* 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.
With potassium carbonate; In acetone; at 60℃; for 5h;
General procedure: 4-Hydroxybenzaldehyde (1.0 g, 8.19 mmol), 3-fluorobenzyl bromide (1.06 mL, 8.64 mmol), potassium carbonate (4.30 g, 32.76 mmol) and acetone (50 mL) were sequentially added to a 100 mL single-neck round bottom flask. ,Reaction at 60 C for 5 h, Cool to room temperature, filter, and collect the filtrate.Purification by direct column chromatography (petroleum ether/ethyl acetate (v/v) = 10/1)The title compound was obtained as a white solid (1.78 g, 94.4%).
With 1,1-diphenyl-2-picrylhydrazyl; potassium carbonate; In acetonitrile; at 50℃; for 24h;
General procedure: 20 mmol (2.44 g) of p-hydroxybenzaldehyde was added to a 250 mL round bottom flask, respectively.20mmol (2.76g) potassium carbonate, 22mmol (4.048g) 4-methylbenzyl bromide, add 50mL acetonitrile and stir evenly, add a few milligrams of 1,1-biphenyl-2-picrylhydryl group, and warm up to 50 C , reaction 24 hours to the end point (TLC test).Cooled to room temperature, suction filtered under reduced pressure, washed with dichloromethane, and then filtered.The organic phases were combined and dried over anhydrous Na 2 SO 4 .The filtrate was concentrated under reduced pressure and the filtrate was concentrated to give an orange solid powder.
2
1-(5-carboxypentyl)-5,6-dichloro-2,3-dimethyl-benzoimidazolium bromide[ No CAS ]
[ 149833-95-4 ]
[ 107-15-3 ]
[ 76-05-1 ]
1-[5-(2-amino-ethylcarbamoyl)-pentyl]-2-{2-[4-(4-bromo-benzyloxy)-phenyl]-vinyl}-5,6-dichloro-3-methyl-3<i>H</i>-benzoimidazol-1-ium; trifluoro-acetate[ No CAS ]
General Method A [44] and [47]a) A Claisen-Schmidt condensation was performed between 4-piperidine hydrochloride monohydrate and the appropriate aryl aldehyde at a molar ratio 1:2 in acetic acid. Dry hydrogen chloride was passed through the mixture for at least 1 h. After stirring at room temperature, the end of the reaction was monitored by TLC. The precipitate was then collected and added to a mixture of saturated aqueous potassium carbonate solution (25% w/v, 25 mL) and acetone (25 ml). The resultant mixture was stirred for 0.5 h. The free base is collected, washed with water (50 mL) and recrystallized from 95% aqueous ethanol. In the case where no precipitate was formed after the water dropping, extraction with 3 ? 50 ml chloroform was performed and the organic base was collected and dried over K2CO3.
With potassium carbonate; In butanone; for 6h;Reflux;
A mixture of 4-hydroxybenzaldehyde (1.22 g, 10 mmol), 4-bromobenzyl bromide (2.5 g, 10 mmol) and anhydrous K2CO3 (2.76 g, 20 mmol) in 2-butanone (25 mL) was refluxed for 6 h. The solvent was removed under reduced pressure to give a residue that was partitioned between water (50 mL) and ethyl acetate (30 mL). The organic phase was washed successively with dilute KOH, water and brine, and then the solvent was evaporated under reduced pressure. The residue was recrystallized from a small volume of ethanol to give the aldehyde (1.95 g, 67%) as a light yellow solid, mp 88-89 C (lit.44 mp 91 C).
With piperidine; acetic acid; In ethanol; for 12h;Reflux;
General procedure: To a suspension of 1 (1.1 mmol) in dry ethanol (10 mL), the 4-[(substitutedbenzyl)oxy]benzaldehydes 5a-j (1 mmol), a catalytic amount of piperidine (0.1 mmol) and glacial acetic acid (0.1 mmol) were added. The mixture was stirred and refluxed overnight. After cooling, the solvent was evaporated in vacuo, dried, and purified by silica gel column chromatography (dichloromethane/methanol, 200:1). The yield, melting point and spectral data of each compound are given below.
With potassium carbonate; In acetonitrile; at 80℃;
General procedure: A mixture of 4-hydroxybenzaldehyde (1.0 g, 8.2 mmol), K2CO3 (2.2 g, 8.2 mmol), and alkyl bromide or benzyl chloride derivatives (8.2 mmol) were placed into a round bottomed flask containing 30 mL of acetonitrile. The mixture was then stirred and heated at 80 C for 12-24 h. After the completion of the reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (30 mL), washed with water (10 mL 3), and then dried over anhydrous MgSO4 to give compounds 6a-w.
