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[ CAS No. 2210-24-4 ] {[proInfo.proName]}

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Chemical Structure| 2210-24-4
Chemical Structure| 2210-24-4
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Product Details of [ 2210-24-4 ]

CAS No. :2210-24-4 MDL No. :MFCD00080617
Formula : C9H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :BPCNEKWROYSOLT-UHFFFAOYSA-N
M.W : 147.17 Pubchem ID :221792
Synonyms :

Calculated chemistry of [ 2210-24-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.09
TPSA : 29.1 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) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 1.75
Log Po/w (WLOGP) : 1.62
Log Po/w (MLOGP) : 1.76
Log Po/w (SILICOS-IT) : 1.7
Consensus Log Po/w : 1.7

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.06
Solubility : 1.28 mg/ml ; 0.0087 mol/l
Class : Soluble
Log S (Ali) : -1.98
Solubility : 1.55 mg/ml ; 0.0105 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.82
Solubility : 0.222 mg/ml ; 0.00151 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.13

Safety of [ 2210-24-4 ]

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 [ 2210-24-4 ]

* 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 [ 2210-24-4 ]

[ 2210-24-4 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 62-53-3 ]
  • [ 79-10-7 ]
  • [ 2210-24-4 ]
YieldReaction ConditionsOperation in experiment
85% With zeolite-HY In neat (no solvent) for 0.833333h; Irradiation;
82% Stage #1: acrylic acid With iodine; triethylamine; phosphorous acid trimethyl ester In dichloromethane for 0.166667h; Cooling with ice; Inert atmosphere; Stage #2: aniline In dichloromethane at 20℃; for 3h; Inert atmosphere; Cooling with ice;
7% Stage #1: acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Stage #2: aniline In dichloromethane at 0 - 20℃; for 11h; 3.S-11.1 Step 1. A solution of acrylic acid (1.10 mL, 16.11 mmol, 1.5 eq), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (3.09 g, 16.11 mmol, 1.5 eq), DIEA (5.6 mL, 32.22 mmol, 3.0 eq), and 1-hydroxybenzotriazole (1.45 g, 10.74 mmol, 1.0 eq) in DCM (20 mL) was stirred at 20° C. for 1 h, after which aniline (1.00 g, 10.74 mmol, 1.0 eq) was added dropwise at 0° C. The reaction was stirred at 20° C. for 11 hours and the reaction progress was monitored by TLC (Petroleum ether:EtOAc=1:3). Upon completion, the mixture was diluted with water (20 mL) and extracted with dichloromethane (20 mL×2). The combined organic layers were washed with brine (50 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (Petroleum ether:EtOAc=10:1) to afford compound SI-17 (300.0 mg, 7%) as an off-white solid.
With vanadium oxide-aluminium oxide catalyst; benzene at 350℃;

  • 2
  • [ 62-53-3 ]
  • [ 814-68-6 ]
  • [ 2210-24-4 ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In lithium hydroxide monohydrate; propan-2-one at 0℃; for 1h; Inert atmosphere;
95% With potassium carbonate In lithium hydroxide monohydrate; propan-2-one at 0℃; for 1h;
95% With potassium carbonate In lithium hydroxide monohydrate; propan-2-one at 0℃; for 1h; Inert atmosphere;
93% With triethylamine In diethyl ether 1) -30 deg C, 1 h; 2) 20 deg C, 3 h;
92% With potassium carbonate In lithium hydroxide monohydrate; propan-2-one at 0℃; Inert atmosphere;
92% With potassium carbonate In lithium hydroxide monohydrate; propan-2-one at 0℃; Inert atmosphere;
91% With triethylamine In dichloromethane at 0 - 20℃; 13 4.2.2.13 Synthesis of N-phenylacrylamide (15) The compound was synthesized similar to the reported procedure [63] . Briefly, aniline (3.03 mL, 33.15 mmol) and triethyl amine (6 mL, 66.29 mmol) were dissolved in dry DCM (30 mL) and the temperature of the solution was lowered to 0 °C. A solution of acryloyl chloride (2.69 mL, 33.15 mmol) in dry DCM (10 mL) was added drop wise. The reaction temperature was increased gradually from 0 °C to room temperature and stirring was continued overnight at room temperature. Solvent was evaporated and the residue was suspended in 10% HCl (20 mL) and then extracted with DCM (2 * 30 mL). The combined organic extracts were washed with saturated solution of sodium carbonate (20 mL), dried over anhydrous sodium sulfate, and evaporated to give the product as a yellow solid (4.44 g, 91%). 1HNMR (400 MHz, CDCl3) δ (ppm): 5.71 (dd, J = 1.6 and 10.0 Hz, 1H), 6.30 (dd, J = 10.0 and 16.8 Hz, 1H), 6.41 (dd, J = 1.6 and 16.8 Hz, 1H), 7.12 (t, J = 7.6, 1H), 7.28 (m, 2H), 7.60 (d, J = 8.0 Hz, 2H), 7.98 (s, 1H); 13CNMR (100 MHz, CDCl3) δ (ppm): 120.15, 124.51, 127.69, 128.99, 131.29, 137.85, 163.86. The spectral data for the synthesized compound was consistent with the reported data in literature [63]
91% With triethylamine In dichloromethane at 0 - 20℃; II.B Synthesis of N-phenylacrylamide (15) 10119] The compound was synthesized similar to the reported procedure.62 Briefly, aniline (3.03 mE, 33.15 mmol) and triethyl amine (6 mE, 66.29 mmol) were dissolved in dry DCM (30 mE) and the temperature of the solution was lowered to 0° C. A solution of acryloyl chloride (2.69 mE, 33.15 mmol) in dry DCM (10 mE) was added drop wise. The reaction temperature was increased gradually from 0° C. to room temperature and stirring was continued overnight at room temperature. Solvent was evaporated and the residue was suspended in 10% HC1 (20 mE) and then extracted with DCM (2x30 mE). The combined organic extracts were washed with saturated solution of sodium carbonate (20 mE), dried over anhydrous sodium sulfate, and evaporated to give the product as a yellow solid (4.44 g, 91%). ‘HNMR (400 MHz, CDC13) ö (ppm): 5.71 (dd, J=1.6 and 10.0 Hz, 1H), 6.30 (dd, J=10.0 and 16.8 Hz, 1H), 6.41 (dd, J=1.6 and 16.8 Hz, 1H), 7.12 (t, J=7.6, 1H), 7.28 (m, 2H), 7.60 (d, J=8.0 Hz, 2H), 7.98 (s, 1H); ‘3CNMR (100 MHz, CDC13) ö (ppm): 120.15, 124.51, 127.69, 128.99, 131.29, 137.85, 163.86. The spectral data for the synthesized compound was consistent with the reported data in literature. 62
88.3% In dichloromethane at 0 - 5℃;
86% With triethylamine In dichloromethane at 0 - 20℃; for 12h;
84% With potassium carbonate In lithium hydroxide monohydrate; propan-2-one at 0℃; for 2h; Schlenk technique; Inert atmosphere;
83% With triethylamine In dichloromethane at 20℃; for 6h;
82% With triethylamine In dichloromethane at 0 - 20℃;
81% With triethylamine In ethyl acetate at 0 - 20℃; for 2h; Inert atmosphere;
79% With triethanolamine In tetrahydrofuran 20.a (a) (a) N1-Phenylacrylamide Acryloyl chloride (28.5 mL; 350 mmol) was added to a stirred solution of phenylamine (30 mL; 320 mmol) and TEA (56 mL; 400 mmol) in THF (1 L) at 0° C. The reaction mixture was stirred for 3 h, poured onto brine and extracted with diethyl ether. The organic layer was dried, concentrated and recrystallized from hexane:EtOAc (3:1) to give the sub-title compound in a 79% yield.
