Name: 20577-73-5|Methyl 2,4-dioxo-4-phenylbutanoate|98%
Brand: Ambeed
SKU: A327408
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1
[ 20577-73-5 ]
[ 51677-09-9 ]
methyl 4-phenyl-2-oxo-4-hydroximinobutyrate [ No CAS ]

Reference： [1]Archiv der Pharmazie,1995,vol. 328,p. 437 - 443

2
[ 553-90-2 ]
[ 98-86-2 ]
[ 20577-73-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: acetophenone With potassium-t-butoxide In tetrahydrofuran at 0℃; for 0.75h; Inert atmosphere; Stage #2: Dimethyl oxalate In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
86%	With sodium methoxide In 5,5-dimethyl-1,3-cyclohexadiene at 40 - 50℃; for 4h;	2.1 Example 2 Synthesis of 5-benzoyl-2-hydroxypyrimidine (1) In a 250 ml three-necked flask,Add 9.5 g (0.174 mol) of sodium methoxide and 100 mL of dry xylene.Stir,A uniform mixed solution of 20.5 g (0.17 mol) of acetophenone and 20.6 g (0.174 mol) of dimethyl oxalate was added dropwise (30 minutes dropwise).The temperature is raised to 40 to 50 ° C.The reaction was stirred for 4 h.Cool to room temperature,Wash with 5% dilute hydrochloric acid solution,And adjust the PH value to 5 to 6,Liquid separation,Collecting the xylene layer,Dry with anhydrous sodium sulfate for 30 minutes.filter,The filtrate pump is distilled under reduced pressure to recover xylene.The residue was recrystallized from 95% ethanol to give methyl ester intermediate I (purity: 98.9%) 30.2 gThe yield was 86%.
65%	With sodium methoxide In methanol for 16h; Ambient temperature;

