Alternatived Products of [ 25855-20-3 ]
Product Details of [ 25855-20-3 ]
CAS No. : | 25855-20-3 |
MDL No. : | MFCD13961838 |
Formula : |
C14H10N2
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
206.24
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 25855-20-3 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 25855-20-3 ]
* 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.
- Upstream synthesis route of [ 25855-20-3 ]
- Downstream synthetic route of [ 25855-20-3 ]
- 1
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[ 25855-20-3 ]
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[ 1022-45-3 ]
Yield | Reaction Conditions | Operation in experiment |
96% |
With dihydrogen peroxide; oxygen; acetic acid at 55℃; for 24h; Sealed tube; Heating; |
32 Control group 32
Add o-aminobenzyl alcohol (1.0mmol), benzonitrile (1.2mmol, 1.2equiv),Cesium hydroxide monohydrate (0.17g, 1.0equiv) and 1,4-dioxane (3.0mL) were placed in a 100mL Schlenk tube and stirred at 100°C for 24 hours.The mixture after completion of the reaction was concentrated in vacuo.The concentrated residue was purified by column chromatography, using petroleum ether and ethyl acetate (petroleum ether: ethyl acetate = 10:1) as eluents,A pale yellow solid was obtained, and 2-phenylquinazoline was obtained with an isolated yield of 79%.Then, 2-phenylquinazoline (20.6mg, 0.1mmol) and hydrogen peroxide (6.8mg, 0.2mmol) were sealed into the reaction tube,After replacing the oxygen 3 times, acetic acid (0.5 mL) was added to the sealed reaction tube via a syringe.Place it in an oil bath at 55°C, and heat and stir to react for 24 hours. After cooling to room temperature, it was concentrated under reduced pressure to obtain a crude product.Purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1), the β-glucuronidase inhibitor was obtained as a pale yellow solid with a yield of 96% |
95% |
With dihydrogen peroxide; oxygen; acetic acid at 55℃; for 24h; Sealed tube; |
|
92% |
With dihydrogen peroxide; oxygen; acetic acid at 55℃; |
|
54% |
With potassium <i>tert</i>-butylate In tetrahydrofuran at 40℃; for 1h; |
|
|
With chromium(VI) oxide; acetic acid |
|
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With oxygen; acetic acid at 55℃; |
|
Reference:
[1]Current Patent Assignee: XIANGTAN UNIVERSITY - CN111606823, 2020, A
Location in patent: Paragraph 0100-0102
[2]Cheng, Xiufang; Wang, Huamin; Xiao, Fuhong; Deng, Guo-Jun
[Green Chemistry, 2016, vol. 18, # 21, p. 5773 - 5776]
[3]Cao, Yue; Wu, Yong; Zhang, Yuanteng; Zhou, Jing; Xiao, Wei; Gu, Dong
[ChemCatChem, 2021, vol. 13, # 16, p. 3679 - 3686]
[4]Zhao, Dan; Shen, Qi; Zhou, Yu-Ren; Li, Jian-Xin
[Organic and Biomolecular Chemistry, 2013, vol. 11, # 35, p. 5908 - 5912]
[5]Bischler; Lang
[Chemische Berichte, 1895, vol. 28, p. 292]
[6]Wu, Yong; Yi, Hong; Lei, Aiwen
[ACS Catalysis, 2018, vol. 8, # 2, p. 1192 - 1196]
- 2
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[ 7672-01-7 ]
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[ 25855-20-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
beim Erhitzen ueber den Schmelzpunkt; |
|
- 3
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[ 43120-25-8 ]
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[ 67-66-3 ]
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[ 271-44-3 ]
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[ 6141-13-5 ]
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[ 25855-20-3 ]
- 4
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[ 43120-25-8 ]
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[ 271-44-3 ]
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[ 6141-13-5 ]
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[ 25855-20-3 ]
- 5
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[ 6141-13-5 ]
