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[ CAS No. 5356-71-8 ] {[proInfo.proName]}

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Chemical Structure| 5356-71-8
Chemical Structure| 5356-71-8
Structure of 5356-71-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5356-71-8 ]

CAS No. :5356-71-8 MDL No. :MFCD00084878
Formula : C15H13N3 Boiling Point : -
Linear Structure Formula :- InChI Key :SXOFMEWDEKEVJU-UHFFFAOYSA-N
M.W : 235.28 Pubchem ID :199969
Synonyms :

Calculated chemistry of [ 5356-71-8 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 73.4
TPSA : 43.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 3.21
Log Po/w (WLOGP) : 3.13
Log Po/w (MLOGP) : 2.96
Log Po/w (SILICOS-IT) : 2.32
Consensus Log Po/w : 2.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.89
Solubility : 0.0305 mg/ml ; 0.000129 mol/l
Class : Soluble
Log S (Ali) : -3.8
Solubility : 0.037 mg/ml ; 0.000157 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.09
Solubility : 0.0019 mg/ml ; 0.00000809 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.28

Safety of [ 5356-71-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5356-71-8 ]

* 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 [ 5356-71-8 ]

[ 5356-71-8 ] Synthesis Path-Downstream   1~93

  • 1
  • [ 614-16-4 ]
  • [ 100-63-0 ]
  • [ 5356-71-8 ]
YieldReaction ConditionsOperation in experiment
78% In a 2-5 mL microwave vial containing a stir bar, 3-oxo-3-phenylpropanenitrile (290 mg, 2 mmol) and 5mL of 1M HCl were combined with stirring to give a 0.4 M solution of starting material. Next, phenylhydrazine (216 mg, 2mmol) was added to the solution. The microwave vial was then sealed with an aluminum cap and irradiated in the microwave reactor at 150 C for 10 m with the absorbance set to ?very high.? After cooling, the resulting solution was basified with 10% NaOH and was sonicated for 5 min. to produce a visible solid precipitate. The precipitate was filtered, washed twice with D.I. water, and then dried to yield the product as a light brown solid (365 mg, 78% yield).
75% at 185℃; for 4h; A mixture of 3-oxo-3- phenylpropanenitrile (1 g, 6.89 mmol) and phenylhydrazine (0.745 g, 6.89 mmol) was heated at 185 C for 4 h. Progress of the reaction was monitored by TLC. Upon completion the reaction mixture was cooled to room temperature and the solid was triturated with diethyl ether, filtered and dried under reduced pressure to afford the title compound (1.2 g, 75%)
In ethanol; at 80℃; for 3h; To a solution of 3-oxo-3-phenylpropanenitrile (7.0 g, 0.048 mol) in EtOH (80 mL) was added dropwise phenylhydrazine (5.2 g, 0.048 mol). The mixture was stirred at 80 C for 3 h. The mixture was cooled and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with petroleum ether/EtOAc = 5 : 1 to afford the title compound as a yellow solid. MS: m/z = 236 (M+H). NMR (300 MHz, DMSO-d6) 8 7.75- 7.77 (br, 2 H), 7.65-7.68 (br, 2H), 7.48-7.54 (br, 2H), 7.30-7.42 (br, 4H), 5.92(s, 1H), 5.46 (br, 2H).
In ethanol; at 80℃; for 3h; Example of reaction scheme VI: Intermediate 31 ,3 -Diphenyl- 1 H-pyrazol-5 -amineStep B: l,3-Diphenyl-lH-pyrazol-5-amineTo a solution of 3-oxo-3-phenylpropanenitrile (7.0 g, 0.048 mol) in EtOH (80 mL) was added dropwise phenylhydrazine (5.2 g, 0.048 mol). The mixture was stirred at 80 C for 3 h. The mixture was cooled and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with petroleum ether/EtOAc = 5: 1 to afford the title compound as a yellow solid. MS: m/z = 236 (M+H). 1H NMR (300 MHz, DMSO-d6) delta 7.75-7.77 (br, 2 H), 7.65-7.68 (br, 2H), 7.48-7.54 (br, 2H), 7.30-7.42 (br, 4H), 5.92(s, 1H), 5.46 (br, 2H).
With hydrogenchloride; In ethanol; water; at 100℃; for 4h; General procedure: To a mixture of appropriate beta-ketonitrile (6a-c, 5.5mmol) and substituted hydrazine or hydrazine hydrochloride(6 mmol) in 20 mL of ethanol was added aqueous 2 M HCl(0.8 mL). The resulting solution was heated at 100 C for 4h. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was poured into ice water and basified with aqueous 10% NaOH. The resulting suspension was extracted with diethyl acetate (3 x20 mL). The combined organic layers were dried over Na2SO4 and then concentrated under reduced pressure to afford the title aminopyrazoles, which were purified by crystallization from ethanol.

  • 2
  • [ 5356-71-8 ]
  • [ 76903-88-3 ]
  • N-(1,3-diphenyl-1H-pyrazol-5-yl)-3,4-difluorobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of 5-amino-1, 3-diphenylpyrazole, 2-1, (100 mg, 0.425 mmol) in was added DIEA (150 uL, 0. 85 mmol) and allowed to stir for 15 minutes followed by the addition of 3,4-difluorobenzoyl chloride (890 mg, 0.51 mmol). The solution stirred at RT until complete by TLC, and then purified by mass-guided preparative HPLC on an Agilent 1100 SYSTEM. 1H NMR (300 MHz, CDC13) : 8 7.92 (m, 2H), 7.45 (m, 12H); Analytical LCMS: single peak (214 nm) at 3.551 min (CH3CN/H20/1% TFA, 4 min gradient), HRMS calc'd for C22H15F2N3 (M+H), 376.1256 ; found 376.1268
  • 3
  • [ 5356-71-8 ]
  • [ 1711-05-3 ]
  • <i>N</i>-(2,5-diphenyl-2<i>H</i>-pyrazol-3-yl)-3-methoxy-benzamide [ No CAS ]
  • 5
  • [ 1076-38-6 ]
  • [ 2058-72-2 ]
  • [ 5356-71-8 ]
  • [ 1198604-97-5 ]
  • 6
  • [ 1677-46-9 ]
  • [ 2058-72-2 ]
  • [ 5356-71-8 ]
  • 5'-bromo-1',5-dimethyl-8,10-diphenyl-10,11-dihydrospiro[benzo[h]pyrazolo[3,4-b][1,6]naphthyridine-7,3'-indoline]-2',6(5H)-dione [ No CAS ]
  • 7
  • [ 2058-72-2 ]
  • [ 5356-71-8 ]
  • [ 126-81-8 ]
  • [ 1221252-27-2 ]
  • 8
  • [ 5356-71-8 ]
  • [ 62348-13-4 ]
  • [ 849337-26-4 ]
  • 9
  • [ 5356-71-8 ]
  • [ 1204-28-0 ]
  • [ 1246523-79-4 ]
  • 10
  • [ 123-39-7 ]
  • [ 5356-71-8 ]
  • [ 1257533-48-4 ]
YieldReaction ConditionsOperation in experiment
97% With trichlorophosphate; at 50 - 60℃;Inert atmosphere; Microwave irradiation; General procedure: The reliable procedure involved the treatment of N-1-phenyl-5-aminopyrazoles (1a-e, 1.0 equiv) with catalytic amount of POCl3 (?3 equiv) with N-methylformamide (2 mL) at 50-60 C with 100 W of microwave energy within 20-30 min. When the reaction was completed, the reaction mixture was concentrated, added to saturate sodium bicarbonate (15 mL), and extracted with dichloromethane (15 mL). The organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residues were purified by column chromatography on silica gel to give the corresponding N-(1H-pyrazol-5-yl)formamidines 3a-e in 76-97% yield.