With potassium carbonate; In acetone;
General procedure: To a solution consisting of hydroxyl benzaldehyde (10 mmol), vanillin or 6-hydroxy-2-naphthaldehyde (10 mmol) and K2CO3 (10 mmol) in dry DMF (20 mL), the corresponding substituted benzyl chloride (10 mmol) was added to the stirred solution 8-12h at 60 oC. After the reaction is completed, the mixture was poured into ice water. The resulting precipitate was filtered, recrystallized with ethanol to obtain crude products which purified by column chromatography (dichloromethane : petroleum ether = 10 : 1).
With potassium carbonate; In acetone; for 4h;Reflux;
General procedure: Compound 6 was synthesized as previously reported [36].A mixture of hydroxyaromatic aldehydes (1.0 mmol), appropriatebenzyl chlorides (1.2 mmol), and anhydrous sodium carbonatewas stirred for 4 h in refluxing acetone. The solvent wasevaporated under reduced pressure and the residue was dissolvedin dichloromethane, washed using water and brine, dried overanhydrous MgSO4, and the solvent was removed under reducedpressure. The resulting residue was purified through silica gel columnchromatography (dichloromethane/PE, 5:1 v/v) to affordcompounds 2-5 as white solids. To a solution of each of compounds2-5 (1.0 mmol) and compound 6 (1.0 mmol) in absoluteethanol (5 mL), was added drops of glacial acetic acid and piperidine.The reaction mixture was stirred at 80 C for 2-6 h, until thecompletion of the reaction as evidenced through TLC. The resultingreaction mixture was concentrated to dryness, and purifiedthrough silica gel column chromatography (dichloromethane/methanol/acetic acid, 100:1:1) to afford the pure products 7-10.The yield, melting point and spectral data of each compound aregiven below.
General procedure: Compound 5 (0.4 g, 2.4 mmol) and triethylamine (3mL) were added in 15 mL of ethanol. The reaction mixture was stirred at 40 C for 1 h, and compounds 6a-w (2.4 mmol) were then added and refluxed for 12-24 h. After the completion of the reaction, NaBH4 (0.5g, 13.2 mmol) was added slowly in an ice bath with stirring, and the mixture was allowed to stir at room temperature for 10 h. After the evaporation of the solvent, the residue was extracted with ethyl acetate (30 mL), washed with water (10 mL 3), and then dried over anhydrous MgSO4. After removing the solvent under reduced pressure, the residue was recrystallized in ethyl acetate to afford compounds 7a-w with yields of 65-80%.
3-(4-(4-bromobenzyloxy)phenyl)-1-(thiophen-2-yl)-2-propen-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
With potassium hydroxide; In methanol;Sonication;
General procedure: A modified Claisen-Schmidt condensation was followed. Equimolar amounts of a suitable substituted acetophenone (10 mmol) and of a suitable substituted aromatic aldehyde (10 mmol) were used. Each reagent was dissolved in methanol, and the total volume of the used solvent was 20 mL. The methanolic solution of the substituted acetophenone was slowly added under stirring in them ethanolic solution of the aldehyde, followed by the addition of 5 mL of potassium hydroxide (15% w/v). The reaction was carried out in an ultrasound bath and has been monitored by thin-layer chromatography. The reaction mixture was cooled by an ice bath and was acidified with an aqueous solution of hydrochloric acid (10%). The precipitate was filtered off and washed repeatedly with water. In case no precipitate was formed, the mixture was extracted with 3 × 40 mL of dichloromethane or chloroform; the organic layer was collected, dried over sodium sulfate, evaporated to dryness and was recrystallized with methanol. Chalcones 1ii, 1iv-vi are referred to in the literature.
72%
With sodium hydroxide; In ethanol; water; at 20℃;
General procedure: To a solution of the aldehyde (5 mmol) in ethanol (minimum volume required to solve the aldehyde at room temperature) was added 2-acetylthiophene (630 mg, 5 mmol) followed by 3-4 drops of 10% aq. NaOH. The mixture was stirred at room temperature overnight, then it was refrigerated for 2 h. The solid was filtered, washed with cold ethanol (5 mL), and recrystallized from the appropriate solvent.