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[ 98-80-6 ]
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[ 25855-20-3 ]
- 6
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[ 3959-05-5 ]
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[ 55-21-0 ]
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[ 25855-20-3 ]
Yield | Reaction Conditions | Operation in experiment |
98% |
With potassium carbonate at 120℃; for 12h; Schlenk technique; Sealed tube; |
General procedure for synthesis of quinazolines catalyzed by Fe3O4*SiO2-SMTU-Cu
General procedure: An oven-dried Schlenk tube was charged with Fe3O4*SiO2-SMTU-Cu (20 mg), K2CO3 (1.5 equiv) amide (1.25 mmol), substituted (2-bromophenyl)methylamine (1 mmol), and PEG-400 (3 ml). The tube was sealed, and the mixture reaction was stirred at 120 °C for 12 h. The progress of the reaction was monitored by TLC. Upon completion of the reaction, the catalyst was separated using magnetic stirring bar and the resulting solution was cooled to room temperature, the solvent was removed, and the residue was purified by silica gel column chromatography to give the desired product. |
87% |
With copper (I) iodide; oxygen; potassium carbonate In isopropanol at 110℃; for 24h; Sealed tube; |
|
71% |
With C24H22N6Ni; sodium tertiary butoxide In N,N-dimethyl-formamide at 70℃; for 24h; Inert atmosphere; Schlenk technique; |
|
Reference:
[1]Riadi, Yassine; M. Kadhim, Mustafa; Jawad Shoja, Sarah; Hussein Ali, Muneam; Fakri Mustafa, Yasser; Sajjadi, Ahmad
[Synthetic Communications, 2022, vol. 52, # 6, p. 875 - 887]
[2]Wang, Chen; Li, Shangfu; Liu, Hongxia; Jiang, Yuyang; Fu, Hua
[Journal of Organic Chemistry, 2010, vol. 75, # 22, p. 7936 - 7938]
[3]Sikari, Rina; Sinha, Suman; Chakraborty, Gargi; Das, Siuli; van Leest, Nicolaas Petrus; Paul, Nanda D.
[Advanced Synthesis and Catalysis, 2019, vol. 361, # 18, p. 4342 - 4353]
- 7
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[ 75-91-2 ]
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[ 529-23-7 ]
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[ 2835-06-5 ]
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[ 25855-20-3 ]
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[ 64113-91-3 ]
- 8
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[ 3959-05-5 ]
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[ 1670-14-0 ]
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[ 25855-20-3 ]
Yield | Reaction Conditions | Operation in experiment |
92% |
Stage #1: 2-bromobenzylamine; benzamidine monohydrochloride With potassium carbonate; copper(I) bromide In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; Schlenk technique;
Stage #2: In dimethyl sulfoxide at 100℃; for 0.5h; Schlenk technique; |
General procedure for synthesis of compounds 3a-v
General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product. |
62% |
With potassium phosphate; copper(l) iodide; Trimethylacetic acid In 1,2-dichloro-benzene at 110℃; for 18h; Sealed tube; |
4.2. General procedure for the CuI-catalyzed synthesis ofcompounds 3a-t
General procedure: Anoven-dried 10mLvialwas charged with CuI (9mg, 0.05mmol),K3PO4 (318 mg, 1.5 mmol), pivalic acid (20 mg, 0.2 mmol), a 1-(2-bromophenyl)methanamine 1 (0.5 mmol), and an amidinium salt 2or an imidate salt 4 (0.5 mmol) under air. After sealing the vial, dry1,2-dichlorobenzene (3 mL) was added by syringe and the reactionmixture was stirred at 110 C (oil bath temperature) for 18 h. Aftercooling to room temperature, the vial was opened and the reactionmixturewas partitioned between CH2Cl2 (30 mL) and brine (20 mL).The aqueous phase was extracted with CH2Cl2 (220 mL). Thecombined organic layers were dried over anhydrous MgSO4 andconcentrated in vacuum. The residue was purified by flash chromatographyon silica gel to afford the desired product. |
