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[ CAS No. 35924-44-8 ] {[proInfo.proName]}

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Chemical Structure| 35924-44-8
Chemical Structure| 35924-44-8
Structure of 35924-44-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 35924-44-8 ]

CAS No. :35924-44-8 MDL No. :MFCD00111013
Formula : C11H8O5 Boiling Point : -
Linear Structure Formula :- InChI Key :XIQQAIQZABTSNZ-UHFFFAOYSA-N
M.W : 220.18 Pubchem ID :711717
Synonyms :

Calculated chemistry of [ 35924-44-8 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.09
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.94
TPSA : 76.74 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 2.17
Log Po/w (WLOGP) : 1.5
Log Po/w (MLOGP) : 0.95
Log Po/w (SILICOS-IT) : 1.81
Consensus Log Po/w : 1.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.9
Solubility : 0.275 mg/ml ; 0.00125 mol/l
Class : Soluble
Log S (Ali) : -3.41
Solubility : 0.0848 mg/ml ; 0.000385 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.12
Solubility : 0.167 mg/ml ; 0.000759 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.51

Safety of [ 35924-44-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 35924-44-8 ]

* 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 [ 35924-44-8 ]

[ 35924-44-8 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 672-13-9 ]
  • [ 141-82-2 ]
  • [ 35924-44-8 ]
YieldReaction ConditionsOperation in experiment
89% In water at 100℃; for 24h;
89% With HZSM-5 zeolite for 0.1h; microwave irradiation;
  • 2
  • [ 672-13-9 ]
  • [ 2033-24-1 ]
  • [ 35924-44-8 ]
YieldReaction ConditionsOperation in experiment
95% With [Cd2(2,2'-((1,4-phenylenebis(methylene))bis((pyridin-2-ylmethyl)azanediyl))diacetamide)(fumarate)2(H2O)2]*2H2O In methanol at 26 - 28℃; for 3h;
93% Stage #1: 2-hydroxy-5-methoxybenzaldehyde; cycl-isopropylidene malonate With potassium phosphate In ethanol at 20℃; for 1h; Stage #2: With ammonium chloride In ethanol
92% With ziconium(IV) oxychloride octahydrate for 0.1h; Neat (no solvent); Sonication;
84% With silica sulfuric acid at 120℃; for 0.533333h;
78% With triethylamine In ethanol at 60℃; for 15h;
65% In water at 75℃; for 2h;
In ethanol at 20℃; for 10h;
Stage #1: 2-hydroxy-5-methoxybenzaldehyde; cycl-isopropylidene malonate With piperdinium acetate at 25℃; Stage #2: In ethanol for 1h; Reflux;

  • 3
  • [ 41459-71-6 ]
  • [ 35924-44-8 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide In ethanol; water monomer for 1h; Reflux;
82% With sodium hydroxide In ethanol at 80℃; for 0.25h; 2.2.5. General synthetic procedure of compounds 12a-t General procedure: Compound 11 (5 mmol) in EtOH (5 mL) were added 10% NaOH (10mL). Next, the mixture was warmed to 80 °C and stirred for 15 min. The resulting mixture poured off in cold water to precipitate a large amount of solid product. The solid product was filtered off and recrystallized by EtOH to afford acid compounds 12a-t (except 12d, 12i, 12m, and 12q)in good yields.
With hydrogenchloride In acetic acid for 2h; Heating;
With hydrogenchloride; water monomer; sodium hydroxide
Stage #1: ethyl 6-methoxy-2-oxo-2H-chromene-3-carboxylate With lithium hydroxyde monohydrate In methanol; water monomer at 20℃; Stage #2: With hydrogenchloride In methanol; water monomer at 20℃; 6.1. General procedure for the synthesis of derivatives 1-58 General procedure: 3-Carbonyl coumarins were obtained by Knoevenagel cyclization between substituted salicylaldehydes (1 mmol) and methyl acetoacetate (1 mmol) or ethyl benzoylacetate (1 mmol) in ethanol (25 mL) with catalytic amounts of piperidine. The ethyl ester of coumarin-3-carboxylic acid was prepared by Knoevenagel reaction between diethyl malonate (1 mmol) and the appropriate salicylaldehyde (1 mmol) with catalytic amounts of piperidine in ethanol (50 mL). Then, if there was an hydroxyl group at position 7, etherification was performed by adding a suitable benzyl bromide (1 mmol) or cycloheptyl bromide (1 mmol), and potassium carbonate (1 mmol) in anhydrous acetone (100 mL), using N,N'-dicyclohexyl-18-crown-6-ether (1 mmol) as a chelating agent. Final products were purified by chromatography. Ethyl ester derivatives (1 mmol) were dissolved and stirred at room temperature in a solution of LiOH.H2O (6 mmol) in H2O/MeOH (1:5, v/v; 50 mL); then HCl 3 N (50 mL) was added. The suspension was filtered and the solid was dried under vacuum. 3-Carboxyhydrazido derivatives were obtained by dissolving at reflux 3-coumarin carboxylic acid (1 mmol) in thionyl chloride (20 mL). After solvent evaporation under vacuum, the reactive acyl chloride (1 mmol) was reacted with a suitable hydrazine hydrochloride (2 mmol) in the presence of sodium acetate (2 mmol) in H2O/CH3CN (1/4, v/v).