65.9%	With sodium methoxide In methanol at 0 - 20℃;
59%	With sodium hydride In N,N-dimethyl-formamide at 20 - 50℃; for 1.5h;
	With sodium methoxide In methanol	131.1 Step 1 Step 1 Preparation methyl 4-phenyl-2,4-dioxobutanoate To a solution of dimethyl oxalate (11.81 g, 100 mmol) in ether (200 mL) is added 24 mL of 25% sodium methoxide in methanol, followed by a solution of acetophenone (12.02 g, 100 mmol) in ether (20 mL) and the mixture stirred overnight at room temperature. The mixture was partitioned between 1N HCl and EtOAc and the organic layer was washed with brine, dried over MgSO4 and concentrated to give 18.4 g of crude butanoate.
	With sodium methoxide In methanol	131.1 Step 1: Step 1: Preparation Methyl 4-phenyl-2,4-dioxobutanoate To a solution of dimethyl oxalate (11.81 g, 100 mmol) in ether (200 mL) is added 24 mL of 25% sodium methoxide in methanol, followed by a solution of acetophenone (12.02 g, 100 mmol) in ether (20 mL) and the mixture stirred overnight at room temperature. The mixture was partitioned between 1N HCl and EtOAc and the organic layer was washed with brine, dried over MgSO4 and concentrated to give 18.4 g of crude butanoate.
	With sodium methoxide In tetrahydrofuran at 20℃; for 8h;
	With sodium methoxide In tetrahydrofuran at 20℃; for 8h;
	Stage #1: acetophenone With sodium hydride In toluene at 0℃; for 0.5h; Stage #2: Dimethyl oxalate In toluene at 80℃;
	With sodium methoxide In methanol at 20℃; for 2h; Inert atmosphere;
	With potassium-t-butoxide In tetrahydrofuran; toluene at 20℃;	General procedure: To a stirred solution of dimethyl oxalate (1.1 eq.) and methyl ketone (1 eq.) in toluene was added a solution of potassium tertbutoxide(1.2 eq.) in THF. The resulting solution was stirred atroom temperature overnight. The reaction was quenched with 1 NHCl and extracted with ethyl acetate. The combined organic layerswere dried over Na2SO4, filtered and concentrated under reducedpressure. The crude product (12a - h) was dissolved in methanoland hydroxylamine hydrochloride was added. The solution washeated to 50 °C for 6 h. The solvents were removed under reducedpressure and the resulting isoxazole ester was purified by flashcolumn chromatography to provide the target compounds.
	With potassium-t-butoxide In tetrahydrofuran; toluene at 20℃;
	With sodium methoxide In methanol at 0 - 20℃; for 12h; Inert atmosphere;	4.1.1. 5-methyl-1-(4-((N-methylsulfiiamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid (12a) General procedure: Step 1. To a solution of acetone (6a, 580 mg, 10 mmol) and dimethyloxalate (7, 1.18 g, 10 mmol) in anhydrous methanol (50 mL) was degassed with argon and cooled to 0 °C in an ice bath. 30% sodium methanolate in methanol (20 mmol) was added dropwise into the coldsolution and the mixture was allowed to warm to room temperature. After 12 h, the resultant mixture was quenched with conc. HCl (5 mL)and concentrated in vacuo. The residue was then diluted with water (50 mL) and extracted with EA (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated to give methyl acetopyruvate (8a) which was directly used in the next step without further purification.
	With sodium methoxide In methanol at 0 - 20℃; for 12h; Inert atmosphere;	4.1.1. 5-methyl-1-(4-((N-methylsulfiiamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid (12a) General procedure: Step 1. To a solution of acetone (6a, 580 mg, 10 mmol) and dimethyloxalate (7, 1.18 g, 10 mmol) in anhydrous methanol (50 mL) was degassed with argon and cooled to 0 °C in an ice bath. 30% sodium methanolate in methanol (20 mmol) was added dropwise into the coldsolution and the mixture was allowed to warm to room temperature. After 12 h, the resultant mixture was quenched with conc. HCl (5 mL)and concentrated in vacuo. The residue was then diluted with water (50 mL) and extracted with EA (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated to give methyl acetopyruvate (8a) which was directly used in the next step without further purification.

