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[ CAS No. 1527-91-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Limited Quantity USD 15-60
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Inaccessible (Haz class 6.1), International USD 150+
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3d Animation Molecule Structure of 1527-91-9
Chemical Structure| 1527-91-9
Chemical Structure| 1527-91-9
Structure of 1527-91-9 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 1527-91-9 ]

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Product Details of [ 1527-91-9 ]

CAS No. :1527-91-9 MDL No. :MFCD00019730
Formula : C13H12N2 Boiling Point : -
Linear Structure Formula :C6H5CNHNHC6H5 InChI Key :MPYOKHFSBKUKPQ-UHFFFAOYSA-N
M.W : 196.25 Pubchem ID :200127
Synonyms :

Calculated chemistry of [ 1527-91-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 63.83
TPSA : 35.88 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 2.71
Log Po/w (WLOGP) : 2.93
Log Po/w (MLOGP) : 3.42
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.16
Solubility : 0.136 mg/ml ; 0.000695 mol/l
Class : Soluble
Log S (Ali) : -3.12
Solubility : 0.15 mg/ml ; 0.000764 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.06
Solubility : 0.0017 mg/ml ; 0.00000865 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 1527-91-9 ]

Signal Word:Danger Class:9
Precautionary Statements:P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501 UN#:3077
Hazard Statements:H302-H319-H332-H372-H400 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1527-91-9 ]

* 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 [ 1527-91-9 ]

[ 1527-91-9 ] Synthesis Path-Downstream   1~97

  • 1
  • [ 2556-46-9 ]
  • [ 19402-64-3 ]
  • [ 1527-91-9 ]
  • 2
  • [ 5333-86-8 ]
  • [ 62-53-3 ]
  • [ 1527-91-9 ]
YieldReaction ConditionsOperation in experiment
In ethanol at 0 - 20℃; Reflux; Inert atmosphere; Benzamidines 1a-e,h,k-o; General Procedure A General procedure: The required amine (20.0 mmol) was added dropwise at 0 °C to a solution of ethyl benzimidate hydrochloride (10.0 mmol) in EtOH (15mL) and the reaction mixture was stirred at r.t. to reflux overnight. EtOH was removed under a reduced pressure and 1 M aq NaOH (15mL) was added. The mixture was extracted with CHCl3 (3 × 10 mL) and the combined organic phases were dried (MgSO4): The solvent was removed under a reduced pressure and the crude N-substituted benzamidine obtained was used for the next reaction without further purification.
  • 3
  • [ 1527-91-9 ]
  • [ 716-79-0 ]
YieldReaction ConditionsOperation in experiment
90% With oxygen; acetic acid; In acetonitrile; at 80.0℃; for 7.0h;Green chemistry;Catalytic behavior; General procedure: A mixture of benzamidine (1 mmol), HOAc (3 eq.) and alpha-ZrP/Uracil/Cu2+ (20 mg: 1.3 mol%) in CH3CN(3 mL) wasrefluxed at 80 C under the direct flow of O2(followed up byTLC). After consumption of benzamidine, the catalyst wasseparated by centrifugation and the reaction mixture wascooled to room temperature. The catalyst was thoroughlywashed with ethyl acetate, and then, the extraction with ethylacetate (3 × 10 ml) was performed on the reaction mixture.The organic extract was dried over anhydrous CaCl2,and thesolvent was vaporized under reduced pressure. The remainingsolid was purified by recrystallization from ethanol.Product specifications are provided in the supplementaryinformation.
  • 4
  • [ 1527-91-9 ]
  • [ 2712-78-9 ]
  • [ 404-24-0 ]
  • N2-Phenylbenzamidin-N2-ium trifluoroacetate [ No CAS ]
  • 2-(phenyl)benzimidazolium trifluoroacetate [ No CAS ]
  • 5
  • [ 3694-57-3 ]
  • [ 1527-91-9 ]
  • 1-(4-Methoxy-benzyl)-3-[1-phenyl-1-phenylamino-meth-(Z)-ylidene]-thiourea [ No CAS ]
  • 6
  • [ 16735-69-6 ]
  • [ 1527-91-9 ]
  • 1-(2-Methyl-benzyl)-3-[1-phenyl-1-phenylamino-meth-(Z)-ylidene]-thiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,2-dichloro-ethane at 55℃;
  • 7
  • [ 615-42-9 ]
  • [ 1527-91-9 ]
  • [ 2622-67-5 ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate; 1,10-Phenanthroline; copper(II) oxide In diethylene glycol dimethyl ether at 140℃; for 24h; Inert atmosphere; regiospecific reaction;
58% With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In 1-methyl-pyrrolidin-2-one at 170℃; Inert atmosphere;
  • 9
  • [ 71838-16-9 ]
  • [ 1527-91-9 ]
  • [ 86318-02-7 ]
  • 10
  • [ 2401-21-0 ]
  • [ 1527-91-9 ]
  • [ 1217102-13-0 ]
  • 11
  • [ CAS Unavailable ]
  • [ 62-53-3 ]
  • [ 1527-91-9 ]
  • [ 493-77-6 ]
YieldReaction ConditionsOperation in experiment
1: 83% 2: 3% Stage #1: benzonitrile With aluminum (III) chloride at 20 - 100℃; Stage #2: aniline at 100℃; for 4h; Stage #3: With sodium hydroxide In water at 20℃;
  • 12
  • [ 113264-43-0 ]
  • [ 1527-91-9 ]
  • [ 1261181-00-3 ]
YieldReaction ConditionsOperation in experiment
55% With sodium hydrogencarbonate; In isopropyl alcohol; at 90.0℃; for 12h;Inert atmosphere; A mixture of N-phenylbenzimidamide (compound 22, 1.0 g, 5.10 mmol), 3-bromo-2-oxovalerate (compound 23, 1.3 g, 6.12 mmol) and NaHCO3 in /-PrOH was stirred at 90 C for 12 hrs. The reaction mixture was concentrated under reduced pressure, then the residue was diluted with EtOAc and washed with H2O. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography (Biotage Isolera FLASH Purification System was used for normal phase column chromatography with EtOAc and hexane) to provide the title compound (0.86 g, 55 %) as a yellow solid.