With sodium hydroxide In ethanol; water monomer for 2h; Reflux;
With sodium hydroxide In ethanol for 0.25h; Reflux; 4.1.9. General procedures for the preparation of compounds 14a-g and16a-r General procedure: To a solution of 13a-g or 15a-r (10 mmol) in EtOH (15 mL) wasadded 15 mL of 10% NaOH and heated under reflux for 15 min.Acidification to pH 2 using concentrated hydrochloric acid and coolingto 0 °C gave a deposit. The solid was filtrated, washed with water anddried to yield acids 14a-g and 16a-r.
With sodium hydroxide In ethanol at 95℃; for 2h; 4.3.3. General Procedures for the Preparation of Coumarin Derivatives 4a~4g General procedure: To a solution of intermediate 3a~3g in EtOH (20 mL), 10% NaOH (20 mL) was added.The reaction system was stirred at 95 C for 2 h, then cooled at room temperature andadjusted to be acidic (pH = 2) with HCl solution. Recrystallisation from the mixture solution(still standing at 0 C) obtained crud solid of coumarin derivatives. The crud solid waswashed with cooled H2O, and concentrated in vacuo to obtain white solid.

Reference: [1]Fonseca, André; Reis, Joana; Silva, Tiago; Matos, Maria João; Bagetta, Donatella; Ortuso, Francesco; Alcaro, Stefano; Uriarte, Eugenio; Borges, Fernanda [Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 7206 - 7212]
[2]Li, Wen-Bo; Qiao, Xue-Peng; Wang, Zi-Xiao; Wang, Shuai; Chen, Shi-Wu [Bioorganic Chemistry, 2020, vol. 105]
[3]Murata, Chiyomi; Masuda, Toshinobu; Kamochi, Yasuko; Todoroki, Kenichiro; Yoshida, Hideyuki; Nohta, Hitoshi; Yamaguchi, Masatoshi; Takadate, Akira [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 7, p. 750 - 758]
[4]Location in patent: experimental part Chimenti, Franco; Bizzarri, Bruna; Bolasco, Adriana; Secci, Daniela; Chimenti, Paola; Granese, Arianna; Carradori, Simone; Rivanera, Daniela; Zicari, Alessandra; Scaltrito, M. Maddalena; Sisto, Francesca [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 16, p. 4922 - 4926]
[5]Location in patent: experimental part Secci, Daniela; Carradori, Simone; Bolasco, Adriana; Chimenti, Paola; Yáñez, Matilde; Ortuso, Francesco; Alcaro, Stefano [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 4846 - 4852]
[6]Fonseca, André; Matos, Maria João; Vilar, Santiago; Kachler, Sonja; Klotz, Karl-Norbert; Uriarte, Eugenio; Borges, Fernanda [Chemical Biology and Drug Design, 2018, vol. 91, # 1, p. 245 - 256]
[7]Bai, Renren; Gu, Jinping; Guo, Jianan; Jiang, Xiaoying; Lv, Yangjing; Mi, Zhisheng; Shi, Yuan; Xie, Yuanyuan; Yao, Chuansheng; Zhang, Changjun; Zhou, Tao [Bioorganic and medicinal chemistry, 2020, vol. 28, # 12]
[8]Lu, Tao; Nie, Xuliang; Peng, Dayong; Wang, Jie; Xiong, Wanming; Yin, Zhongping; Zeng, Fanxin [Molecules, 2022, vol. 27, # 7]
  • 4
  • [ 35924-44-8 ]
  • [ 62-53-3 ]
  • N-phenyl-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;
  • 5
  • [ 672-13-9 ]
  • [ 35924-44-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: piperidine / ethanol / 0.5 h / Heating 2: aq. HCl / acetic acid / 2 h / Heating
Multi-step reaction with 2 steps 1.1: piperidine / ethanol 2.1: lithium hydroxyde monohydrate / methanol; water monomer / 20 °C 2.2: 20 °C
Multi-step reaction with 2 steps 1: PYRIMIDINE / ethanol / Reflux 2: sodium hydroxide / ethanol; water monomer / 1 h / Reflux
Multi-step reaction with 2 steps 1: piperidine / Reflux 2: sodium hydroxide / ethanol; water monomer / 2 h / Reflux
Stage #1: 2-hydroxy-5-methoxybenzaldehyde With piperidine; acetic acid In ethanol for 6h; Inert atmosphere; Reflux; Stage #2: With water monomer; sodium hydroxide In ethanol for 0.5h; Inert atmosphere; Reflux; Synthesis of compounds 3a-h; general procedure General procedure: A stirred solution of intermediate 2 (10 mmol) in EtOH was treatedwith methylmalonate (11 mmol), piperidine (50 μL) and glacial aceticacid. The mixture was heated under reflux for 6 h. This mixture wastreated slowly with a 0.5% NaOH aqueous solution and stirred for0.5 h at this temperature. The mixture was then poured into cool water,acidified to pH 2 with HCl (2 N), filtered and washed with alcohol togive the compounds 3a-h. The melting points of compounds 3a-h aregiven in the ESI.