78% With ruthenium(III) 2,4-pentanedionate at 25℃; for 0.5h;
72.8% With triethylamine In dichloromethane at 0 - 20℃;
68% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 23℃; for 1h;
64% With triethylamine In dichloromethane at 0 - 20℃; for 12h;
61% With potassium carbonate In lithium hydroxide monohydrate; propan-2-one at 20℃;
60% With triethylamine In dichloromethane at 20℃; Cooling with ice; 6.1; 9.1 1. Preparation of N-phenylacrylamide Add 2-nitroaniline (8.1mmol) to dichloromethane (20mL),Acryloyl chloride (7.5 mmol) dissolved in dichloromethane (10 mL) was slowly added dropwise to triethylamine (24.4 mmol) in an ice bath.After completion of the dropwise addition, the mixture was transferred to room temperature and stirred for 5-12 hours.The reaction was detected by TLC, and the organic phase was extracted with water and dichloromethane.Column chromatography separated a light yellow solid, namely N-phenylacrylamide, with a yield of 60%.
60% With triethylamine In dichloromethane at 0 - 20℃; 2.1. General procedure for compounds 3a-3g. General procedure: Aniline or 2-nitroanilines 1a-d (8.1 mmol) and triethylamine (24.4 mmol) were stirred in dichloromethane (25 mL), then acryloyl chloride 2a or methacryloyl chloride 2b (7.5 mmol) was slowly added to the reaction system under ice bath condition. The reaction was stirred at room temperature for 5-12 hours until the TLC showed the disappearance of the starting material. The mixture was partitioned between dichloromethane (30 mL) and water (30 mL). The organic extract was washed with water (30 mL×3), dried (MgSO4) and dichloromethane was removed under reduced pressure. The crude product was purified by column chromatography to obtain compounds 3a-3g.
60% With triethylamine In dichloromethane at 0 - 20℃; 2.1. General procedure for compounds 3a-3g. General procedure: Aniline or 2-nitroanilines 1a-d (8.1 mmol) and triethylamine (24.4 mmol) were stirred in dichloromethane (25 mL), then acryloyl chloride 2a or methacryloyl chloride 2b (7.5 mmol) was slowly added to the reaction system under ice bath condition. The reaction was stirred at room temperature for 5-12 hours until the TLC showed the disappearance of the starting material. The mixture was partitioned between dichloromethane (30 mL) and water (30 mL). The organic extract was washed with water (30 mL×3), dried (MgSO4) and dichloromethane was removed under reduced pressure. The crude product was purified by column chromatography to obtain compounds 3a-3g.
56% With pyridine In diethyl ether 1.) 0 deg C, 10 min, 2.) room temperature, 4 h;
50% With triethylamine In dichloromethane at 0 - 20℃;
46% With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
With benzene
With Potassium bicarbonate; 1-n-butyl-3-methylimidazolium tetrafluoroborate at 20℃; for 6h;
In dichloromethane
In N,N-dimethyl acetamide
With triethylamine
In dichloromethane at 0 - 20℃;
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 18h;
With triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;
With sodium hydroxide In N,N-dimethyl acetamide; lithium hydroxide monohydrate at -5 - 20℃; for 2h; Inert atmosphere;
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;
With triethylamine In tetrahydrofuran at 65℃; for 6h;
In dichloromethane at 0 - 20℃;
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;
With triethylamine In dichloromethane
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;
With triethylamine In dichloromethane at 0℃; for 0.5h;
With triethylamine In dichloromethane at 20℃; 2.2.1. Synthesis of N-alkyl acrylamide General procedure: N-alkyl acrylamides were prepared based onthe methods in literature [12]. In detail, N-alkylacryl amine (12 mmol) and anhydrous triethylamine(12 mmol, 1.7 mL) were dissolved in anhydrous DCM(50 mL). Acryloyl chloride (10 mmol, 820 L) was dripped slowly into the solution under 0 °C. The reaction mixture was left under room temperature overnight. The solution was concentrated and dissolved again in ethyl acetate. The precipitate was removed by filtration and the filtrate was concentrated.The obtained crude product was purified by column chromatography using a mixture of ethylacetate and pentane (v/v 1/2) as eluent to yield the corresponding N-alkyl acrylamide.
With triethylamine In dichloromethane at 0 - 20℃; for 2h;
With triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;

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  • 3
  • [ 2210-24-4 ]
  • [ 101-79-1 ]
  • [ 57181-48-3 ]
  • 4
  • [ 3460-04-6 ]
  • [ 5099-95-6 ]
  • [ 2210-24-4 ]
  • 5
  • [ 100-42-5 ]
  • [ 2210-24-4 ]
  • [ 3056-73-3 ]
YieldReaction ConditionsOperation in experiment
69% With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 15h;
  • 6
  • [ 2210-24-4 ]
  • [ 77022-44-7 ]
  • (E)-7-(Tetrahydro-pyran-2-yloxy)-hept-2-enoic acid phenylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 15h;
  • 7
  • [ 590-92-1 ]
  • [ 62-53-3 ]
  • [ 2210-24-4 ]
  • 8
  • [ 3460-04-6 ]
  • [ 2210-24-4 ]
  • N-phenyl-N-(2-phenylcarbamoylethyl)acrylamide [ No CAS ]
  • 9
  • [ 3460-04-6 ]
  • <i>N</i>-phenyl-<i>N</i>-{2-[phenyl-(2-phenylcarbamoyl-ethyl)-carbamoyl]-ethyl}-acrylamide [ No CAS ]
  • [ 2210-24-4 ]
  • N-phenyl-N-(2-phenylcarbamoylethyl)acrylamide [ No CAS ]
  • 10
  • N,N’-cystamine-bis-acrylamide [ No CAS ]
  • [ 2210-24-4 ]
  • [ 79-06-1 ]
  • None [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium peroxydisulfate; N,N,N,N,-tetramethylethylenediamine In ethanol; water at 25℃; for 15.5h; 2 Copolymerization of acrylamide (AAm), bisacryloylcystamine (BAC), and N-phenylacrylamide (NPA) was carried out at acrylic mole ratios of 94/4/2 at 5% (w/w) in 25% ethanol (25:75=ethanol:water v/v). Nitrogen was bubbled through the solution for about 30 minutes to remove any dissolved oxygen prior to the initiation of the polymerization. The reaction was initiated by adding 2.1% (w/w) of tetramethylethylenediamine and 0.4% (w/w) of ammonium persulfate and allowed to proceed for 15 hours at 25° C. Because of the limited solubility of BAC in water, aqueous ethanol was used as the solvent. The resulting gel was removed from the beaker, swelled in 500 mL of water for two days, crushed into small pieces and washed with distilled water. The copolymeric gel was labeled AB4N2SS indicating that it contained disulfide (-SS-) bonds by incorporating 4 acrylic mole % of BAC and 2 acrylic mole % of NPA. The liquefaction of crushed gels (AB4N2SS) was achieved by the addition of dithiothreitol (DTT) (10 mol/mol of BAC used) to the crushed hydrogels. The reduction was carried out at pH 7.0 for 4 hours, while nitrogen was bubbled through the solution with stirring. After complete solubilization, the copolymer solution was acidified to pH 4 using 10% (v/v) HCl and precipitated in methanol (pH 4) with vigorous stirring. The precipitated -SH copolymer was filtered, dried under vacuum, and stored under reduced pressure at all times. The above obtained thiol containing water-soluble copolymer, from AB4N2SS was labeled AB4N2SH. A 5% (w/v) solution of AB4N2SH was prepared in water (N2 saturated) initially at pH 4 and after the complete dissolution, the pH was adjusted to 7 using 7 μL of 5 M NaOH. Then, 162 μL of 0.5M DTDP (pH=7) was added to reform the hydrogel. The total volume of the composition was 3 ml. Similarly, 7%, 9%, and 11% (w/v) solutions of AB4N2SH were also prepared and used for the formation of hydrogels. The hydrogels were analyzed for their modulus values. The polymer solution (9, 11%) exhibited “honey-like” consistency, shear thinning when injected through the syringe, and almost instantaneously set within the porcine capsular bag as a physical gel without leaking. This physical gel was then transformed into a chemical gel.