  • 13
  • [ 57332-84-0 ]
  • [ 1527-91-9 ]
  • [ 1261181-00-3 ]
  • 14
  • [ 96424-68-9 ]
  • [ 1527-91-9 ]
  • [ 1350629-03-6 ]
  • 15
  • [ 1193-72-2 ]
  • [ 1527-91-9 ]
  • [ 1350629-00-3 ]
  • 16
  • [ 2732-80-1 ]
  • [ 1527-91-9 ]
  • [ 1350629-08-1 ]
  • 17
  • [ 95-50-1 ]
  • [ 1527-91-9 ]
  • [ 2622-67-5 ]
YieldReaction ConditionsOperation in experiment
96% With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction;
30% With potassium phosphate; 1,10-Phenanthroline; copper(II) oxide In diethylene glycol dimethyl ether at 140℃; for 24h; Inert atmosphere; regiospecific reaction;
  • 18
  • [ 1527-91-9 ]
  • [ 583-53-9 ]
  • [ 2622-67-5 ]
YieldReaction ConditionsOperation in experiment
99% With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction;
51% With potassium phosphate; 1,10-Phenanthroline; copper(II) oxide In diethylene glycol dimethyl ether at 140℃; for 24h; Inert atmosphere; regiospecific reaction;
  • 19
  • [ 6942-39-8 ]
  • [ 1527-91-9 ]
  • 6-fluoro-2,3-diphenylquinazolin-4(3H)-one [ No CAS ]
  • 20
  • [ 3179-10-0 ]
  • [ 1527-91-9 ]
  • [ 1423126-02-6 ]
YieldReaction ConditionsOperation in experiment
67% With copper(I) bromide; In dimethyl sulfoxide; at 80.0℃; for 24.0h; General procedure: Amidine 1 (0.5 mmol), nitroolefin 2 (0.75 mmol) and CuBr (0.5mmol) were mixed in DMSO (2 mL) and heated at 80 C for 24h. After being cooled to room temperature, the mixture was diluted with 25 mL of ethyl acetate, washed with 25 mL of brine, and dried over anhydrous Na2SO4. The solvent was removed under vacuum. The residue was purified by column chromatography (petroleum ether/ethylacetate 20:1 or petroleum ether/ dichloromethane 4:1) to afford pure 3.
  • 21
  • [ 7559-36-6 ]
  • [ 1527-91-9 ]
  • 1,2-diphenyl-4-(p-tolyl)-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With copper(I) bromide; In dimethyl sulfoxide; at 80.0℃; for 24.0h; General procedure: Amidine 1 (0.5 mmol), nitroolefin 2 (0.75 mmol) and CuBr (0.5mmol) were mixed in DMSO (2 mL) and heated at 80 C for 24h. After being cooled to room temperature, the mixture was diluted with 25 mL of ethyl acetate, washed with 25 mL of brine, and dried over anhydrous Na2SO4. The solvent was removed under vacuum. The residue was purified by column chromatography (petroleum ether/ethylacetate 20:1 or petroleum ether/ dichloromethane 4:1) to afford pure 3.
  • 22
  • [ 705-60-2 ]
  • [ 1527-91-9 ]
  • [ 74554-36-2 ]
YieldReaction ConditionsOperation in experiment
64% With copper(I) bromide; In dimethyl sulfoxide; at 80.0℃; for 24.0h; General procedure: Amidine 1 (0.5 mmol), nitroolefin 2 (0.75 mmol) and CuBr (0.5mmol) were mixed in DMSO (2 mL) and heated at 80 C for 24h. After being cooled to room temperature, the mixture was diluted with 25 mL of ethyl acetate, washed with 25 mL of brine, and dried over anhydrous Na2SO4. The solvent was removed under vacuum. The residue was purified by column chromatography (petroleum ether/ethylacetate 20:1 or petroleum ether/ dichloromethane 4:1) to afford pure 3.
  • 23
  • [ 17354-63-1 ]
  • [ 1527-91-9 ]
  • [ 1423126-05-9 ]
YieldReaction ConditionsOperation in experiment
58% With copper(I) bromide; In dimethyl sulfoxide; at 80.0℃; for 24.0h; General procedure: Amidine 1 (0.5 mmol), nitroolefin 2 (0.75 mmol) and CuBr (0.5mmol) were mixed in DMSO (2 mL) and heated at 80 C for 24h. After being cooled to room temperature, the mixture was diluted with 25 mL of ethyl acetate, washed with 25 mL of brine, and dried over anhydrous Na2SO4. The solvent was removed under vacuum. The residue was purified by column chromatography (petroleum ether/ethylacetate 20:1 or petroleum ether/ dichloromethane 4:1) to afford pure 3.
  • 24
  • [ 102-96-5 ]
  • [ 1527-91-9 ]
  • [ 56839-21-5 ]
YieldReaction ConditionsOperation in experiment
70% With copper(I) bromide; In dimethyl sulfoxide; at 80.0℃; for 24.0h; General procedure: Amidine 1 (0.5 mmol), nitroolefin 2 (0.75 mmol) and CuBr (0.5mmol) were mixed in DMSO (2 mL) and heated at 80 C for 24h. After being cooled to room temperature, the mixture was diluted with 25 mL of ethyl acetate, washed with 25 mL of brine, and dried over anhydrous Na2SO4. The solvent was removed under vacuum. The residue was purified by column chromatography (petroleum ether/ethylacetate 20:1 or petroleum ether/ dichloromethane 4:1) to afford pure 3.
  • 25
  • [ 3179-09-7 ]
  • [ 1527-91-9 ]
  • [ 1602636-63-4 ]
YieldReaction ConditionsOperation in experiment
56% With copper(I) bromide; In dimethyl sulfoxide; at 80℃; for 24h; General procedure: Amidine 1 (0.5 mmol), nitroolefin 2 (0.75 mmol) and CuBr (0.5mmol) were mixed in DMSO (2 mL) and heated at 80 C for 24h. After being cooled to room temperature, the mixture was diluted with 25 mL of ethyl acetate, washed with 25 mL of brine, and dried over anhydrous Na2SO4. The solvent was removed under vacuum. The residue was purified by column chromatography (petroleum ether/ethylacetate 20:1 or petroleum ether/ dichloromethane 4:1) to afford pure 3.
