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CAS No. : | 613-69-4 | MDL No. : | MFCD00003316 |
Formula : | C9H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DUVJMSPTZMCSTQ-UHFFFAOYSA-N |
M.W : | 150.17 | Pubchem ID : | 11950 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 43.13 |
TPSA : | 26.3 Ų |
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) : | -5.73 cm/s |
Log Po/w (iLOGP) : | 2.03 |
Log Po/w (XLOGP3) : | 2.09 |
Log Po/w (WLOGP) : | 1.9 |
Log Po/w (MLOGP) : | 1.44 |
Log Po/w (SILICOS-IT) : | 2.31 |
Consensus Log Po/w : | 1.95 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.29 |
Solubility : | 0.764 mg/ml ; 0.00509 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.27 |
Solubility : | 0.802 mg/ml ; 0.00534 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.86 |
Solubility : | 0.208 mg/ml ; 0.00138 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.17 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With oxygen In toluene at 110℃; for 5 h; | General procedure: A mixture of 1b (100 mg, 0.818 mmol), SS-Pd (918 mg, 0.04 mmol Pd) and 3 ml of toluene was purged with molecular oxygen and stirred at 110 °C for 5 h. The progress of reaction was monitored on TLC. After completion of reaction, the reaction was cooled, diluted with ethyl acetate and filtered through cotton bed. The combined organic layer was evaporated under reduced pressure and crude residue was purified by silica gel (mesh 60-120) column chromatography (Hexane/EtOH 95:5) afforded 2b as colorless liquid (94 mg, 96percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium carbonate In N,N-dimethyl-formamide for 36 h; Inert atmosphere | General procedure: Salicylaldehyde (5) (3.66 g, 3.2 mL, 30 mmol) was added to asuspension of potassium carbonate (8.29 g, 60 mmol) in DMF(50 mL). Alkyl halide was then added dropwise and the solutionwas stirred for 36 h under an atmosphere of argon.Water (150 mL)was added and the mixture was extracted with diethyl ether(3 50 mL). The combined organic layers were washed with 2MNaOH (3 50 mL), dried over Na2SO4, filtered and evaporated invacuo to afford the 2-alkoxy benzaldehyde 6a-b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With lemon juice; at 25 - 30℃;Irradiation; | General procedure: To a solution of hippuric acid (1a, 0.18 g, 1.0 mmol) and benzaldehyde (2a, 0.127 g, 1.2 mmol) in PEG-400 (2 mL) was added lemon juice (5 mL) and the mixture was stirred at room temperature for 5 min. The mixture was then stirred under ultrasound at room temperature (25-30C) for 60 min. Upon completion of the reaction as indicated by TLC, the mixture was treated with a saturated aqueous solution of Na2CO3 to remove the unreacted hippuric acid if any. The mixture was extracted with CH2Cl2, dried over anhydrous Na2SO4, filtered, and the solvent was removed under vacuum. The residue obtained was purified by recrystallization from EtOH to give 3a as a yellow solid; m.p. 168-170 oC. All other compounds were prepared following the procedure described above. Physical and spectroscopic characterization data of compounds synthesized are given in the supplementary material. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With acetic acid; In ethanol;Reflux; | General procedure: Nicotinic/isonicotinic hydrazides (1 mmol), substituted aromatic aldehyde (1 mmol) and glacial acetic acid (few drops) were taken in ethanol (10 mL) and refluxed for 3 h. Progress of the reaction was monitored by TLC. After the completion of the reaction,mixture was left for evaporation of solvent, and then crude product washed with dichloromethane and hexane, and dried to afford compounds 1-54. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With cyclohexylamine; at 120℃;Microwave irradiation; | General procedure: To a solution of the appropriate benzaldehyde (3.6 mmol) in glacial acetic acid (4 mL) was added the nitroalkane (7.2mmol) followed by cyclohexylamine (3.6 mmol, 0.4 mL). The reaction mixture was heated under microwave irradiation at 120 C for 30 min. After cooling, water (10 mL) was added to the reaction and it was allowed to stand. The precipitated nitroethene was isolated by filtration. The filtrate was further diluted with water (20 mL) and extracted with dichloromethane (3 x 10 mL). The organic phases were combined and washed with saturated aqueous NaHCO3 (3 x10 mL). The solution was dried over anhydrous Na2SO4, filtered and all solvent removed in vacuo, to give an oil which was purified by flash column chromatography over silica gel (eluent: dichloromethane/hexane) and recrystallised from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium tetrahydroborate; sodium hydroxide; In water; at 20℃; for 4h; | General procedure: These compounds 7a-b were prepared using the generalmethod described by Zartler and Sharpiro [34]. A solution of sodiumborohydride (0.37 eq, 28 mg, 0.74 mmol) in 2M NaOH (40 mL)diluted withwater (360 mL)was added dropwise to a solution of the2-alkoxy benzaldehyde (6a-b) (2 mmol) in methanol (2 mL) at18e25 C. The reaction mixture was stirred for 4 h at room temperatureand then evaporated in vacuo. Methanol (2 10 mL) wasadded and evaporated in vacuo. HCl (5%, 10 mL) was added to theresidue which was extracted with diethyl ether (2 20 mL). Thecombined organic layers were dried over Na2SO4, filtered andevaporated in vacuo to afford 7a-b. |
65% | With formic acid; water; palladium diacetate; tricyclohexylphosphine; In 1,4-dioxane; at 90℃; for 18h;Inert atmosphere; Sealed tube; | General procedure: An oven-dried pressure tube containing a Teflon-coated stirring bar was charged with Pd(OAc)2 (11.2 mg, 5 mol%), PCy3 (21 mg, 7.5 mol%) and aldehyde(1 mmol).The tube was sealed, evacuated and backfilled with N2. 1 mL of dioxane was subsequently injected. After the mixture was stirred at room temperature for 15 min, H2O (180 mg, 10 equiv) and HCO2H (184 mg, 4 equiv) were injected and the reaction was heated to 90 oC for 18 h. After the reaction was completed, the solvent was removed under vacuo. The residues were purified by flash column chromatography on silica gel to afford 87 mg of benzyl alcohol in 81 % yield. |
With methanol; sodium tetrahydroborate; for 1h;Cooling with ice; | General procedure: To a solution of compound 7a (1.06 g, 10 mmol) in methanol(10 mL) was added NaBH4 (0.57 g, 15 mmol). After stirring for 1 hwhile cooled with an ice-water bath, methanol was evaporatedand the residue was dissolved in EtOAc (100 mL). The organic layerwas washed with water (3 100 mL) and brine (3 100 mL), anddried over MgSO4 overnight. EtOAc was evaporated to give 8a ascolorless oil (2.01 g, yield: 94%). ESI-MS m/z 109.4 [M+H]+. The crude product was used directly in the next reaction without furtherpurification. Compounds 8b-8u, 8aa-8ff, 10v-10w, 17a-17b and 22a-22hwere prepared using the same procedure described above |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With Selectfluor; In neat (no solvent); at 20℃; for 0.916667h;Green chemistry; | General procedure: Method A A mixture of aldehyde (1 mmol), freshly distilled Ac2O (2 mmol), and selectfluor (0.035 g, 0.1 mmol) was stirred at room temperature for appropriate time as shown in Table 3. After the completion of the reaction was monitored byTLC (hexane/ethyl acetate, 5:1), CH2Cl2 (15 ml) was added to the mixture and filtered, then the solid material (Selectfluor) was again washed with CH2Cl2(2 x 5 ml) and collected for reuse. Evaporation of the solvent followed by column chromatography on silica gel afforded the pure compound corresponding to 1,1-diacetates. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium carbonate; In N,N-dimethyl-formamide; for 36h;Inert atmosphere; | General procedure: Salicylaldehyde (5) (3.66 g, 3.2 mL, 30 mmol) was added to asuspension of potassium carbonate (8.29 g, 60 mmol) in DMF(50 mL). Alkyl halide was then added dropwise and the solutionwas stirred for 36 h under an atmosphere of argon.Water (150 mL)was added and the mixture was extracted with diethyl ether(3 50 mL). The combined organic layers were washed with 2MNaOH (3 50 mL), dried over Na2SO4, filtered and evaporated invacuo to afford the 2-alkoxy benzaldehyde 6a-b. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 140 - 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With oxygen; [5,6]fullerene-C70 In chloroform; toluene at 20℃; for 24h; Sealed tube; Irradiation; | |