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 0 - 20℃; for 16h;Inert atmosphere;
General procedure: To a stirred and ice-bath cooled mixture of the phenol (1 equiv) in anhydrous THF (9 ml), was added the alcohol (1 equiv). Triphenylphosphine (PPh3) (1.1 equiv) was added portionwise to this mixture and the system was kept under nitrogen by evacuation and filling with nitrogen three times. Subsequently, diisopropyl azodicarboxylate (DIAD) (94 wt % solution in toluene, 1.1 equiv) was added in a strictly dropwise fashion. The reaction mixture was first stirred for 1h at 0C and then overnight at room temperature. After completion of the reaction as indicated by TLC, the reaction mixture was concentrated under reduced pressure. The residue was extracted with EtOAc (2x) and the combined extract was washed successively with saturated aqueous NaHCO3 and sodium chloride (NaCl) solutions, dried over anhydrous MgSO4 and concentrated in-vacuo affording an oily residue. The crude oil was chromatographed on flash column to yield the desired ether derivative.
With piperidine; benzoic acid; In toluene; for 16h;Reflux; Dean-Stark;
General procedure: To a stirred solution of the appropriate benzaldehyde derivative (1 equiv) in toluene (50 ml) were sequentially added thiazolidine-2,4-dione (3; 1 equiv), benzoic acid (0.5 equiv) and piperidine (0.5 equiv). The flask was connected to a Dean-Stark apparatus and a reflux condenser. After refluxing overnight, the reaction mixture is reduced then cooled and placed in the fridge overnight. In case of formed precipitant, the reaction suspension was filtered and the residue was washed with cold water and hexane. The washed residue was dried in oven at 45C overnight affording the desired derivatives of the 5-benzylidenethiazolidine-2,4-dione as canary yellow residues. However, in case of absence of precipitant, the reaction mixture was extracted with EtOAc (2x), washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated in vacuo affording the canary yellow crude residues. In both cases, the residue was used for the next step without further purification or analysis.
With copper; potassium carbonate; In nitrobenzene; for 6h;Reflux; Inert atmosphere;
The 501mg (3mmol) carbazole, 873mg (3mmol) 4- (4- bromo-benzyloxy) benzaldehyde, 828mg (6mmol)Of anhydrous potassium carbonate and 95mg (1.5mmol) of copper powder placed 100mL single jar, add 30mL nitrobenzene, nitrogenUnder the protection of air heated to reflux 6h, the reaction was stopped, cooled, filtered, and evaporated under reduced pressure nitrobenzene, column chromatography (ethylAcetate: petroleum ether = 1:30) to give yellow needles, NMR confirmed the molecular structure, yield = 53%.
6-(4-((4-bromobenzyl)oxy)phenyl)-N<SUP>2</SUP>,N<SUP>2</SUP>-dimethyl-3,6-dihydro-1,3,5-triazine-2,4-diamine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
With acetic acid;Reflux;
General procedure: Synthesized intermediate compounds (1 mmol) and Moroxydine hydrochloride or Metformin hydrochloride (1 mmol) were refluxed in glacial acetic acid (10 mL) at 120 oCfor 4-6 h. The whole processes of the reactions were traced by TLC, then removed solvent under reduced pressure. The crude products were purified by column chromatography (dichloromethane : methanol = 20 : 1).
(1S*,2R*)-N-(4-((4-bromobenzyl)oxy)benzyl)-2-phenylcyclopropan-1-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
72%
General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound.
2-(4-((4-bromobenzyl)oxy)benzylidene)malononitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
95%
With silica sodium carbonate nanoparticles; In acetonitrile; at 70℃;Sonication; Green chemistry;
General procedure: 4-morpholinobenzaldehyde (1 mmol, 0.191 g) was added to a stirred mixture of malononitrile (1.5 mmol, 0.099 g), and catalytic amount of SSC NPs (0.012 g, 2 mol%) in ace-tonitrile (10 mL). It was allowed to the mixture to stir at 70 C under sonication about 25-60 minutes. After completion of the reaction (the reaction progress was monitored by TLC using EtOAc/n-hexane (1:1) as eluent), the reaction mixture was filtered to separate precipitate. Next, the pre-cipitate was dissolved in boiling ethanol and then was fil-trated to separate catalyst. Finally, pure crystalline product was obtained from filtrate. Since the catalyst is reusable, at the end of the reaction, it was washed by boiling methanol three times (3 × 2 mL), dried at 90 C for 2 h and re-used in further cycles. Also, in the following, we explain more details about reusability results of the catalyst on model reaction.