  • 26
  • [ 403-42-9 ]
  • [ 1527-91-9 ]
  • [ 1423126-00-4 ]
YieldReaction ConditionsOperation in experiment
72% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide; In 1,2-dichloro-benzene; at 120.0℃; for 2.0h;Green chemistry; General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120 C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 27
  • [ 445-27-2 ]
  • [ 1527-91-9 ]
  • [ 1610784-73-0 ]
YieldReaction ConditionsOperation in experiment
68% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide In 1,2-dichloro-benzene at 120℃; for 2h; Green chemistry; regioselective reaction; 4.1. Typical procedure for the preparation of multisubstituted imidazoles 3 General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120° C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 28
  • [ 1136-86-3 ]
  • [ 1527-91-9 ]
  • [ 1610784-75-2 ]
YieldReaction ConditionsOperation in experiment
76% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide; In 1,2-dichloro-benzene; at 120.0℃; for 2.0h;Green chemistry; General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120 C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 29
  • [ 1527-91-9 ]
  • [ 586-37-8 ]
  • [ 1602636-63-4 ]
YieldReaction ConditionsOperation in experiment
82% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide; In 1,2-dichloro-benzene; at 120.0℃; for 2.0h;Green chemistry; General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120 C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 30
  • [ 1527-91-9 ]
  • [ 577-16-2 ]
  • [ 1610784-76-3 ]
YieldReaction ConditionsOperation in experiment
77% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide; In 1,2-dichloro-benzene; at 120.0℃; for 2.0h;Green chemistry; General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120 C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 31
  • [ 1527-91-9 ]
  • [ 585-74-0 ]
  • [ 1610784-77-4 ]
YieldReaction ConditionsOperation in experiment
81% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide; In 1,2-dichloro-benzene; at 120.0℃; for 2.0h;Green chemistry; General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120 C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 32
  • [ 122-00-9 ]
  • [ 1527-91-9 ]
  • 1,2-diphenyl-4-(p-tolyl)-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide; In 1,2-dichloro-benzene; at 120.0℃; for 2.0h;Green chemistry; General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120 C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 33
  • [ 99-90-1 ]
  • [ 1527-91-9 ]
  • [ 1210045-72-9 ]
YieldReaction ConditionsOperation in experiment
81% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide; In 1,2-dichloro-benzene; at 120.0℃; for 2.0h;Green chemistry; General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120 C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 34
  • [ 99-91-2 ]
  • [ 1527-91-9 ]
  • [ 1393347-06-2 ]
YieldReaction ConditionsOperation in experiment
80% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide; In 1,2-dichloro-benzene; at 120.0℃; for 2.0h;Green chemistry; General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120 C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 35
  • [ 56894-99-6 ]
  • [ 1527-91-9 ]
  • [ 1610784-79-6 ]
YieldReaction ConditionsOperation in experiment
83% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide; In 1,2-dichloro-benzene; at 120.0℃; for 2.0h;Green chemistry; General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120 C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 36
  • [ 1527-91-9 ]
  • [ 93-08-3 ]
  • [ 1423126-06-0 ]
YieldReaction ConditionsOperation in experiment
84% With 1,10-Phenanthroline; copper diacetate; aniline; lithium bromide; zinc(II) iodide; In 1,2-dichloro-benzene; at 120.0℃; for 2.0h;Green chemistry; General procedure: Synthesis of 1,2,4-triphenyl-1H-imidazole (3a): the reaction was carried out in a round-bottom sidearm flask (10 mL), 1a (0.24 mmol), 2a (0.2 mmol), Cu(OAc)2 (10 mol %), ZnI2 (10 mol %), aniline (5 mol %), 1,10-phenanthroline (20 mol %), LiBr(3.0 equiv) and DCB (2 mL) were added to the flask with a magnetic stirring bar at 120 C under air. After 6 h stirring at this temperature,the flask was took out and cooled to room temperature. The mixture was filtered with ethyl acetate (350 mL), and the filtrate was concentrated under reduced pressure to distill ethyl acetate. Subsequently, the crude product with DCB was dried under heat gun, which was further purified by silica gel chromatography (petroleum/ethyl acetate10:1 as eluent) to obtain product 3a.
  • 37
  • [ 94-41-7 ]
  • [ 1527-91-9 ]
  • phenyl(1,2,4-triphenyl-1H-imidazole-5-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With iron(III) chloride; iodine; oxygen; In chlorobenzene; at 110.0℃; for 10.0h; 0.6 mmol of <strong>[1527-91-9]N-phenylbenzamidine</strong>,0.5 mmol chalcone,0.01 mmol of ferric chloride and 0.05 mmol of iodine were added to a 25 mL round bottom flask containing 2 mL of chlorobenzene,Heated to 110 C, reacted in an oxygen atmosphere for 10 h.After completion of the reaction (TLC monitoring), the mixture was cooled to room temperature.The iodine was removed with saturated sodium thiosulfate solution,Ethyl acetate (15 mL x 3) was added three times and then washed with saturated brine,Dehydrated with anhydrous sodium sulfate, concentrated with ethyl acetate / petroleum ether (1: 5) silica gel column chromatography,To give 170 mg of a yellow solid in 85% yield.
  • 38
  • [ 1527-91-9 ]
  • [ 956-02-5 ]
  • (4-chlorophenyl)(1,2,4-triphenyl-1H-imidazol-5-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With 1,10-Phenanthroline; iron(III) chloride hexahydrate; iodine In 1,2-dichloro-benzene at 110℃; for 18h; regioselective reaction;
81% With iodine; oxygen; iron(III) chloride In chlorobenzene at 110℃; for 10h; regioselective reaction;
  • 39
  • [ 583-55-1 ]
  • [ 1527-91-9 ]
  • [ 2622-67-5 ]
YieldReaction ConditionsOperation in experiment
86% With potassium phosphate; 1,10-Phenanthroline; copper(II) oxide In diethylene glycol dimethyl ether at 140℃; for 24h; Inert atmosphere; regiospecific reaction;
  • 40
  • [ 589-18-4 ]
  • [ 1527-91-9 ]
  • C28H23N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 41
  • [ 1527-91-9 ]
  • (4-((trifluoromethyl)thio)phenyl)methanol [ No CAS ]
  • C28H20F3N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 42
  • [ 6966-10-5 ]
  • [ 1527-91-9 ]
  • C29H25N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With Cu/OMS-2; In toluene; at 90℃; for 20h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 43
  • [ 1805-32-9 ]
  • [ 1527-91-9 ]
  • C27H19Cl2N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With Cu/OMS-2; In toluene; at 90℃; for 20h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 44
  • [ 768-59-2 ]
  • [ 1527-91-9 ]
  • C29H25N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 45
  • [ 1592-38-7 ]
  • [ 1527-91-9 ]
  • C31H23N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 46
  • [ 1527-91-9 ]
  • [ 4407-36-7 ]
  • C29H23N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 47
  • [ 586-98-1 ]
  • [ 1527-91-9 ]
  • C26H20N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 48
  • [ 636-72-6 ]
  • [ 1527-91-9 ]
  • C25H19N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 49
  • [ 71-23-8 ]
  • [ 1527-91-9 ]
  • C23H21N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 50
  • [ 1527-91-9 ]
  • [ 71-36-3 ]
  • C24H23N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 51
  • [ 1527-91-9 ]
  • [ 100-51-6 ]
  • 1,2,4,6-tetraphenyl-1,2-dihydro-1,3,5-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With Cu/OMS-2; In toluene; at 90.0℃; for 20.0h; General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.
  • 52
  • [ 100-47-0 ]
  • [ 1527-91-9 ]
  • [ 1043-46-5 ]
YieldReaction ConditionsOperation in experiment
75% With 1,10-Phenanthroline; copper(II) acetate monohydrate; sodium carbonate; In toluene; at 110.0℃; for 24.0h; Take 10mmolN- phenyl benzamidine and 40mmol benzonitrile to 100mL round bottom flask, and then further added 1mmolCu (OAc)2.H2O and 1mmol phenanthroline, 40mmol Na2CO3 and 30mL of toluene was stirred at 110C for 24 hours. After the reaction, the product was extracted with ethyl acetate, and dried to give the crude product, the crude product was purified by silica gel column chromatography (solvent volume ratio of petroleum ether: ethyl acetate = 20: 1) to give a pink solid that is 1,3,5-phenyl-1H-triazole 75% yield, mp 85C
74% With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide; In chlorobenzene; at 130.0℃; for 36.0h;Sealed tube; A sealed tube equipped with a stirrer bar was charged with <strong>[1527-91-9]N-phenylbenzamidine</strong>(1a; 0.0393 g, 0.2 mmol), benzonitrile (2a; 41 muL, 0.40mmol), CuI (0.0190 g, 0.10 mmol), ZnI2 (0.0063 g, 0.02 mmol),phenanthroline (0.0040 g, 0.02 mmol) and chlorobenzene (1 mL). The resulting mixture was stirred at 130 C for 36 h. After reaction completion,the residue was directly purified by flash column chromatography(EtOAc-petroleum ether) to afford pure product 3aa. White solid; yield: 44 mg (74%); mp 100-105 C.IR: 3430.2, 1592.1, 1517.8, 1496.1, 1476.3, 1441.6, 1397.9, 1350.4,1271.9, 1138.5, 1070.7, 1025.8, 990.4, 923.3, 848.4, 771.7, 728.5,695.3 cm-1.1H NMR (300 MHz, CDCl3): delta = 8.24 (dd, J = 7.9, 1.5 Hz, 2 H), 7.56 (dd,J = 8.0, 1.4 Hz, 2 H), 7.52-7.32 (m, 11 H).13C NMR (75 MHz, CDCl3): delta = 162.12, 154.93, 138.47, 130.91, 130.18,129.58, 129.17, 129.00, 128.76, 128.20, 126.78, 125.61.HRMS (ESI): m/z [M + H]+ calcd for C20H16N3+: 298.1344; found:298.1344.