  • 11
  • [ 1187-58-2 ]
  • [ 5356-71-8 ]
  • [ 1257533-50-8 ]
YieldReaction ConditionsOperation in experiment
93% With trichlorophosphate at 30 - 40℃; Microwave irradiation;
  • 12
  • [ 1076-38-6 ]
  • [ 2058-72-2 ]
  • [ 5356-71-8 ]
  • [ 1217110-04-7 ]
  • 17
  • [ 606-23-5 ]
  • [ 667463-64-1 ]
  • [ 5356-71-8 ]
  • [ 1315268-75-7 ]
  • 18
  • [ 606-23-5 ]
  • [ 5356-71-8 ]
  • [ 91-56-5 ]
  • [ 1315268-67-7 ]
YieldReaction ConditionsOperation in experiment
93% at 60℃; for 0.35h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 19
  • [ 67-52-7 ]
  • [ 5356-71-8 ]
  • [ 91-56-5 ]
  • [ 1152724-46-3 ]
YieldReaction ConditionsOperation in experiment
95% at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 20
  • [ 67-52-7 ]
  • [ 608-05-9 ]
  • [ 5356-71-8 ]
  • [ 1152724-54-3 ]
YieldReaction ConditionsOperation in experiment
95% at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 21
  • [ 67-52-7 ]
  • [ 2058-72-2 ]
  • [ 5356-71-8 ]
  • [ 1152724-60-1 ]
  • 22
  • [ 5356-71-8 ]
  • [ 77287-34-4 ]
  • [ 77746-92-0 ]
YieldReaction ConditionsOperation in experiment
96% With trichlorophosphate; In dichloromethane; at 80 - 90℃;Inert atmosphere; General procedure: The reliable procedure involved the treatment of N-1-phenyl-5-aminopyrazoles, N-1-phenyl-5-aminopyrazoles (1a-e, 1.0 equiv), N-1-(2-pyridinyl)-5-aminopyrazoles (4a-e 1.0 equiv), or N-1-(2-quinolinyl)-5-aminopyrazoles (5a-e, 1.0 equiv) with catalytic amount of POCl3 (?3 equiv) with formamide (2 mL) in CH2Cl2 solution at 80-90 C within 0.5-1 h. When the reaction was completed, the reaction mixture was concentrated, added to saturate sodium bicarbonate (15 mL), and extracted with dichloromethane (15 mL). The organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residues were purified by column chromatography on silica gel to give the corresponding pyrazolo[3,4-d]pyrimidine products 12a-e, 13a-e or 14a-e were obtained in 91-96%, 81-88%, or 82-91% yield, respectively.
  • 23
  • [ 5356-71-8 ]
  • [ 77287-34-4 ]
  • [ 1400634-58-3 ]
YieldReaction ConditionsOperation in experiment
96% With phosphorus tribromide; at 50 - 60℃;Inert atmosphere; General procedure: The reliable procedure involved the treatment of 5-aminopyrazoles (1-28, 1.0 equiv) with catalytic amount of PBr3 (~3 equiv) in formamide solution (2 mL) at 50-60 C within 0.5-1 h. When the reaction was completed, the reaction mixture was added to saturate sodium bicarbonate (15 mL) and extracted with dichloromethane (15 mL). The organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue solution was purified by column chromatography on silica gel to give the corresponding pyrazolo[3,4-d]pyrimidine products (29-56) in 76-96% yields.
  • 24
  • [ 5356-71-8 ]
  • [ 1414568-50-5 ]
YieldReaction ConditionsOperation in experiment
87% With N-chloro-succinimide; In acetonitrile; at 20℃; for 3h; To a solution of l,3-diphenyl-lH-pyrazol-5-amine (Table 1; 0.100 g, 0.425 mmol) in acetonitrile (2 mL) was added N-chlorosuccinimide (0.0568 g, 0.425 mmol). The pale yellow solution was stirred at ambient temperature for 3 hours, then concentrated in vacuo and purified by silica column chromatography eluting with 20% EtOAc/Hexanes to afford the product as a light brown oil (0.10 g, 87% yield). MS (apci) m/z = 270.0 (M+H).
87% With N-chloro-succinimide; In acetonitrile; at 20℃; for 3h; Intermediate PI 15 4-chloro- 1 ,3-diphenyl- 1 H-pyrazol-5-amine [00394] To a solution of l,3-diphenyl-lH-pyrazol-5-amine (Table 1 ; 0.100 g, 0.425 mmol) in acetonitrile (2 mL) was added N-chlorosuccinimide (0.0568 g, 0.425 mmol). The pale yellow solution was stirred at ambient temperature for 3 hours, then concentrated in vacuo and purified by silica column chromatography eluting with 20% EtOAc/Hexanes to afford the product as a light brown oil (0.10 g, 87% yield). MS (apci) m/z = 270.0 (M+H).
87% With N-chloro-succinimide; In acetonitrile; at 20℃; for 3h; (005781 To a solution of <strong>[5356-71-8]1,3-diphenyl-1H-pyrazol-5-amine</strong> (Table 1; 0.100 g, 0.425 mmol) in acetonitrile (2 mL) was added N-chlorosuccinimide (0.0568 g, 0.425 mmol). The pale yellow solution was stirred at ambient temperature for 3 hours, then concentrated in vacuo and purified by silica column chromatography eluting with 20% EtOAc/Hexanes to afford the product as a light brown oil (0.10 g, 87% yield). MS (apci) mlz = 270.0 (M+H).
87% With N-chloro-succinimide; In acetonitrile; at 20℃; for 3h; Intermediate P115 4-chloro- 1 ,3 -diphenyl- 1 H-pyrazol-5-amine [00509] To a solution of l,3-diphenyl-lH-pyrazol-5-amine (Table 1; 0.100 g, 0.425 mmol) in acetonitrile (2 mL) was added N-chlorosuccinimide (0.0568 g, 0.425 mmol). The pale yellow solution was stirred at ambient temperature for 3 hours, then concentrated in vacuo and purified by silica column chromatography eluting with 20% EtOAc/Hexanes to afford the product as a light brown oil (0.10 g, 87% yield). MS (apci) m/z = 270.0 (M+H).
87% With N-chloro-succinimide; In acetonitrile; at 20℃; for 3h; To a solution of l,3-diphenyl-lH-pyrazol-5-amine (Table 1; 0.100 g, 0.425 mmol) in acetonitrile (2 mL) was added N-chlorosuccinimide (0.0568 g, 0.425 mmol). The pale yellow solution was stirred at ambient temperature for 3 hours, then concentrated in vacuo and purified by silica column chromatography eluting with 20% EtOAc/Hexanes to afford the product as a light brown oil (0.10 g, 87% yield). MS (apci) m/z = 270.0 (M+H).
87% With N-chloro-succinimide; In acetonitrile; at 20℃; for 3h; Intermediate P115 4-chloro- 1 ,3-diphenyl- 1 H-pyrazol-5-amine(007071 To a solution of <strong>[5356-71-8]1,3-diphenyl-1H-pyrazol-5-amine</strong> (Table 1; 0.100 g, 0.425 mmol) in acetonitrile (2 mL) was added N-chlorosuccinimide (0.0568 g, 0.425 mmol). The pale yellow solution was stirred at ambient temperature for 3 hours, then concentrated in vacuo and purified by silica column chromatography eluting with 20% EtOAc/Hexanes to afford the product as a light brown oil (0.10 g, 87% yield). MS (apci) mlz - 270.0 (M+H).
87% With N-chloro-succinimide; In acetonitrile; at 20℃; for 3h; To a solution of l,3-diphenyl-lH-pyrazol-5-amine (Table 1; 0.100 g, 0.425 mmol) in acetonitrile (2 mL) was added N-chlorosuccinimide (0.0568 g, 0.425 mmol). The pale yellow solution was stirred at ambient temperature for 3 hours, then concentrated in vacuo and purified by silica column chromatography eluting with 20% EtOAc/Hexanes to afford the product as a light brown oil (0.10 g, 87% yield). MS (apci) m/z - 270.0 (M+H).