methyl (E)-3-(4-((4-bromobenzyl)oxy)phenyl)-2-cyanoacrylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
95%
With silica sodium carbonate nanoparticles; In acetonitrile; at 70℃;Sonication; Green chemistry;
General procedure: 4-morpholinobenzaldehyde (1 mmol, 0.191 g) was added to a stirred mixture of malononitrile (1.5 mmol, 0.099 g), and catalytic amount of SSC NPs (0.012 g, 2 mol%) in ace-tonitrile (10 mL). It was allowed to the mixture to stir at 70 C under sonication about 25-60 minutes. After completion of the reaction (the reaction progress was monitored by TLC using EtOAc/n-hexane (1:1) as eluent), the reaction mixture was filtered to separate precipitate. Next, the pre-cipitate was dissolved in boiling ethanol and then was fil-trated to separate catalyst. Finally, pure crystalline product was obtained from filtrate. Since the catalyst is reusable, at the end of the reaction, it was washed by boiling methanol three times (3 × 2 mL), dried at 90 C for 2 h and re-used in further cycles. Also, in the following, we explain more details about reusability results of the catalyst on model reaction.
ethyl (E)-3-(4-((4-bromobenzyl)oxy)phenyl)-2-cyanoacrylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
98%
With silica sodium carbonate nanoparticles; In acetonitrile; at 70℃;Sonication; Green chemistry;
General procedure: 4-morpholinobenzaldehyde (1 mmol, 0.191 g) was added to a stirred mixture of malononitrile (1.5 mmol, 0.099 g), and catalytic amount of SSC NPs (0.012 g, 2 mol%) in ace-tonitrile (10 mL). It was allowed to the mixture to stir at 70 C under sonication about 25-60 minutes. After completion of the reaction (the reaction progress was monitored by TLC using EtOAc/n-hexane (1:1) as eluent), the reaction mixture was filtered to separate precipitate. Next, the pre-cipitate was dissolved in boiling ethanol and then was fil-trated to separate catalyst. Finally, pure crystalline product was obtained from filtrate. Since the catalyst is reusable, at the end of the reaction, it was washed by boiling methanol three times (3 × 2 mL), dried at 90 C for 2 h and re-used in further cycles. Also, in the following, we explain more details about reusability results of the catalyst on model reaction.
98%
With molybdenum(VI) oxide; In ethanol; water; at 20℃; for 1h;Green chemistry;
General procedure: 4(morpholinoethoxy)benzaldehyde (1 mmol, 0.235 g)was added to a stirring mixture of ethyl cyanoacetate(1.5 mmol, 0.170 g), and the catalytic amount of MoO3NPs (0.004 g, 3 mol%) in EtOH/H2O (4:1). It was allowedto the mixture to stir at room temperature for the timeindicated in Table II. After compilation of the reaction (thereaction progress was controlled by TLC EtOAc/n-hexane(1:1) as eluent), the reaction mixture was filtered to separateprecipitate. Next, the precipitate was dissolved in boilingethanol and filtrated to separate catalyst. In the end,formed crystalline product was filtrated to obtain the crystallinepure product.
Corresponding aldehydes containing alkylamine ethers was synthesized according to the procedure reported in the lit-erature,[45a] and all structures were confirmed by compari-son with their physical and chemical data reported in literature. Also p-benziloxybenzaldehyde derivatives were prepared by treated with 4-hydroxybenzaldehyde with ap-propriate benzylchloride/bromide derivatives in the pres-ence of K2CO3 as catalyst. The physical and chemical properties of all obtained substrates were compared with the ones reported in literature and all of their structures were confirmed.[46]
2-amino-4-(4-((4-bromobenzyl)oxy)phenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
93%
With molybdenum(VI) oxide; In ethanol; water; at 80℃; for 0.666667h;Green chemistry;
General procedure: 4-hydroxycoumarin (1 mmol, 0.162 g) was added to a stirred mixture of malononitrile (1.5 mmol 0.01 g), MoO3 NPs (0.007 g, 5 mol%) and para-(4-morpholinoethoxy)-benzaldehyde (1 mmol, 0.235 g) in EtOH/H2O (4:1). The mixture was heated at 80 C for the times indicated in Table 2 (see ??Results and discussion??. After compilation of the reaction progress (which was controlled by TLC CHCl3/CH3OH (10:1) as eluent), the mixture was precipitated and then filtrated to separatethe crude product., which was dissolved in boiling ethanol and filtrated to separate the catalyst. Finally, a crystalline pure product was obtained in solution and isolatedby filtration.