  • 53
  • [ 874-90-8 ]
  • [ 1527-91-9 ]
  • 3-(4-methoxyphenyl)-1,5-diphenyl-1H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide; In chlorobenzene; at 130.0℃; for 36.0h;Sealed tube; General procedure: A sealed tube equipped with a stirrer bar was charged with <strong>[1527-91-9]N-phenylbenzamidine</strong>(1a; 0.0393 g, 0.2 mmol), benzonitrile (2a; 41 muL, 0.40mmol), CuI (0.0190 g, 0.10 mmol), ZnI2 (0.0063 g, 0.02 mmol),phenanthroline (0.0040 g, 0.02 mmol) and chlorobenzene (1 mL). The resulting mixture was stirred at 130 C for 36 h. After reaction completion,the residue was directly purified by flash column chromatography(EtOAc-petroleum ether) to afford pure product 3aa.
  • 54
  • [ 1527-91-9 ]
  • [ 619-72-7 ]
  • 3-(4-nitrophenyl)-1,5-diphenyl-1H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide; In chlorobenzene; at 130.0℃; for 36.0h;Sealed tube; General procedure: A sealed tube equipped with a stirrer bar was charged with <strong>[1527-91-9]N-phenylbenzamidine</strong>(1a; 0.0393 g, 0.2 mmol), benzonitrile (2a; 41 muL, 0.40mmol), CuI (0.0190 g, 0.10 mmol), ZnI2 (0.0063 g, 0.02 mmol),phenanthroline (0.0040 g, 0.02 mmol) and chlorobenzene (1 mL). The resulting mixture was stirred at 130 C for 36 h. After reaction completion,the residue was directly purified by flash column chromatography(EtOAc-petroleum ether) to afford pure product 3aa.
  • 55
  • [ 1194-02-1 ]
  • [ 1527-91-9 ]
  • 3-(4-fluorophenyl)-1,5-diphenyl-1H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide; In chlorobenzene; at 130.0℃; for 36.0h;Sealed tube; General procedure: A sealed tube equipped with a stirrer bar was charged with <strong>[1527-91-9]N-phenylbenzamidine</strong>(1a; 0.0393 g, 0.2 mmol), benzonitrile (2a; 41 muL, 0.40mmol), CuI (0.0190 g, 0.10 mmol), ZnI2 (0.0063 g, 0.02 mmol),phenanthroline (0.0040 g, 0.02 mmol) and chlorobenzene (1 mL). The resulting mixture was stirred at 130 C for 36 h. After reaction completion,the residue was directly purified by flash column chromatography(EtOAc-petroleum ether) to afford pure product 3aa.
  • 56
  • [ 766-84-7 ]
  • [ 1527-91-9 ]
  • 3-(3-chlorophenyl)-1,5-diphenyl-1H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide; In chlorobenzene; at 130.0℃; for 36.0h;Sealed tube; General procedure: A sealed tube equipped with a stirrer bar was charged with <strong>[1527-91-9]N-phenylbenzamidine</strong>(1a; 0.0393 g, 0.2 mmol), benzonitrile (2a; 41 muL, 0.40mmol), CuI (0.0190 g, 0.10 mmol), ZnI2 (0.0063 g, 0.02 mmol),phenanthroline (0.0040 g, 0.02 mmol) and chlorobenzene (1 mL). The resulting mixture was stirred at 130 C for 36 h. After reaction completion,the residue was directly purified by flash column chromatography(EtOAc-petroleum ether) to afford pure product 3aa.
  • 57
  • [ 623-03-0 ]
  • [ 1527-91-9 ]
  • [ 87277-50-7 ]
YieldReaction ConditionsOperation in experiment
72% With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide; In chlorobenzene; at 130.0℃; for 36.0h;Sealed tube; General procedure: A sealed tube equipped with a stirrer bar was charged with <strong>[1527-91-9]N-phenylbenzamidine</strong>(1a; 0.0393 g, 0.2 mmol), benzonitrile (2a; 41 muL, 0.40mmol), CuI (0.0190 g, 0.10 mmol), ZnI2 (0.0063 g, 0.02 mmol),phenanthroline (0.0040 g, 0.02 mmol) and chlorobenzene (1 mL). The resulting mixture was stirred at 130 C for 36 h. After reaction completion,the residue was directly purified by flash column chromatography(EtOAc-petroleum ether) to afford pure product 3aa.
  • 58
  • [ 6574-99-8 ]
  • [ 1527-91-9 ]
  • 3-(3,4-dichlorophenyl)-1,5-diphenyl-1H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide; In chlorobenzene; at 130℃; for 36h;Sealed tube; General procedure: A sealed tube equipped with a stirrer bar was charged with N-phenylbenzamidine(1a; 0.0393 g, 0.2 mmol), benzonitrile (2a; 41 muL, 0.40mmol), CuI (0.0190 g, 0.10 mmol), ZnI2 (0.0063 g, 0.02 mmol),phenanthroline (0.0040 g, 0.02 mmol) and chlorobenzene (1 mL). The resulting mixture was stirred at 130 C for 36 h. After reaction completion,the residue was directly purified by flash column chromatography(EtOAc-petroleum ether) to afford pure product 3aa.
  • 59
  • [ 623-00-7 ]
  • [ 1527-91-9 ]
  • 3-(4-bromophenyl)-1,5-diphenyl-1H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide; In chlorobenzene; at 130.0℃; for 36.0h;Sealed tube; General procedure: A sealed tube equipped with a stirrer bar was charged with <strong>[1527-91-9]N-phenylbenzamidine</strong>(1a; 0.0393 g, 0.2 mmol), benzonitrile (2a; 41 muL, 0.40mmol), CuI (0.0190 g, 0.10 mmol), ZnI2 (0.0063 g, 0.02 mmol),phenanthroline (0.0040 g, 0.02 mmol) and chlorobenzene (1 mL). The resulting mixture was stirred at 130 C for 36 h. After reaction completion,the residue was directly purified by flash column chromatography(EtOAc-petroleum ether) to afford pure product 3aa.