Multi-step reaction with 2 steps 1: piperidine; acetic acid / ethanol / Reflux 2: sodium hydroxide / ethanol / 0.25 h / Reflux
Multi-step reaction with 2 steps 1: acetic acid; piperidine / ethanol / 95 °C 2: sodium hydroxide / ethanol / 2 h / 95 °C

  • 6
  • [ 872-85-5 ]
  • [ 931-53-3 ]
  • [ 35924-44-8 ]
  • [ 106-49-0 ]
  • N-cyclohexyl-8-methoxy-3,4-dioxo-1-(pyridin-4-yl)-2-p-tolyl-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% In methanol at 20℃; diastereoselective reaction;
  • 7
  • [ 872-85-5 ]
  • [ 931-53-3 ]
  • [ 35924-44-8 ]
  • [ 106-47-8 ]
  • 2-(4-chlorophenyl)-N-cyclohexyl-8-methoxy-3,4-dioxo-1-(pyridin-4-yl)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In methanol at 20℃; diastereoselective reaction;
  • 8
  • [ 872-85-5 ]
  • [ 931-53-3 ]
  • [ 35924-44-8 ]
  • [ 62-53-3 ]
  • N-cyclohexyl-8-methoxy-3,4-dioxo-2-phenyl-1-(pyridin-4-yl)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% In methanol at 20℃; diastereoselective reaction;
  • 9
  • [ 872-85-5 ]
  • [ 7188-38-7 ]
  • [ 35924-44-8 ]
  • [ 106-49-0 ]
  • N-tert-butyl-8-methoxy-3,4-dioxo-2-p-tolyl-1-(pyridin-4-yl)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% In methanol at 20℃; diastereoselective reaction;
  • 10
  • [ 872-85-5 ]
  • [ 7188-38-7 ]
  • [ 35924-44-8 ]
  • [ 106-47-8 ]
  • N-tert-butyl-2-(4-chlorophenyl)-8-methoxy-3,4-dioxo-1-(pyridin-4-yl)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In methanol at 20℃; diastereoselective reaction;
  • 11
  • [ 872-85-5 ]
  • [ 627-36-1 ]
  • [ 35924-44-8 ]
  • [ 104-94-9 ]
  • 8-methoxy-2-(4-methoxyphenyl)-3,4-dioxo-2-phenyl-N-propyl-1-(pyridin-4-yl)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% In methanol at 20℃; diastereoselective reaction;
  • 12
  • [ 872-85-5 ]
  • [ 627-36-1 ]
  • [ 35924-44-8 ]
  • [ 62-53-3 ]
  • 8-methoxy-3,4-dioxo-2-phenyl-N-propyl-1-(pyridin-4-yl)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In methanol at 20℃; diastereoselective reaction;
  • 13
  • [ 4279-77-0 ]
  • [ 35924-44-8 ]
  • [ 1366125-55-4 ]
YieldReaction ConditionsOperation in experiment
91% With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 12h;
  • 14
  • 4-4´dimethoxytrityl cysteine methyl ester [ No CAS ]
  • [ 35924-44-8 ]
  • C36H33NO8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-hydroxy-7-aza-benzotriazole; triethylamine; HATU In dichloromethane at 20℃; for 2h; Synthesis of Fluorescent Thiol Compound 6 Compound 6 was synthesized from 6-methoxy-coumarin-3-carboxylic acid and 4,4´-dimethoxytrityl protected cysteine methylester:A mixture of L-cysteine methyl ester hydrochloride (1 eq.) and 4,4'-dimethoxytriphenylmethyl chloride (1 eq.) in DMSO was stirred at RT overnight. Thereaction mixture was diluted with water and extracted with ethyl acetate. The combinedorganic extracts were dried over MgSO4 and the solvent was evaporated. 4-4´dimethoxytritylcysteine methylester was purified by silica-gel column chromatography with an ethylacetate/cyclohexane mobile phase.A mixture of 6-methoxy-coumarin-3-carboxylic acid (1 eq.), HATU (1.2 eq.), HOAT (1.2 eq.)and triethylamine (3 eq.) in dichloromethane was cooled in an ice-bath. 4-4´dimethoxytritylcysteine methylester (1 eq.) was added and the reaction mixture was allowed to come to RT. After stirring for 2 h, it was washed with 1 M KHSO4 and water. The organic phase wasseparated and dried over MgSO4. The product was isolated by silica-gel columnchromatography with an ethyl acetate/cyclohexane mobile phase.The 4-4´dimethoxytrityl protecting group was removed by 0.5% TFA in dichloromethane andthe final product 6 purified by silica-gel column chromatography with an ethylacetate/cyclohexane mobile phase.