With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 0℃; for 12h;Inert atmosphere;
General procedure: A 100mL oven-dried three-neck flask was charged with magnetic bead, 20mmol of 6 (6a-6f), flushed with dry nitrogen gas followed by addition of ethanol (40mL), dry THF (20mL), and NaBH4 (1.14g, 30mmol) under inert conditions at 0C. The mixture was then stirred for 12h. When TLC analysis confirmed that the reaction was completed, 2N HCl was drop-wise added to decompose excess NaBH4 while stirring was continued. The solution was evaporated and the residue was extracted with dichloromethane followed by its washing with water. Combined organic phases were dried over Na2SO4 and concentrated to give desired product 7 (7a-7f) in 93%-96% yields.
3-(4-((4-bromobenzyl)oxy)phenyl)-2-(4-bromophenyl)acrylic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
22%
With acetic anhydride; triethylamine; for 5h;Reflux;
General procedure: The titlecompounds were prepared by a Knoevenangel reaction, as shown in Scheme 1, according to literaturemethods [17-19]. A suitable aldehyde (0.015 mol) was condensed with 4-bromophenylacetic acidor 4-hydroxyphenylacetic acid (0.015 mol) and acetic acid anhydride (10 mL) in the presence oftriethylamine (5 mL). The reaction mixture was refluxed for approximately 5 h (while monitoringcompletion of the reaction). The solution was poured into 2 N HCl, and ice and the precipitate formedwas collected by filtration and recrystallized from 50% v/v aqueous ethanol. In case that no precipitatewas formed an extraction with 3 x 100 mL CHCl3 was made and the organic phase was collected,dried over MgSO4 and evaporated to dryness affording a residue that was recrystallized from 50%aqueous ethanol.
3-(4-((4-bromobenzyl)oxy)phenyl)-2-(4-hydroxyphenyl)acrylic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
7%
With acetic anhydride; triethylamine; for 5h;Reflux;
General procedure: The titlecompounds were prepared by a Knoevenangel reaction, as shown in Scheme 1, according to literaturemethods [17-19]. A suitable aldehyde (0.015 mol) was condensed with 4-bromophenylacetic acidor 4-hydroxyphenylacetic acid (0.015 mol) and acetic acid anhydride (10 mL) in the presence oftriethylamine (5 mL). The reaction mixture was refluxed for approximately 5 h (while monitoringcompletion of the reaction). The solution was poured into 2 N HCl, and ice and the precipitate formedwas collected by filtration and recrystallized from 50% v/v aqueous ethanol. In case that no precipitatewas formed an extraction with 3 x 100 mL CHCl3 was made and the organic phase was collected,dried over MgSO4 and evaporated to dryness affording a residue that was recrystallized from 50%aqueous ethanol.
(2E,2'E)-1,1'-((propane-1,3-diylbis(oxy))bis(4,1-phenylene))bis(3-(4-((4-bromobenzyl)oxy)phenyl)prop-2-en-1-one)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
89%
With potassium hydroxide; In ethanol; water; at 20℃;Sonication;
General procedure: A Claisen-Schmidt condensation was performed between (1,10-((propane-1,3-diyl-bis(oxy)) bis-(4,1-phenylene))diethanone) and the appropriate substituted aromatic aldehyde at a molar ratio 1:2 in absolute ethanol (10 mL). Three milliliter (3 mL) aqueous KOH (20%) was added. The mixture was stirred at room temperature in a US-bath. The end of the reaction was monitored by TLC. After the completion of the reaction the mixture was treated with aqueous HCl 10% and adjusted to acidic pH. The precipitate was either ltered and washed with cold water or extracted with CHCl3 (30 mL×3). The combined organic layers were washed with water and brine and dried under anhydrous MgSO4. The product was evaporated to dryness and puried by recrystallization from a proper solvent.