Reference： [1]Wang, Ziqian; Song, Ting; Feng, Yingang; Guo, Zongwei; Fan, Yudan; Xu, Wenjie; Liu, Lu; Wang, Anhui; Zhang, Zhichao [Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3152 - 3162]
[2]Current Patent Assignee: BAYNOE CHEM (SUZHOU) CO LTD - CN108148003, 2018, A Location in patent: Paragraph 0090; 0091
[3]Penning, Thomas D.; Talley, John J.; Bertenshaw, Stephen R.; Carter, Jeffery S.; Collins, Paul W.; Docter, Stephen; Graneto, Matthew J.; Lee, Len F.; Malecha, James W.; Miyashiro, Julie M.; Rogers, Roland S.; Rogier; Yu, Stella S.; Anderson, Gary D.; Burton, Earl G.; Cogburn, J. Nita; Gregory, Susan A.; Koboldt, Carol M.; Perkins, William E.; Seibert, Karen; Veenhuizen, Amy W.; Zhang, Yan Y.; Isakson, Peter C. [Journal of Medicinal Chemistry, 1997, vol. 40, # 9, p. 1347 - 1365]
[4]Veeraswamy; Kurumurthy; Santhosh Kumar; Sambasiva Rao; Thelakkat, Kavya; Kotamraju, Srigiridhar; Narsaiah [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 9, p. 1369 - 1375]
[5]Tanaka, Akira; Terasawa, Takeshi; Hagihara, Hiroyuki; Sakuma, Yuri; Ishibe, Noriko; Sawada, Masae; Takasugi, Hisashi; Tanaka, Hirokazu [Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2390 - 2410]
[6]Current Patent Assignee: PFIZER INC - US5756529, 1998, A
[7]Current Patent Assignee: ZOETIS INC. - US5760068, 1998, A
[8]Location in patent: scheme or table Kamal, Ahmed; Tamboli, Jaki R.; Ramaiah, M. Janaki; Adil; KoteswaraRao; Viswanath; Mallareddy, Adla; Pushpavalli; Pal-Bhadra, Manika [ChemMedChem, 2012, vol. 7, # 8, p. 1453 - 1464]
[9]Kamal, Ahmed; Tamboli, Jaki R.; Vishnuvardhan; Adil; Nayak, V. Lakshma; Ramakrishna [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 273 - 280]
[10]Jaiswal, Pradeep K.; Sharma, Vashundhra; Kumar, Surendra; Mathur, Manas; Swami, Ajit K.; Yadav, Dharmendra K.; Chaudhary, Sandeep [Archiv der Pharmazie, 2018, vol. 351, # 3-4]
[11]Vickers, Clare F.; Silva, Ana P. G.; Chakraborty, Ajanta; Fernandez, Paulina; Kurepina, Natalia; Saville, Charis; Naranjo, Yandi; Pons, Miquel; Schnettger, Laura S.; Gutierrez, Maximiliano G.; Park, Steven; Kreiswith, Barry N.; Perlin, David S.; Thomas, Eric J.; Cavet, Jennifer S.; Tabernero, Lydia [Journal of Medicinal Chemistry, 2018, vol. 61, # 18, p. 8337 - 8352]
[12]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - EP1176140, 2002, A1 Location in patent: Page 49
[13]Ye, Jiqing; Yang, Xiao; Xu, Min; Chan, Paul Kay-sheung; Ma, Cong [European Journal of Medicinal Chemistry, 2019, vol. 182]
[14]Ye, Jiqing; Lin, Lin; Xu, Jinyi; Chan, Paul Kay-Sheung; Yang, Xiao; Ma, Cong [Pharmaceuticals, 2021, vol. 14, # 4]
[15]Fan, Yan; Fang, Zhen; Guo, Nihong; Guo, Yinping; Li, Linli; Liu, Yang; Mu, Bo; Xia, Anjie; Xiang, Rong; Xiong, Liang; Yang, Shengyong; Yao, Rui; Zhang, Hailin; Zhang, Rong [European Journal of Medicinal Chemistry, 2022, vol. 238]
[16]Fan, Yan; Fang, Zhen; Guo, Nihong; Guo, Yinping; Li, Linli; Liu, Yang; Mu, Bo; Xia, Anjie; Xiang, Rong; Xiong, Liang; Yang, Shengyong; Yao, Rui; Zhang, Hailin; Zhang, Rong [European Journal of Medicinal Chemistry, 2022, vol. 238]

3
[ 20577-73-5 ]
[ 56426-35-8 ]

Yield	Reaction Conditions	Operation in experiment
69%	With hydrazine hydrate; acetic acid; at 118℃; for 2h;	Methyl 2,4-dioxo-4-phenylbutanoate (470mg, 2.28mmol) was dissolved in AcOH (5mL), hydrazine hydrate (122uL, 2.51mmol) was added and the reaction mixture was heated under reflux at 118C for 2h. The reaction mixture was concentrated in vacuo to give the title compound (320mg, 69%) as a yellow solid. LCMS: ES+ 203.0 [MH]+.
69%	With hydrazine hydrate; acetic acid; at 118℃; for 2h;	Methyl 2,4-dioxo-4-phenylbutanoate (470mg, 2.28mmol) was dissolved in AcOH (5mL), hydrazine hydrate (122uL, 2.Slmmol) was added and the reaction mixture was heated under reflux at 118C for 2h. The reaction mixture was concentrated in vacuo to0 . + +give the title compound (320mg, 69/o) as a yellow solid. LCMS: ES 203.0 [IVIH]
1.3 g	With hydrazinium monoacetate; acetic acid; at 20℃;	6.02.02.39 5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester 983 mg hydrazine acetate was added to 2 g 2,4-Dioxo-4-phenyl-butyric acid methyl ester in 10 mL concentrated acetic acid. The mixture was stirred over night at RT. Then water was added. The precipitate was filtered, stirred with diisopropylether and again filtered to give 1.3 g desired product. Rt: 1.39 min (method O), (M+H)+: 203