  • 15
  • [ 118-48-9 ]
  • [ 2769-71-3 ]
  • [ 35924-44-8 ]
  • N-(2-carbamoylphenyl)-1-(2,6-dimethylphenyl)-4-(2-hydroxy-5-methoxyphenyl)-2, 5-dioxopyrrolidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With ammonium acetate In ethanol at 20℃; for 24h; 1 General procedure for the preparation of 2,5-dioxopyrrolidines General procedure: A mixture of coumarin-3-carboxylic acid (1 mmol), isocyanides (1 mmol), isatoic anhydride (1 mmol) and ammonium acetate (1 mmol) in ethanol (5 mL) was stirred at room temperature for 24 h. After completion of the reaction (TLC, eluent: EtOAc/n-hexane,1:1), the precipitated product was filtered and washed with EtOH (5 mL) to afford the pure product.
  • 16
  • [ 4279-77-0 ]
  • [ 35924-44-8 ]
  • (R)-S-phenyl 2-(6-methoxy-2-oxochroman-4-yl)ethanethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With C29H30N4O3S In tetrahydrofuran at 20℃; for 24h; Molecular sieve; Inert atmosphere; enantioselective reaction;
  • 17
  • [ 7188-38-7 ]
  • [ 35924-44-8 ]
  • [ 137-07-5 ]
  • 2-(5-methoxy-2-hydroxyphenyl)-N-(tert-butyl)-2-(2,3,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]thiazepin-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With immobilized Aspergillus niger lipase bonded on Fe3O4 nanoparticles In ethanol at 20℃; for 1h; Green chemistry; 3.1 General Procedure for the Preparation of Benzothiazepines General procedure: A mixture of coumarin-3-carboxylic acid derivative (1 mmol),alkyl isocyanide (1 mmol), aminobenzothiol (0.104 ml,1 mmol), and NBC (0.025 g) in 5 ml ethanol was stirred atroom temperature for 1 h. When the reaction (TLC, eluent:AcOEt/n-hexane 1:1) was completed, the nano biocatalyst was separated using a magnet, the solvent was removed under reduced pressure and the residue was separated by chromatography plates using n-hexane/AcOEt as eluent.
  • 18
  • [ 931-53-3 ]
  • [ 35924-44-8 ]
  • [ 137-07-5 ]
  • 2-(5-methoxy-2-hydroxyphenyl)-N-cyclohexyl-2-(2,3,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]thiazepin-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With immobilized Aspergillus niger lipase bonded on Fe3O4 nanoparticles In ethanol at 20℃; for 1h; Green chemistry; 3.1 General Procedure for the Preparation of Benzothiazepines General procedure: A mixture of coumarin-3-carboxylic acid derivative (1 mmol),alkyl isocyanide (1 mmol), aminobenzothiol (0.104 ml,1 mmol), and NBC (0.025 g) in 5 ml ethanol was stirred atroom temperature for 1 h. When the reaction (TLC, eluent:AcOEt/n-hexane 1:1) was completed, the nano biocatalyst was separated using a magnet, the solvent was removed under reduced pressure and the residue was separated by chromatography plates using n-hexane/AcOEt as eluent.
  • 19
  • [ 35924-44-8 ]
  • [ 108-44-1 ]
  • N-(3′-methylphenyl)-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;
73% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-amino-3-methylbenzene In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 20
  • [ 35924-44-8 ]
  • [ 108-42-9 ]
  • N-(3′-chlorophenyl)-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;
48% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 3-chloro-aniline In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 21
  • [ 35924-44-8 ]
  • [ 591-27-5 ]
  • N-(3′-hydroxyphenyl)-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;
57% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: m-Hydroxyaniline In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 22
  • [ 35924-44-8 ]
  • [ 106-49-0 ]
  • N-(4′-methylphenyl)-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;
61% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: <i>p</i>-toluidine In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 23
  • [ 35924-44-8 ]
  • [ 106-47-8 ]
  • N-(4′-chlorophenyl)-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;
49% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 4-chloro-aniline In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 24
  • [ 123-30-8 ]
  • [ 35924-44-8 ]
  • N-(4′-hydroxyphenyl)-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;
59% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 4-amino-phenol In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 25
  • [ 931-53-3 ]
  • [ 35924-44-8 ]
  • [ 17356-08-0 ]
  • N-carbamothioyl-1-cyclohexyl-4-(2-hydroxy-5-methoxyphenyl)-2,5-dioxopyrrolidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With lipase from Aspergillus niger; iron oxide In 1,4-dioxane at 60℃; for 4h; Green chemistry; diastereoselective reaction; 3.1. General procedure for the preparation of 2,5-dioxopyrrolidines General procedure: A mixture of coumarin-3-carboxylic acid derivative (1 mmol), alkyl isocyanide (1 mmol), thiourea derivative (1 mmol), and NBC (25 mg) in 10 mL of dioxane was stirred at 60 °C for 4 h. When the reaction (TLC, eluent: AcOEt/n-hexane 2/3) was completed, the NBC was separated using a magnet. The solvent was removed under reduced pressure and the residue was separated by chromatography plates using n-hexane/AcOEt as an eluent.