  • 60
  • [ 100-54-9 ]
  • [ 1527-91-9 ]
  • 3-(1,5-diphenyl-1H-1,2,4-triazol-3-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With copper(l) iodide; 1,10-Phenanthroline; zinc(II) iodide; In chlorobenzene; at 130.0℃; for 36.0h;Sealed tube; General procedure: A sealed tube equipped with a stirrer bar was charged with <strong>[1527-91-9]N-phenylbenzamidine</strong>(1a; 0.0393 g, 0.2 mmol), benzonitrile (2a; 41 muL, 0.40mmol), CuI (0.0190 g, 0.10 mmol), ZnI2 (0.0063 g, 0.02 mmol),phenanthroline (0.0040 g, 0.02 mmol) and chlorobenzene (1 mL). The resulting mixture was stirred at 130 C for 36 h. After reaction completion,the residue was directly purified by flash column chromatography(EtOAc-petroleum ether) to afford pure product 3aa.
  • 61
  • [ 2009-97-4 ]
  • [ 1527-91-9 ]
  • [ 36779-16-5 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: N-phenylbenzamidine With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cesium acetate; acetic acid In 1,2-dichloro-ethane Inert atmosphere; Sealed tube; Stage #2: ethyl 2-diazo-3-oxobutanoate In 1,2-dichloro-ethane at 40℃; for 16h; Inert atmosphere; Sealed tube;
  • 62
  • [ 623-03-0 ]
  • [ 1527-91-9 ]
  • [ 87277-53-0 ]
YieldReaction ConditionsOperation in experiment
91% With copper(II) acetate monohydrate; sodium carbonate; In toluene; at 110.0℃; for 24.0h; taking 10mmolN- phenyl benzamidine and 15mmol4- chlorobenzonitrile in 100mL of round bottom flask, and then further added 1mmolCu(OAc)2·H2O 20 mmolNa2CO3And 30mL of toluene was stirred at 110 C for 24 hours. After the reaction, the product was extracted with ethyl acetate, and dried to give the crude product, the crude product was purified by silica gel column chromatography (solvent volume ratio of petroleum ether: ethyl acetate = 5: 1) 3-(4-chlorophenyl)-5-phenyl-1H-1,2,4-triazole to give a white solid which yield 91%, mp 233C
  • 63
  • [ 1694-31-1 ]
  • [ 1527-91-9 ]
  • tert-butyl 4-methyl-1,2-diphenyl-1H-imidazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With carbon tetrabromide; In acetonitrile; at 80.0℃; for 5.0h;Sealed tube; General procedure: The reactions were carried out in a sealed test tube. 1a (0.6 mmol), 2b (0.2 mmol), CBr4 (2 equiv), and MeCN (1.5 mL) were added to the tube with magnetic stirring bar. The mixture was stirred at 80 C for 5 h. When the reaction was completed (detected by TLC), the mixture was cooled to room temperature. The product 3ab was purified by column chromatography on silica gel (petroleum ether/EtOAc = 5:1).
  • 64
  • [ 94-02-0 ]
  • [ 1527-91-9 ]
  • [ 1345509-63-8 ]
YieldReaction ConditionsOperation in experiment
84% With carbon tetrabromide; In acetonitrile; at 80.0℃; for 5.0h;Sealed tube; General procedure: The reactions were carried out in a sealed test tube. 1a (0.6 mmol), 2b (0.2 mmol), CBr4 (2 equiv), and MeCN (1.5 mL) were added to the tube with magnetic stirring bar. The mixture was stirred at 80 C for 5 h. When the reaction was completed (detected by TLC), the mixture was cooled to room temperature. The product 3ab was purified by column chromatography on silica gel (petroleum ether/EtOAc = 5:1).
  • 65
  • [ 1527-91-9 ]
  • [ 123-54-6 ]
  • 1-(4-methyl-1,2-diphenyl-1H-imidazole-5-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With carbon tetrabromide; In acetonitrile; at 80.0℃; for 5.0h;Sealed tube; General procedure: The reactions were carried out in a sealed test tube. 1a (0.6 mmol), 2b (0.2 mmol), CBr4 (2 equiv), and MeCN (1.5 mL) were added to the tube with magnetic stirring bar. The mixture was stirred at 80 C for 5 h. When the reaction was completed (detected by TLC), the mixture was cooled to room temperature. The product 3ab was purified by column chromatography on silica gel (petroleum ether/EtOAc = 5:1).
  • 66
  • [ 1527-91-9 ]
  • [ 4949-44-4 ]
  • ethyl 4-ethyl-1,2-diphenyl-1H-imidazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With carbon tetrabromide In acetonitrile at 80℃; for 5h; Sealed tube; Procedure 3ab General procedure: The reactions were carried out in a sealed test tube. 1a (0.6 mmol), 2b (0.2 mmol), CBr4 (2 equiv), and MeCN (1.5 mL) were added to the tube with magnetic stirring bar. The mixture was stirred at 80 °C for 5 h. When the reaction was completed (detected by TLC), the mixture was cooled to room temperature. The product 3ab was purified by column chromatography on silica gel (petroleum ether/EtOAc = 5:1).
  • 67
  • [ 1226-42-2 ]
  • [ 1527-91-9 ]
  • [ 77290-63-2 ]
  • [ 7465-88-5 ]
  • 68
  • m-fluorobenzenesulfonyl azide [ No CAS ]
  • [ 1527-91-9 ]
  • 1-((3-fluorophenyl)sulfonyl)-2-phenyl-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With phenylacetic acid; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) triflimide; In 1,2-dichloro-ethane; at 80.0℃; for 12.0h; A solution of <strong>[1527-91-9]N-phenylbenzamidine</strong> 0.2 mmol, m-fluorobenzenesulfonyl azide 0.3 mmol, dichloro (pentamethylcyclopentadienyl) iridium(III) dimer, 0.032 mmol of bis-trifluoromethanesulfonimide silver salt and 0.2 mmol of phenylacetic acid were added to a solution containing Stirring the tube and adding 2mL 1,2-dichloroethane solvent, placed in 80 oil bath, the reaction 12h, the reaction removed from the heat source, cooled to room temperature. The reaction mixture was concentrated and purified by column chromatography to give 68.9 mg of the desired product in a yield of 93%.
  • 69
  • [ 4547-68-6 ]
  • [ 1527-91-9 ]
  • [ 15728-52-6 ]
YieldReaction ConditionsOperation in experiment
90% With phenylacetic acid; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) triflimide; In 1,2-dichloro-ethane; at 80.0℃; for 12.0h; A solution of <strong>[1527-91-9]N-phenylbenzamidine</strong> 0.2 mmol, p-chlorobenzenesulfonyl azide 0.3 mmol, dichloro (pentamethylcyclopentadienyl) iridium(III) dimer, 0.032 mmol of bis-trifluoromethanesulfonimide silver salt and 0.2 mmol of phenylacetic acid were added to a solution containing Stirring the tube and adding 2mL 1,2-dichloroethane solvent, placed in 80 oil bath, the reaction 12h, the reaction removed from the heat source, cooled to room temperature. The reaction solution was concentrated and purified by column chromatography to obtain 69.8 mg of the desired product in a yield of 90%.
  • 70
  • [ 624-90-8 ]
  • [ 1527-91-9 ]
  • 1-(methylsulfonyl)-2-phenyl-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With phenylacetic acid; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) triflimide; In 1,2-dichloro-ethane; at 80.0℃; for 12.0h; A solution of <strong>[1527-91-9]N-phenylbenzamidine</strong> 0.2 mmol, methylbenzenesulfonyl azide 0.3 mmol, dichloro (pentamethylcyclopentadienyl) iridium(III) dimer, 0.032 mmol of bis-trifluoromethanesulfonimide silver salt and 0.2 mmol of phenylacetic acid were added to a solution containing Stirrer in a test tube and add 2 mL of 1,2-dichloroethane solvent, placed in 80 oil bath, the reaction 12h, the reaction removed Heat source, cool to room temperature. The reaction solution was concentrated and purified by column chromatography to obtain 62.9 mg of the desired product in a yield of 99%.