  • 25
  • [ 591-50-4 ]
  • [ 5356-71-8 ]
  • [ 94863-16-8 ]
YieldReaction ConditionsOperation in experiment
78% With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 30h;Inert atmosphere; General procedure: A 5-amino-pyrazole substrates (1.0 mmol, 1.0 equiv), arylhalides (PhCl, PhBr, PhI, p-MeO-PhI, or tolyl iodide, 1.0 mmol, 1.0 equiv), and K2CO3 (1.2 mmol, 1.2 equiv) with catalytic amount CuI (0.1 mmol, 0.1 equiv) and 1,10-phenanthroline (0.1 mmol, 0.1 equiv) in DMF at 70 or 140 C within 1-48 h under nitrogen gas. After 5-amino-pyrazoles were completely consumed, the reaction mixture was work-up, extracted with CH2Cl2 (20 mL×2), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give the corresponding 5-arylamino-1-arylpyrazole products in 17-96%.4.1.11 5-Anilino-1,3-diphenyl-1H-pyrazole (24) Yellow powder; mp 152-153 C; 1H NMR (CDCl3, 300 MHz) delta 5.55 (br, 1H, NH), 6.52 (s, 1H, Py), 6.99 (d, 2H, J=7.8 Hz, ArH), 7.18-7.50 (m, 9H, ArH), 7.63 (d, 2H, J=7.7 Hz, ArH), 7.86 (d, 2H, J=7.2 Hz, ArH); 13C NMR (CDCl3, 75 MHz) delta 93.72, 115.91, 120.94, 124.38, 125.61, 127.67, 127.93, 128.50, 129.34, 129.44, 133.18, 138.33, 142.17, 142.98, 151.47; IR (diffuse reflectance) 3233 (m), 3004 (m), 2935 (m), 1596 (s), 1494 (m), 1452 (m), 1361 (m), 1301 (m), 1255 (w), 1165 (m) cm-1; MS (ESI) m/z: 312 (M+H)+. HRMS (ESI) calcd for C21H18N3 (M+H)+ 312.1501, found 312.1503.
  • 26
  • [ 5356-71-8 ]
  • 6-(4,6-dichloro-1,3,5-triazin-2-ylamino)-7-hydroxynaphthalene-2-sulfonic acid [ No CAS ]
  • sodium 6-(4,6-dichloro-1,3,5-triazin-2-ylamino)-8-((1,3-diphenyl-1H-pyrazol-5-yl) diazenyl)-7-hydroxynaphthalene-2-sulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% General procedure: Nitrosyl sulphuric acid was prepared by dissolving sodium nitrite (0.20g, 2.1mmol) in sulphuric acid (20ml) at 0C. 5-Amino-3-substituted-1-phenylpyrazoles 2a-c (2.1mmol) was dissolved in hot glacial acetic acid (2.5ml) and rapidly cooled in ice/salt bath to 0-5C. The solution was added in portions over 30min to nitrosylsulphuric acid at 0-5C and the mixture stirred for a further 1h at the same temperature. The resulting diazonium solution was added slowly over 1h to compounds 1 and 4 at a pH of 7 by the addition NaOH (5N). The stirring was continued for 4h at 0-5C. A solution of disodium hydrogen phosphate (0.2g), and potassium dihydrogen phosphate (0.4g) in water followed by a sufficient NaCl (7.5g) was added to precipitate the product. The reaction mixture was stirred at 0C for 2h and the colored solid formed was filtered, washed with water and crystallized from ethanol to give compounds 3a-c and 5a-c.
  • 27
  • [ 5356-71-8 ]
  • [ 7538-88-7 ]
  • sodium 5-(4,6-dichloro-1,3,5-triazin-2-ylamino)-3-((1,3-diphenyl-1H-pyrazol-5-yl)diazenyl)-4-hydroxynaphthalene-2,7-disulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% General procedure: Nitrosyl sulphuric acid was prepared by dissolving sodium nitrite (0.20g, 2.1mmol) in sulphuric acid (20ml) at 0C. 5-Amino-3-substituted-1-phenylpyrazoles 2a-c (2.1mmol) was dissolved in hot glacial acetic acid (2.5ml) and rapidly cooled in ice/salt bath to 0-5C. The solution was added in portions over 30min to nitrosylsulphuric acid at 0-5C and the mixture stirred for a further 1h at the same temperature. The resulting diazonium solution was added slowly over 1h to compounds 1 and 4 at a pH of 7 by the addition NaOH (5N). The stirring was continued for 4h at 0-5C. A solution of disodium hydrogen phosphate (0.2g), and potassium dihydrogen phosphate (0.4g) in water followed by a sufficient NaCl (7.5g) was added to precipitate the product. The reaction mixture was stirred at 0C for 2h and the colored solid formed was filtered, washed with water and crystallized from ethanol to give compounds 3a-c and 5a-c.
  • 28
  • [ 5356-71-8 ]
  • [ 4996-21-8 ]
  • (1,3-diphenyl-1,4,6,7-tetrahydropyrazolo[3,4-d][1,3]oxazine-4,6-diyl)bis((4-chlorophenyl)methanone) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With acetic acid; at 20℃; General procedure: In a 25-mL reaction vial, 1-(4-chlorophenyl)-2,2-dihydroxyethanone (1a, 2.2 mmol), 3-methyl-1-phenyl-1H-pyrazol-5-amine (2a, 1.0 mmol) and HOAc (1.5 mL) were then successively added. Subsequently, the mixture was stirred at room temperature until TLC revealed that conversion of the starting material 2a was complete. Then the solid was obtained through filtration and washed with 2mL 95% EtOH to give the almost pure product 3a, which were further purified by recrystallization from 95% EtOH to afford the desired 3a.
  • 29
  • [ 5356-71-8 ]
  • [ 16208-14-3 ]
  • (1,3-diphenyl-1,4,6,7-tetrahydropyrazolo[3,4-d][1,3]oxazine-4,6-diyl)bis(p-tolylmethanone) [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With acetic acid; at 20℃; General procedure: In a 25-mL reaction vial, 1-(4-chlorophenyl)-2,2-dihydroxyethanone (1a, 2.2 mmol), 3-methyl-1-phenyl-1H-pyrazol-5-amine (2a, 1.0 mmol) and HOAc (1.5 mL) were then successively added. Subsequently, the mixture was stirred at room temperature until TLC revealed that conversion of the starting material 2a was complete. Then the solid was obtained through filtration and washed with 2mL 95% EtOH to give the almost pure product 3a, which were further purified by recrystallization from 95% EtOH to afford the desired 3a.
  • 30
  • [ 5356-71-8 ]
  • [ 31686-94-9 ]
  • ethyl 4-(4-fluorophenyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-6-carboxylate [ No CAS ]
  • 31
  • [ 5356-71-8 ]
  • [ 5814-38-0 ]
  • ethyl 4-(4-chlorophenyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-6-carboxylate [ No CAS ]
  • 32
  • [ 5356-71-8 ]
  • [ 5814-37-9 ]
  • ethyl 1,3-diphenyl-4-p-tolyl-1H-pyrazolo[3,4-b]pyridine-6-carboxylate [ No CAS ]
  • 33
  • [ 5356-71-8 ]
  • [ 15971-92-3 ]
  • 6-cyclohexyl-1,3-diphenyl-1,7-dihydro-4H-pyrazolo[3,4-b]pyridin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With polyphosphoric acid; at 120 - 130℃; for 2h; General procedure: Cyclization in polyphosphoric acid (Method A): A mixture of 5-aminopyrazole 7d-r (0.5 mmol), the appropriated beta-ketoester 9s-w (0.55 mmol) and polyphosphoric acid (3 g)was heated under stirring at 120C for 2 h. The reaction mixture was poured into ice and water and neutralized with aqueous NaOH 10%. The crude solid was filtered off and washed with cold water. The residue was purified by column chromatography, eluted with Petroleum ether/ EtOAc 9/ 1.
  • 34
  • [ 675-10-5 ]
  • [ 5356-71-8 ]
  • [ 635-93-8 ]
  • 10-chloro-5-(2-oxopropyl)-1,3-diphenylchromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% General procedure: A mixture of salicylaldehydes 1 (1 mmol), 4-hydroxy-6-methyl-2H-pyran-2-one 2 (1mmol) and L-proline (0.10 mmol) in EtOH (10 mL) was stirred at 80 C for 1 h. Then pyrazol-5-amines 3(1 mmol) and CuSO4 (0.20 mmol) was added to the reactor and stirred at 80 C for 4-48 h. Aftercompletion of the reaction confirmed by TLC (eluent acetone/petroleum ether (PE), V/V = 1:3), thereaction mixture was concentrated in vacuo to remove the solvent. The product purified by columnchromatography (PE-acetone = 5:1) to afford the pure product 4.