  • 11
  • [ 2210-24-4 ]
  • [ 101961-58-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) NO, Et3SiH, 2) K2CO3 / 1) N,N'-bis(2-ethoxycarbonyl-3-oxobutylidene)ethylenediaminatocobalt(II) (Co(eobe)) / 1) 1,2-dichloroethane, room temp., 60 h, 2) ethanol, room temp., 2 h 2: H2 / Raney Ni / ethanol / 5 h / 75 °C / 760 Torr
Multi-step reaction with 2 steps 1: NO, Et3SiH / N,N'-bis(2-ethoxycarbonyl-3-oxobutylidene)ethylenediaminatocobalt(II) (Co(eobe)) / 1,2-dichloro-ethane / 60 h / Ambient temperature 2: H2 / Raney Ni / ethanol / 5 h / 75 °C / 760 Torr
  • 12
  • [ 2210-24-4 ]
  • [ 69407-32-5 ]
  • N1-phenyl-3-(7-benzyl-3,7-diazabicyclo[3.3.1]non-3-yl)-propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% In ethanol 20.b (b) (b) N1-Phenyl-3-(7-benzyl-3,7-diazabicyclo[3.3.1]non-3-yl)propanamide N1-Phenylacrylamide (1.0 g; 6.8 mmol; from step (a) above) was added to a stirred solution of 3-benzyl-3,7-diazabicyclo[3.3.1]nonane (1.5 g; 6.8 mmol; see Example E above) in EtOH (7 mL). The reaction mixture was stirred for 10 h and concentrated to give the sub-title compound in a 97% yield.
  • 13
  • [ 2210-24-4 ]
  • potassium 3-trifluoroborato-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: N-acryloylaniline With potassium <i>tert</i>-butylate; bis(pinacol)diborane; bis[2-(diphenylphosphino)phenyl] ether; copper(l) chloride In tetrahydrofuran; methanol at 0 - 20℃; Inert atmosphere; Stage #2: With potassium hydrogenfluoride In water; acetonitrile at 0℃; Saturated solution;
  • 14
  • [ 1295-35-8 ]
  • [ 2210-24-4 ]
  • [ 2622-14-2 ]
  • [ 1286680-08-7 ]
  • 15
  • [ 2210-24-4 ]
  • [ 100-63-0 ]
  • cinnamanilide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With Bathocuproine; palladium diacetate; acetic acid In methanol; chlorobenzene at 40℃;
  • 16
  • [ 2210-24-4 ]
  • [ 74-88-4 ]
  • [ 6273-94-5 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: N-acryloylaniline With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;
62% Stage #1: N-acryloylaniline With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 4h; Schlenk technique; Inert atmosphere;
Stage #1: N-acryloylaniline With sodium hydride In diethyl ether at 0 - 20℃; Stage #2: methyl iodide In diethyl ether at 0 - 20℃;
Stage #1: N-acryloylaniline With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3h; Inert atmosphere;
Stage #1: N-acryloylaniline With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: methyl iodide at 0 - 20℃;
Stage #1: N-acryloylaniline With sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 5h;

  • 17
  • [ 1013634-99-5 ]
  • [ 2210-24-4 ]
  • [ 1412410-82-2 ]
YieldReaction ConditionsOperation in experiment
72% With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 100℃; for 0.116667h; Microwave irradiation; 6.3 General procedure for the synthesis of compounds 7 and 8 General procedure: To a solution of compound 5 (6) (3 mmol) and substituted acrylamide (3.3 mmol) in dry DMF was added Pd(OAc)2 (3%) and triethylamine (6 mmol). The reaction mixture was stirred under 100 °C via microwave (500 w) for 7 min. Then the mixture was poured into 10% HCl ice water (200 ml) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compounds 7 or 8.
With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 80℃; for 0.0833333h; Microwave irradiation; Green chemistry; 4.3. General experimental procedure for Heck reaction under microwave heating condition General procedure: To a solution of 3-iodo-chromone (4 mmol) and olefin (4.8 mmol) in solvent was added catalyst (5 mmol %) and base (8 mmol). The reaction mixture was stirred via microwave heating under air. Then the mixture was poured into 10% HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give resulting product.
  • 18
  • [ 2210-24-4 ]
  • [ 73220-42-5 ]
  • [ 1412410-76-4 ]
YieldReaction ConditionsOperation in experiment
94.2% With triethylamine at 80℃; for 2h; 3.2. general experimental for ILPd-MNPs catalyzed heck cross coupling reaction and catalyst recycling General procedure: The solution of 3-iodo-7-methoxy-4H-chromen-4-one (1)(1 mmol), methy acrylate (2) (1.2mmol) was allowed to reactin presence of freshly prepared ILPd MNP (0.1 g) with 0.250 mmol of the base as per the reaction condition defined in Table 2. After cooling the reaction mass the volatile materials were under reduced pressure at 40oC for 20 minutes.Then the reaction product was isolated with diethyl ether(5x2mL) washing. Then the purification of the reaction product was carried out with flash chromatography (eluent:AcOEt: n-hexane=1: 3) to achieve the pure Heck reaction product.
79% With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 100℃; for 0.116667h; Microwave irradiation; 6.3 General procedure for the synthesis of compounds 7 and 8 General procedure: To a solution of compound 5 (6) (3 mmol) and substituted acrylamide (3.3 mmol) in dry DMF was added Pd(OAc)2 (3%) and triethylamine (6 mmol). The reaction mixture was stirred under 100 °C via microwave (500 w) for 7 min. Then the mixture was poured into 10% HCl ice water (200 ml) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compounds 7 or 8.
With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 80℃; for 0.0833333h; Microwave irradiation; Green chemistry; 4.3. General experimental procedure for Heck reaction under microwave heating condition General procedure: To a solution of 3-iodo-chromone (4 mmol) and olefin (4.8 mmol) in solvent was added catalyst (5 mmol %) and base (8 mmol). The reaction mixture was stirred via microwave heating under air. Then the mixture was poured into 10% HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give resulting product.
  • 19
  • [ 2210-24-4 ]
  • 3-iodo-7,4'-dimethoxyflavone [ No CAS ]
  • [ 1412410-90-2 ]
YieldReaction ConditionsOperation in experiment
74.4% With triethylamine at 80℃; for 2h; 3.2. general experimental for ILPd-MNPs catalyzed heck cross coupling reaction and catalyst recycling General procedure: The solution of 3-iodo-7-methoxy-4H-chromen-4-one (1)(1 mmol), methy acrylate (2) (1.2mmol) was allowed to reactin presence of freshly prepared ILPd MNP (0.1 g) with 0.250 mmol of the base as per the reaction condition defined in Table 2. After cooling the reaction mass the volatile materials were under reduced pressure at 40oC for 20 minutes.Then the reaction product was isolated with diethyl ether(5x2mL) washing. Then the purification of the reaction product was carried out with flash chromatography (eluent:AcOEt: n-hexane=1: 3) to achieve the pure Heck reaction product.