Reference： [1]Patent: WO2014/20350,2014,A1 .Location in patent: Page/Page column 51
[2]Patent: WO2014/20351,2014,A1 .Location in patent: Page/Page column 36
[3]Journal of Medicinal Chemistry,1998,vol. 41,p. 2390 - 2410
[4]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 273 - 280
[5]Patent: US2013/143870,2013,A1 .Location in patent: Paragraph 0547; 0548

4
[ 20577-73-5 ]
[ 51677-09-9 ]

Yield	Reaction Conditions	Operation in experiment
90.1%	With hydroxylamine hydrochloride; In methanol;Reflux;	Compound 2 (4.12 g, 0.02 mol) and hydroxylaminehydrochloride (1.67 g, 0.024 mol) were and refluxed for2-3 h in methanol (200 mL), while judging the completionof the reaction by TLC (hexane:ethyl acetate 3:1). Methanolwas removed under vacuum and the content was pouredover crushed ice. The solid separated out was filtered,washed with water and recrystallized from ethanol to obtaincompound 3 (3.66 g; 90.1%; m.p.: 86-87 C, lit. 86-88 C)(Veeraswamy et al. 2012).
	With hydroxylamine hydrochloride; In methanol; at 50℃; for 6h;	General procedure: To a stirred solution of dimethyl oxalate (1.1 eq.) and methyl ketone (1 eq.) in toluene was added a solution of potassium tertbutoxide(1.2 eq.) in THF. The resulting solution was stirred atroom temperature overnight. The reaction was quenched with 1 NHCl and extracted with ethyl acetate. The combined organic layerswere dried over Na2SO4, filtered and concentrated under reducedpressure. The crude product (12a - h) was dissolved in methanoland hydroxylamine hydrochloride was added. The solution washeated to 50 C for 6 h. The solvents were removed under reducedpressure and the resulting isoxazole ester was purified by flashcolumn chromatography to provide the target compounds.

Reference： [1]Medicinal Chemistry Research,2019,vol. 28,p. 1488 - 1501
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 2390 - 2410
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 8337 - 8352
[4]Journal of Molecular Structure,2009,vol. 919,p. 47 - 53
[5]Indian Journal of Heterocyclic Chemistry,2011,vol. 20,p. 279 - 280
[6]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 1097 - 1102
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2012,vol. 51,p. 1369 - 1375
[8]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 273 - 280
[9]Indian Journal of Heterocyclic Chemistry,2012,vol. 22,p. 27 - 30
[10]European Journal of Medicinal Chemistry,2019,vol. 182

5
[ 20577-73-5 ]
[ 179057-19-3 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2390 - 2410

6
[ 100-52-7 ]
[ 21190-16-9 ]
[ 20577-73-5 ]
[ 1104807-32-0 ]

Reference： [1]Russian Journal of Organic Chemistry,2008,vol. 44,p. 478 - 480

7
[ 67565-48-4 ]
[ 20577-73-5 ]
C₂₄H₁₈N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate In ethanol at 120℃; for 0.116667h; Microwave irradiation;	6.2 Step 2:(reference: Gein V.L., Kasimova N.N.; Russian Journal of General Chemistry, 2005, 75, 254-260)A solution of compound 6.1 (705 mg, 2.74 mmol), ammonium acetate (1.06 g, 13.7 mmol, Aldrich) and methyl 2,4-dioxo-4-phenylbutanoate (604 mg, 2.93 mmol, Bionet) in EtOH (9 mL) is heated for 7 min at 120°C in a microwave apparatus (Biotage Initiator). To the resulting solution is added AcOH (9 mL) and hydrazine monohydrate (686 μ, 13.7 mmol, Aldrich). The reaction mixture is then heated for 1 1 min at 140°C in the microwave. The reaction mixture is cooled to RT and the resulting solid is collected by filtration. The solid is washed with EtOH and dried under vacuum to afford compound 1033.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2011/143772, 2011, A1 Location in patent: Page/Page column 24