(E)-3-(4-((4-bromobenzyl)oxy)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76%
With potassium hydroxide; In ethanol; water; at 20℃;Sonication;
General procedure: A modied Claisen-Schmidt condensation was performed between 4-hydroxy acetophenone and the suitable substituted aryl aldehyde at a molar ratio 1:1 in absolute ethanol (10 mL) [29]. Three milliliters (3 mL) aqueous KOH (20%) was added. The mixture was stirred at room temperature in a US-bath. The end of the reaction was monitored by TLC. The mixture was treated with aqueous HCl 10% and adjusted to acidic pH. The precipitate was either ltered and washed with cold water or extracted with CHCl3 (30 mL × 3). The combined organic layers were washed with water and brine and dried under anhydrous MgSO4. The product was evaporated to dryness and puried by recrystallization from a proper solvent.
(E)-3-(4-((4-bromobenzyl)oxy)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
With potassium hydroxide; In ethanol; water; at 20℃;Sonication;
General procedure: A modied Claisen-Schmidt condensation was performed between 2-hydroxy acetophenone and the suitable substituted aryl aldehyde at a molar ratio 1:1 in absolute ethanol (10 mL). Three milliliters (3 mL) of aqueous KOH (20%) was added. The mixture was stirred at room temperature in a US-bath. The end of the reaction was monitored by TLC. The mixture was treated with aqueous HCl 10% and adjustedtoacidicpH.Theprecipitatewaseitherlteredandwashedwithcoldwaterorextractedwith CHCl3 (30 mL×3). The combined organic layers were washed with water and brine and dried under anhydrous MgSO4. The product was evaporated to dryness and puried by recrystallization from a proper solvent.
(Z)-2-(5-(4-(4-bromobenzyloxy)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-(1H-indol-3-yl)propanoic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With piperidine; acetic acid; In ethanol; at 80℃;
General procedure: Compound 6 was synthesized as previously reported [36].A mixture of hydroxyaromatic aldehydes (1.0 mmol), appropriatebenzyl chlorides (1.2 mmol), and anhydrous sodium carbonatewas stirred for 4 h in refluxing acetone. The solvent wasevaporated under reduced pressure and the residue was dissolvedin dichloromethane, washed using water and brine, dried overanhydrous MgSO4, and the solvent was removed under reducedpressure. The resulting residue was purified through silica gel columnchromatography (dichloromethane/PE, 5:1 v/v) to affordcompounds 2-5 as white solids. To a solution of each of compounds2-5 (1.0 mmol) and compound 6 (1.0 mmol) in absoluteethanol (5 mL), was added drops of glacial acetic acid and piperidine.The reaction mixture was stirred at 80 C for 2-6 h, until thecompletion of the reaction as evidenced through TLC. The resultingreaction mixture was concentrated to dryness, and purifiedthrough silica gel column chromatography (dichloromethane/methanol/acetic acid, 100:1:1) to afford the pure products 7-10.The yield, melting point and spectral data of each compound aregiven below.
(Z)-2-(4-((4-bromobenzyl)oxy)benzylidene)-1H-indene-1,3(2H)-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
32.45%
With piperidine; In ethanol; for 8h;Reflux;
General procedure: In a round bottom flask 0.0068 mol 1,3-indandione and 0.0075 mol of the corresponding arylaldehyde were added and diluted in 30 mL of absolute ethanol using piperidine (0.06 mL) as catalyst. The mixture was heated reflux for approximately 8 h monitoring with TLC (petroleum ether/ethyl acetate, 7/3) for the completion of the reaction. The excess of the solvent was removed with rotary evaporator. The residue was ltered and puried either with recrystallization with EtOH 95or ethanol/water or with preparative TLC using CH3COOC2H5: petroleum ether (1:2).
2-amino-4-(4-((4-bromobenzyl)oxy)phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
95%
With nickel ferrite; In ethanol; for 0.5h;Reflux; Green chemistry;
General procedure: To a stirring mixture of 4-(2-morpholinoethoxy)benzaldehyde(0.235 g, 1 mmol) and malononitrile (0.132 g,2 mmol) dissolved in 10 cm3 EtOH, in the presence ofNiFe2O4 NPs (0.012 g, 5 mol%), dimedone (0.140 g,1 mmol) was added. The mixture was heated under refluxconditions for the time indicated in Table II. After completionof reaction which was found out by monitoring onTLC, the mixture was poured into boiling THF (10 mL)and then the catalyst was separated by a magnet, washedwith boiling acetone (5 cm3, and dried at 100 C for1 h to use in further cycles. The mixture was evaporatedto obtain crude product. In final step, crud product was recrystallized in boiling EtOH to afford crystalline pureproduct 4a.
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