60.4% With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 110℃; for 1.5h; Microwave irradiation; Green chemistry; 4.3. General experimental procedure for Heck reaction under microwave heating condition General procedure: To a solution of 3-iodo-chromone (4 mmol) and olefin (4.8 mmol) in solvent was added catalyst (5 mmol %) and base (8 mmol). The reaction mixture was stirred via microwave heating under air. Then the mixture was poured into 10% HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give resulting product.
  • 20
  • 3-iodo-6,7-dimethoxy-2-phenylchromone [ No CAS ]
  • [ 2210-24-4 ]
  • [ 1412410-95-7 ]
YieldReaction ConditionsOperation in experiment
55.8% With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 110℃; for 1.5h; Microwave irradiation; Green chemistry; 4.3. General experimental procedure for Heck reaction under microwave heating condition General procedure: To a solution of 3-iodo-chromone (4 mmol) and olefin (4.8 mmol) in solvent was added catalyst (5 mmol %) and base (8 mmol). The reaction mixture was stirred via microwave heating under air. Then the mixture was poured into 10% HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give resulting product.
  • 21
  • [ 2210-24-4 ]
  • [ 1412411-09-6 ]
  • [ 1412411-02-9 ]
YieldReaction ConditionsOperation in experiment
48.1% With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 110℃; for 1.5h; Microwave irradiation; Green chemistry; 4.3. General experimental procedure for Heck reaction under microwave heating condition General procedure: To a solution of 3-iodo-chromone (4 mmol) and olefin (4.8 mmol) in solvent was added catalyst (5 mmol %) and base (8 mmol). The reaction mixture was stirred via microwave heating under air. Then the mixture was poured into 10% HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give resulting product.
  • 22
  • [ 591-50-4 ]
  • [ 79-06-1 ]
  • [ 2210-24-4 ]
YieldReaction ConditionsOperation in experiment
79% With copper(I) thiophene-2-carboxylate; sodium t-butanolate In dimethyl sulfoxide at 100℃; for 6h; Inert atmosphere;
71% With copper(ll) sulfate pentahydrate; sodium ascorbate; sodium t-butanolate In dimethyl sulfoxide at 100℃; for 7h; 1 General procedure for N-arylation of primary amides General procedure: CuSO4*5H2O (0.15 mmol), NaAsc (0.3 mmol), aryl iodides (1mmol), primary amides (1.2mmol), t-BuONa (2.0 mmol), and DMSO (3mL) were added to a flask. The reaction mixture was stirred under air, and then cooled to room temperature and extracted with ethyl acetate (3×10 mL). The organic layer was then dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The secondary amides were finally obtained by column chromatography on silica gel eluted with ethyl acetate/petroleum ether.
  • 23
  • [ 31121-11-6 ]
  • [ 2210-24-4 ]
  • [ 1606589-45-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1H-imidazole / dichloromethane / 2 h / 20 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C 5: 1,4-diaza-bicyclo[2.2.2]octane / <i>tert</i>-butyl alcohol / 6 h / Reflux
Multi-step reaction with 5 steps 1: 1H-imidazole / dichloromethane / 2 h / 20 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C 5: 1,4-diaza-bicyclo[2.2.2]octane / <i>tert</i>-butyl alcohol / 6 h / Reflux
  • 24
  • [ 1003869-22-4 ]
  • [ 2210-24-4 ]
  • (2E)-3-(9-tert-butyl-6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepin-2-yl)-N-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 150℃; for 0.916667h; Inert atmosphere; 5.1.2 General procedure for the synthesis of 2a-2j General procedure: 9-tert-Butyl-2-iodo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one (6; 215mg, 0.500mmol), the indicated amount of a suitable acryl amide, palladium(II)acetate (11mg, 0.049mmol) and triethylamine (2mL) are stirred under nitrogen at 150°C in DMF (5mL). The reaction is monitored by TLC. As soon as all starting material 6 is consumed, the mixture is filtered. After addition of silicagel (1.5g) the filtrate is evaporated to dryness. The residue is eluted over a short silica gel column (3.5cm) using mild vacuum and the indicated eluent. The solution is evaporated and the solid residue is purified by crystallization from the indicated solvent.
  • 25
  • [ 2210-24-4 ]
  • 11-iodo-7,12-dihydropyrido[2',3':2,3]azepino[4,5-b]indol-6(5H)-one [ No CAS ]
  • (E)-3-(6-oxo-5,6,7,12-tetrahydropyrido[2',3':2,3]azepino[4,5-b]indol-11-yl)-N-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.4% With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 100℃; for 0.666667h; Microwave irradiation; 5.1.9. (E)-3-(6-oxo-5,6,7,12-tetrahydropyrido[2',3':2,3]azepino[4,5-b]indol-11-yl)-N-phenylacrylamide (5e) A mixture of 11-iodo-7,12-dihydropyrido[2',3':2,3]azepino[4,5-b]indol-6(5H)-one (11b, 200 mg, 0.530 mmol), N-phenylacrylamide(13, 87 mg, 0.59 mmol), triethylamine (101 mg, 1.00 mmol,0.14 mL), Pd(OAc)2 (7 mg, 0.03 mmol), and DMF (3 mL) were heated for 40 min to 100 °C (power: 100 W; pressure 150 PSI) in a microwave device in a sealed microwave reaction vessel. After filtration of the mixture through a charcoal frit, ethyl acetate (220 mL) was added to the filtrate. A solid precipitated, which was filtered off and washed with n-hexane (320 mL). Further material precipitated from the washing liquid, which was collected by filtration and combined with the material collected previously. Crystallization of the combined materials from ethanol yielded a gray-brown solid (168 mg, 80.4%); decomposition starting at 289 °C; IR (KBr): 3435(NH), 2908 (CH aliphat.), 1652 (C=O), 1624 (C=O), 1442,1359 cm-1; 1H NMR (400 MHz, DMSO-d6): δ = 12.03 (s, 1H), 10.40(s, 1H), 10.25 (s, 1H), 8.46 (dd, 1H, 3JH,H = 4.7 Hz, 4JH,H = 1.8 Hz), 8.42-8.32 (m, 2H), 7.83-7.72 (m, 3H), 7.58 (d, 1H, 3JH,H = 7.4 Hz),7.44-7.29 (m, 3H), 7.21 (t, 1H, 3JH,H = 7.7 Hz), 7.13-7.04 (m, 1H), 6.99(d, 1H, 3JH,H = 15.5 Hz), 3.65 (s, 2H); 13C NMR (100.6 MHz, DMSO-d6): δ = 171.4, 163.8, 147.7, 139.4, 136.7, 131.3, 127.5, 119.1, 117.5, 108.4(quat C); 147.6, 136.3, 135.6, 128.8 (2C), 123.3, 122.3, 119.9, 119.8,119.4, 119.2 (2C), 119.1 (tert C); 31.8 (sec C); C24H18N4O2 (394.43);MS (EI): m/z 394 ([M], 52), 302 ([C18H12N3O2], 100), 274([C17H12N3O], 99), 259 (56); HRMS (EI): m/z ([M]) calcd. 394.14243, found 394.14233; HPLC: 98.1% at 254 nm, 98.9% at 280 nm, tN = 8.5 min, tM = 1.09 min (ACN/H2O; 40:60).