With oxalic acid; dimethyl sulfoxide; O-phenyl phosphorodichloridate; triethylamine 1.) -10 deg C, 15 min, CH2Cl2, 2.) -10 deg C to 20 deg C, 45 min, 3.) 20 deg C, 30 min; Yield given. Multistep reaction; | ||
With 4-phenylnaphthalene-1,2-dione; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With oxygen; In toluene; at 110℃; for 5h; | General procedure: A mixture of 1b (100 mg, 0.818 mmol), SS-Pd (918 mg, 0.04 mmol Pd) and 3 ml of toluene was purged with molecular oxygen and stirred at 110 C for 5 h. The progress of reaction was monitored on TLC. After completion of reaction, the reaction was cooled, diluted with ethyl acetate and filtered through cotton bed. The combined organic layer was evaporated under reduced pressure and crude residue was purified by silica gel (mesh 60-120) column chromatography (Hexane/EtOH 95:5) afforded 2b as colorless liquid (94 mg, 96%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With ethanolamine; In ethanol; water; for 24h;Schlenk technique; Inert atmosphere; Reflux; | General procedure: A 250mL flask was charged with hydantoin (10.0g, 100mmol), aromatic aldehyde (100mmol), ethanolamine (3.05g, 50mmol) and 100mL of solvent (ethnol/water=1/1, v/v). The reaction mixture was then heated and stirred at reflux for 24h. After cooling to room temperature, a large amount of crystals were formed. The mixture was filtered and the filter cake was washed with 20mL of cold ethanol. The crystals were then collected and dried under reduced pressure. Yield: 81%; Colorless crystal, mp=219.4-220.7C; 1H NMR (300MHz, d6-DMSO) delta (ppm): 1.37 (t, J=6.9Hz, 3H), 4.06-4.13 (m, 2H), 6.66 (s, 1H), 6.93-7.04 (m, 1H), 7.27-7.33 (m, 1H), 7.57-7.60 (m, 1H), 7.58 (dd, J1=7.8Hz, J2=1.5Hz, 1H), 10.31 (br s, 1H), 11.15 (br s, 1H); 13C NMR (125MHz, d6-DMSO) delta (ppm): 166.0, 156.9, 155.9, 130.5, 129.8, 128.4, 122.0, 120.9, 112.4, 103.4, 64.1, 15.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a salicylilaldehyde I (10 mmol, 1 equiv) dissolved in propanone (30 mL) was added an alkyl halide R1-X (12 mmol, 1.2 equiv) in the presence of K2CO3 (20 mmol, 2 equiv) and the mixture was refluxed for 3 h. The solvent was then evaporated and the residue was purified by a flash column chromatography to yield II. A terminal alkyne (2.4 mmol, 1.2 equiv) was dissolved in dry THF (5 mL) and cooled to -78C. A solution of butyl lithium (n-BuLi 2.5 M in hexanes, 2.4 mmol, 1.2 equiv) was added dropwise and the mixture was stirred at -78C for 30 minutes. Compound II (2 mmol, 1 equiv) dissolved in dry THF (5 mL) was then added and the mixture was stirred at -78C for 1 h then at -20C for 2 h. A saturated solution of NH4Cl (10 mL) was then added, the mixture was diluted with water (20 mL) and extracted with ethyl acetate (3x10 mL). The organic layer was washed twice with water (20 mL), dried over MgSO4 and the solvent was evaporated. The residue was purified by a flash column chromatography to yield III. To a solution of III (2 mmol, 1equiv) in CH2Cl2 (20 mL) was added MnO2 (30 mmol, 15 equiv) and the mixture was stirred at room temperature for 12 h. The MnO2 was removed by filtration and the solvent was evaporated to yield 1, 5a, 5c-d, 5f-i that were used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With dipotassium peroxodisulfate; In water; dimethyl sulfoxide; at 100℃;Sealed tube; Microwave irradiation; | We intended to synthesize compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold by using microwave assisted protocol (Scheme 1). In this direction we started the studies for optimization of synthesis of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The optimization studies were initiated by screening of different oxidizing agents as depicted in Table1, see Supplementary data using DMSO:Water in 1:1 proportion to see the conversion in desired product. Amongst all oxidants, the best result was observed with K2S2O8, in equivalence studies for catalyst, 3eq. of catalyst has given maximum yields (Table1, see Supplementary data). Therefore, all reactions were conducted using this condition after optimization of catalyst. However, oxone has also given the product 3a with minor yields. After screening of the catalyst we started study of selectivity for solvent that could affect the formation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The solvent screening was carried out to find out the best conversion, the mixture of DMSO:H2O in 1:1 proportion has given the best results with excellent yields (Table2, see Supplementary data). The microwave protocols were optimized for this reaction as mentioned in Table 3, see Supplementary data; the reactions carried under different microwave Watt powers have given varied results. Wherein, entry 3(b) (Table3, see Supplementary data) was found to be the best condition for maximum conversion. A series of compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold was synthesized using these optimized conditions, wherein, all kind of substrates with diversity around aryl ring were chosen for conversion and in all cases products obtained in good to excellent yields (Table1). |
91.4% | To a 250 ml three-necked flask was added 8.15 g of <strong>[613-69-4]2-ethoxybenzaldehyde</strong>, 9.6 g of 1-methyl-3-propyl-4-aminopyrazole-5-carboxamide and 150 ml of isopropanol, 3 hours; to the reaction system into the oxygen, add 8.56g anhydrous ferric chloride, temperature 60 C reaction 3 hours; reaction is completed, add 180ml of purified water, cooled to room temperature filtration, drying solid 15.78. Yield: | |