  • 26
  • [ 7188-38-7 ]
  • [ 35924-44-8 ]
  • [ 17356-08-0 ]
  • 1-(tert-butyl)-N-carbamothioyl-4-(2-hydroxy-5-methoxyphenyl)-2,5-dioxopyrrolidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With lipase from Aspergillus niger; iron oxide In 1,4-dioxane at 60℃; for 4h; Green chemistry; diastereoselective reaction; 3.1. General procedure for the preparation of 2,5-dioxopyrrolidines General procedure: A mixture of coumarin-3-carboxylic acid derivative (1 mmol), alkyl isocyanide (1 mmol), thiourea derivative (1 mmol), and NBC (25 mg) in 10 mL of dioxane was stirred at 60 °C for 4 h. When the reaction (TLC, eluent: AcOEt/n-hexane 2/3) was completed, the NBC was separated using a magnet. The solvent was removed under reduced pressure and the residue was separated by chromatography plates using n-hexane/AcOEt as an eluent.
  • 27
  • [ 931-53-3 ]
  • [ 35924-44-8 ]
  • [ 102-08-9 ]
  • 1-cyclohexyl-4-(2-hydroxy-5-methoxyphenyl)-2,5-dioxo-N-phenyl-N-(phenylcarbamothioyl)pyrrolidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With lipase from Aspergillus niger; iron oxide In 1,4-dioxane at 60℃; for 4h; Green chemistry; diastereoselective reaction; 3.1. General procedure for the preparation of 2,5-dioxopyrrolidines General procedure: A mixture of coumarin-3-carboxylic acid derivative (1 mmol), alkyl isocyanide (1 mmol), thiourea derivative (1 mmol), and NBC (25 mg) in 10 mL of dioxane was stirred at 60 °C for 4 h. When the reaction (TLC, eluent: AcOEt/n-hexane 2/3) was completed, the NBC was separated using a magnet. The solvent was removed under reduced pressure and the residue was separated by chromatography plates using n-hexane/AcOEt as an eluent.
  • 28
  • [ 35924-44-8 ]
  • [ 95-53-4 ]
  • N-(2′-methylphenyl)-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: <i>o</i>-toluidine In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 29
  • [ 90-04-0 ]
  • [ 35924-44-8 ]
  • N-(2'-methoxyphenyl)-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-methoxy-phenylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 30
  • [ 35924-44-8 ]
  • [ 95-51-2 ]
  • N-(2′-chlorophenyl)-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: o-chloroaniline In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 31
  • [ 536-90-3 ]
  • [ 35924-44-8 ]
  • N-(3'-methoxyphenyl)-6-methoxycoumarin-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: m-Anisidine In dichloromethane at 20℃; for 4h; Inert atmosphere;
  • 32
  • [ 35924-44-8 ]
  • (1R,3aR,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol [ No CAS ]
  • C30H40O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Microwave irradiation; Synthesis of compounds 4a-e, 5a-d,f-h under microwave irradiation; general procedure General procedure: A mixture of coumarin-3-carboxylic acid (6 mmol), vitamin D2 orvitamin D2 CD-ring alcohol (5 mmol), DCC (5 mmol) and DMAP(0.5 mmol) was irradiated in a MAS-1 microwave reactor apparatus at 400 W for 15 min. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate (2 × 50 mL), washed with water (2 × 60 mL) and brine (2 × 60 mL), and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified by silica gel column chromatography to give compounds 4a-e, 5a-d,f-h.
  • 33
  • [ 35924-44-8 ]
  • [ 108-98-5 ]
  • S-phenyl 6-methoxy-2-oxo-2H-chromene-3-carbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;
  • 34
  • [ 20432-44-4 ]
  • [ 35924-44-8 ]
  • 2-(2-methoxy-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-7-yl)acetaldehyde [ No CAS ]
  • 2-(2-methoxy-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-7-yl)acetaldehyde [ No CAS ]
  • 2-((6aS,7S,10aR)-2-methoxy-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-7-yl)acetaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 95% 2: 96 % ee With (-)-(S)-α,α-diphenylpyrrolidine-2-methanol methyl(diphenyl)silyl ether; p-N,N-dimethylaminobenzoic acid In chloroform at 20℃; for 24h; Overall yield = 95 %; diastereoselective reaction;
  • 35
  • [ 1287715-28-9 ]
  • [ 35924-44-8 ]
  • C20H16N2O4S [ No CAS ]
  • C20H16N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.429 % de In acetonitrile at 20℃; for 0.25h; Overall yield = 81 %; Overall yield = 61.6 mg; diastereoselective reaction; Compounds 3a-o; General Procedure General procedure: A solution of 1 (0.20 mmol) and 2 (0.22 mmol) in CH3CN (2.0 mL) was stirred at rt for 15 min. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc, 10:1 to 5:1) to furnish the corresponding product 3 as a white solid.