  • 71
  • [ 70284-09-2 ]
  • [ 1527-91-9 ]
  • 1-(ethylsulfonyl)-2-phenyl-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With phenylacetic acid; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) triflimide; In 1,2-dichloro-ethane; at 80.0℃; for 12.0h; A solution of <strong>[1527-91-9]N-phenylbenzamidine</strong> 0.2 mmol, ethylsulfonyl azide 0.3 mmol, dichloro (pentamethylcyclopentadienyl) iridium(III) dimer, 0.032 mmol of bis-trifluoromethanesulfonimide silver salt and 0.2 mmol of phenylacetic acid were added to a solution containing Stirring the tube and adding 2mL 1,2-dichloroethane solvent, placed in 80 oil bath, the reaction 12h, the reaction removed from the heat source, cooled to room temperature. The reaction solution was concentrated and purified by column chromatography to give 47.0 mg of the desired product in 80% yield.
  • 72
  • [ 6972-27-6 ]
  • [ 1527-91-9 ]
  • N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)-N'-phenylbenzamidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A solution of the above crude N-substituted benzamidine (10.0mmol) in DMF (5 mL) was added dropwise at 0 C to a solution of NaH (20.0 mmol) in DMF (5 mL) and stirred for 30 min. A solution of 1,3-dimethyl-6-chlorouracil (5.0 mmol) in DMF (5 mL) was added dropwise at 0 C and the reaction mixture was stirred at 80 C overnight. Sat. aq NH4Cl (20 mL) was added at 0 C and the mixture was extracted with EtOAc (5 × 10 mL). The combined organic phases were washed with H2O (2 × 10 mL) and brine (1 × 10 mL), and dried (MgSO4). The solvent was removed under reduced pressure and the crude material was purified by silica gel column chromatography to give 1a-e,h,k-o.
  • 73
  • [ 13565-43-0 ]
  • [ 1527-91-9 ]
  • o-tolyl(1,2,4-triphenyl-1H-imidazol-5-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With iron(III) chloride; (1-(4-bromophenyl)-2,4-diphenyl-1H-imidazol-5-yl)(phenyl)methanone; oxygen; In chlorobenzene; at 110.0℃; for 10.0h; 0.6 mmol of <strong>[1527-91-9]N-phenylbenzamidine</strong>,0.5 mmol(2E) -1- (2-methylphenyl) -3-phenyl-2-propenyl-1-one,0.01 mmol of ferric chloride and0.05 mmol of iodine added to the containing2mL chlorobenzene25 mL of a round bottom flask and heated to 110 C, reacted in an oxygen atmosphere for 10 h. After completion of the reaction (TLC monitoring), the mixture was cooled to room temperature. With saturated sodium thiosulfate Solution was added to iodine, ethyl acetate (15 mL x 3) was added three times and then washed with saturated brine, washed with anhydrous sodium sulfate Water, concentrated and chromatographed on silica gel using ethyl acetate / petroleum ether (1: 5) to give 166 mg of yellow solid in 80% yield.
  • 74
  • [ 941-55-9 ]
  • [ 1527-91-9 ]
  • [ 15728-51-5 ]
YieldReaction ConditionsOperation in experiment
97% With phenylacetic acid; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) triflimide; In 1,2-dichloro-ethane; at 80.0℃; for 12.0h; A solution of <strong>[1527-91-9]N-phenylbenzamidine</strong>, 0.2 mmol,P-toluenesulfonyl azide 0.3 mmol,Dichloro (pentamethylcyclopentadienyl) iridium(IIl) dimer 0.008 mmol,2-trifluoromethanesulfonimide silver salt, 0.032 mmol,0.01 mmol of phenylacetic acid was added to the solution Stirring the tube and adding 2mL 1,2-dichloroethane solvent, placed in 80 oil bath, the reaction 12h, the reaction removed from the heat source, cooled to room temperature. The reaction solution was concentrated and purified by column chromatography to give 75.9 mg of the desired product in a yield of 97%.
  • 75
  • [ 2579-22-8 ]
  • [ 64-17-5 ]
  • [ 1527-91-9 ]
  • 5-(ethoxy(phenyl)methyl)-1,2-diphenyl-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With silver(I) acetate; toluene-4-sulfonic acid; In toluene; at 100.0℃; for 10.0h;Inert atmosphere; Schlenk technique; To 25mL-schlenk tube have been added<strong>[1527-91-9]N-phenylbenzamidine</strong> (0.20 mmol), AgOAc (2.5 mol%),TsOH (5 mol%), toluene (2 mL),Phenylpropynylaldehyde (0.20 mmol),Ethanol (0.60 mmol),Subsequently, N2 was introduced into the schlenk tube and stirred for 10 h in an oil bath at 100 C,After completion of the reaction by TLC, the mixture was cooled to room temperature, 10 mL of saturated brine was added to the reaction mixture,And extracted with ethyl acetate (10 mL x 3). The organic layers were combined and washed with saturated brine,Dry with anhydrous MgSO4. The resulting organic phase was distilled under reduced pressure to remove most of the solvent,The crude product was purified by column chromatography.
  • 76
  • [ 2579-22-8 ]
  • [ 802294-64-0 ]
  • [ 1527-91-9 ]
  • (1,2-diphenyl-1H-imidazol-5-yl)(phenyl)methyl propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With silver(I) acetate; In dichloromethane; at 60.0℃; for 10.0h;Inert atmosphere; Schlenk technique; N-Phenylbenzamidine (0.20 mmol), phenylpropiolaldehyde(0.20 mmol), Acetic acid (0.60mmol), were added successively into a 25ml of Schlenktube, then N2 was passed and the reacted at 60 C for 10h. After completion of the reaction detected by TLC, the reaction was cooled to room temperature , then 10 ml of saturated brine added to the reaction mixture and carried out extraction with Ethyl acetate (10mL X 3). The combined organic layers were washed with saturated brine and dried over anhydrous MgSO4. The resulting organic phase was distilled under reduced pressure to remove most of the solvent, and the crude product was separated and purified by column chromatography
  • 77
  • [ 104-09-6 ]
  • [ 1527-91-9 ]
  • [ 82221-51-0 ]
YieldReaction ConditionsOperation in experiment
83% With tert-Butyl peroxybenzoate; iodine In 1,4-dioxane at 100℃; for 5h; Green chemistry; regioselective reaction;
  • 78
  • [ 1736-67-0 ]
  • [ 1527-91-9 ]
  • [ 1393902-34-5 ]
YieldReaction ConditionsOperation in experiment
78% With tert-Butyl peroxybenzoate; iodine In 1,4-dioxane at 100℃; for 5h; Green chemistry; regioselective reaction;
  • 79
  • [ 1527-91-9 ]
  • [ 75321-85-6 ]
  • C21H15FN2 [ No CAS ]
  • 80
  • [ 2579-22-8 ]
  • [ 7170-38-9 ]
  • [ 1527-91-9 ]
  • (1,2-diphenyl-1H-imidazol-5-yl)(phenyl)methyl 3-phenoxypropionate [ No CAS ]
  • 81
  • [ 1527-91-9 ]
  • [ 1878-68-8 ]
  • [ 1210045-72-9 ]
YieldReaction ConditionsOperation in experiment
60% With [2,2]bipyridinyl; nitromethane; copper(II) sulfate; In nitromethane; N,N-dimethyl-formamide; at 130.0℃; for 8.0h; General procedure: A round-bottom flask was charged with arylacetic acid 1 (1.5 mmol), N-arylbenzamidine 2 or 4 (1.0 mmol), CuSO4 (10 mol%), and 2,2?-bipyridyl (20 mol%). A pre-oxygen degassed solvent system of DMF/nitroalkane (1.5:0.5 mL) was added to above mixture. The resulting mixture was heated at 130 C for 8 h. The reaction progress was monitored by using TLC. After completion of the reaction, water was added to the mixture and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (anhyd Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography (230-400 mesh silica gel, EtOAc/n-hexane) to afford imidazoles 3 or 5.