83% | Step 7: Synthesis of 5-(2-ethoxyphenyl)-1 -methyl-3-propyl-1H-pyrazolo[4,3- d]pyrimidin-7(611)-one:- 4-amino-i -methyi-3-propyi- 1 H-pyrazole-5-earboxamide (7.0gm 3.84 m.ml) and 2-ethoxybenz- aldehyde (6.0 gm 4.0 m.ml) were suspended in ethanol and the mixture was heated at 70 C for 1.5 hours after conformation of forming of imine by TLC. Added CuC12 (15.4 gm 11.5 m ml) and the reaction mixture heated at 70 C under 02 for 1.5 hours. After there action was completed, the ethanol was removed under vacuum. Then work up was carried out using ethyl acetate and water.The organic layer was separated and water layer re-extracted with 100 ml ethyl acetate. The combined organic layers are washed with brine solution, concentrated under vacuum; Yield 83%. ?H NMR (400 MHz CDC13): 10.80(s 1H), 8.46(m 1H), 7.47(m 1H), 7.14(m 1H) 7.06(m 1H) 4.38 (q, J=7.OHz 2H), 4.27(s 3H), 2.94(t, J= 7.6 Hz 2H), 1 .87(m 2H), 1 .64(t, J = 7.0Hz 3H). 1 .03(t J = 7.2Hz 3H). ppm MASS: ESI [M + H] :313.14 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With zinc trifluoromethanesulfonate; In neat (no solvent); at 100℃; for 0.833333h; | General procedure: To a 25 mL flask, sequentially added aldehydes 1a-k (1.0 mmol), amine 2a-c (1.2 mmol),alkyne 3a-b (1.5 mmol) and Zn(OTf)2 (0.05 mmol) under an air atmosphere. The reaction mixture was stirred at 100C till the complete consumption of starting aldehydes (TLC monitoring). The reaction mixture was cooled to room temperature and diluted with ethylacetate, and then washed with cold water (2 X 5 mL). The organic phase was separated, and the aqueous layer was washed with ethyl acetate (2 X 5 mL). Concentration of the combined organic layer afforded the crude product, which was further purified by by column chromatography on 100-200 silica gel (hexane/ethyl acetate, 20:1) to afford propargylamines 4a-t. The catalyst was recovered from the aqueous layer via evaporation under reduced pressure and dried at 120C for 2 h to get pure Zn(OTf)2. The recovered catalyst was reused for the next run in the same way. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With L-proline; In acetonitrile; at 20℃; for 3h; | General procedure: To a mixture of aldehyde 1 (1 mmol),amine 2 (1 mmol), and trimethylsilyl cyanide 3 (TMSCN) (1.2 mmol) inacetonitrile (5 mL) L-proline (20 mol %) was added and the reaction mixturewas stirred for the time specified in Table 3. After completion of the reaction asindicated by TLC, the reaction mixture was quenched with aqueous saturatedNaHCO3 followed by brine solution and then extracted with ethylacetate, driedover Na2SO4, concentrated under vacuum, and the crude mixture was purifiedby column chromatography on silica gel (hexane:ethylacetate 2:1) (Merck100-200 mesh) to afford the corresponding pure a-aminonitriles 4a-4y(Table 3). All the products are well characterized by spectral analysis (IR, 1HNMR,13C NMR, MS) elemental analysis, and were found to be identical withthose reported in the literature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / ethanol / 1 h / Heating 2: 85 percent / tBuOK / 2-methyl-propan-2-ol / Heating | ||
Multi-step reaction with 2 steps 1: ethanol / 1.5 h / 70 °C 2: copper dichloride; oxygen / ethanol / 1.5 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 87 percent / pyridine / ethanol / 1 h / Heating 2: 15 percent / 650 °C / 0.03 Torr 3: 27 percent / K2CO3 / dimethylformamide / 21 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 90 percent / pyridine / ethanol / 1 h / Heating 2: 3 percent / 650 °C / 0.03 Torr 3: 88 percent / K2CO3 / dimethylformamide / 21 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; In methanol; for 2h;Heating / reflux; | Intermediate Ia (9.Og, 47mmol), 2-ethoxybenzaldehyde (6.60 mL, 47mmol) and piperidine (2mL) are dissolved in methanol (100 mL) and heated under reflux for 2 hours. The solution is allowed to cool to room temperature and the resulting precipitate is collected via filtration and washed with methanol and then ether and dried under reduced pressure to give the desired product 1-01 (13.4g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium borohydrid; In ethanol; dichloromethane; chloroform; | Example 9 Synthesis of alpha-(2-Ethoxyphenyl)-N-cyclobutylnitrone 2-Ethoxybenzaldehyde was combined with cyclobutylamine hydrochloride in chloroform and the solution was refluxed for 22 hours. Upon completion of the reaction, the solution was cooled to room temperature and concentrated under vacuum to give an oily residue, which was N-cyclobutyl-(2-ethoxy)phenyl imine. The oily residue was dissolved in ethanol and the solution was cooled with an ice bath. Sodium borohydride was added in portions and the reaction mixture was stirred at ambient temperature for 21 hours. The solution was then concentrated under vacuum and the residue was suspended in dichloromethane. A precipitate formed which was filtered. The filtrate was concentrated to give a liquid, which was passed through a silica gel filled funnel (eluding with hexane/ethyl acetate, 2:1) to afford N-cyclobutyl-(2-ethoxy)phenylamine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium cyanoborohydride; sodium hydrogencarbonate In methanol; acetic acid | 42.A A. A. 2-Ethoxy-N-[(2-ethoxyphenyl)methyl]-benzenemethanamine 2-Ethoxybenzenemethanamine (300 mg, 0.30 mL, 1.98 mmol) and 2-ethoxybenzaldehyde (297 mg, 0.28 mL, 1.98 mmol) were dissolved in dry methanol (10 mL). Glacial acetic acid (0.2 mL) was added and sodium cyanoborohydride (124 mg, 1.98 mmol) was added portionwise over 1 hour. The reaction mixture was stirred for 16 hours. The mixture was cooled to 0°C and saturated NaHCO3 (20 mL) was slowly added. The mixture was concentrated and the product was extracted into ethyl acetate (100 mL). The ethyl acetate layer was washed with water (100 mL) and brine (50 mL), dried (MgSO4), concentrated and chromatographed (silica gel, 4.1 X 15 cm, 40% ethyl acetate, 60% hexanes). Fractions containing the desired product were combined and concentrated to yield compound A as a clear oil (450 mg, 80%), MS: (M+H)+ 286+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: malonic acid; 2-ethoxylbenzaldehyde With piperidine; pyridine Reflux; Stage #2: With hydrogenchloride In water at 25℃; | ||
With piperidine In pyridine at 80℃; for 6h; | General procedure for the preparation of furoxan oxynitride 9a-9g General procedure: Step 1: To a solution of aryl formaldehyde (6a~6g, 20 mmol) and malonic acid in pyridine (40 mL) was added piperidine (2.55 g, 30 mmol). The resulting mixture was heated to 80 °C for 6 hours until no starting material was detected by TLC. Then the solvent was removed in vacuum to give viscous liquid. The crude product was diluted with 1 M aqueous NaOH solution (200 mL) and was washed with EtOAc (100 mL × 3). The aqueous layer was acidified to pH=1 with HCl (aq., 2M), and extracted with EtOAc (150 mL × 3). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuum to afford aryl acrylic acid as white solid in 60-78% yields. Step 2: To a solution of aryl acrylic acid 7a~7j (10 mmol) in anhydrous THF under argon at 0 °C was added a solution of BH3 (1.0 M in THF, 15 mL) drop wise. The resulting solution was stirred at room temperature until no starting material was detected by TLC. The reaction was quenched with H2O (100 mL) and extracted with EtOAc (80 mL × 3). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuum to give the crude product, which was purified by silica gel column chromatography (PE : EA = 4 : 1) to obtain the aryl propylene alcohol 8a~8g as light yellow oil in 67 % to 92 % yields. Step 3: To a solution of aryl propylene alcohol 8a~8g (5 mmol) in AcOH (1 mL) at 0 °C under argon was added a saturated aqueous NaNO2 (1.04 g, 15 mmol) solution drop wise over 30 min. The mixture was stirred at room temperature overnight. The reaction was quenched with H2O (30 mL) and extracted with EtOAc (50 mL × 3). The combined organic layer was washed with saturated Na2CO3 and brine, dried with anhydrous Na2SO4, and concentrated in vacuum. The crude product was purified by silica gel column chromatography (PE:EA = 10 : 1 to 5 : 1) to afford 3-(hydroxymethyl)-4-aryl-furoxan as white or yellow solid. Step 4: The product in step 3 (1 mmol) was dissolved in anhydrous DCM at 0 °C. Then TEA (151 mg, 1.5 mmol) and MsCl (125 mg, 1.1 mmol) were added successively. The resulting mixture was stirred at room temperature until no starting material was detected by TLC, The solvent was then removed in vacuum and the residue was purified by silica gel column chromatography (PE : EA = 20 : 1) to give the furoxan derivatives 9a~9g in 29 % to 46 % yield for 2 steps. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1-methyl-pyrrolidin-2-one; methanol at 70 - 80℃; for 2h; Combinatorial reaction / High throughput screening (HTS); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere; | General procedure: To a stirred solution of aldehyde 7a (48.0 muL, 0.5 mmol, 1.0 equiv) in THF (2.0 mL) was added ethyl cyanoformate (98.0 muL, 1.0 mmol, 2.0 equiv) at room temperature under argon atmosphere. After that the solution was then cooled to 0 C and IPr (2.0 mg, 1 mol %) was added. The mixture was stirred at room temperature until the starting aldehyde was fully consumed as indicated by TLC concentration and the crude material was purified by column chromatography (PE-EtOAc: 9:1) to afford product 8a (100 mg, 98%) as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | General procedure: N-Pivaloyl-4-chloroaniline (33, 595 mg, 2.81 mmol) was dissolved in THF (50 ml), and the solution was added sec-butyl lithium c-hexane, n-hexane solution (0.99 M, 5.96 ml, 6.18 mmol) at -78 C, and then stirred at 0 C for 2 h. The mixture was added 2-chloro-3-fluoro-benzaldehyde (490 mg, 3.09 mmol) at the same temperature for 30 min. The reaction mixture was poured saturated with NH4Claq and AcOEt. The organic layer was washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (n-hexane/AcOEt = 9:1) to give the title compound (676 mg, 65%) as light yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.1% | With triethylamine; In xylene; at 15℃; for 3h; | Reference Example 1 Into a 300 ml flask was charged 10.00 g (0.066 mol) of <strong>[613-69-4]2-ethoxybenzaldehyde</strong> [compound represented by the formula (1) in which X represents an ethoxy group and m=0], 25.00 g of xylene and 0.07 g (0.00066 mol) of triethylamine and they were mixed, then, cooled down to 15C while stirring. Then, into the mixture, 3.60 g (0.13 mol) of hydrogen cyanide was dropped over a period of 2 hours, thereby adding hydrogen cyanide in an amount of 2.0 mol with respect to 1 mol of <strong>[613-69-4]2-ethoxybenzaldehyde</strong>. After completion of dropping, the reaction mixture was stirred at 15C for 1 hour. This reaction mixture was analyzed to find that the conversion of <strong>[613-69-4]2-ethoxybenzaldehyde</strong> was 90.1%, the residual ratio thereof was 9.9% and the yield of 2-ethoxymandelonitrile [compound represented by the formula (2) in which X represents an ethoxy group and m=0] was 90.1%. |
90.1% | With triethylamine; In xylene; at 15℃; for 3h; | Reference Example 1; Into a 300 ml flask was charged 10.00 g (0.066 mol) of <strong>[613-69-4]2-ethoxybenzaldehyde</strong> [compound represented by the formula (1) in which X represents an ethoxy group and m=0], 25.00 g of xylene and 0.07 g (0.00066 mol) of triethylamine and they were mixed, then, cooled down to 15 C. while stirring. Then, into the mixture, 3.60 g (0.13 mol) of hydrogen cyanide was dropped over a period of 2 hours, thereby adding hydrogen cyanide in an amount of 2.0 mol with respect to 1 mol of <strong>[613-69-4]2-ethoxybenzaldehyde</strong>. After completion of dropping, the reaction mixture was stirred at 15 C. for 1 hour. This reaction mixture was analyzed to find that the conversion of <strong>[613-69-4]2-ethoxybenzaldehyde</strong> was 90.1%, the residual ratio thereof was 9.9% and the yield of 2-ethoxymandelonitrile [compound represented by the formula (2) in which X represents an ethoxy group and m=0] was 90.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In ethanol; water; for 0.5h;Reflux; | General procedure: In a 200 mL round bottom flask, 1.54 g (12 mmol) of barbituric acid (25) were dissolved in 50 mL of hot distilled water. To this solution it was added a solution of the aldehyde (1-24) (12 mmol) in 10 mL of 95% ethanol. The mixture was kept under reflux and agitation for 30 min with the formation of a precipitate. The solid was separated by filtration and recrystallized in methanol to obtain the pure form of the respective benzylidene barbiturate, in yields from 90% to 99%. The data for the synthesis of the benzylidene barbiturates 26-49 is shown in Table 3, and the specific synthetic procedure data for the four new compounds is described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene; In 1,2-dichloro-ethane; at 0 - 20℃;Inert atmosphere; | General procedure: To a stirred solution of aldehyde 7f (70.0 mg, 0.5 mmol, 1.0 equiv) in 1,2-DCE (2.0 mL) was added acetyl cyanide (80.0 muL, 1.0 mmol, 2.0 equiv) at room temperature under argon atmosphere. After that the solution was then cooled to 0 C and IPr (19.4 mg, 10 mol %) was added. The mixture was stirred at room temperature until the starting aldehyde was fully consumed as indicated by TLC concentration, the crude material was purified by column chromatography (PE-EtOAc: 15:1) to afford product 10f (92 mg, 82%) as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With potassium hydroxide; In ethanol; at 20℃; | General procedure: To a solution of 1 (100 mg, 0.316 mmol) in 95% EtOH (10 mL) was added solid KOH (35 mg, 0.632 mmol) and aldehyde (1.2 equiv). The mixture was stirred at room temperature for 24-48 h, then the reaction was quenched with 10% HCl. The reaction mixture was extracted with ethyl acetate (3×15 mL). The organic layers were combined, washed with brine (3×10 mL), dried over anhydrous MgSO4, filtered, and concentrated. The residue was subjected to silica gel chromatographic with petroleum ether/EtOAc (4:1 to 3:1) to give 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.5% | General procedure: The appropriate quinoline derivative (2,5 mmol) in acetic anhydride was mixed thoroughly with 2 equiv aldehyde and heated under inert gas atmosphere (N2) during 16 h at 130 C. Then the liquid was evaporated in vacuo, pyridine and water in ratio 3:1 were added and the mixture further heated for 3 h at 100 C. Then mixture was evaporated to dryness and solid was crystallized or chromatographed |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With zinc(II) oxide; In ethanol; at 25℃; for 0.166667h; | General procedure: A mixture of the required aldehyde (1 mmol), N-benzoylglycine/N-acetylglycine (1 mmol),acetic anhydride (3 mmol), ZnO as a catalyst (0.05 mmol) and 15 mL ethanol was stirred atroom temperature, 25 C (Scheme 1). After a certain period, the syrupy reaction mixture was solidified and the reaction was completed (Table I). After the final product had been obtained,20 mL more of cold ethanol was added. The solid was filtered off, dried and washed with hotwater before recrystallization of the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With acetic acid; In ethanol; for 12h;Reflux; | General procedure: A mixture of compound E (10mmol), appropriate aldehyde (10mmol) and few drops of glacial acetic acid in ethanol (50mL) was refluxed for 12h. The product was precipitated, collected by filtration and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With bismuth(III) chloride; hydrazine; In water; at 20℃; for 0.0166667h;Sonication; Green chemistry; | General procedure: A reaction flask containing benzaldehyde (1mmol), hydrazine hydrate 55% (Sigma Alrich) (1mL) and catalytic (0.1mol%) amounts of BiCl3 was immersed in an ultrasonic bath containing water at room temperature. The reaction mixture was exposed to ultrasound irradiation for 1-2min (reaction complete based on TLC analysis). The resulting precipitate is filtered and washed with water to afford pure desired product (yellow crystals). Only, when necessary, final products were re-crystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; | General procedure: Glycine ethyl ester hydrochloride (1.12 g, 8 mmol) was dissolved inH2O (2.5 mL) and 5% sulfuric acid (0.76 mL, w/w) was added and a 4-mL syringe was equipped with the mixture. Next, NaNO2 (664 mg, 10 mmol) was dissolved in H2O (3.9mL) and another 4-mL syringe was equipped with this solution. The two syringes were connected to a flow setup with a T-piece mixer and a 0.9-mL coil (PTFE, i.d. = 0.5mm). 