  • 26
  • [ 2210-24-4 ]
  • C15H10IN3O [ No CAS ]
  • (E)-3-(6-oxo-5,6,7,12-tetrahydropyrido[2',3':2,3]azepino[4,5-b]indol-9-yl)-N-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36.4% With palladium diacetate; triethylamine In N,N-dimethyl-formamide at 100℃; for 0.666667h; Microwave irradiation; (E)-3-(6-Oxo-5,6,7,12-tetrahydropyrido[2',3':2,3]azepino[4,5-b]indol-9-yl)-N-phenyl-acrylamide (4f) A mixture of 9-iodo-7,12-dihydropyrido[2‘,3‘:2,3]azepino[4,5-b]indol-6(5H)-one (11a, 200mg, 0.530mmol), N-phenylacrylamide (13, 87mg, 0.59mmol), triethylamine (101mg, 1.00mmol, 0.14mL), and Pd(OAc)2 (7mg, 0.03mmol) in DMF (3 mL) was heated for 40 min to 100 °C in a sealed microwave reaction vial by means of a mono mode microwave device (100 W, 150 PSI, CEM Discover, CEM GmbH, Kamp-Lintfort, Germany). After cooling to room temperature the mixture was filtered through a charcoal frit. Upon addition of ethyl acetate (220 mL) to the filtrate a precipitate formed, which was filtered off, dried and crystallized from ethanol to yield a brown solid (76.0 mg, 36.4%), dec. starting at 236 °C; IR (KBr): 3242 (NH), 1660 (C=O), 1438 cm-1; 1H NMR (400MHz, DMSO-d6): δ = 11.96 (s, 1H), 10.42 (s, 1H), 10.12 (s, 1H), 8.45 (dd, 1H, 3JH,H = 4.7 Hz, 4JH,H = 1.8 Hz), 8.19 (dd, 1H, 3JH,H = 7.8 Hz, 4JH,H = 1.8 Hz), 8.01 (s, 1H), 7.78 - 7.66 (m, 3H), 7.52 (d, 2H, 4JH,H = 1.1 Hz), 7.41 - 7.29 (m, 3H), 7.13 - 7.01 (m, 1H), 6.83 (d, 1H, 3JH,H = 15.6 Hz), 3.68 (s, 2H); 13C NMR (100.6 MHz, DMSO-d6): δ = 171.2, 164.0, 147.8, 139.5, 138.6, 131.5, 126.8, 126.4, 117.5, 108.4 (quat C); 147.7, 141.6, 135.4, 128.7 (2C), 123.0, 121.7, 119.2 (2C), 119.1, 119.0 (2C), 112.1 (tert C); 31.8 (sec C); C24H18N4O2 (394.43); MS (EI): m/z = 394 ([M]+, 38), 302 ([C18H12N3O2]+, 100), 274 ([C17H12N3O]+, 94); HRMS (EI): m/z ([M]+) calcd. 394.14243, found 394.14244; HPLC: 94.9% at 254 nm, 96.4% at 280 nm, tN = 5.2 min, tM = 1.09 min (ACN/H2O; 40:60), max = 330, 347, 353 nm.
  • 27
  • [ 2058-74-4 ]
  • [ 2210-24-4 ]
  • 2-(3-hydroxy-1-methyl-2-oxoindolin-3-yl)-N-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With 1,4-diaza-bicyclo[2.2.2]octane; phenol In acetonitrile at 20℃; for 48h; Inert atmosphere; Procedure for the MBH reaction of N-phenylacrylamide (1a) with N-methylisatin (2a) DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.
  • 28
  • [ 1217-89-6 ]
  • [ 2210-24-4 ]
  • 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)-N-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With 1,4-diaza-bicyclo[2.2.2]octane; phenol In acetonitrile at 20℃; for 48h; Inert atmosphere; General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.
  • 29
  • [ 149096-95-7 ]
  • [ 2210-24-4 ]
  • 2-(3-hydroxy-2-oxo-1-(prop-2-ynyl)indolin-3-yl)-N-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With 1,4-diaza-bicyclo[2.2.2]octane; phenol In acetonitrile at 20℃; for 48h; Inert atmosphere; General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.
  • 30
  • [ 60434-13-1 ]
  • [ 2210-24-4 ]
  • 2-(5-chloro-3-hydroxy-1-methyl-2-oxoindolin-3-yl)-N-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With 1,4-diaza-bicyclo[2.2.2]octane; phenol; In acetonitrile; at 20℃; for 24h;Inert atmosphere; General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.
  • 31
  • [ 2058-72-2 ]
  • [ 2210-24-4 ]
  • 2-(5-bromo-3-hydroxy-1-methyl-2-oxoindolin-3-yl)-N-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With 1,4-diaza-bicyclo[2.2.2]octane; phenol; In acetonitrile; at 20℃; for 24h;Inert atmosphere; General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.
  • 32
  • [ 2210-24-4 ]
  • [ 189368-12-5 ]
  • (E)-3-(2-oxo-6-phenyl-2H-pyran-5-yl)-N-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With bis(benzonitrile)palladium(II) dichloride; oxygen; p-benzoquinone In dimethyl sulfoxide at 32℃; for 38h; Sealed tube;
  • 33
  • [ 421-83-0 ]
  • [ 2210-24-4 ]
  • 2-chloro-4,4,4-trifluoro-N-phenylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With dipotassium hydrogenphosphate; [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In 1,2-dichloro-ethane at 20℃; Sealed tube; Inert atmosphere; Irradiation;
48% With pyridine; copper dichloride In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; Schlenk technique; 4.2 General procedure for chlorotrifluoromethylation of alkenes General procedure: CuCl2 (7 mg, 10 mol%), alkene (0.5 mmol), 1,4-dioxane (2 mL), CF3SO2Cl (152 mg, 1.8 eq.) and pyridine (4 mg, 10 mol%) were added into a Schlenk tube under a N2 atmosphere. The reaction mixture was stirred at 100 °C for 1 h. After being cooled to room temperature, the solid was removed by filtration and washed with DCM (30 mL). The combined organic solution was evaporated, and the resulting crude product was purified by flash column chromatography to give the products 3 or 4.
  • 34
  • [ 31121-11-6 ]
  • [ 2210-24-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1H-imidazole / dichloromethane / 2 h / 20 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C 5: dmap / N,N-dimethyl-formamide / 1 h / Reflux
  • 35
  • [ 2210-24-4 ]
  • [ 108-98-5 ]
  • N-phenyl-3-(phenylsulfinyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tert.-butylhydroperoxide; methanesulfonic acid In decane; acetonitrile at 40℃; General procedure: General procedure: To a 1 mL screw cap vial charged with a magnetic stirring bar, dry acetonitrile (0.5ml), the olefin substrate (0.5 mmol, 1 equivalent), the thiol substrate (1.0 mmol, 2equiv.) and tBuOOH (5.5M solution in decane, 1.5 mmol, 3 equiv.) were added in thatorder. To the solution, methanesulfonic acid (3.55 μL, 10 mol%) was added and the reaction mixture was heated at 40°C (in an aluminum heating block) and stirred at 300 rpm. The vials were closed and only contained a small headspace of air, but nospecial treatment was necessary to exclude air or moisture. The reaction mixtures were analyzed by thin-layer-chromatography in order to determine the time when full conversion was reached. The reaction mixture was diluted, a small amount of silica was added and the solvent was removed under vacuum. The resulting powder was purified by column chromatography on silica gel using mixtures of hexane and acetone to afford the desired product.