  • 82
  • [ 622-47-9 ]
  • [ 1527-91-9 ]
  • 1,2-diphenyl-4-(p-tolyl)-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With [2,2]bipyridinyl; nitromethane; copper(II) sulfate; In nitromethane; N,N-dimethyl-formamide; at 130.0℃; for 8.0h; General procedure: A round-bottom flask was charged with arylacetic acid 1 (1.5 mmol), N-arylbenzamidine 2 or 4 (1.0 mmol), CuSO4 (10 mol%), and 2,2?-bipyridyl (20 mol%). A pre-oxygen degassed solvent system of DMF/nitroalkane (1.5:0.5 mL) was added to above mixture. The resulting mixture was heated at 130 C for 8 h. The reaction progress was monitored by using TLC. After completion of the reaction, water was added to the mixture and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (anhyd Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography (230-400 mesh silica gel, EtOAc/n-hexane) to afford imidazoles 3 or 5.
  • 83
  • [ 104-01-8 ]
  • [ 1527-91-9 ]
  • [ 1423126-02-6 ]
YieldReaction ConditionsOperation in experiment
71% With [2,2]bipyridinyl; nitromethane; copper(II) sulfate; In nitromethane; N,N-dimethyl-formamide; at 130.0℃; for 8.0h; General procedure: A round-bottom flask was charged with arylacetic acid 1 (1.5 mmol), N-arylbenzamidine 2 or 4 (1.0 mmol), CuSO4 (10 mol%), and 2,2?-bipyridyl (20 mol%). A pre-oxygen degassed solvent system of DMF/nitroalkane (1.5:0.5 mL) was added to above mixture. The resulting mixture was heated at 130 C for 8 h. The reaction progress was monitored by using TLC. After completion of the reaction, water was added to the mixture and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (anhyd Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography (230-400 mesh silica gel, EtOAc/n-hexane) to afford imidazoles 3 or 5.
  • 84
  • [ 5462-71-5 ]
  • [ 1527-91-9 ]
  • [ 1571142-49-8 ]
YieldReaction ConditionsOperation in experiment
69% With [2,2]bipyridinyl; nitromethane; copper(II) sulfate; In nitromethane; N,N-dimethyl-formamide; at 130℃; for 8h; General procedure: A round-bottom flask was charged with arylacetic acid 1 (1.5 mmol), N-arylbenzamidine 2 or 4 (1.0 mmol), CuSO4 (10 molpercent), and 2,2?-bipyridyl (20 molpercent). A pre-oxygen degassed solvent system of DMF/nitroalkane (1.5:0.5 mL) was added to above mixture. The resulting mixture was heated at 130 °C for 8 h. The reaction progress was monitored by using TLC. After completion of the reaction, water was added to the mixture and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (anhyd Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography (230?400 mesh silica gel, EtOAc/n-hexane) to afford imidazoles 3 or 5.
  • 85
  • [ 1527-91-9 ]
  • [ 581-96-4 ]
  • [ 1423126-06-0 ]
YieldReaction ConditionsOperation in experiment
47% With [2,2]bipyridinyl; nitromethane; copper(II) sulfate In nitromethane; N,N-dimethyl-formamide at 130℃; for 8h; regioselective reaction; Multisubstituted Imidazoles 3 and 5; General Procedure General procedure: A round-bottom flask was charged with arylacetic acid 1 (1.5 mmol), N-arylbenzamidine 2 or 4 (1.0 mmol), CuSO4 (10 mol%), and 2,2′-bipyridyl (20 mol%). A pre-oxygen degassed solvent system of DMF/nitroalkane (1.5:0.5 mL) was added to above mixture. The resulting mixture was heated at 130 °C for 8 h. The reaction progress was monitored by using TLC. After completion of the reaction, water was added to the mixture and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (anhyd Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography (230-400 mesh silica gel, EtOAc/n-hexane) to afford imidazoles 3 or 5.
  • 86
  • [ 63104-44-9 ]
  • [ 1527-91-9 ]
  • dimethyl 3-methyl-4-(2-phenylquinazolin-4-yl)cyclopent-3-ene-1,1-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 2,6-dimethylbenzoic acid; lithium carbonate; silver carbonate In 1-methyl-pyrrolidin-2-one; ethanol; water; N,N-dimethyl-formamide at 80℃; for 21h; 10 Example 10 Add [Cp*RhCl2]2 (3.9 mg, 0.0063 mmol) to the reaction vessel.Ag2CO3 (3.5mg, 10mol%), 2,6-dimethylbenzoic acid (1equiv),Li2CO3 (0.8equiv),Amidine compound 1a (0.5mmol),Diacetylene compound 2b (0.125 mmol),DMF/EtOH/NMP (2:1:2) (6 mL) and H2O (4 equiv),Warming to 80°C,Reaction for 21 hours.Cool the reaction to room temperatureAfter removing the solvent under reduced pressure,Column chromatographic separation of the corresponding quinazoline derivative (ie quinazoline product 3ab),Determine its structure through nuclear magnetic and single crystal methods,See Figure 7-8 and Figure 17Yield up to 50%.
50% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 2,6-dimethylbenzoic acid; water; lithium carbonate; silver carbonate In 1-methyl-pyrrolidin-2-one; ethanol at 80℃; for 21h;
  • 87
  • [ 6921-27-3 ]
  • [ 1527-91-9 ]
  • 4-(4-methyl-2,5-dihydrofuran-3-yl)-2-phenylquinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 2,6-dimethylbenzoic acid; lithium carbonate; silver carbonate; In 1-methyl-pyrrolidin-2-one; ethanol; water; N,N-dimethyl-formamide; at 80.0℃; for 21.0h; Add [Cp*RhCl2]2 (3.9 mg, 0.0063 mmol) to the reaction vessel.Ag2CO3 (3.5mg, 10mol%),2,6-Dimethylbenzoic acid (1equiv),Li2CO3 (0.8equiv),Amidine compound 1a (0.5mmol),Diacetylene compound 2c (0.125 mmol),DMF/EtOH/NMP (2:1:2) (6 mL) and H2O (4 equiv),Warming to 80C,Reaction for 21 hours.Cool the reaction to room temperatureAfter removing the solvent under reduced pressure,Chromatographic separation of the corresponding quinazoline derivative (ie quinazoline product 3ac),Determine its structure through nuclear magnetic and single crystal methods,See Figure 9-10, Figure 18,Yield up to 73%.