Reference:
[1]Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei
[Synlett, 2013, vol. 24, # 16, p. 2089 - 2094]
[2]Omar, Mohamed A.; Conrad, Jürgen; Beifuss, Uwe
[Tetrahedron, 2014, vol. 70, # 18, p. 3061 - 3072]
- 9
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[ 5344-90-1 ]
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[ 100-52-7 ]
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[ 25855-20-3 ]
Yield | Reaction Conditions | Operation in experiment |
93% |
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; cerium(III) nitrate hexahydrate; oxygen; ammonium chloride; copper(l) chloride; potassium hydroxide In acetonitrile at 30 - 80℃; for 48h; Schlenk technique; |
|
91% |
With [2,2]bipyridinyl; ammonium cerium (IV) nitrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; cesium hydroxide; oxygen; copper(l) chloride In acetonitrile at 30 - 60℃; for 48h; Schlenk technique; |
3.2. General Procedure for the Synthesis of 2-Arylquinazolins
To a Schlenk tube were added (2-aminophenyl)methanols 1 (0.2 mmol), aldehydes 2 (0.3 mmol), CAN (0.3 mmol), CuCl (0.02 mmol), 2,2'-bipyridine (0.02 mmol), TEMPO (0.02 mmol), CsOH(0.5 mmol), and CH3CN (2 mL). Next the tube was charged with O2 (1 atm), and was stirred constantly at 30 °C for 24 h, then at 60 °C for 24 h. After the completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with brine. After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous MgSO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products 3. |
Reference:
[1]Chen, Zhongyan; Chen, Jiuxi; Liu, Miaochang; Ding, Jinchang; Gao, Wenxia; Huang, Xiaobo; Wu, Huayue
[Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11342 - 11348]
[2]Ye, Leping; Yu, Lin; Zhu, Lijun; Xia, Xiaodong
[Molecules, 2013, vol. 18, # 11, p. 13860 - 13869]
- 10
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[ 3959-05-5 ]
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[ 5333-86-8 ]
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[ 25855-20-3 ]
Yield | Reaction Conditions | Operation in experiment |
57% |
With potassium phosphate; copper(l) iodide; Trimethylacetic acid In 1,2-dichloro-benzene at 110℃; for 18h; Sealed tube; |
4.2. General procedure for the CuI-catalyzed synthesis ofcompounds 3a-t
General procedure: Anoven-dried 10mLvialwas charged with CuI (9mg, 0.05mmol),K3PO4 (318 mg, 1.5 mmol), pivalic acid (20 mg, 0.2 mmol), a 1-(2-bromophenyl)methanamine 1 (0.5 mmol), and an amidinium salt 2or an imidate salt 4 (0.5 mmol) under air. After sealing the vial, dry1,2-dichlorobenzene (3 mL) was added by syringe and the reactionmixture was stirred at 110 C (oil bath temperature) for 18 h. Aftercooling to room temperature, the vial was opened and the reactionmixturewas partitioned between CH2Cl2 (30 mL) and brine (20 mL).The aqueous phase was extracted with CH2Cl2 (220 mL). Thecombined organic layers were dried over anhydrous MgSO4 andconcentrated in vacuum. The residue was purified by flash chromatographyon silica gel to afford the desired product. |
- 11
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[ 39959-51-8 ]
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[ 1670-14-0 ]
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[ 25855-20-3 ]
Yield | Reaction Conditions | Operation in experiment |
63% |
With potassium phosphate; copper(l) iodide; Trimethylacetic acid; In 1,2-dichloro-benzene; at 110℃; for 18h;Sealed tube; |
General procedure: Anoven-dried 10mLvialwas charged with CuI (9mg, 0.05mmol),K3PO4 (318 mg, 1.5 mmol), pivalic acid (20 mg, 0.2 mmol), a 1-(2-bromophenyl)methanamine 1 (0.5 mmol), and an amidinium salt 2or an imidate salt 4 (0.5 mmol) under air. After sealing the vial, dry1,2-dichlorobenzene (3 mL) was added by syringe and the reactionmixture was stirred at 110 C (oil bath temperature) for 18 h. Aftercooling to room temperature, the vial was opened and the reactionmixturewas partitioned between CH2Cl2 (30 mL) and brine (20 mL).The aqueous phase was extracted with CH2Cl2 (220 mL). Thecombined organic layers were dried over anhydrous MgSO4 andconcentrated in vacuum. The residue was purified by flash chromatographyon silica gel to afford the desired product. |