  • 36
  • [ 1426132-09-3 ]
  • [ 35924-44-8 ]
  • C21H18N2O4S [ No CAS ]
  • C21H18N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.615 % de In acetonitrile at 20℃; for 0.25h; Overall yield = 80 %; Overall yield = 63.1 mg; diastereoselective reaction; Compounds 3a-o; General Procedure General procedure: A solution of 1 (0.20 mmol) and 2 (0.22 mmol) in CH3CN (2.0 mL) was stirred at rt for 15 min. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc, 10:1 to 5:1) to furnish the corresponding product 3 as a white solid.
  • 37
  • [ 1354636-91-1 ]
  • [ 35924-44-8 ]
  • C25H18N2O4S [ No CAS ]
  • C25H18N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.615 % de In acetonitrile at 20℃; for 0.25h; Overall yield = 76 %; Overall yield = 67.2 mg; diastereoselective reaction; Compounds 3a-o; General Procedure General procedure: A solution of 1 (0.20 mmol) and 2 (0.22 mmol) in CH3CN (2.0 mL) was stirred at rt for 15 min. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc, 10:1 to 5:1) to furnish the corresponding product 3 as a white solid.
  • 38
  • [ 1287715-31-4 ]
  • [ 35924-44-8 ]
  • C26H20N2O4S [ No CAS ]
  • C26H20N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.5 % de In acetonitrile at 20℃; for 0.25h; Overall yield = 77 %; Overall yield = 70.2 mg; diastereoselective reaction; Compounds 3a-o; General Procedure General procedure: A solution of 1 (0.20 mmol) and 2 (0.22 mmol) in CH3CN (2.0 mL) was stirred at rt for 15 min. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc, 10:1 to 5:1) to furnish the corresponding product 3 as a white solid.
  • 39
  • [ 35924-44-8 ]
  • [ 149457-89-6 ]
  • N-(2-(3-hydroxy-2-methyl-4-oxopyridin-1(4H)-yl)ethyl)-6-methoxy-2-oxo-2H-chromene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.5% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; 2-mercaptothiazoline; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Stage #2: 1-(β-aminoethyl)-3-(benzyloxy)-2-methyl-4(1H)-pyridinone In dichloromethane at 20℃; for 24h; Stage #3: With boron trichloride In dichloromethane at -48 - 20℃; for 12h; Inert atmosphere; 7 Add 3-carboxy-6-methoxycoumarin (0.220g, 1mmol), dichloromethane (10mL), and then add dicyclohexylcarbodiimide (0.226g, 1.1mmol) in a 100mL single-neck flask, 2-Mercaptothiazoline (0.130g, 1.1mmol), 4-dimethylaminopyridine (5mg, 0.04mmol), reacted at room temperature for 24h, after the reaction, filtered, and the filtrate was concentrated for use.Add 1-(2-aminoethyl)-2-methyl-3-benzyloxypyridin-4-one (0.258g, 1mmol) and dichloromethane (10mL) into a 100mL single-neck flask, and add the above filtrate dropwise, React at room temperature for 24 hours. After the reaction is completed, the reaction solution is concentrated and purified by silica gel column chromatography (dichloromethane: methanol = 100:1-20:1 gradient elution) to obtain a white solid (0.158 g) with a yield of 34.4%.Add the above white solid (0.276g, 0.6mmol), anhydrous dichloromethane (10mL) to a 100mL single-necked flask, and dissolve 1.0mol/L boron trichloride (1.8mL) in anhydrous dichloromethane (15mL). In the constant pressure dropping funnel, N2Protect, slowly add boron trichloride dropwise at -48°C, after the drop, warm to room temperature and react for 12 hours.The reaction was monitored by TLC. After the conversion of the raw material was completed, methanol (10mL) was added dropwise to quench the reaction. After the drop was completed, after 0.5h of reaction, the reaction solution was concentrated and recrystallized with methanol/ether to obtain a white solid a3b1 (0.183g). Yield 82.5%.
Multi-step reaction with 2 steps 1.1: dicyclohexyl-carbodiimide; 2-mercaptothiazoline; dmap / dichloromethane / 24 h / 20 °C 1.2: 24 h / 20 °C 2.1: boron trichloride / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere
  • 40
  • [ 35924-44-8 ]
  • [ 149457-89-6 ]
  • N-(2-(3-(benzyloxy)-2-methyl-4-oxopyridin-1(4H)-yl)ethyl)-6-methoxy-2-oxo-2H-chromene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; 2-mercaptothiazoline; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Stage #2: 1-(β-aminoethyl)-3-(benzyloxy)-2-methyl-4(1H)-pyridinone In dichloromethane at 20℃; for 24h; 4.1.10. General procedures for the preparation of compounds 17a-f and19a-w General procedure: To a vigorously stirred suspension of coumarin-3-carboxylic acids14a-g or 16a-r (1 mmol) in DCM (10 mL) were added DCC (0.226 g, 1.1mmol), 2-mercaptothiazoline (0.130 g, 1.1 mmol), and a catalyticamount of DMAP (5 mg) in sequence. The mixture was stirred for 24 hat room temperature, the white precipitate N,N’-dicyclohexylurea(DCU) filtered from the yellow solution, the filtrate added to the amine3a-c, 8a-b, 11a-b (1 mmol) dissolved in DCM (10 mL), and the reactionmixture allowed to stir 24 h. After the reaction was complete, the solventwas removed in vacuo. The residue was further purified by columnchromatography on silica gel (eluant: DCM:MeOH = 100:1-20:1 gradientelution) to afford 17a-f or 19a-w as yellow solids.