1,8-Diazabicycloundec-7-ene (596 muL, 4 mmol) was dissolved in dimethylsulfoxide (3.4 mL) and charged into a 4-mL syringe. Aldehyde (4 mmol) was dissolved in the required amount of DMSO to have a solution of exactly 4mL volume. This mixture was charged into another 4-mL syringe. Both syringes were put to another syringe pump and connected with two T-pieces to the outlet of the first coil as well as to the inlet of the second coil. The second coil consisted of a 2-mL coil (PTFE, i.d. = 0.8 mm). The pumps were set to 4 mL/h and the entire setup ran for 28 min to reach the steady state. Afterwards, the product was collected for 20-30 min in NaHCO3 as quenching agent. Extraction was performed with CH2Cl2 (3 × 10 mL), the combined organic layers were washed with H2O thoroughly (3 × 10mL) and dried over anhyd MgSO4. After evaporating the solvent in vacuo, the diazoalcohol was purified by column chromatography (hexane-EtOAc gradient, 100% hexane to 85% hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10%; 85% | With dipotassium peroxodisulfate; In water; dimethyl sulfoxide; at 80℃; for 0.0833333h;Sealed tube; Microwave irradiation; | We intended to synthesize compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold by using microwave assisted protocol (Scheme 1). In this direction we started the studies for optimization of synthesis of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The optimization studies were initiated by screening of different oxidizing agents as depicted in Table1, see Supplementary data using DMSO:Water in 1:1 proportion to see the conversion in desired product. Amongst all oxidants, the best result was observed with K2S2O8, in equivalence studies for catalyst, 3eq. of catalyst has given maximum yields (Table1, see Supplementary data). Therefore, all reactions were conducted using this condition after optimization of catalyst. However, oxone has also given the product 3a with minor yields. After screening of the catalyst we started study of selectivity for solvent that could affect the formation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The solvent screening was carried out to find out the best conversion, the mixture of DMSO:H2O in 1:1 proportion has given the best results with excellent yields (Table2, see Supplementary data). The microwave protocols were optimized for this reaction as mentioned in Table 3, see Supplementary data; the reactions carried under different microwave Watt powers have given varied results. Wherein, entry 3(b) (Table3, see Supplementary data) was found to be the best condition for maximum conversion. A series of compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold was synthesized using these optimized conditions, wherein, all kind of substrates with diversity around aryl ring were chosen for conversion and in all cases products obtained in good to excellent yields (Table1). |
75%; 20% | With dipotassium peroxodisulfate; In water; dimethyl sulfoxide; at 80℃; for 0.05h;Sealed tube; Microwave irradiation; | We intended to synthesize compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold by using microwave assisted protocol (Scheme 1). In this direction we started the studies for optimization of synthesis of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The optimization studies were initiated by screening of different oxidizing agents as depicted in Table1, see Supplementary data using DMSO:Water in 1:1 proportion to see the conversion in desired product. Amongst all oxidants, the best result was observed with K2S2O8, in equivalence studies for catalyst, 3eq. of catalyst has given maximum yields (Table1, see Supplementary data). Therefore, all reactions were conducted using this condition after optimization of catalyst. However, oxone has also given the product 3a with minor yields. After screening of the catalyst we started study of selectivity for solvent that could affect the formation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The solvent screening was carried out to find out the best conversion, the mixture of DMSO:H2O in 1:1 proportion has given the best results with excellent yields (Table2, see Supplementary data). The microwave protocols were optimized for this reaction as mentioned in Table 3, see Supplementary data; the reactions carried under different microwave Watt powers have given varied results. Wherein, entry 3(b) (Table3, see Supplementary data) was found to be the best condition for maximum conversion. A series of compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold was synthesized using these optimized conditions, wherein, all kind of substrates with diversity around aryl ring were chosen for conversion and in all cases products obtained in good to excellent yields (Table1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With dipotassium peroxodisulfate; In ethanol; at 100℃;Sealed tube; Microwave irradiation; | We intended to synthesize compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold by using microwave assisted protocol (Scheme 1). In this direction we started the studies for optimization of synthesis of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The optimization studies were initiated by screening of different oxidizing agents as depicted in Table1, see Supplementary data using DMSO:Water in 1:1 proportion to see the conversion in desired product. Amongst all oxidants, the best result was observed with K2S2O8, in equivalence studies for catalyst, 3eq. of catalyst has given maximum yields (Table1, see Supplementary data). Therefore, all reactions were conducted using this condition after optimization of catalyst. However, oxone has also given the product 3a with minor yields. After screening of the catalyst we started study of selectivity for solvent that could affect the formation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The solvent screening was carried out to find out the best conversion, the mixture of DMSO:H2O in 1:1 proportion has given the best results with excellent yields (Table2, see Supplementary data). The microwave protocols were optimized for this reaction as mentioned in Table 3, see Supplementary data; the reactions carried under different microwave Watt powers have given varied results. Wherein, entry 3(b) (Table3, see Supplementary data) was found to be the best condition for maximum conversion. A series of compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold was synthesized using these optimized conditions, wherein, all kind of substrates with diversity around aryl ring were chosen for conversion and in all cases products obtained in good to excellent yields (Table1). |