- 12
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[ 108-86-1 ]
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[ 201230-82-2 ]
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[ 1774-35-2 ]
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[ 4403-69-4 ]
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[ 25855-20-3 ]
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[ 620-94-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; catacxium A In N,N-dimethyl-formamide at 140℃; for 36h; Inert atmosphere; Autoclave; |
|
- 13
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[ 538-86-3 ]
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[ 4403-69-4 ]
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[ 25855-20-3 ]
Yield | Reaction Conditions | Operation in experiment |
70% |
With oxygen In dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Sealed tube; Green chemistry; |
General procedure for the synthesis of N-heterocyclic compounds
General procedure: A 25 mL Schlenk-type tube equipped with a magnetic stir bar was charged with o-substituted aniline 1a-1f. The reaction tube was evacuated and back-filled with O2. Under oxygen atmospheres, ethers or alcohols 2a-2n and DMSO were added at room temperature, then the reaction mixture was stirred at 120 C for 12 h. The reaction was monitored by TLC. After completion of the reaction, the resulting solution was cooled to room temperature, and neutralized with saturated NaHCO3 aqueous solution. The product was extracted with EtOAc or CHCl3, dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel to give N-heterocyclic compounds 3. |
Reference:
[1]Chen, Xiuling; Qi, Hongxue; Wu, Shaofeng; Liu, Leng; Wen, Jianhui; Li, Wanxi; Guo, Fang; Bian, Yongjun; Li, Jun
[Heterocycles, 2017, vol. 94, # 1, p. 86 - 94]
- 14
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[ 100-47-0 ]
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[ 221910-19-6 ]
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[ 25855-20-3 ]
- 15
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[ 100-47-0 ]
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[ 157869-15-3 ]
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[ 25855-20-3 ]
- 16
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[ 1022-45-3 ]
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[ 25855-20-3 ]
Yield | Reaction Conditions | Operation in experiment |
60% |
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); phenylsilane In toluene at 120℃; for 12h; Inert atmosphere; Sealed tube; |
Typical procedure for the synthesis of 5a
General procedure: The mixture of 3-methyl-2-phenylquinazolin-4(3H)-one 4a (47 mg, 0.2 mmol), PhSiH3 (43 mg, 0.4 mmol), RuHCl(CO)(PPh3)3 (5 mol%, 9 mg), and toluene (2 mL) were added successively to a Schlenk tube (50 mL) equipped with a magnetic stirrer bar, the Schlenk tube was then closed and the resulting reaction mixture was heated at 120 °C for 12 h under N2 atmosphere. After cooling to room temperature, the reaction mixture was filtrated and then concentrated under vacuum. The residue was directly purified by preparative TLC on silica, eluting with petroleum ether (60-90°C): ethyl acetate (4:1) to give 3-methyl-2-phenyl-3,4-dihydroquinazoline (5a) as oil (35 mg, 80%). |
Reference:
[1]Zhang, Xiangyu; Luo, Chujun; Chen, Xiaoyong; Ma, Weilin; Li, Bin; Lin, Zirui; Chen, Xiuwen; Li, Yibiao; Xie, Feng
[Tetrahedron Letters, 2021, vol. 66]