  • 36
  • [ 2210-24-4 ]
  • [ 1538551-54-0 ]
  • [ 621-15-8 ]
YieldReaction ConditionsOperation in experiment
65% With 4-trifluoromethylbenzenethiol; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; caesium carbonate In N,N-dimethyl-formamide at 25℃; for 6h; Schlenk technique; Inert atmosphere; Irradiation;
  • 37
  • [ 2210-24-4 ]
  • [ 84379-72-6 ]
  • [ 74973-26-5 ]
YieldReaction ConditionsOperation in experiment
90% With 4-trifluoromethylbenzenethiol; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; caesium carbonate In N,N-dimethyl-formamide at 25℃; for 3h; Schlenk technique; Inert atmosphere; Irradiation;
  • 38
  • [ 2210-24-4 ]
  • 1-(tert-butyl) 2-(1,3-dioxoisoindolin-2-yl) (S)-pyrrolidine-1,2-dicarboxylate [ No CAS ]
  • tert-butyl 2-(3-oxo-3-(phenylamino)propyl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With 4-trifluoromethylbenzenethiol; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; caesium carbonate In N,N-dimethyl-formamide at 25℃; for 4h; Schlenk technique; Inert atmosphere; Irradiation;
  • 39
  • [ 2210-24-4 ]
  • 1,3-dioxoisoindolin-2-yl (tert-butoxycarbonyl)valinate [ No CAS ]
  • tert-butyl (2-methyl-6-oxo-6-(phenylamino)hexan-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 4-trifluoromethylphenyl disulfide; caesium carbonate In N,N-dimethyl-formamide at 25℃; for 5h; Schlenk technique; Inert atmosphere; Irradiation;
  • 40
  • [ 111-88-6 ]
  • [ 2210-24-4 ]
  • 3-(octylthio)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With C8H18NO3(1+)*C2H4NO2(1-) In water at 25℃; for 10h; Schlenk technique; Green chemistry;
73% With C9H20NO2(1+)*C2H3O2(1-) In water at 25℃; for 10h; Schlenk technique; Green chemistry; General procedure for the Michael condensation. General procedure: Sulfur or nitrogen nucleophile 1 (0.5 mmol), α,β-unsaturated amides 2 (0.5 mmol), [Nmp-PDO][OAc] (10 mol %) and water (1 mL) was added into a 25 mL Schlenk tube, and stirred at room temperature. Upon completion of the recation (monitored by TLC). The reaction mixture was extracted with ethyl acetate (3×5 mL), The organic and aqueous layers were separated, and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated and purified by column chromatography on silica gel employing petroleum ether/ethyl acetate as eluent to afford target product 3.
  • 41
  • [ 2210-24-4 ]
  • [ 108-98-5 ]
  • [ 126400-65-5 ]
YieldReaction ConditionsOperation in experiment
91% With C8H18NO3(1+)*C2H4NO2(1-) In water at 25℃; for 10h; Schlenk technique; Green chemistry;
81% With C9H20NO2(1+)*C2H3O2(1-) In water at 25℃; for 10h; Schlenk technique; Green chemistry; General procedure for the Michael condensation. General procedure: Sulfur or nitrogen nucleophile 1 (0.5 mmol), α,β-unsaturated amides 2 (0.5 mmol), [Nmp-PDO][OAc] (10 mol %) and water (1 mL) was added into a 25 mL Schlenk tube, and stirred at room temperature. Upon completion of the recation (monitored by TLC). The reaction mixture was extracted with ethyl acetate (3×5 mL), The organic and aqueous layers were separated, and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated and purified by column chromatography on silica gel employing petroleum ether/ethyl acetate as eluent to afford target product 3.
  • 42
  • [ 2210-24-4 ]
  • [ 106-45-6 ]
  • N-phenyl-3-(p-tolylthio)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With C8H18NO3(1+)*C2H4NO2(1-) In water at 25℃; for 10h; Schlenk technique; Green chemistry;
87% With C9H20NO2(1+)*C2H3O2(1-) In water at 25℃; for 10h; Schlenk technique; Green chemistry; General procedure for the Michael condensation. General procedure: Sulfur or nitrogen nucleophile 1 (0.5 mmol), α,β-unsaturated amides 2 (0.5 mmol), [Nmp-PDO][OAc] (10 mol %) and water (1 mL) was added into a 25 mL Schlenk tube, and stirred at room temperature. Upon completion of the recation (monitored by TLC). The reaction mixture was extracted with ethyl acetate (3×5 mL), The organic and aqueous layers were separated, and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated and purified by column chromatography on silica gel employing petroleum ether/ethyl acetate as eluent to afford target product 3.
  • 43
  • [ 2210-24-4 ]
  • [ 204711-96-6 ]
  • (S)-methyl 2-(tert-butoxycarbonylamino)-8-oxo-8-(phenylamino)octanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 2h; Inert atmosphere; Reflux; General procedure for cross metathesis General procedure: This was carried out in a manner as described in [36]. Grubb’ssecond generation catalyst 12 (10 mg, 0.012 mmol, 2.5 mol %)was added to a stirring solution of olefin 11 (130 mg,0.50 mmol) in dry DCM (1 mL) and then a solution of theappropriate electron-deficient olefin 13 (1.5 mmol) in dry DCM (1 mL) was added dropwise under an argon atmosphere. The resulting reaction mixture was then heated to reflux for 2 h. Thereaction mixture was allowed to cool to room temperature andthen concentrated in vacuo. The residue was subjected tocolumn chromatographic purification over silica gel using anappropriate mixture of ethyl acetate in hexane to provide thecoupled product as colorless viscous liquid.
  • 44
  • [ 2210-24-4 ]
  • methyl (S)-4-benzylhept-6-enoate [ No CAS ]
  • methyl (S,E)-4-benzyl-8-oxo-8-(phenylamino)oct-6-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 50 - 60℃; for 48h; Inert atmosphere; 14 4.2.2.14 Synthesis of methyl (S,E)-4-benzyl-8-oxo-8-(phenylamino)oct-6-enoate ((S)-16) To a solution of (S)-14 (162 mg, 0.7 mmol) in dry DCM (20 mL) was added 15 (103 mg, 0.7 mmol), and then air was replaced with argon. Grubbs' second generation catalyst (35 mg, 5 mol%) was added and the reaction was heated to 50-60 °C for 20 h. A second addition of Grubbs' second generation catalyst (35 mg, 5 mol%) was done and the reaction was heated to 50-60 °C for 28 h. The solvent was evaporated and the product was purified by flash silica-gel chromatography (ethyl acetate:hexanes 1:15 followed by 1:7-1:3), which yielded (S)-16 in 46% yield (112 mg). 1HNMR (400 MHz, CDCl3) δ (ppm): 1.67 (m, 2H), 1.88 (m, 1H), 2.18 (m, 2H), 2.33 (t, J = 8.0 Hz, 2H), 2.51 (dd, J = 7.6 and 13.6 Hz, 1H), 2.63 (dd, J = 6.4 and 13.6 Hz, 1H), 3.66 (s, 3H), 5.92 (d, J = 15.2 Hz, 1H), 6.91 (m, 1H), 7.12 (m, 3H), 7.21 (t, J = 7.2 Hz, 1H), 7.31 (m, 4H), 7.36 (s, 1H), 7.57 (dd, J = 7.6 Hz, 2H); 13CNMR (100 MHz, CDCl3) δ (ppm): 28.45, 31.67, 35.61, 38.93, 40.07, 51.65, 119.81, 124.27, 126.00, 126.16, 128.41, 129.01, 129.13, 138.02, 140.03, 143.84, 163.75, 173.97. IR: 3301, 3136, 3062, 3027, 2926, 1733, 1670, 1640, 1600, 1542, 1497, 1441 cm-1. LRMS (LC-SQMS, m/z); found: [M+H], 352.07, calculated for C22H26NO3, 352.19, found: [M+Na], 374.05, calculated for C22H25NO3Na, 374.17.
