dimethyl sulfoxide at 20℃; for 12h; Sealed tube; 7 Example 7 In a 15 mL pressure bottle, add 0.125 mmol of 1-phenyl-2-phenoxyethanone, 0.0125 mmol of copper acetate, 0.625 mmol of dimethylamine (40% aqueous solution), and then add 1 mL of dimethyl sulfoxide. After the fresh air was replaced, the mixture was sealed, and the reaction was stirred at room temperature for 12 hours. After the reaction was completed, the product was chromatographed, and the yields of the amide and phenol were shown in Table 1.
1: 62 %Chromat. 2: 56 %Chromat. With copper(II) acetate monohydrate In dimethyl sulfoxide at 25℃; for 9h;
  • 45
  • [ 67-56-1 ]
  • [ 721-04-0 ]
  • [ 121-98-2 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
1: 87% 2: 73% Stage #1: 2-phenoxy-1-phenylethanone With tri-n-propylamine; oxygen; copper diacetate In dimethyl sulfoxide at 20℃; for 12h; Sealed tube; Stage #2: methanol With sulfuric acid In dimethyl sulfoxide 16 Example 16 In a 15 mL pressure bottle, 0.125 mmol of 1-phenyl-2-phenoxyethanone, 0.0125 mmol of copper acetate, 0.625 mmol of tripropylamine, and 1 mL of dimethyl sulfoxide were added, and after replacement with pure oxygen, it was sealed. The mixture was stirred and stirred at room temperature for 12 hours. After completion of the reaction, it was esterified with a methanol solution of H 2SO 4, and the product was obtained by chromatography. The yield of aromatic acid (ester) and phenol is shown in Table 3.
  • 46
  • [ 770-35-4 ]
  • [ 721-04-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium salt of dibutyl phosphate; Methyl thioglycolate; [Ir(ppy)2(dtbpy)]PF6 / N,N-dimethyl acetamide / 72 h / 25 °C / Sealed tube; Irradiation; Inert atmosphere 2: potassium carbonate / acetone / 4 h / 20 °C / Reflux
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  • [ 4249-72-3 ]
  • [ 721-04-0 ]
  • [ 100-52-7 ]
  • [ 1864-94-4 ]
  • [ 65-85-0 ]
  • [ 108-95-2 ]
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  • [ 183303-74-4 ]
  • [ 721-04-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; oxygen / 16 h / 180 °C / 3750.38 Torr / Autoclave 2.1: potassium carbonate / acetone / 0.5 h / 20 °C 2.2: 24 h / 20 °C
  • 49
  • [ 721-04-0 ]
  • [ 70110-65-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetone; water; ethanol / 4 h / 20 °C 2: sodium tetrahydroborate; water / tetrahydrofuran / 1 h / 20 °C
Multi-step reaction with 2 steps 1: potassium carbonate / acetone; water / 24 h / 20 °C 2: sodium tetrahydroborate / tetrahydrofuran; water / 5 h / 20 °C
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  • [ 1864-94-4 ]
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  • [ 721-04-0 ]
  • [ 103-65-1 ]
  • [ 93-54-9 ]
  • [ 1123-86-0 ]
  • [ 17264-02-7 ]
  • [ 108-93-0 ]
  • [ 108-95-2 ]
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  • [ 721-04-0 ]
  • [ 1636-34-6 ]
  • [ 13323-81-4 ]
  • [ 108-95-2 ]
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  • [ 721-04-0 ]
  • [ 1575-37-7 ]
  • [ 1741-50-0 ]
  • [ 4887-88-1 ]
  • [ 108-95-2 ]
YieldReaction ConditionsOperation in experiment
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 2-methoxy-ethanol; at 120℃; for 24.0h;Sealed tube; Put 0.1mmol oxidized lignin model substrate 1 in a 10mL pressure tube, add 0.01mmol HNO3, 1mL DMSO and 0.2mmol o-phenylenediamine 2,After tightening the cap, heat the resulting reaction solution (the concentration of oxidized lignin in the reaction solution is 0.1 mmol/mL) in an oil bath at 100C for 12 hours,The decomposition reaction is carried out. After the reaction is completed, the obtained product is taken out and the solvent is drained and separated by a column to obtain two nitrogen-containing heterocyclic products.