  • 35
  • [ 675-10-5 ]
  • [ 5356-71-8 ]
  • [ 148-53-8 ]
  • 8-methoxy-5-(2-oxopropyl)-1,3-diphenylchromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% General procedure: A mixture of salicylaldehydes 1 (1 mmol), 4-hydroxy-6-methyl-2H-pyran-2-one 2 (1mmol) and L-proline (0.10 mmol) in EtOH (10 mL) was stirred at 80 C for 1 h. Then pyrazol-5-amines 3(1 mmol) and CuSO4 (0.20 mmol) was added to the reactor and stirred at 80 C for 4-48 h. Aftercompletion of the reaction confirmed by TLC (eluent acetone/petroleum ether (PE), V/V = 1:3), thereaction mixture was concentrated in vacuo to remove the solvent. The product purified by columnchromatography (PE-acetone = 5:1) to afford the pure product 4.
  • 36
  • [ 673-22-3 ]
  • [ 675-10-5 ]
  • [ 5356-71-8 ]
  • 9-methoxy-5-(2-oxopropyl)-1,3-diphenylchromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% General procedure: A mixture of salicylaldehydes 1 (1 mmol), 4-hydroxy-6-methyl-2H-pyran-2-one 2 (1mmol) and L-proline (0.10 mmol) in EtOH (10 mL) was stirred at 80 C for 1 h. Then pyrazol-5-amines 3(1 mmol) and CuSO4 (0.20 mmol) was added to the reactor and stirred at 80 C for 4-48 h. Aftercompletion of the reaction confirmed by TLC (eluent acetone/petroleum ether (PE), V/V = 1:3), thereaction mixture was concentrated in vacuo to remove the solvent. The product purified by columnchromatography (PE-acetone = 5:1) to afford the pure product 4.
  • 37
  • [ 5356-71-8 ]
  • [ 1198083-53-2 ]
  • 2-(4-benzoyl-1,3,6-triphenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-N-(4-methoxyphenyl)-2-oxoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% In 1,4-dioxane; at 60℃; for 4.5h; General procedure: A solution of 4,5-dibenzoyl-1-(4-methoxyphenyl)-1H-pyrrole-2,3-dione (6a; 411 mg, 1.0 mmol) and 3-methyl-1-phenyl-1H-pyrazol-5-amine (7a; 173 mg, 1.0 mmol) in anhyd 1,4-dioxane (5 mL) was stirred at 60 C for 4.5 h. Upon completion, the solvent was removed under reduced pressure and the residue was recrystallized from EtOH to afford compound 10aa.
  • 38
  • [ 5356-71-8 ]
  • [ 112641-20-0 ]
  • 8-(trifluoromethyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline [ No CAS ]
  • 39
  • [ 5356-71-8 ]
  • [ 93118-03-7 ]
  • 8-(trifluoromethyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline [ No CAS ]
  • 1,3,5,7-tetraphenyl-4-[2-chloro-3-(trifluoromethyl)phenyl]-bispyrazolo[3,4-b,4',3'-e]pyridine [ No CAS ]
  • 40
  • [ 5356-71-8 ]
  • [ 82386-89-8 ]
  • 6-(trifluoromethyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline [ No CAS ]
  • 1,3,5,7-tetraphenyl-4-[2-chloro-5-(trifluoromethyl)phenyl]-bispyrazolo[3,4-b,4',3'-e]pyridine [ No CAS ]
  • 41
  • [ 5356-71-8 ]
  • [ 146137-72-6 ]
  • 5-iodo-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoline [ No CAS ]
  • 1,3,5,7-tetraphenyl-4-(2-fluoro-6-iodophenyl)-bis-pyrazolo[3,4-b,4',3'-e]pyridine [ No CAS ]
  • 42
  • [ 5356-71-8 ]
  • [ 609-73-4 ]
  • (2,5-diphenyl-2H-pyrazol-3-yl)(2-nitrophenyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 24h;Inert atmosphere; General procedure: The appropriate 4-substituted-1-iodo-2-nitrobenzene 10 (1mmol), appropriate 1,3-disubstituted-5-aminopyrazole 11 (1.3mmol), and anhydrous potassium carbonate (248mg, 1.8mmol) were heated in the presence of rac-BINAP (23mg, 0.036mmol, 3.7mol%), Pd2dba3 (23mg, 0.024mmol, 2.5mol%), and 18-crown-6 (10mg, 0.038mmol) in toluene (8mL, purged with argon) at 100C. The reaction was carried out under argon for 24h. After cooling the reaction mixture was filtered and purified using column chromatography on aluminium oxide with toluene, or a toluene-ethyl acetate mixture (10:1) as an eluent. The product was recrystallized from toluene. 4.6.1 (2,5-Diphenyl-2H-pyrazol-3-yl)-(2-nitrophenyl)-amine (12a) (0035) Red long plates, 345mg, 97%, mp. 130-131C; 1H NMR (600MHz, CDCl3, ppm): delta=9.42 (s, 1H), 8.2 (dd, J=8.5, 1.5Hz, 1H), 7.9 (d, J=7.1Hz, 2H), 7.59 (dd, J=8.6, 1.2Hz, 2H), 7.47-7.34 (m, 5H), 7.37-7.34 (m, 2H), 7.22 (dd, J=8.5, 1.0Hz, 1H), 6.87 (dtd, J=7.8, 1.2, 1.3Hz, 1H), 6.7 (s 1H); 13C NMR (150MHz, CDCl3, ppm): delta=151.7, 141.6, 138.1, 138.0, 136.2, 132.8, 129.4, 128.7, 128.4, 128.3, 128.1, 126.53, 125.56, 124.0, 119.0, 116.3, 98.8; IR (ATR): nu=3246, 3056, 1609, 1587, 1555, 1506, 1494, 1341, 1270, 1238, 1140, 1071, 954, 777, 737, 691, 616, 515, 470cm-1. Anal. Calcd for C21H16N4O2: C, 70.77; H,4.53; N, 15.72. Found: C, 71.28; H, 4.61; N, 15.25.
  • 43
  • [ 5356-71-8 ]
  • [ 5446-05-9 ]
  • (2,5-diphenyl-2H-pyrazol-3-yl)(4-chloro-2-nitrophenyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 24h;Inert atmosphere; General procedure: The appropriate 4-substituted-1-iodo-2-nitrobenzene 10 (1mmol), appropriate 1,3-disubstituted-5-aminopyrazole 11 (1.3mmol), and anhydrous potassium carbonate (248mg, 1.8mmol) were heated in the presence of rac-BINAP (23mg, 0.036mmol, 3.7mol%), Pd2dba3 (23mg, 0.024mmol, 2.5mol%), and 18-crown-6 (10mg, 0.038mmol) in toluene (8mL, purged with argon) at 100C. The reaction was carried out under argon for 24h. After cooling the reaction mixture was filtered and purified using column chromatography on aluminium oxide with toluene, or a toluene-ethyl acetate mixture (10:1) as an eluent. The product was recrystallized from toluene.
  • 44
  • [ 5356-71-8 ]
  • [ 112671-42-8 ]
  • (2,5-diphenyl-2H-pyrazol-3-yl)(4-bromo-2-nitrophenyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 24h;Inert atmosphere; General procedure: The appropriate 4-substituted-1-iodo-2-nitrobenzene 10 (1mmol), appropriate 1,3-disubstituted-5-aminopyrazole 11 (1.3mmol), and anhydrous potassium carbonate (248mg, 1.8mmol) were heated in the presence of rac-BINAP (23mg, 0.036mmol, 3.7mol%), Pd2dba3 (23mg, 0.024mmol, 2.5mol%), and 18-crown-6 (10mg, 0.038mmol) in toluene (8mL, purged with argon) at 100C. The reaction was carried out under argon for 24h. After cooling the reaction mixture was filtered and purified using column chromatography on aluminium oxide with toluene, or a toluene-ethyl acetate mixture (10:1) as an eluent. The product was recrystallized from toluene.
  • 45
  • [ 5356-71-8 ]
  • [ 112671-42-8 ]
  • 6-bromo-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoxaline [ No CAS ]
  • 46
  • [ 5356-71-8 ]
  • [ 364-77-2 ]
  • (2,5-diphenyl-2H-pyrazol-3-yl)(4-fluoro-2-nitrophenyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 24h;Inert atmosphere; General procedure: The appropriate 4-substituted-1-iodo-2-nitrobenzene 10 (1mmol), appropriate 1,3-disubstituted-5-aminopyrazole 11 (1.3mmol), and anhydrous potassium carbonate (248mg, 1.8mmol) were heated in the presence of rac-BINAP (23mg, 0.036mmol, 3.7mol%), Pd2dba3 (23mg, 0.024mmol, 2.5mol%), and 18-crown-6 (10mg, 0.038mmol) in toluene (8mL, purged with argon) at 100C. The reaction was carried out under argon for 24h. After cooling the reaction mixture was filtered and purified using column chromatography on aluminium oxide with toluene, or a toluene-ethyl acetate mixture (10:1) as an eluent. The product was recrystallized from toluene.