  • 41
  • [ 672-13-9 ]
  • [ 105-53-3 ]
  • [ 35924-44-8 ]
YieldReaction ConditionsOperation in experiment
99.2% Stage #1: 2-hydroxy-5-methoxybenzaldehyde; diethyl malonate With piperidine; acetic acid In ethanol for 9h; Reflux; Stage #2: With ethanol; water; sodium hydroxide for 0.25h; Reflux; 7 Add 2-hydroxy-5-methoxybenzaldehyde (3.04g, 20mmol), diethyl malonate (3.84g, 24mmol), piperidine (0.2mL), 2 drops of acetic acid, ethanol ( 24mL), reflux and react for 9h. After the reaction is over, cool and pour into 40mL ice water to precipitate a solid, filter, wash with 50% ice ethanol, and recrystallize with 50% ice ethanol to obtain a yellow-green solid (4.69g). The rate is 94.6%.Add the above-mentioned yellow-green solid (2.48g, 10mmol), 10% sodium hydroxide (15mL), ethanol (15mL) to a 100mL single-necked flask, and react at reflux for 15min. After the reaction, add hydrochloric acid dropwise to adjust pH 2, precipitate solids, and filter , Washed with water and dried to obtain 3-carboxy-6-methoxycoumarin (2.18g) as a yellow-green solid, with a yield of 99.2%.
  • 42
  • [ 35924-44-8 ]
  • [ 149457-89-6 ]
  • 6-hydroxy-N-(2-(3-hydroxy-2-methyl-4-oxopyridin-1(4H)-yl)ethyl)-2-oxo-2H-chromene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.2% Stage #1: 6-methoxycoumarin-3-carboxylic acid With dmap; 2-mercaptothiazoline; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Stage #2: 1-(β-aminoethyl)-3-(benzyloxy)-2-methyl-4(1H)-pyridinone In dichloromethane at 20℃; for 24h; Stage #3: With boron trichloride In dichloromethane at -48 - 20℃; for 12h; Inert atmosphere; 9 Add 3-carboxy-6-methoxycoumarin (0.220g, 1mmol), dichloromethane (10mL), and then add dicyclohexylcarbodiimide (0.226g, 1.1mmol) in a 100mL single-neck flask, 2-Mercaptothiazoline (0.130g, 1.1mmol), 4-dimethylaminopyridine (5mg, 0.04mmol), reacted at room temperature for 24h, after the reaction, filtered, and the filtrate was concentrated for use.Add 1-(2-aminoethyl)-2-methyl-3-benzyloxypyridin-4-one (0.258g, 1mmol) and dichloromethane (10mL) into a 100mL single-neck flask, and add the above filtrate dropwise, React at room temperature for 24 hours. After the reaction is completed, the reaction solution is concentrated and purified by silica gel column chromatography (dichloromethane: methanol = 100:1-20:1 gradient elution) to obtain a white solid (0.158 g) with a yield of 34.4%.Add the above white solid (0.276g, 0.6mmol), anhydrous dichloromethane (10mL) to a 100mL single-neck flask, dissolve boron tribromide (1.503g, 6.0mmol) in anhydrous dichloromethane (15mL) and place in a constant temperature. In the pressure dropping funnel, under N 2 protection, slowly add boron tribromide dropwise at -48°C, after the drop is completed, the temperature is raised to room temperature and reacted for 12 hours. The reaction was monitored by TLC. After the conversion of the raw materials was completed, methanol (10mL) was added dropwise to quench the reaction. After the drop was completed, after 0.5h of reaction, the reaction solution was concentrated and recrystallized with methanol/ether to obtain a white solid a5b1 (0.205g). Yield 96.2%.
  • 43
  • [ 96826-11-8 ]
  • [ 35924-44-8 ]
  • 3,4-bis(benzyloxy)phenethyl 6-methoxy-2-oxo-2H-chromene-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; Inert atmosphere; 2.2.6. General synthetic procedure of compounds 13a-t General procedure: To a solution of 9 (1.0 mmol) and 12 (1.2 mmol) in dry DCM (5 mL), DMAP (2.0 mmol) and EDCI (1.2 mmol) were added under an atmosphere of argon, and the mixture was allowed to stir for 24 h. Next, the resulting mixture was washed with 1 M HCl (5 mL). The organic phases were dried, filtered, and evaporated in vacuo. Compounds 13b-t were obtained by chromatography column (PE: EA = 10:1), but 13q and 13rwere used directly in the next reaction without purification.