  • 54
  • [ 110-91-8 ]
  • [ 721-04-0 ]
  • [ 6425-41-8 ]
  • [ 100-41-4 ]
YieldReaction ConditionsOperation in experiment
1: 35 %Chromat. 2: 21.4 %Chromat. With palladium 10% on activated carbon; hydrogen In m-xylene at 170℃; for 24h; Autoclave; Green chemistry;
  • 55
  • [ 721-04-0 ]
  • [ 183303-74-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / tetrahydrofuran; water / 6 h / 20 °C 2: palladium 10% on activated carbon; sodium formate / toluene / 12 h / 150 °C / Inert atmosphere 3: potassium carbonate / acetone / 5 h / 20 °C 4: sodium tetrahydroborate / tetrahydrofuran; water / 6 h / 20 °C
Multi-step reaction with 5 steps 1: potassium carbonate / acetone; water / 24 h / 20 °C 2: sodium tetrahydroborate / tetrahydrofuran; water / 5 h / 20 °C 3: palladium 10% on activated carbon; sodium formate / toluene / 12 h / 150 °C / Inert atmosphere 4: potassium carbonate / acetone / 5 h / 20 °C 5: sodium tetrahydroborate / tetrahydrofuran; water / 6 h / 20 °C
  • 56
  • [ 37952-93-5 ]
  • [ 109524-10-9 ]
  • [ 721-04-0 ]
YieldReaction ConditionsOperation in experiment
27% With [NiBr2(phen)]; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; lithium bromide In N,N-dimethyl acetamide for 24h; Inert atmosphere; Irradiation;
  • 57
  • [ 721-04-0 ]
  • [ 1741-50-0 ]
  • 58
  • [ 18065-04-8 ]
  • [ 93-56-1 ]
  • [ 721-04-0 ]
YieldReaction ConditionsOperation in experiment
1: 9% 2: 12% With oxygen; 9-(4-bromophenyl)-10-methylacridinium tetrafluoroborate In methanol; lithium hydroxide monohydrate; (methylsulfinyl)methane at 20℃; for 12h; Irradiation; 2 Example 2: Screening of acridinium-based photoredox catalysts in oxidation of 0-O- 4 lignin’s model to aromatics To test the performance of the modular acridinium catalysts, 2-(2- methoxyphenoxy)-1 -phenylethanol (1) was selected as a simple nonphenolic /3-O-4 -type model substrate owing to this linkage is the most abundant in native Lignin (45-60%). The acridinium-based photoredox catalysts (OPC1 to 8) from example 1 were tested. Results are summarized in Table 2 below. The reaction was carried out in the presence of 0.75 mol% of OPC in DMSO/MeOH/water as solvent mixtures in 8:8:1 mixing ratio under atmospheric pressure of O2 and blue LEDs irradiation for 12h (further tests have shown the reaction can also be done under atmospheric pressure of air and blue LEDs irradiation for 12h). We firstly examined the catalytic activity of commercially available Fukuzumi’s catalyst, but a moderate conversion of 1 was observed with the formation of oxidized product 2 in only 5% (Table 2, entry 1). Surprisingly, 1-phenylethane-1 ,2-diol (3) resulting from the C-O bond breakage was the major product, albeit in a very poor yield. This highlights the fact that acridiniums can be an effective OPC for oxidative C-O bond cleavage of the lignin’s models using oxygen associated with visible-light as sustainable oxidant systems, all encouraging us to screen other acridinium-based structures to obtain higher yield in favor of 3. 9-Phenyl-10- methylacridium, bromo, ester, and acetyl, para-substituted 9-phenyl-10-methylacridiums give a similar trend of reactivity (Table 2, entries 2-5). Interestingly, 10-methylacridium substituted by an ortho-substituted aryl group at C9-position give higher conversion. When the reaction is carried out with the photocatalyst OPC5 with a 2-bromophenyl at the C9 position, the C-O bond cleavage occurred in high yield affording 3 in 84% isolated yield without the formation of overoxidized products 4 and 5 (Table 2, entry 6). The catalyst OPC6 and OPC7 with 2- iodophenyl and 2-biphenyl C9-substituent, respectively, gives a slightly lower yield in 3, suggesting that 2-bromophenyl is the best design for this transformation (Table 2, entries e OPC8 bearing a 2-bromo and 4-methyl substituents on the C9aryl also od reactivity affording 3 in 78% yield (Table 2, entry 9).
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  • [ 18065-04-8 ]
  • [ 93-56-1 ]
  • [ 721-04-0 ]
  • [ 65-85-0 ]
YieldReaction ConditionsOperation in experiment
1: 8% 2: 15% 3: 9% With 10-methyl-9-phenyl-9,10-dihydroacridin-9-ylium tetrafluoroborate; oxygen In methanol; lithium hydroxide monohydrate; (methylsulfinyl)methane at 20℃; for 12h; Irradiation; 2 Example 2: Screening of acridinium-based photoredox catalysts in oxidation of 0-O- 4 lignin’s model to aromatics To test the performance of the modular acridinium catalysts, 2-(2- methoxyphenoxy)-1 -phenylethanol (1) was selected as a simple nonphenolic /3-O-4 -type model substrate owing to this linkage is the most abundant in native Lignin (45-60%). The acridinium-based photoredox catalysts (OPC1 to 8) from example 1 were tested. Results are summarized in Table 2 below. The reaction was carried out in the presence of 0.75 mol% of OPC in DMSO/MeOH/water as solvent mixtures in 8:8:1 mixing ratio under atmospheric pressure of O2 and blue LEDs irradiation for 12h (further tests have shown the reaction can also be done under atmospheric pressure of air and blue LEDs irradiation for 12h). We firstly examined the catalytic activity of commercially available Fukuzumi’s catalyst, but a moderate conversion of 1 was observed with the formation of oxidized product 2 in only 5% (Table 2, entry 1). Surprisingly, 1-phenylethane-1 ,2-diol (3) resulting from the C-O bond breakage was the major product, albeit in a very poor yield. This highlights the fact that acridiniums can be an effective OPC for oxidative C-O bond cleavage of the lignin’s models using oxygen associated with visible-light as sustainable oxidant systems, all encouraging us to screen other acridinium-based structures to obtain higher yield in favor of 3. 9-Phenyl-10- methylacridium, bromo, ester, and acetyl, para-substituted 9-phenyl-10-methylacridiums give a similar trend of reactivity (Table 2, entries 2-5). Interestingly, 10-methylacridium substituted by an ortho-substituted aryl group at C9-position give higher conversion. When the reaction is carried out with the photocatalyst OPC5 with a 2-bromophenyl at the C9 position, the C-O bond cleavage occurred in high yield affording 3 in 84% isolated yield without the formation of overoxidized products 4 and 5 (Table 2, entry 6). The catalyst OPC6 and OPC7 with 2- iodophenyl and 2-biphenyl C9-substituent, respectively, gives a slightly lower yield in 3, suggesting that 2-bromophenyl is the best design for this transformation (Table 2, entries e OPC8 bearing a 2-bromo and 4-methyl substituents on the C9aryl also od reactivity affording 3 in 78% yield (Table 2, entry 9).
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