  • 47
  • [ 5356-71-8 ]
  • [ 5326-39-6 ]
  • (2,5-diphenyl-2H-pyrazol-3-yl)(4-methyl-2-nitrophenyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 24h;Inert atmosphere; General procedure: The appropriate 4-substituted-1-iodo-2-nitrobenzene 10 (1mmol), appropriate 1,3-disubstituted-5-aminopyrazole 11 (1.3mmol), and anhydrous potassium carbonate (248mg, 1.8mmol) were heated in the presence of rac-BINAP (23mg, 0.036mmol, 3.7mol%), Pd2dba3 (23mg, 0.024mmol, 2.5mol%), and 18-crown-6 (10mg, 0.038mmol) in toluene (8mL, purged with argon) at 100C. The reaction was carried out under argon for 24h. After cooling the reaction mixture was filtered and purified using column chromatography on aluminium oxide with toluene, or a toluene-ethyl acetate mixture (10:1) as an eluent. The product was recrystallized from toluene.
  • 48
  • [ 5356-71-8 ]
  • [ 5326-39-6 ]
  • 6-methyl-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoxaline [ No CAS ]
  • 49
  • [ 5356-71-8 ]
  • [ 58755-70-7 ]
  • (2,5-diphenyl-2H-pyrazol-3-yl)(4-methoxy-2-nitrophenyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 24h;Inert atmosphere; General procedure: The appropriate 4-substituted-1-iodo-2-nitrobenzene 10 (1mmol), appropriate 1,3-disubstituted-5-aminopyrazole 11 (1.3mmol), and anhydrous potassium carbonate (248mg, 1.8mmol) were heated in the presence of rac-BINAP (23mg, 0.036mmol, 3.7mol%), Pd2dba3 (23mg, 0.024mmol, 2.5mol%), and 18-crown-6 (10mg, 0.038mmol) in toluene (8mL, purged with argon) at 100C. The reaction was carried out under argon for 24h. After cooling the reaction mixture was filtered and purified using column chromatography on aluminium oxide with toluene, or a toluene-ethyl acetate mixture (10:1) as an eluent. The product was recrystallized from toluene.
  • 50
  • [ 5356-71-8 ]
  • [ 91-56-5 ]
  • [ 614-16-4 ]
  • C32H21N5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With sulfonic acid-functionalized mesoporous MCM-41; In neat (no solvent); at 80℃; for 0.333333h;Green chemistry; General procedure: For the synthesis of spiro-1H-pyrazolo-[3,4-b]pyridines,a mixture of isatin or ninhydrin (1 mmol), 3-oxo-3-phenylpropanenitrile (1 mmol), 1H-pyrazol-5-amine(1 mmol) and PTPSAMCM-41 (10 mg) was stirred at80 C under solvent-free conditions for 20 min (monitoredby TLC, eluent: n-hexane/ethyl acetate, 6:1). The workup was performed as mentioned above to give the pure product.
  • 51
  • [ 3132-99-8 ]
  • [ 5356-71-8 ]
  • [ 614-16-4 ]
  • C31H21BrN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sulfonic acid-functionalized mesoporous MCM-41; In neat (no solvent); at 80℃; for 0.333333h;Green chemistry; General procedure: A mixture of aldehyde (1 mmol), 3-oxo-3-phenylpropanenitrile(1 mmol), 1H-pyrazol-5-amine (1 mmol) andPTPSAMCM-41 (10 mg) was stirred at 80 C under solvent-free conditions. After completion of the reaction(monitored by TLC, eluent: n-hexane/ethyl acetate, 6:1),acetone (10 mL) was added; the catalyst was filtered and washed with acetone. The solvent was evaporated under reduced pressure, and the residue was purified by recrystallization from EtOH to give the pure product.
  • 52
  • [ 5356-71-8 ]
  • [ 387-45-1 ]
  • [ 614-16-4 ]
  • C31H20ClFN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sulfonic acid-functionalized mesoporous MCM-41; In neat (no solvent); at 80℃; for 0.333333h;Green chemistry; General procedure: A mixture of aldehyde (1 mmol), 3-oxo-3-phenylpropanenitrile(1 mmol), 1H-pyrazol-5-amine (1 mmol) andPTPSAMCM-41 (10 mg) was stirred at 80 C under solvent-free conditions. After completion of the reaction(monitored by TLC, eluent: n-hexane/ethyl acetate, 6:1),acetone (10 mL) was added; the catalyst was filtered and washed with acetone. The solvent was evaporated under reduced pressure, and the residue was purified by recrystallization from EtOH to give the pure product.
  • 53
  • [ 5356-71-8 ]
  • [ 614-16-4 ]
  • [ 99-61-6 ]
  • C31H21N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sulfonic acid-functionalized mesoporous MCM-41; In neat (no solvent); at 80℃; for 0.333333h;Green chemistry; General procedure: A mixture of aldehyde (1 mmol), 3-oxo-3-phenylpropanenitrile(1 mmol), 1H-pyrazol-5-amine (1 mmol) andPTPSAMCM-41 (10 mg) was stirred at 80 C under solvent-free conditions. After completion of the reaction(monitored by TLC, eluent: n-hexane/ethyl acetate, 6:1),acetone (10 mL) was added; the catalyst was filtered and washed with acetone. The solvent was evaporated under reduced pressure, and the residue was purified by recrystallization from EtOH to give the pure product.
  • 54
  • [ 4397-53-9 ]
  • [ 5356-71-8 ]
  • [ 614-16-4 ]
  • C38H28N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With sulfonic acid-functionalized mesoporous MCM-41; In neat (no solvent); at 80℃; for 0.333333h;Green chemistry; General procedure: A mixture of aldehyde (1 mmol), 3-oxo-3-phenylpropanenitrile(1 mmol), 1H-pyrazol-5-amine (1 mmol) andPTPSAMCM-41 (10 mg) was stirred at 80 C under solvent-free conditions. After completion of the reaction(monitored by TLC, eluent: n-hexane/ethyl acetate, 6:1),acetone (10 mL) was added; the catalyst was filtered and washed with acetone. The solvent was evaporated under reduced pressure, and the residue was purified by recrystallization from EtOH to give the pure product.
  • 55
  • [ 5356-71-8 ]
  • [ 614-16-4 ]
  • [ 123-72-8 ]
  • C28H24N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With sulfonic acid-functionalized mesoporous MCM-41; In neat (no solvent); at 80℃; for 0.333333h;Green chemistry; General procedure: A mixture of aldehyde (1 mmol), 3-oxo-3-phenylpropanenitrile(1 mmol), 1H-pyrazol-5-amine (1 mmol) andPTPSAMCM-41 (10 mg) was stirred at 80 C under solvent-free conditions. After completion of the reaction(monitored by TLC, eluent: n-hexane/ethyl acetate, 6:1),acetone (10 mL) was added; the catalyst was filtered and washed with acetone. The solvent was evaporated under reduced pressure, and the residue was purified by recrystallization from EtOH to give the pure product.
  • 56
  • [ 5356-71-8 ]
  • C15H10BrN3O [ No CAS ]
  • 5-amino-6-(4-bromophenyl)-1,3,4-triphenyl-1H-pyrazolo[3,4-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium tert-butylate; In N,N-dimethyl-formamide; at 25℃; for 0.0833333h; General procedure: A mixture of alpha-azidochalcone 1a (R?=?Ar = C6H5, 0.249 g, 1.0 mmol), 3-methyl-1-phenyl-1H-pyrazol-5-amine 2a (R??=?CH3, R???=?C6H5, 0.173?g, 1.0 mmol) and t-BuOK (0.056?g, 0.5?mmol) in DMF (4?mL) was stirred at 25?C for 5?min. After completion of the reaction as was indicated by TLC monitoring, water (10?mL) was added to the mixture and extracted into EtOAc (3?x?15?mL). The combined organic extracts were washed with brine and the solvent was removed under the reduced pressure. The residue was purified by column chromatography using n-hexane/EtOAc (10:1) as eluent to afford pure product 3a.