8
[ 1258624-04-2 ]
[ 20577-73-5 ]
C₂₄H₁₈N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate In ethanol at 120℃; for 0.116667h; Microwave irradiation;	13.2 Step 2:A solution of compound 13.1 (16 mg, 0.067 mmol), ammonium acetate (21 mg, 0.27 mmol, Aldrich) and methyl 2,4-dioxo-4-phenylbutanoate (1 1 mg, 0.053 mmol, Aldrich) in EtOH (1.5 mL) is heated for 7 min at 120°C in a microwave apparatus (Biotage Initiator). The resulting mixture is concentrated under vacuum to dryness. AcOH (1.5 mL) and hydrazine monohydrate (1 1 μ, 0.27 mmol, Aldrich) are added and the reaction mixture is heated for 1 1 min at 140°C in the microwave. The reaction mixture is filtered and directly injected onto a semi-preparative HPLC to isolate product 1047.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2011/143772, 2011, A1 Location in patent: Page/Page column 27-28

9
[ 1350614-59-3 ]
[ 20577-73-5 ]
C₃₀H₂₉N₃O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate In ethanol at 120℃; for 0.116667h; Microwave irradiation;	14.5 Step 5:(reference: Gein V.L., Kasimova N.N.; Russian Journal of General Chemistry, 2005, 75, 254-260)A solution of compound 14.4 (35 mg, 0.091 mmol), ammonium acetate (35 mg, 0.46 mmol, Aldrich) and methyl 2,4-dioxo-4-phenylbutanoate (20 mg, 0.091 mmol, Aldrich) in EtOH (1 mL) is heated for 7 min at 120°C in a microwave apparatus (Biotage Initiator). To the resulting solution is added AcOH (1 mL) and hydrazine monohydrate (22 μΙ_, 0.46 mmol, Aldrich). The reaction mixture is then heated for 1 1 min at 140°C in the microwave and concentrated under vacuum to dryness. To the residue in DCM (1 mL) is added TFA (140 μΙ_, 1.8 mmol) and the reaction mixture is stirred for 16 h at RT. The reaction mixture is concentrated under vacuum to dryness and the residue is dissolved in AcOH, filtered and directly injected onto a semi-preparative HPLC to isolate product 14.5.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2011/143772, 2011, A1 Location in patent: Page/Page column 29-30

10
[ 3829-80-9 ]
[ 100-52-7 ]
[ 20577-73-5 ]
[ 371225-96-6 ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

11
[ 28466-21-9 ]
[ 100-52-7 ]
[ 20577-73-5 ]
C₂₃H₂₁N₃O₃ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

12
[ 2289-75-0 ]
[ 100-52-7 ]
[ 20577-73-5 ]
[ 615278-87-0 ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

13
[ 17647-70-0 ]
[ 100-52-7 ]
[ 20577-73-5 ]
C₂₀H₁₅N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-amino-4-methylfurazan; benzaldehyde; methyl 4-phenyl-2,4-dioxobutanoate With chloro-trimethyl-silane In N,N-dimethyl-formamide Sealed tube; Heating; Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 2h; Sonication;

Reference： [1]Ryabukhin, Sergey V.; Panov, Dmitriy M.; Plaskon, Andrey S.; Grygorenko, Oleksandr O. [ACS Combinatorial Science, 2012, vol. 14, # 12, p. 631 - 635]

14
[ 93-85-6 ]
[ 100-52-7 ]
[ 20577-73-5 ]
C₂₅H₁₆N₂O₅S [ No CAS ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