  • 88
  • [ 1805-32-9 ]
  • [ 1527-91-9 ]
  • 4-(3,4-dichlorophenyl)-2-phenylquinazoline [ No CAS ]
  • 89
  • [ 766-96-1 ]
  • [ 26496-94-6 ]
  • [ 1527-91-9 ]
  • ethyl 4-(5-(4-bromobenzoyl)-1,2-diphenyl-1H-imidazol-4-yl)benzoate [ No CAS ]
  • 90
  • [ 4209-02-3 ]
  • [ 1527-91-9 ]
  • (4-bromophenyl)(2-phenyl-1H-indol-3-yl)methanone [ No CAS ]
  • 91
  • [ 1527-91-9 ]
  • [ 2196-99-8 ]
  • [ 103056-99-1 ]
YieldReaction ConditionsOperation in experiment
83% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium hydrogencarbonate In methanol at 90℃; for 24h; Inert atmosphere; regioselective reaction;
  • 92
  • [ 51336-95-9 ]
  • [ 1527-91-9 ]
  • (3,4-difluorophenyl)(2-phenyl-1H-indol-3-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium hydrogencarbonate In methanol at 90℃; for 24h; Inert atmosphere; regioselective reaction;
  • 93
  • [ 20718-17-6 ]
  • [ 1527-91-9 ]
  • [ 56839-21-5 ]
YieldReaction ConditionsOperation in experiment
83% With trifluoroacetic acid; In 1,2-dichloro-ethane; at 110.0℃; for 12.0h;Green chemistry; All the reactions were carried out in a reaction vessel (10 mL), <strong>[1527-91-9]N-phenylbenzamidine</strong> (1a, 0.1 mmol), sulfoxonium ylides (2a,0.2 mmol), trifluoroacetate (50 mol%) and DCE (2 ml) were successfully mixed in the flask using a magnetic stir bar and reacted at 110 C for 12 h in the presence of air. Then the mixture was removed from the oil bath and cooled to room temperature. The mixture was filtered and washed with ethyl acetate (3×50 mL) and the crude product was obtained by concentrating under reduced pressure. Finally, product 3a was isolated as a yellow oil by silica gel chromatography (petroleum ether/ethyl acetate = 10/1 as the eluent).The remaining substituted imidazoles were prepared in a similar manner.
  • 94
  • 2-[dimethyl(oxo)-λ6-sulfaneylidene]-1-(o-tolyl)ethan-1-one [ No CAS ]
  • [ 1527-91-9 ]
  • [ 1610784-76-3 ]
YieldReaction ConditionsOperation in experiment
75% With trifluoroacetic acid; In 1,2-dichloro-ethane; at 110.0℃; for 12.0h;Green chemistry; General procedure: All the reactions were carried out in a reaction vessel (10 mL), <strong>[1527-91-9]N-phenylbenzamidine</strong> (1a, 0.1 mmol), sulfoxonium ylides (2a,0.2 mmol), trifluoroacetate (50 mol%) and DCE (2 ml) were successfully mixed in the flask using a magnetic stir bar and reacted at 110 C for 12 h in the presence of air. Then the mixture was removed from the oil bath and cooled to room temperature. The mixture was filtered and washed with ethyl acetate (3×50 mL) and the crude product was obtained by concentrating under reduced pressure. Finally, product 3a was isolated as a yellow oil by silica gel chromatography (petroleum ether/ethyl acetate = 10/1 as the eluent).The remaining substituted imidazoles were prepared in a similar manner.
  • 95
  • 2-(dimethyl(oxo)- λ6-sulfanylidene)-1-(m-tolyl)ethan-1-one [ No CAS ]
  • [ 1527-91-9 ]
  • [ 1610784-77-4 ]
YieldReaction ConditionsOperation in experiment
76% With trifluoroacetic acid; In 1,2-dichloro-ethane; at 110.0℃; for 12.0h;Green chemistry; General procedure: All the reactions were carried out in a reaction vessel (10 mL), <strong>[1527-91-9]N-phenylbenzamidine</strong> (1a, 0.1 mmol), sulfoxonium ylides (2a,0.2 mmol), trifluoroacetate (50 mol%) and DCE (2 ml) were successfully mixed in the flask using a magnetic stir bar and reacted at 110 C for 12 h in the presence of air. Then the mixture was removed from the oil bath and cooled to room temperature. The mixture was filtered and washed with ethyl acetate (3×50 mL) and the crude product was obtained by concentrating under reduced pressure. Finally, product 3a was isolated as a yellow oil by silica gel chromatography (petroleum ether/ethyl acetate = 10/1 as the eluent).The remaining substituted imidazoles were prepared in a similar manner.
  • 96
  • C12H16O2S [ No CAS ]
  • [ 1527-91-9 ]
  • 4-(4-ethylphenyl)-1,2-diphenyl-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With trifluoroacetic acid; In 1,2-dichloro-ethane; at 110.0℃; for 12.0h;Green chemistry; General procedure: All the reactions were carried out in a reaction vessel (10 mL), <strong>[1527-91-9]N-phenylbenzamidine</strong> (1a, 0.1 mmol), sulfoxonium ylides (2a,0.2 mmol), trifluoroacetate (50 mol%) and DCE (2 ml) were successfully mixed in the flask using a magnetic stir bar and reacted at 110 C for 12 h in the presence of air. Then the mixture was removed from the oil bath and cooled to room temperature. The mixture was filtered and washed with ethyl acetate (3×50 mL) and the crude product was obtained by concentrating under reduced pressure. Finally, product 3a was isolated as a yellow oil by silica gel chromatography (petroleum ether/ethyl acetate = 10/1 as the eluent).The remaining substituted imidazoles were prepared in a similar manner.
  • 97
  • 2-[dimethyl(oxo)-λ6-sulfaneylidene]-1-(4-methoxyphenyl)ethan-1-one [ No CAS ]
  • [ 1527-91-9 ]
  • [ 1423126-02-6 ]
YieldReaction ConditionsOperation in experiment
91% With trifluoroacetic acid; In 1,2-dichloro-ethane; at 110.0℃; for 12.0h;Green chemistry; General procedure: All the reactions were carried out in a reaction vessel (10 mL), <strong>[1527-91-9]N-phenylbenzamidine</strong> (1a, 0.1 mmol), sulfoxonium ylides (2a,0.2 mmol), trifluoroacetate (50 mol%) and DCE (2 ml) were successfully mixed in the flask using a magnetic stir bar and reacted at 110 C for 12 h in the presence of air. Then the mixture was removed from the oil bath and cooled to room temperature. The mixture was filtered and washed with ethyl acetate (3×50 mL) and the crude product was obtained by concentrating under reduced pressure. Finally, product 3a was isolated as a yellow oil by silica gel chromatography (petroleum ether/ethyl acetate = 10/1 as the eluent).The remaining substituted imidazoles were prepared in a similar manner.
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