46% With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 50 - 60℃; for 48h; Inert atmosphere; II.B Synthesis of methyl (S,E)-4-benzyl-8-oxo-8-(phe- nylamino)oct-6-enoate ((S)-i 6) To a solution of(S)-14 (162 mg, 0.7 mmol) in dry DCM (20 mE) was added 15 (103 mg, 0.7 mmol), and then air was replaced with argon. Grubbs’ second generation catalyst (35 mg, 5 mol %) was added and the reaction was heated to 50-60° C. for 20 hours. A second addition of Grubbs’ second generation catalyst (35 mg, 5 mol %) was done and the reaction was heated to 50-60° C. for 28 hours. The solvent was evaporated and the product was purified by flash silica-gel chromatography (ethyl acetate:hexanes 1:15 followed by 1:7-1:3), which yielded (S)-16 in 46% yield (112 mg). ‘HNMR (400 MHz, CDC13) ö (ppm): 1.67 (m, 2H), 1.88 (m, 1H), 2.18 (m, 2H), 2.33 (t, J=8.0 Hz, 2H), 2.51 (dd, J=7.6 and 13.6 Hz, 1H), 2.63 (dd, J=6.4 and 13.6 Hz, 1H), 3.66 (s, 3H), 5.92 (d, J=15.2 Hz, 1H), 6.91 (m, 1H),7.12 (m, 3H), 7.21 (t, J=7.2 Hz, 1H), 7.31 (m, 4H), 7.36 (s, 1H), 7.57 (dd, J=7.6 Hz, 2H); ‘3CNMR (100 MHz, CDC13) ö (ppm): 28.45, 31.67, 35.61, 38.93, 40.07, 51.65, 119.81, 124.27, 126.00, 126.16, 128.41, 129.01, 129.13, 138.02,140.03, 143.84, 163.75, 173.97. IR: 3301, 3136, 3062, 3027, 2926, 1733, 1670, 1640, 1600, 1542, 1497, 1441 cm’. ERMS (EC-SQMS, mlz); found: [M+H], 352.07, calculated for C22H26N03, 352.19, found: [M+Na], 374.05, calculated for C22H25NO3Na, 374.17.
  • 45
  • [ 2210-24-4 ]
  • methyl (R)-4-benzylhept-6-enoate [ No CAS ]
  • methyl (R,E)-4-benzyl-8-oxo-8-(phenylamino)oct-6-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 50 - 60℃; for 48h; Inert atmosphere; 15 4.2.2.14 Synthesis of methyl (S,E)-4-benzyl-8-oxo-8-(phenylamino)oct-6-enoate ((S)-16) General procedure: To a solution of (S)-14 (162 mg, 0.7 mmol) in dry DCM (20 mL) was added 15 (103 mg, 0.7 mmol), and then air was replaced with argon. Grubbs' second generation catalyst (35 mg, 5 mol%) was added and the reaction was heated to 50-60 °C for 20 h. A second addition of Grubbs' second generation catalyst (35 mg, 5 mol%) was done and the reaction was heated to 50-60 °C for 28 h. The solvent was evaporated and the product was purified by flash silica-gel chromatography (ethyl acetate:hexanes 1:15 followed by 1:7-1:3), which yielded (S)-16 in 46% yield (112 mg).
  • 46
  • [ 2210-24-4 ]
  • [ 98-74-8 ]
  • (E)-3-((4-nitrophenyl)sulfonyl)-N-phenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tris(bipyridine)ruthenium(II) dichloride hexahydrate In acetonitrile at 20℃; for 4h; Irradiation; Inert atmosphere; chemoselective reaction; Preparation of products General procedure: A 10 mL reaction vessel with a magnetic stirring bar wasequipped with sulfonyl chloride(0.5 mmol), alkene (0.5 mmol), Ru(bpy)3Cl2·6H2O (1mol%), and acetonitrile (2 mL). The mixture was irradiated with a blue LED (5 W)and stirred under at r.t. in an air atmosphere for 4h. The distance of the reaction vialfrom the light is about 2 centimeter. After the reaction, the solvent was removed underreduced pressure. Purification of the crude product was achieved by flash columnchromatography using petrol ether/ethyl acetate (6:1~10:1) as eluent.
  • 47
  • [ 50-00-0 ]
  • [ 2210-24-4 ]
  • [ 442900-08-5 ]
YieldReaction ConditionsOperation in experiment
22% With 1,4-diaza-bicyclo[2.2.2]octane In water; <i>tert</i>-butyl alcohol; phenol at 55℃; Inert atmosphere; Sealed tube;
10% With 1,4-diaza-bicyclo[2.2.2]octane; phenol In water; <i>tert</i>-butyl alcohol at 55℃; for 72h; 7 Reference Example 7 N-phenylacrylamide (1.2 g, 8.15 mmol),1, 4-diazabicyclo [2.2.2] octane (914 mg, 8.15 mmol), paraformaldehyde (1.2 g, 40.8 mmol)Phenol (192 mg, 2.04 mmol)tert-butyl alcohol: water (volume ratio 3: 7)(4.0 mL), and reacted at 55 ° C. for 72 hours.Water (50 mL) was added to the reaction solution,And extracted with dichloromethane (100 mL × 3).The organic layer was washed with saturated brine (50 mL) and then dried over anhydrous sodium sulfate.The solvent was distilled off under reduced pressure,The obtained residue was purified by silica gel chromatography (50% ethyl acetate / hexane)2- (hydroxymethyl) -N-phenylacrylamide (146 mg, yield 10%) as a white solid.
  • 48
  • [ 626-58-4 ]
  • [ 2210-24-4 ]
  • 3-(4-methylpiperidin-1-yl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With C9H20NO2(1+)*C2H3O2(1-) In water at 25℃; for 10h; Schlenk technique; Green chemistry; General procedure for the Michael condensation. General procedure: Sulfur or nitrogen nucleophile 1 (0.5 mmol), α,β-unsaturated amides 2 (0.5 mmol), [Nmp-PDO][OAc] (10 mol %) and water (1 mL) was added into a 25 mL Schlenk tube, and stirred at room temperature. Upon completion of the recation (monitored by TLC). The reaction mixture was extracted with ethyl acetate (3×5 mL), The organic and aqueous layers were separated, and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated and purified by column chromatography on silica gel employing petroleum ether/ethyl acetate as eluent to afford target product 3.
  • 49
  • [ 2210-24-4 ]
  • [ 100-46-9 ]
  • [ 119852-06-1 ]
YieldReaction ConditionsOperation in experiment
82% With C9H20NO2(1+)*C2H3O2(1-) In water at 25℃; for 8h; Schlenk technique; Green chemistry; General procedure for the Michael condensation. General procedure: Sulfur or nitrogen nucleophile 1 (0.5 mmol), α,β-unsaturated amides 2 (0.5 mmol), [Nmp-PDO][OAc] (10 mol %) and water (1 mL) was added into a 25 mL Schlenk tube, and stirred at room temperature. Upon completion of the recation (monitored by TLC). The reaction mixture was extracted with ethyl acetate (3×5 mL), The organic and aqueous layers were separated, and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were dried over anhydrous Na2SO4, concentrated and purified by column chromatography on silica gel employing petroleum ether/ethyl acetate as eluent to afford target product 3.
  • 50
  • [ 50-00-0 ]
  • [ 5326-87-4 ]
  • [ 2210-24-4 ]
YieldReaction ConditionsOperation in experiment
71% With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; potassium carbonate; triphenylphosphine In acetonitrile at 20℃; for 4h; Schlenk technique; Inert atmosphere; Irradiation; 10 Example 10 In a Schlenk tube equipped with a magnetic stirrer, 163.2 mg of K2CO3 (1.5:1 molar ratio to N-bromoacetylaniline) and 314.4 mg of triphenylphosphine (with N-bromoacetylaniline) were added. The molar ratio is 1.5:1), 4.6 mg [Ir(ppy)2dtbbpy]PF6 (molar ratio to N-bromoacetylaniline is 0.005:1), 90 mg paraformaldehyde, 10 mL acetonitrile, 213 mg N-bromoacetylaniline, argon gas was bubbled for 5 minutes, under visible light, normal temperature, reaction time was 4 h, and the product was isolated and purified by petroleum ether-ethyl acetate to give the product as N-acryloylaniline (formula 10) 104 mg, yield 71 %.