  • 44
  • [ 35924-44-8 ]
  • [ 21103-33-3 ]
  • 6‐methoxy‐N‐{4‐[4‐(2‐methoxyphenyl)piperazin‐1‐yl]butyl}‐2‐oxo‐2H‐chromene‐3‐carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;
  • 45
  • [ 16179-97-8 ]
  • [ 35924-44-8 ]
  • 6-methoxy-4-[(pyridin-2-yl)methyl]-3,4-dihydro-2H-1-benzopyran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 4-methyl-morpholine In tetrahydrofuran at 20℃; Sealed tube; 4.2. General Procedure General procedure: An ordinary screw-cap vial was charged with a magnetic stirring bar; the correspondingcoumarin-3-carboxylic acid 2 or chromone-3-carboxylic acid 3 (0.1 mmol, 1equivalent), THF (0.2 mL), N-methyl morpholine (0.17 mmol, 1.7 equivalent), and pyridylaceticacid hydrochloride 1 or 6 (0.15 mmol, 1.5 equivalent) was added. The reactionmixture was stirred at room temperature and monitored by 1H NMR spectroscopy. Afterthe complete consumption of the carboxylic acid 2a or 3a, the mixture was directly subjectedto FC on silica gel (n-hexane:ethyl acetate 3:1 or 2:1) to afford the pure products 4,5 or 7.The ultrasound variant of the reaction proceeded under the same reaction conditions,however without a stirring bar and with the shorter reaction time of 1.5 h.
  • 46
  • [ 100-42-5 ]
  • [ 35924-44-8 ]
  • (E)-6-methoxy-3-styryl-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With C44H36Cl2PdSe2; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 10h; regioselective reaction;
  • 47
  • C22H31N3 [ No CAS ]
  • [ 35924-44-8 ]
  • 6-methoxy-2-oxo-N-(5-((4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)amino)pentyl)-2H-chromene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; 4.4.3. General Procedures for the Preparation of Coumarin-BMT Hybrids 7a~9g General procedure: To a solution of intermediate 6a~6c (1 mmol) and coumarin derivatives 4a~4g (1 mmol)in CH2Cl2 (20 mL), benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate(PyBOP, 1.3 mmol) and triethylamine (2.6 mmol) were added. The reaction systemwas stirred at room temperature until the reaction was fully carried out, then washed by10% citric acid solution, 10% NaHCO3 solution and distilled water in turn, extracted byCH2Cl2 three times. The organic layer was dried over anhydrous MgSO4, concentrated invacuo and purified by flash column chromatography with PE/EA/triethylamine.
  • 48
  • C23H33N3 [ No CAS ]
  • [ 35924-44-8 ]
  • 6-methoxy-2-oxo-N-(6-((4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)amino)hexyl)-2H-chromene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; 4.4.3. General Procedures for the Preparation of Coumarin-BMT Hybrids 7a~9g General procedure: To a solution of intermediate 6a~6c (1 mmol) and coumarin derivatives 4a~4g (1 mmol)in CH2Cl2 (20 mL), benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate(PyBOP, 1.3 mmol) and triethylamine (2.6 mmol) were added. The reaction systemwas stirred at room temperature until the reaction was fully carried out, then washed by10% citric acid solution, 10% NaHCO3 solution and distilled water in turn, extracted byCH2Cl2 three times. The organic layer was dried over anhydrous MgSO4, concentrated invacuo and purified by flash column chromatography with PE/EA/triethylamine.
  • 49
  • C24H35N3 [ No CAS ]
  • [ 35924-44-8 ]
  • 6-methoxy-2-oxo-N-(7-((4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)amino)heptyl)-2H-chromene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; 4.4.3. General Procedures for the Preparation of Coumarin-BMT Hybrids 7a~9g General procedure: To a solution of intermediate 6a~6c (1 mmol) and coumarin derivatives 4a~4g (1 mmol)in CH2Cl2 (20 mL), benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate(PyBOP, 1.3 mmol) and triethylamine (2.6 mmol) were added. The reaction systemwas stirred at room temperature until the reaction was fully carried out, then washed by10% citric acid solution, 10% NaHCO3 solution and distilled water in turn, extracted byCH2Cl2 three times. The organic layer was dried over anhydrous MgSO4, concentrated invacuo and purified by flash column chromatography with PE/EA/triethylamine.
  • 50
  • [ 100-48-1 ]
  • [ 35924-44-8 ]
  • 6-methoxy-4-(pyridin-4-yl)chroman-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With fac-tris(2-phenylpyridinato-C<SUP>2</SUP>,N)iridium(III); triethylamine In dimethyl sulfoxide at 20℃; for 48h; Schlenk technique; Irradiation; Inert atmosphere;
Same Skeleton Products
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