In ethanol; at 70℃; for 1.5h; | General procedure: 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide (5.0g, 2.74mmol) and <strong>[613-69-4]2-ethoxybenzaldehyde</strong> (4.32g, 2.88mmol) were suspended in ethanol and the mixture was heated at 70C for 1.5h after confirmation of forming an imine by TLC. Added CuCl2 (10.87g, 8.2mmol) and the reaction mixture again heated at 70C under O2 for 1.5h. After completion of reaction, ethanol was removed under vacuum and to this crude residue was added ethyl acetate (50mL) and water (50mL). The organic layer was separated and water layer was re-extracted with (2×50mL) ethyl acetate. The combined organic layers were washed with brine solution, concentrated under vacuum and purified by using Column chromatography afforded the title compound as a white solid. Yield 85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With copper(II) choride dihydrate; In ethanol; for 16h;Reflux; | General procedure: In a typical procedure, 2-arylquinazolin-4(3H)-ones 1-25 were synthesized by mixing anthranilamide (2 mmol), substituted benzaldehydes (2.1 mmol) and CuCl2*2H2O (4 mmol) in ethanol (15 mL). The mixtures were refluxed for 16 h, while progress of the reaction was monitored through thin layer chromatography. After completion of reaction, the reaction mixtures were cooled to room temperature and distilled water was added until the formation of precipitates. The precipitates were filtered and washed with distilled water. This reaction afforded good yields of title compounds. 4.4.19 2-[2'-(Ethyloxy)phenyl]quinazolin-4(3H)-one (19) Yield: 97%; 1H NMR: (400 MHz, DMSO-d6): deltaH 12.03 (s, 1H, NH), 8.14 (t, 1H, J5(6,7) = 6.8 Hz, H-5), 7.84 (m, 1H, H-7), 7.76 (dd, 1H, J6',5' = 7.2 Hz, J6',4' = 1.2 Hz, H-6'), 7.70 (d, 1H, J8,7 = 8.0 Hz, H-8), 7.53 (m, 2H, H-6, H-3'), 7.18 (d, 1H, J3',4' = 8.4 Hz, H-3'), 7.09 (t, 1H, J4'(3',5') = 7.2 Hz, H-4'), 4.16 (q, 2H, J(CH2,CH3) = 7.2 Hz, CH2), 1.35 (t, 3H, J(CH3,CH2) = 6.8 Hz, CH3); EI-MS: m/z (rel. abund.%), 266 (M+, 23.9), 251 (51.8), 238 (14.6), 222 (21.2), 119 (100). Anal. Calcd for C16H14N2O2: C, 72.16; H, 5.30; N, 10.52; O, 12.02. Found: C, 72.15; H, 5.32; N, 10.55. |
With copper(II) choride dihydrate; In ethanol; for 16h;Reflux; | General procedure: 2-Aminobenzamide (1 eq.), substituted benzaldehydes (1.1 eq)and CuCl22H2O (4 eq.) were mixed in ethanol (15 mL) and refluxedfor 16 h. The reaction was periodically monitored by thin layerchromatography. Water was added to the reaction mixtures untilthe appearance of precipitates. These precipitates were filtered,washed with water, and dried under vacuum. Good yields of titlecompounds were obtained [33]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dodecatungstosilic acid; phosphorus pentoxide In neat (no solvent, solid phase) at 20℃; for 0.05h; Green chemistry; | General method for the synthesis of Schiff bases 1-25 General procedure: A mixture of 1-aminoanthraquinone (1 mmol), a substituted aromatic aldehyde or ketone (1 mmol) and dodecatungstosilicic acid/P2O5 (0.2 g, 1 mol % of 1-aminoanthraquinone/P2O5) as a catalyst was ground in a mortar with a pestle under solvent-free conditions at room temperature for 1-3 min, Scheme 1. The reaction mixture turned to a pasty material that indicated the completion of the reaction. Crushed ice was added to afford precipitates of the Schiff bases. In order to remove the catalyst, the product was washed several times with ice-cold water. The solid products were obtained in excellent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With cesium fluoride; In water; at 20℃; | General procedure: In a typical reaction, a catalytic amount of CsF (5 mol%)was added to the solution of an aromatic aldehyde (1.0equiv) in 10 cm3 de-ionized water at room temperatureslowly and gradually 0.49 g pyarazolone (2.0 equiv) wasadded and the reaction mixture was swirled for 5-10 min. The product formation was monitored by TLC analysis andresulting precipitates were washed with distilled water togive the pure products in excellent yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide; In toluene; at 60℃; | General procedure: Hydrazine (1, 1.2mmol) and methylenemalononitrile (2, 1.0mmol) were mixed in toluene, then NaOH (0.2mmol) and aldehyde (3, 1.2mmol) was added at 60C. At the end of the reaction (TLC monitoring), the reaction mixture was extracted with EtOAc (3×20mL). Then the organic layer was evaporated under reduced pressure. The crude product was washed by ethanol and then filtered. The filter cake was dried and purified by crystallization from ethanol to afford pure 4.4.2.6 6-(2-Ethoxyphenyl)-1-phenyl-1,5-dihydro-4H-pyrazolo [3,4-d]pyrimidin-4-one (4f) 28 Yellow solid; mp 210-212 C; IR (KBr, v, cm-1): 3078, 2973, 1685; 1H NMR (400 MHz, DMSO-d6) (delta, ppm): 12.17 (s, 1H), 8.37 (s, 1H), 8.37-8.10 (m, 2H), 7.83-7.80 (m, 1H), 7.59-7.53 (m, 3H), 7.42-7.38 (m, 1H), 7.22-7.20 (m, 1H), 7.14-7.10 (m, 1H), 4.18 (q, J=8.0 Hz, 2H), 1.36 (t, J=8.0 Hz, 3H); 13C NMR (100 MHz, DMSO-d6) (delta, ppm): 157.8, 157.3, 156.0, 136.5, 133.4, 131.1, 129.7, 127.4, 122.2, 121.1, 113.5, 106.3, 64.7, 14.9; ESI-MS (m/z)=333 ([M+H]+). |
90% | With sodium hydroxide; In toluene; at 60℃; | In 50 ml single-port flask is added in 20 ml toluene, after hydrazine (1.1 mmol), ethoxy methylene malononitrile (1 mmol), heating to 60 C, then adding sodium hydroxide (0.2 mmol), benzaldehyde (1.2 mmol). Thin layer chromatographic detection, after the reaction, cooling to room temperature. Water and ethyl acetate extraction, the organic phase after drying with anhydrous sodium sulfate, and steaming and get the crude product. The crude product recrystallized with ethanol to get the yellow solid. The yield is 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydroxide; In ethanol; at 20 - 23℃; for 24h; | General procedure: A mixture of 0.033 mol of 1,1'-diacetylferrocene I, 0.01 mol of benzaldehyde or substituted alkoxybenzaldehyde II, and 0.005 mol of NaOH in 50 mL of 96% ethanol was stirred at 20-23C during 24 h. The reaction mixture was diluted with 150 mL of water, and the precipitate was filtered off, washed with large amount of distilled water (1.5-2 L), and dried at 35-40C in air. Compounds III-XXXV were purified via low-temperature recrystallization from 80% ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | General procedure: To a solution of N-(5-chloropyridin-2-yl)pivalamide 2 [24](1 equiv) in freshly distilled THF (15 mL), tBuLi (2.7 equiv) wasinjected dropwise at 78 C under Ar, and the mixture was stirredfor 15 min, and 2 h more at 0 C. Then, reaction was taken to 78 C,and the arylaldehyde (1.1 equiv) in freshly distilled THF (5 mL) wasdropwisely added. Then, the reaction mixture was allowed to reachroom temperature slowly, and stirred for 2 h more. Reaction wasterminated by addition of water (15 mL), and extracted with ether(3 40 mL). Then, organic layer was treated with NaHCO3(3 30 mL), dried over anhydrous MgSO4, filtered and evaporated,to produce a yellowish wax, which was further purified byautomatized flash chromatography with ethyl acetate/hexane aseluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 130℃; for 16h;Inert atmosphere; | The appropriate quinoline derivative (2.5 mmol) in acetic anhydride was thoroughly mixed with two equiv aldehyde and heated in an inert gas atmosphere (N2) for 16 h at 130C. Then, the mixture was evaporated to dryness and a solid was crystallized from EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