  • 51
  • [ 4687-25-6 ]
  • [ 2210-24-4 ]
  • 4-methyl-2-phenylbenzofuro[3,2-c]pyridin-3(2H)-one [ No CAS ]
  • 53
  • [ 25637-18-7 ]
  • [ 2210-24-4 ]
  • N-phenyl-3-(tetrahydro-2H-pyran-4-yl)propanamide [ No CAS ]
  • 54
  • [ 64-17-5 ]
  • [ 2210-24-4 ]
  • [ 91247-36-8 ]
YieldReaction ConditionsOperation in experiment
58% With Quinuclidine; 2,2-bis(4-(trifluoromethyl)phenyl)-1,3,2λ4-oxazaborolidine; Ir[dF(CF3)ppy]2(4,4′-di-tert-butyl-2,2′-bipyridine)PF6 In acetonitrile at 25 - 33℃; for 14h; Irradiation; Sealed tube; Inert atmosphere; regioselective reaction; General Procedure for Photocatalytic C-H Alkylation of Alcohols General procedure: [Ir(dF(CF3)ppy)2(dtbpy)][PF6] (4a, 1.1 mg, 1.0 μmol, 1 mol%), quinuclidine (5a, 1.1 mg, 0.010 mmol, 10 mol%), and 2,2-bis(4-(trifluoromethyl)phenyl)-1,3,2λ4-oxazaborolidine (6j, 3.6 mg, 0.010 mmol, 10 mol%) were added to a dried screw-cap vial. Degassed MeCN (1.0 mL, [acceptor]final = 0.1 M), alcohol 1 (0.20 mmol, 2.0 eq), and Michael acceptor 2 (0.10 mmol, 1.0 eq) were added to the vial under an argon atmosphere or in a glove box, before the vial was sealed with the screw cap. The resulting mixture was then placed near the 430 nm light source (Valore VBP-L24-C2 with a 38W LED lamp; VBL-SE150-BBB(430)). The temperature (25- 33 °C) was controlled using a strong fan, and the vial was irradiated for 14 h with the blue LEDs under constant stirring. After evaporation of all volatiles, the residue was purified by flash column chromatography (GPC was used for the purification of 3aj and 3ie) to afford the targeted C-H alkylation product.
45% With quinuclidin-3-yl benzenesulfonate; 3,3,3',3'-tetrakis(trifluoromethyl)-1,1'(3H,3'H)-spirobi<2,1-benzoxasilole>; C36H16F16IrN4(1+)*F6P(1-) In acetonitrile at 20℃; for 14h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;
  • 55
  • [ 2210-24-4 ]
  • N-phenyl-3-sulfamoylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With tris-(trimethylsilyl)silane; sulphamoyl chloride; Eosin Y In acetonitrile at 20℃; for 16h; Irradiation;
  • 56
  • [ 1873-77-4 ]
  • [ 2210-24-4 ]
  • [ 13360-57-1 ]
  • [ 5565-32-2 ]
  • 3-(N,N-dimethylsulfamoyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 83% 2: 69% With Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 57
  • [ 20588-68-5 ]
  • [ 2210-24-4 ]
  • 3-(N,N-diethylsulfamoyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 58
  • [ 371150-44-6 ]
  • [ 2210-24-4 ]
  • 3-(N,N-bis(2-methoxyethyl)sulfamoyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 16h; Irradiation;
  • 59
  • [ 2210-24-4 ]
  • [ 36959-70-3 ]
  • 3-(N-benzyl-N-methylsulfamoyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 60
  • [ 1689-02-7 ]
  • [ 2210-24-4 ]
  • N-phenyl-3-(pyrrolidin-1-ylsulfonyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 61
  • [ 35856-62-3 ]
  • [ 2210-24-4 ]
  • N-phenyl-3-(piperidin-1-ylsulfonyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 62
  • [ 2210-24-4 ]
  • [ 41483-72-1 ]
  • 3-(azepan-1-ylsulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 63
  • [ 1828-66-6 ]
  • [ 2210-24-4 ]
  • 3-(morpholinosulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 64
  • [ 2210-24-4 ]
  • C6H9ClN2O2S [ No CAS ]
  • 3-((4-cyanopiperidin-1-yl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 65
  • [ 2210-24-4 ]
  • [ 765962-70-7 ]
  • ethyl 1-((3-oxo-3-(phenylamino)propyl)sulfonyl)piperidine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 66
  • [ 2210-24-4 ]
  • C6H12ClNO3S [ No CAS ]
  • 3-((3-(methoxymethyl)pyrrolidin-1-yl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 67
  • [ 2210-24-4 ]
  • C3H4ClF2NO2S [ No CAS ]
  • 3-((3,3-difluoroazetidin-1-yl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 68
  • [ 2210-24-4 ]
  • C4H8ClNO3S [ No CAS ]
  • 3-((3-methoxyazetidin-1-yl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 16h; Irradiation;
  • 69
  • [ 10438-96-7 ]
  • [ 2210-24-4 ]
  • 3-(N-methylsulfamoyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tris-(trimethylsilyl)silane; Eosin Y In acetonitrile at 20℃; for 16h; Irradiation;
  • 70
  • [ 1873-77-4 ]
  • [ 2210-24-4 ]
  • 3-(1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilan-2-yl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With Eosin Y In acetonitrile at 20℃; for 4h; Irradiation;
  • 71
  • [ 2210-24-4 ]
  • [ 4363-35-3 ]
  • (E)-N,5-diphenylpent-4-enamide [ No CAS ]
  • 72
  • [ 1873-77-4 ]
  • [ 2210-24-4 ]
  • [ 349-88-2 ]
  • [ 5565-32-2 ]
  • 3-((4-fluorophenyl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 82% 2: 69% With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In acetonitrile at 20℃; for 1h; Irradiation;
  • 73
  • [ 2210-24-4 ]
  • [ 98-68-0 ]
  • 3-((4-methoxyphenyl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 74
  • [ 2210-24-4 ]
  • [ 2991-42-6 ]
  • N-phenyl-3-((4-(trifluoromethyl)phenyl)sulfonyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 75
  • [ 2210-24-4 ]
  • [ 98-74-8 ]
  • 3-((4-nitrophenyl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 76
  • [ 2210-24-4 ]
  • [ 49584-26-1 ]
  • 3-((4-cyanophenyl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 77
  • [ 55854-46-1 ]
  • [ 2210-24-4 ]
  • 3-((5-bromothiophen-2-yl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 78
  • [ 16133-25-8 ]
  • [ 2210-24-4 ]
  • N-phenyl-3-(pyridin-3-ylsulfonyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 79
  • [ 2210-24-4 ]
  • C5H5ClN2O3S2 [ No CAS ]
  • 3-((5-acetamidothiazol-2-yl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 80
  • [ 2210-24-4 ]
  • [ 139631-62-2 ]
  • 3-(cyclopropylsulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 81
  • [ 10147-37-2 ]
  • [ 2210-24-4 ]
  • 3-(isopropylsulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 82
  • [ 2210-24-4 ]
  • [ 124-63-0 ]
  • N-phenyl-3-methanesulfonylpropionamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 83
  • [ 3518-65-8 ]
  • [ 2210-24-4 ]
  • 3-((chloromethyl)sulfonyl)-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 84
  • [ 2210-24-4 ]
  • [ 1311315-85-1 ]
  • benzyl 3-((3-oxo-3-(phenylamino)propyl)sulfonyl)azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
  • 85
  • tetrahydrofuran-3-ylsulfonyl chloride [ No CAS ]
  • [ 2210-24-4 ]
  • N-phenyl-3-((tetrahydrofuran-3-yl)sulfonyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 1h; Irradiation;
Same Skeleton Products
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