  • 57
  • [ 5356-71-8 ]
  • 1-(p-Chlorphenyl)-2-azido-3-(p-chlorphenyl)-2-propen-1-on [ No CAS ]
  • 5-amino-4,6-bis(4-chlorophenyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium tert-butylate; In N,N-dimethyl-formamide; at 25℃; for 0.0833333h; General procedure: A mixture of alpha-azidochalcone 1a (R?=?Ar = C6H5, 0.249 g, 1.0 mmol), 3-methyl-1-phenyl-1H-pyrazol-5-amine 2a (R??=?CH3, R???=?C6H5, 0.173?g, 1.0 mmol) and t-BuOK (0.056?g, 0.5?mmol) in DMF (4?mL) was stirred at 25?C for 5?min. After completion of the reaction as was indicated by TLC monitoring, water (10?mL) was added to the mixture and extracted into EtOAc (3?x?15?mL). The combined organic extracts were washed with brine and the solvent was removed under the reduced pressure. The residue was purified by column chromatography using n-hexane/EtOAc (10:1) as eluent to afford pure product 3a.
  • 58
  • [ 5356-71-8 ]
  • C16H12BrN3O [ No CAS ]
  • 5-amino-4-(4-bromophenyl)-6-(4-methylphenyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With potassium tert-butylate; In N,N-dimethyl-formamide; at 25℃; for 0.0833333h; General procedure: A mixture of alpha-azidochalcone 1a (R?=?Ar = C6H5, 0.249 g, 1.0 mmol), 3-methyl-1-phenyl-1H-pyrazol-5-amine 2a (R??=?CH3, R???=?C6H5, 0.173?g, 1.0 mmol) and t-BuOK (0.056?g, 0.5?mmol) in DMF (4?mL) was stirred at 25?C for 5?min. After completion of the reaction as was indicated by TLC monitoring, water (10?mL) was added to the mixture and extracted into EtOAc (3?x?15?mL). The combined organic extracts were washed with brine and the solvent was removed under the reduced pressure. The residue was purified by column chromatography using n-hexane/EtOAc (10:1) as eluent to afford pure product 3a.
  • 59
  • [ 5356-71-8 ]
  • [ 91-56-5 ]
  • [ 126-81-8 ]
  • 7',7'-dimethyl-1',3'-diphenyl-1',7',8',9'-tetrahydrospiro[indoline-3,4'-pyrazolo[3,4-b]quinoline]-2,5'(6'H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 60
  • [ 3859-41-4 ]
  • [ 5356-71-8 ]
  • [ 91-56-5 ]
  • C28H20N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% at 60℃; for 0.283333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 61
  • [ 5356-71-8 ]
  • [ 91-56-5 ]
  • [ 504-02-9 ]
  • C29H22N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 62
  • [ 608-05-9 ]
  • [ 5356-71-8 ]
  • [ 126-81-8 ]
  • C32H28N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% at 60℃; for 0.25h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 63
  • [ 608-05-9 ]
  • [ 5356-71-8 ]
  • [ 504-02-9 ]
  • C30H24N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 64
  • [ 5356-71-8 ]
  • [ 87-48-9 ]
  • [ 126-81-8 ]
  • C31H25BrN4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 65
  • [ 611-09-6 ]
  • [ 5356-71-8 ]
  • [ 126-81-8 ]
  • C31H25N5O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% at 60℃; for 0.416667h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 66
  • [ 6326-79-0 ]
  • [ 5356-71-8 ]
  • [ 126-81-8 ]
  • C31H25BrN4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 67
  • [ 1127-59-9 ]
  • [ 5356-71-8 ]
  • [ 126-81-8 ]
  • C32H28N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% at 60℃; for 0.3h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 68
  • [ 1127-59-9 ]
  • [ 3859-41-4 ]
  • [ 5356-71-8 ]
  • C29H22N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% at 60℃; for 0.216667h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 69
  • [ 317-20-4 ]
  • [ 5356-71-8 ]
  • [ 126-81-8 ]
  • C31H25FN4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% at 60℃; for 0.266667h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 70
  • [ 7477-63-6 ]
  • [ 5356-71-8 ]
  • [ 126-81-8 ]
  • C31H25ClN4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% at 60℃; for 0.283333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 71
  • [ 67-52-7 ]
  • [ 7477-63-6 ]
  • [ 5356-71-8 ]
  • C27H17ClN6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% at 60℃; for 0.3h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 72
  • [ 7477-63-6 ]
  • [ 3859-41-4 ]
  • [ 5356-71-8 ]
  • C28H19ClN4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% at 60℃; for 0.25h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 73
  • [ 606-23-5 ]
  • [ 7477-63-6 ]
  • [ 5356-71-8 ]
  • C32H19ClN4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 74
  • [ 2058-74-4 ]
  • [ 5356-71-8 ]
  • [ 126-81-8 ]
  • C32H28N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% at 60℃; for 0.333333h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 75
  • [ 606-23-5 ]
  • [ 39755-95-8 ]
  • [ 5356-71-8 ]
  • C33H22N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% at 60℃; for 0.416667h;Microwave irradiation; Green chemistry; General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C - H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.
  • 76
  • [ 5356-71-8 ]
  • [ 100-52-7 ]
  • [ 1384105-56-9 ]
YieldReaction ConditionsOperation in experiment
64% With iron(III) chloride; In dimethyl sulfoxide; at 130℃; for 24h; General procedure: A mixture of 5-amimoamimo amimo pyrazolepyrazolepyrazole pyrazolepyrazole s (1a-c, 1 , 1.0 mmol), mmol), aromatic aldehydes (2a-t, 0.5 mmol), FeCl3 (12 mg, 0.075 mmol) and DMSO (3 mL) was reacted at 130 C for 24 h. After completion of the reaction, the mixture was cooled to room temperature. In case there are some solids precipitated from the mixture, which were filtered and washed by ethanol/petroleum ether. The remaining solution was poured into the water and extracted with dichloromethane (3×15 mL). The combined organic layers were dried over anhydrous magnesium sulfate and filtered. After removal of the solvent, the residue was purified by flash column chromatography on silica gel using the mixture of petroleum ether/ethyl acetate (v:v, 20:1 to 1:1) as the eluent to afford the target products.
  • 77
  • [ 5356-71-8 ]
  • [ 1122-91-4 ]
  • 4-(4-bromophenyl)-1,3,5,7-tetraphenyl-1,7-dihydropyrazolo[3,4-b:4′,3′-e]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With iron(III) chloride; In dimethyl sulfoxide; at 130℃; for 24h; General procedure: A mixture of 5-amimoamimo amimo pyrazolepyrazolepyrazole pyrazolepyrazole s (1a-c, 1 , 1.0 mmol), mmol), aromatic aldehydes (2a-t, 0.5 mmol), FeCl3 (12 mg, 0.075 mmol) and DMSO (3 mL) was reacted at 130 C for 24 h. After completion of the reaction, the mixture was cooled to room temperature. In case there are some solids precipitated from the mixture, which were filtered and washed by ethanol/petroleum ether. The remaining solution was poured into the water and extracted with dichloromethane (3×15 mL). The combined organic layers were dried over anhydrous magnesium sulfate and filtered. After removal of the solvent, the residue was purified by flash column chromatography on silica gel using the mixture of petroleum ether/ethyl acetate (v:v, 20:1 to 1:1) as the eluent to afford the target products.
  • 78
  • [ 53750-82-6 ]
  • [ 5356-71-8 ]
  • 1,3-diphenyl-5,6-dihydropyrano[3,4-b]pyrazolo[4,3-e]-pyridin-8(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With acetic acid; at 100℃; for 36h;Reflux; General procedure: Method I. A solution of enone 11, 12,or 13a-c (50 mmol) in AcOH (20 ml) was added to asolution of NCC-binucleophile 7a-e, 8b,c, 9, or 19(50 mmol) in AcOH (30 ml) upon stirring at room temperature.The resulting mixture was refluxed for 36 h, thenmost of AcOH was evaporated under reduced pressure. The residue was recrystallized from EtOH (ca. 10 ml).