244 mg | In butan-1-ol; at 110℃; | General procedure: The vial containing the crude diaminopyridine was equipped with a magnetic stir bar and sealed with a teflon screw cap. Aldehyde (2 mol eqwith respect to the theoretical yield of the first reaction) and then nBuOH was added via syringe to give a diaminopyridine concentration of 0.3 M based on the theoretical yield of the first reaction. The reaction mixture was stirred at 110 C for 18-24 h with needle inserted in septum to expose reaction to air. The mixture was cooled to room temperature, diluted with ethyl acetate, and poured into aqueous saturated NaHCO3. The organic phase was separated and the aqueous phase was extracted twice more into ethyl acetate. The combined organic phases were driedover Na2SO4. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel, typically using EtOAc, 0 ->10% MeOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium hydrogensulfite; In N,N-dimethyl acetamide; at 150℃; for 2 - 3h; | General procedure: Sodium hydrogen sulfite (208 mg, 2 mmol) was added to a solution of 5-diethylaminoanthranilamide 5 (207 mg, 1 mmol) and substituted benzaldehyde (1 mmol) in N,N-dimethylacetamide (5 mL). The mixture was heated at 150C with stirring for 2-3 h, poured into water and extracted with ethyl acetate. Compounds 1e-1l were obtained as yellow solid after purification by column chromatography (silicagel; ethyl acetate) followed by recrystallization from EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With hydrogenchloride; In ethanol; water; at 20℃; | General procedure: The synthesis of hydrazide based Schiff bases were carried out in two steps. First methyl salicylate (1 mmol) was mixed with hydrazine hydrate (1 mmol) in methanol (10 ml) as solvent with 2-3 drops of acetic acid under continuous stirring for 4 h to obtain hydrazide. The reaction completion was monitored by TLC through depletion of starting material spot and formation of hydrazide fluorescent spot established the reaction completion. After completiondistilled water was added into the reaction mixture whichgives white precipitate. The product obtained was then further purified by washing with n-hexane. In step-2, the hydrazide was mixed with different aldehydes (1:1) in EtOH with 1-2 drops of HCl and stirred for 2-3 h to obtain various Schiff bases of hydrazones (1-28). The reaction completion was checked by TLC. The Schiff bases obtained were then washed with ethanol and n-hexane. 4.7.20 N'-[(Z)-(2-ethoxyphenyl)methylidene]-2-hydroxybenzohydrazide (20) Yield: 0.27 g (94%); m.p. 194-196 C; 1H NMR (400 MHz, DMSO-d6) delta (ppm): 11.98 (s, 1H, -OH), 11.91 (s, 1H, -NH), 8.80 (s, 1H, N=C-H), 7.89 (d, 2H, J6,5/6',5' = 8.8 Hz, H-6/6'), 7.42 (m, 2H, H-4/4'), 7.09 (d, 1H, J3',4' = 8 Hz, H-3'), 7.01 (t, 1H, J5'(4',6') = 7.4 Hz, H-5'), 6.93 (m, 2H, H-3/5), 4.13 (q, 2H, -OCH2-), 1.39 (t, 3H, -CH3); EI-MS: m/z (rel. abund.%), 284 (M+, 23.5), 148 (10), 137 (71), 133 (84.6), 121 (100), 120 (80), 105 (25), 93 (20.4), 91 (11.3), 77 (9), 65 (26.3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With nano-TiCl2/cellulose; at 70℃; for 2h; | General procedure: A mixture of 2-aminobenzothiazole I (1 mmol), aldehyde II (1 mmol), ethyl acetoacetate III (1 mmol), and PEG-400 (0.5 mL) was heated at 70 C in the presence of nano-TiCl2/cellulose (0.03 g). After completion of the reaction (monitored by TLC), hot ethanol (10 mL) was added to the mixture and filtered off for separation of catalyst. By adding water to filtrate, the product appeared as a pure solid in high yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With acetic acid; In methanol; for 1h;Reflux; | General procedure: A mixture of 2 mmol of carbohydrazonamide 1, 2 mmol of the corresponding aldehyde (or 1 mmol of diformylferrocene), 30 mL of anhydrous methanol, and 3 drops of glacial acetic acid was refluxed for 1 h. The hot solution was filtered, cooled, and maintained for 10-15 h at 0-5C. The resulting compounds 2-23 were separated by filtration on a glass porous filter, washed with a small amount (5-10 mL) of cold methanol, and dried in air. The condensation of carbohydrazonamide 1 with 1,1'-diacetylferrocene was carried out in benzene at refluxat a ratio of 1 : diacetylferrocene = 2 : 1. The product was isolated in a similar manner, but washed with cold benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-ethoxylbenzaldehyde With sodium tetrahydroborate In ethanol at 20℃; for 1h; Stage #2: With phosphorus tribromide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With ammonium hydroxide; In water; acetonitrile; at 80℃; for 4h; | In 100 ml round-bottom flask is added in 40 ml acetonitrile and 10 ml water, stirring, add 10mmol <strong>[613-69-4]2-ethoxybenzaldehyde</strong>, adding 25mmol malononitrile, then adding 100mmol concentrated ammonia water, the mixed solution 80 C lower, stirring and heating by magnetic force 4.0h. After the reaction is finished, direct filtering, to obtain the solid mixture. Recrystallization with ethanol, to obtain light yellow crystal (7), yield 82% (recrystallization mother liquor recovery), m.p. > 300 C. 2-ethoxy formaldehyde and propandinitrile, ammonia reaction equation is: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With piperidine; In ethanol; at 90℃;Inert atmosphere; | General procedure: The appropriate aldehyde (1 equiv) was added to EtOH (3 mL/0.2 mmol) and the mixture was stirred until complete solution. Theoxindole (1 equiv) and piperidine (0.1 equiv) were added, and themixture was heated to 90C for 3-7 h, and cooled. The resultingprecipitatewas filtered, washed with cold ethanol and dried to givethe pure compound. If necessary, additional recrystallization inethanol was applied to obtain the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-naphthylmethyltriphenylphosphonium chloride With potassium <i>tert</i>-butylate In tetrahydrofuran at -78 - 23℃; for 0.5h; Stage #2: 2-ethoxylbenzaldehyde In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With toluene-4-sulfonic acid; In ethanol; at 120℃; for 1h;Inert atmosphere; | General procedure: To a solution of 4-{4-(methylamino)thieno[3,2-d]pyrimidin-2-yl}benzohydrazide (11) (100 mg, 0.33 mmol) in ethanol (4 mL) were added an aldehyde (0.33 mmol) and PTSA (catalytic amount). The mixture was heated at 120 C for 1 h. The reaction mixture was poured into ice cold water (4 mL). The precipitate was filtered off and washed with ethyl acetate to afford a compounds 11a-11k. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With acetic acid; at 20℃; for 3h; | General procedure: In a flask containing 5 ml of glacial acetic acid and 2 mmol of indole (0.234 gm) or 5-chloroindole 0.303 gm or 6-chloroindole 0.303 gm was added under stirring until all the indole was dissolved. Then 1 mmol of the appropriate aromatic or heterocyclic aldehyde was added under vigorous stirring. The reaction mixture was allowed to stir over 4 to 6 h, where the reaction solution turned from light yellow to light pink to dark red colour. The product was detected by TLC (100 % CH2Cl2), and when the reaction was finished 10 ml of water were added and the solution was extracted with ethyl acetate, washed with water and 100 ml brine, driedover anhydrous sodium sulphate and concentrated in vacuum.The product was purified by passing over a column and eluted with dichloromethane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With potassium hydroxide; In ethanol; water; at 20℃; | General procedure: To a solution of 2-methoxybenzaldehyde (25?mg, 0.18?mmol) and 2'-hydroxy-5'-methoxyacetophenone (30?mg, 0.18?mmol) in EtOH (0.2?mL) was added 40% aqueous KOH (0.2?mL), and the mixture was stirred at room temperature. After the reaction was complete, ice-water was added to the reaction mixture, which was then neutralized with 1?N HCl. The mixture was extracted with EtOAc and the resultant organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with hexane-EtOAc (15:1) to give 2'-hydroxy-2,5'-dimethoxychalcone (13) (44?mg, 0.15?mmol) in 85% yield as an yellow solid. Chalcones 16, 17, 20, 26-29, and 32 were produced by the same procedure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: triethyl 2-ethylphosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 2-ethoxylbenzaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h; Inert atmosphere; | 5.1 Step 1: To a stirred suspension of NaH (60% dispersion in mineral oil) (226 mg, 5.66 mmol) in THF (7 mL) was added ethyl 2-(diethoxyphosphoryl)butanoate (1 .18 mL, 4.95 mmol) in THF (3 mL) drop wise at 0 °C under nitrogen atmosphere. After completion of the addition, the reaction mixture was stirred at RT for 1 h. Again, the mixture was cooled to 0 °C and 2- ethoxybenzaldehyde (500 mg, 3.33 mmol) was added and the mixture was stirred at RT for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with cold water (20 mL) and extracted with EtOAc (3 x 20 mL). Separated organic layer was washed with saturated NaHC03solution (30 mL) and brine (30 mL). Organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Obtained crude material was purified through silica gel column chromatography using 4% EtOAc/ hexane to afford ethyl (E)-2-(2-ethoxybenzylidene)butanoate (500 mg, 60%) as colourless syrup.ethyl (E)-2-(2-ethoxybenzylidene)butanoate:1H NMR (400MHz, CDCI3): δ 7.28-7.26 (m, 1 H), 7.23-7.14 (m, 1 H), 6.97-6.78 (m, 3H), 4.28 (q, J = 7.1 Hz, 2H), 4.1 1 -4.00 (m, 2H), 2.52-2.44 (m, 2H), 1.45-1.40 (m, 3H), 1.35 (t, J=7.2 Hz, 3H), 1 .18-1 .13 (m, 3H); LC-MS (ESI): 70.79%; m/z 249.0 [M + H]+at RT 3.09 min; (column; column; Ascentis Express C-18 (50 3.0mm, 2.7μη); 0.025% Aq TFA + 5% ACN: ACN + 5% 0.025% Aq TFA; 1.2 mL/min). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With palladium diacetate; potassium hydrogencarbonate; DL-Pro-NHMe; In tert-Amyl alcohol; at 120℃; for 24h;Inert atmosphere; | General procedure: A mixture of arylaldehyde (0.1 g, 1 mmol), dihaloarene (0.565 g, 2 mmol), Pd(OAc)2 (0.022 g, 10.0 mol%), N-phenylpicolinamide (L7, 0.019 g, 15.0 mol%) and potassium hydrogen carbonate (0.5 g, 5 mmol) in tert-amyl alcohol (5.0 ml) was taken in 100.0 ml round bottom flask under N2 atmosphere and stirred for 120C for 24 h. Progress of the reaction was monitored continuously by TLC with ethyl acetate: hexane (2:3) eluent system. After completion of reaction, crude was poured into crushed ice and then filter the reaction mixture. Filtrate then extracted with ethyl acetate (3 times). Organic layer was separated, dried (over anhydrous Na2SO4) and evaporated under reduced pressure and purified by column chromatography to obtain desired product. Characterization data of compounds 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3v and 3x were found exactly similar as reported in the literature (References of above compound are mentioned in Supplementary data). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | General procedure: To a suspension of 0.001 mol of compound 2 in methanol,0.001 mol of the appropriate arylaldehyde was added.Then the mixture was heated under reflux for 1h. Next, 0.5ml of concentrated acetic acid was added, and heating wascontinued for 4-5 h. After cooling, the mixture was left overnight.The precipitate was then filtered off and recrystallizedfrom methanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With diethoxymethylane; ferric benzoylacetonate; In iso-butanol; at 80℃; for 24h; | In the air, a 25 mL reaction flask was charged with benzoylacetone ferrous (0.05 mmol), alkene 1 s (0.5 mmol), and methyldiethoxysilane (2.0 mmol).Secondary butanol (2.0 mL). After mixing at room temperature,The reaction mixture is reacted at 80 C24h. The reaction was completed, the reaction was completed, and the yield was obtained by direct chromatography to give a yield of 84%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With triethylamine; In methanol; at 20℃; for 18h; | Triethylamine (125 mL, 0.89 mmol) was added to a suspension of4a (218 mg, 0.85 mmol) and 4-ethoxybenzaldehyde (5a) (0.24 mL,1.74 mmol) in methanol (10 mL). The mixture was stirred at roomtemperature, and the solids dissolved in approximately 1 h. Thesolution was stirred for another 24 h, during which solid precipitatesgradually formed. The mixture was filtered and washedwith cold EtOH and Et2O to obtain the 8-oxopurine-6-carboxamide1a (182 mg, 53% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.6% | With tert-butylsulfenyl iodide; potassium hydroxide; at 80℃; for 2h; | The First Step 2-(2-Ethoxyphenyl)ethylene oxide 2-Ethoxy-benzaldehyde 6a (5.00 g, 33.3 mmol) and tert-butylthiohypoiodite (8.16 g, 39.9 mmol) were dissolved in 20 mL dimethylsulfoxide, and potassium hydroxide (5.6 g, 99.9 mmol) were added, and the mixture was heated to 80 C. to react for 2 h. The reaction mixture was cooled to room temperature and filtered. 100 mL water was added into the filtrate, and the filtrate was extracted with ethyl acetate (40 mL*3). The organic phases were combined, successively washed with water (40 mL*2) and saturated sodium chloride solution (40 mL*2), dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: A system) to obtain 2-(2-ethoxyphenyl)ethylene oxide 6b (5.0 g, light yellow oily product); yield: 91.6%. MS m/z(ESI):165.0 [M+1] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With acetic acid; In ethanol; at 83℃; for 0.333333h;Microwave irradiation; | General procedure: Compound 2 and the corresponding aldehyde were placed in a round-bottom flask, at a ratioof 1:1. Then, 5 mL of ethanol and 3 drops of acetic acid were added. The mixture was exposed tomicrowave irradiation for 20 min in conditions of 50 W and 83 C. The obtained compounds werefiltered and washed with ethanol. The general route for the synthesis is presented in Figure 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sulphonated graphene oxide / chloroform / 0.27 h / 120 °C / 12751.3 Torr / Flow reactor 2: chlorosulfonic acid / chloroform / 0.17 h / 25 °C / Flow reactor 3: chloroform / 0.08 h / 25 °C / Flow reactor |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sulphonated graphene oxide / chloroform / 0.27 h / 120 °C / 12751.3 Torr / Flow reactor 2: chlorosulfonic acid / chloroform / 0.17 h / 25 °C / Flow reactor 3: chloroform / 0.08 h / 25 °C / Flow reactor |
Tags: 613-69-4 synthesis path| 613-69-4 SDS| 613-69-4 COA| 613-69-4 purity| 613-69-4 application| 613-69-4 NMR| 613-69-4 COA| 613-69-4 structure
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