  • 79
  • 5,6-dihydro-4<i>H</i>-pyran-3-carboxylic acid ethyl ester [ No CAS ]
  • [ 5356-71-8 ]
  • ethyl 5-(3-hydroxypropyl)-1,3-diphenyl-1H-pyrazolo-[3,4-b]pyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% General procedure: Method III. 4 N HCl in 1,4-dioxane (15 ml, 60 mmol)was added to a solution of NCC-binucleophile 7a-e(10 mmol) in EtOH (15 ml) at room temperature. Theresulting mixture was stirred at room temperature for15 min, then enone 12 (11.5 mmol) was added. Thereaction mixture was stirred at 100C for 18 h, then cooledto room temperature and concentrated under reducedpressure. The residue was diluted with H2O (30 ml) andextracted with CH2Cl2 (2×30 ml). The combined organicextracts were dried over anhydrous Na2SO4. Crude compounds16a-e were purified by column chromatography(SiO2, gradient elution with EtOAc-hexane, 0:1?7:3). After chromatographic purification, compounds 16c,e wereadditionally recrystallized from hexane-MTBE, 10:1.
  • 80
  • [ 931-53-3 ]
  • [ 5356-71-8 ]
  • [ 3128-06-1 ]
  • N-cyclohexyl-1-(1,3-diphenyl-1H-pyrazol-5-yl)-2-methyl-6-oxopiperidine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% In neat (no solvent); at 100℃; under 12751.3 Torr; for 0.333333h;Microwave irradiation; General procedure: A mixture of a ketoacid 1-3 (1.0 mmol) with various amino-pyrazoles 4-6 (1.0 mmol) and cyclohexylisocyanide 7 (1.0 mmol) was continuously stirred in a capped 10 mL microwave-vessel (Borosilicate glass vial sealed) which was placed in a microwave cavity. Pressure was set at 17 bar and power adjusted at 75 W. The reaction mixture was heated to 100C for 20 min and tested by TLC. After the reaction vessel was cooled down to ambient temperature, the crude product was dissolved in DCM (20 mL), washed with HCl (2M, 10 mL), sat. NaHCO 3 (10 mL), and dried over Na 2 SO 4 . The residual mixture was concentrated and puri ed by ash chromatography (petroleum ether-ethyl acetate, 7 : 3) to produce the corresponding pure product 8-16.
  • 81
  • [ 931-53-3 ]
  • [ 5356-71-8 ]
  • [ 123-76-2 ]
  • N-cyclohexyl-1-(1,3-diphenyl-1H-pyrazol-5-yl)-2-methyl-5-oxopyrrolidine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In neat (no solvent); at 100℃; under 12751.3 Torr; for 0.333333h;Microwave irradiation; General procedure: A mixture of a ketoacid 1-3 (1.0 mmol) with various amino-pyrazoles 4-6 (1.0 mmol) and cyclohexylisocyanide 7 (1.0 mmol) was continuously stirred in a capped 10 mL microwave-vessel (Borosilicate glass vial sealed) which was placed in a microwave cavity. Pressure was set at 17 bar and power adjusted at 75 W. The reaction mixture was heated to 100C for 20 min and tested by TLC. After the reaction vessel was cooled down to ambient temperature, the crude product was dissolved in DCM (20 mL), washed with HCl (2M, 10 mL), sat. NaHCO 3 (10 mL), and dried over Na 2 SO 4 . The residual mixture was concentrated and puri ed by ash chromatography (petroleum ether-ethyl acetate, 7 : 3) to produce the corresponding pure product 8-16.
  • 82
  • [ 931-53-3 ]
  • [ 5356-71-8 ]
  • [ 90199-73-8 ]
  • 2-(but-3-en-1-yl)-N-cyclohexyl-1-(1,3-diphenyl-1H-pyrazol-5-yl)-5-oxopyrrolidine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In neat (no solvent); at 100℃; under 12751.3 Torr; for 0.333333h;Microwave irradiation; General procedure: A mixture of a ketoacid 1-3 (1.0 mmol) with various amino-pyrazoles 4-6 (1.0 mmol) and cyclohexylisocyanide 7 (1.0 mmol) was continuously stirred in a capped 10 mL microwave-vessel (Borosilicate glass vial sealed) which was placed in a microwave cavity. Pressure was set at 17 bar and power adjusted at 75 W. The reaction mixture was heated to 100C for 20 min and tested by TLC. After the reaction vessel was cooled down to ambient temperature, the crude product was dissolved in DCM (20 mL), washed with HCl (2M, 10 mL), sat. NaHCO 3 (10 mL), and dried over Na 2 SO 4 . The residual mixture was concentrated and puri ed by ash chromatography (petroleum ether-ethyl acetate, 7 : 3) to produce the corresponding pure product 8-16.
  • 83
  • [ 5356-71-8 ]
  • [ 66447-80-1 ]
  • 3-(1,3-diphenyl-5-(p-tolyl)-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With toluene-4-sulfonic acid In ethanol for 6h; Reflux; chemoselective reaction; 3-{1,3,5-Triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl}indolin-2-one (5a); Typical Procedure General procedure: Benzoylacetonitrile (1a, 0.25 mmol) and phenylhydrazine (2a,0.25 mmol) were mixed in neat conditions and heated at 120 °Cfor 2.0 h. After completion of the reaction, the reaction mixturewas cooled to room temperature. Then, 3-(2-aryl-2-oxoethylidene)indolin-2-one (4a, 0.25 mmol) PTSA·H2O (0.05 mmol)and EtOH (2.5 mL) were added to the reaction mixture. Afterwards,the mixture was stirred for 6 h under reflux conditions.Upon the completion of the reaction (monitored by TLC), thereaction mixture was cooled to room temperature. The precipitatewas collected by filtration and washed with cold ethanol togive the pure product 5a (93 mg, yield 80%).
  • 84
  • [ 5356-71-8 ]
  • [ 66447-83-4 ]
  • 3-(5-(4-bromophenyl)-1,3-diphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With toluene-4-sulfonic acid In ethanol for 6h; Reflux; chemoselective reaction; 3-{1,3,5-Triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl}indolin-2-one (5a); Typical Procedure General procedure: Benzoylacetonitrile (1a, 0.25 mmol) and phenylhydrazine (2a,0.25 mmol) were mixed in neat conditions and heated at 120 °Cfor 2.0 h. After completion of the reaction, the reaction mixturewas cooled to room temperature. Then, 3-(2-aryl-2-oxoethylidene)indolin-2-one (4a, 0.25 mmol) PTSA·H2O (0.05 mmol)and EtOH (2.5 mL) were added to the reaction mixture. Afterwards,the mixture was stirred for 6 h under reflux conditions.Upon the completion of the reaction (monitored by TLC), thereaction mixture was cooled to room temperature. The precipitatewas collected by filtration and washed with cold ethanol togive the pure product 5a (93 mg, yield 80%).
  • 85
  • [ 5356-71-8 ]
  • C17H12ClNO2 [ No CAS ]
  • 4-chloro-7-methyl-3-(1,3,5-triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With toluene-4-sulfonic acid In ethanol for 6h; Reflux; chemoselective reaction; 3-{1,3,5-Triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl}indolin-2-one (5a); Typical Procedure General procedure: Benzoylacetonitrile (1a, 0.25 mmol) and phenylhydrazine (2a,0.25 mmol) were mixed in neat conditions and heated at 120 °Cfor 2.0 h. After completion of the reaction, the reaction mixturewas cooled to room temperature. Then, 3-(2-aryl-2-oxoethylidene)indolin-2-one (4a, 0.25 mmol) PTSA·H2O (0.05 mmol)and EtOH (2.5 mL) were added to the reaction mixture. Afterwards,the mixture was stirred for 6 h under reflux conditions.Upon the completion of the reaction (monitored by TLC), thereaction mixture was cooled to room temperature. The precipitatewas collected by filtration and washed with cold ethanol togive the pure product 5a (93 mg, yield 80%).
  • 86
  • [ 5356-71-8 ]
  • [ 23336-93-8 ]
  • 3-(5-(4-chlorophenyl)-1,3-diphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With toluene-4-sulfonic acid In ethanol for 6h; Reflux; chemoselective reaction; 3-{1,3,5-Triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl}indolin-2-one (5a); Typical Procedure General procedure: Benzoylacetonitrile (1a, 0.25 mmol) and phenylhydrazine (2a,0.25 mmol) were mixed in neat conditions and heated at 120 °Cfor 2.0 h. After completion of the reaction, the reaction mixturewas cooled to room temperature. Then, 3-(2-aryl-2-oxoethylidene)indolin-2-one (4a, 0.25 mmol) PTSA·H2O (0.05 mmol)and EtOH (2.5 mL) were added to the reaction mixture. Afterwards,the mixture was stirred for 6 h under reflux conditions.Upon the completion of the reaction (monitored by TLC), thereaction mixture was cooled to room temperature. The precipitatewas collected by filtration and washed with cold ethanol togive the pure product 5a (93 mg, yield 80%).
  • 87
  • [ 27230-23-5 ]
  • [ 5356-71-8 ]
  • 1-methyl-3-(1,3,5-triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With toluene-4-sulfonic acid In ethanol for 6h; Reflux; chemoselective reaction; 3-{1,3,5-Triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl}indolin-2-one (5a); Typical Procedure General procedure: Benzoylacetonitrile (1a, 0.25 mmol) and phenylhydrazine (2a,0.25 mmol) were mixed in neat conditions and heated at 120 °Cfor 2.0 h. After completion of the reaction, the reaction mixturewas cooled to room temperature. Then, 3-(2-aryl-2-oxoethylidene)indolin-2-one (4a, 0.25 mmol) PTSA·H2O (0.05 mmol)and EtOH (2.5 mL) were added to the reaction mixture. Afterwards,the mixture was stirred for 6 h under reflux conditions.Upon the completion of the reaction (monitored by TLC), thereaction mixture was cooled to room temperature. The precipitatewas collected by filtration and washed with cold ethanol togive the pure product 5a (93 mg, yield 80%).
  • 88
  • [ 847-00-7 ]
  • [ 5356-71-8 ]
  • 3-(5-(4-chlorophenyl)-1,3-diphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl)-1-methylindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With toluene-4-sulfonic acid In ethanol for 6h; Reflux; chemoselective reaction; 3-{1,3,5-Triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl}indolin-2-one (5a); Typical Procedure General procedure: Benzoylacetonitrile (1a, 0.25 mmol) and phenylhydrazine (2a,0.25 mmol) were mixed in neat conditions and heated at 120 °Cfor 2.0 h. After completion of the reaction, the reaction mixturewas cooled to room temperature. Then, 3-(2-aryl-2-oxoethylidene)indolin-2-one (4a, 0.25 mmol) PTSA·H2O (0.05 mmol)and EtOH (2.5 mL) were added to the reaction mixture. Afterwards,the mixture was stirred for 6 h under reflux conditions.Upon the completion of the reaction (monitored by TLC), thereaction mixture was cooled to room temperature. The precipitatewas collected by filtration and washed with cold ethanol togive the pure product 5a (93 mg, yield 80%).
  • 89
  • [ 5356-71-8 ]
  • 5-bromo-3-(2-(4-chlorophenyl)-2-oxoethylidene)indolin-2-one [ No CAS ]
  • 5-bromo-3-(5-(4-chlorophenyl)-1,3-diphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With toluene-4-sulfonic acid In ethanol for 6h; Reflux; chemoselective reaction; 3-{1,3,5-Triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl}indolin-2-one (5a); Typical Procedure General procedure: Benzoylacetonitrile (1a, 0.25 mmol) and phenylhydrazine (2a,0.25 mmol) were mixed in neat conditions and heated at 120 °Cfor 2.0 h. After completion of the reaction, the reaction mixturewas cooled to room temperature. Then, 3-(2-aryl-2-oxoethylidene)indolin-2-one (4a, 0.25 mmol) PTSA·H2O (0.05 mmol)and EtOH (2.5 mL) were added to the reaction mixture. Afterwards,the mixture was stirred for 6 h under reflux conditions.Upon the completion of the reaction (monitored by TLC), thereaction mixture was cooled to room temperature. The precipitatewas collected by filtration and washed with cold ethanol togive the pure product 5a (93 mg, yield 80%).
  • 90
  • [ 5356-71-8 ]
  • 1-methyl-3-(2-(4-methylphenyl)-2-oxoethylidene)indolin-2-one [ No CAS ]
  • 3-(1,3-diphenyl-5-(p-tolyl)-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl)-1-methylindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With toluene-4-sulfonic acid In ethanol for 6h; Reflux; chemoselective reaction; 3-{1,3,5-Triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl}indolin-2-one (5a); Typical Procedure General procedure: Benzoylacetonitrile (1a, 0.25 mmol) and phenylhydrazine (2a,0.25 mmol) were mixed in neat conditions and heated at 120 °Cfor 2.0 h. After completion of the reaction, the reaction mixturewas cooled to room temperature. Then, 3-(2-aryl-2-oxoethylidene)indolin-2-one (4a, 0.25 mmol) PTSA·H2O (0.05 mmol)and EtOH (2.5 mL) were added to the reaction mixture. Afterwards,the mixture was stirred for 6 h under reflux conditions.Upon the completion of the reaction (monitored by TLC), thereaction mixture was cooled to room temperature. The precipitatewas collected by filtration and washed with cold ethanol togive the pure product 5a (93 mg, yield 80%).
  • 91
  • [ 31541-39-6 ]
  • [ 5356-71-8 ]
  • 1-benzyl-3-(1,3,5-triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With toluene-4-sulfonic acid In ethanol for 6h; Reflux; chemoselective reaction; 3-{1,3,5-Triphenyl-1,6-dihydropyrrolo[2,3-c]pyrazol-4-yl}indolin-2-one (5a); Typical Procedure General procedure: Benzoylacetonitrile (1a, 0.25 mmol) and phenylhydrazine (2a,0.25 mmol) were mixed in neat conditions and heated at 120 °Cfor 2.0 h. After completion of the reaction, the reaction mixturewas cooled to room temperature. Then, 3-(2-aryl-2-oxoethylidene)indolin-2-one (4a, 0.25 mmol) PTSA·H2O (0.05 mmol)and EtOH (2.5 mL) were added to the reaction mixture. Afterwards,the mixture was stirred for 6 h under reflux conditions.Upon the completion of the reaction (monitored by TLC), thereaction mixture was cooled to room temperature. The precipitatewas collected by filtration and washed with cold ethanol togive the pure product 5a (93 mg, yield 80%).
  • 92
  • [ 5356-71-8 ]
  • [ 1147550-11-5 ]
  • [ 19688-93-8 ]
YieldReaction ConditionsOperation in experiment
87% With oxygen In dimethyl sulfoxide at 20℃; Irradiation; Green chemistry; 1. General Remarks General procedure: First, add pyrazole (0.3 mmol), ammonium thiocyanate (0.9 mmol), dimethyl sulfoxide (3 mL) to a glass tube with g-C3N4 (30 mg). Then flush oxygen into the reaction tube, the reaction mixture was by blue light irradiation (450 nm, 0.1 w/cm2), stirring at room temperature, the reaction was tracked by TLC (Thin layer chromatography). After the reaction was completed, the catalyst was filtered out, the solvent was removed by distillation under reduced pressure, and the initial product was subjected to column chromatography to obtain the target product.
78% With dihydrogen peroxide In water at 20℃;
  • 93
  • [ 5356-71-8 ]
  • [ 34772-98-0 ]
  • (E)-3-(1,3-diphenyl-1H-pyrazol-5-yl)amino-1-(thiophen-2-yl)prop-2-en-1-one [ No CAS ]
  • (Z)-3-(1,3-diphenyl-1H-pyrazol-5-yl)amino-1-(thiophen-2-yl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol at 20℃; for 1.5h; Overall yield = 80 percent; Overall yield = 1 g; 4.1.1. General method for the synthesis of compounds 4a-g General procedure: A mixture of the appropriate enaminone (3a-g) (5 mmol) and1,3-diphenyl-1H-pyrazol-5-amine (2) (1.17 g, 5 mmol) were stirredat RT for 1.5 h (for 4a, b, f and g) and 4 h (for 4c-e). The mixturewaspoured onto crushed ice, and the separated solid was filtered,washed with water, dried, and crystallized from ethanol.4.1.1.1. (E/Z)-3-(1,3-diphenyl-1H-pyrazol-5-ylamino)-1-phenylprop-2-en-1-one (4a). Yellow crystals; yield: (1.63 g, 89%
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