15
[ 3829-80-9 ]
[ 104-88-1 ]
[ 20577-73-5 ]
[ 371922-20-2 ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

16
[ 28466-21-9 ]
[ 104-88-1 ]
[ 20577-73-5 ]
[ 1015516-97-8 ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

17
[ 2289-75-0 ]
[ 104-88-1 ]
[ 20577-73-5 ]
[ 615277-66-2 ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

18
[ 17647-70-0 ]
[ 104-88-1 ]
[ 20577-73-5 ]
C₂₀H₁₄ClN₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-amino-4-methylfurazan; 4-chlorobenzaldehyde; methyl 4-phenyl-2,4-dioxobutanoate With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;

Reference： [1]Ryabukhin, Sergey V.; Panov, Dmitriy M.; Plaskon, Andrey S.; Grygorenko, Oleksandr O. [ACS Combinatorial Science, 2012, vol. 14, # 12, p. 631 - 635]

19
[ 93-85-6 ]
[ 104-88-1 ]
[ 20577-73-5 ]
C₂₅H₁₅ClN₂O₅S [ No CAS ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

20
[ 3829-80-9 ]
[ 123-11-5 ]
[ 20577-73-5 ]
[ 433253-78-2 ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

21
[ 28466-21-9 ]
[ 123-11-5 ]
[ 20577-73-5 ]
C₂₄H₂₃N₃O₄ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

22
[ 2289-75-0 ]
[ 123-11-5 ]
[ 20577-73-5 ]
[ 636988-38-0 ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

23
[ 17647-70-0 ]
[ 123-11-5 ]
[ 20577-73-5 ]
C₂₁H₁₇N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-amino-4-methylfurazan; 4-methoxy-benzaldehyde; methyl 4-phenyl-2,4-dioxobutanoate With acetic acid Reflux; Stage #2: With water at 20℃; for 2h; Sonication;

Reference： [1]Ryabukhin, Sergey V.; Panov, Dmitriy M.; Plaskon, Andrey S.; Grygorenko, Oleksandr O. [ACS Combinatorial Science, 2012, vol. 14, # 12, p. 631 - 635]

24
[ 93-85-6 ]
[ 123-11-5 ]
[ 20577-73-5 ]
C₂₆H₁₈N₂O₆S [ No CAS ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

25
[ 106-49-0 ]
[ 27258-33-9 ]
[ 20577-73-5 ]
C₂₂H₁₉N₃O₃ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 631 - 635

26
[ 20577-73-5 ]
[ 5071-61-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 273 - 280

27
[ 20577-73-5 ]
[ 144537-05-3 ]

Reference： [1]Indian Journal of Heterocyclic Chemistry,2011,vol. 20,p. 279 - 280

28
[ 100-83-4 ]
[ 20577-73-5 ]
[ 929-06-6 ]
C₂₁H₂₁NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.2%	In 1,4-dioxane at 20℃; for 24h;	5-Aryl-4-aroyl-3-hydroxy-1-[2-(2-hydroxyethoxy)-ethyl]-3-pyrrolin-2-ones (1-6) General procedure: A solution of 0.05 mol of methyl aroylpyruvate in 10 mL of dioxane was mixed with equimolar amounts of an aromatic aldehyde and 2-(2-aminoethoxy)ethanol and incubated at room temperature during 1 day. The precipitate formed was filtered off, recrystallized from ethanol, and dried.

Reference： [1]Gein; Rogachev; Bobyleva; Apushkin, D. Yu.; Veikhman; Nasakin [Russian Journal of General Chemistry, 2015, vol. 85, # 11, p. 2568 - 2570][Zh. Obshch. Khim., 2015, vol. 85, # 11, p. 1826 - 1829,3]

29
[ 67-56-1 ]
[ 104-88-1 ]
[ 57-13-6 ]
[ 20577-73-5 ]
methyl 5-benzoyl-4-methoxy-6-(4-chlorophenyl)-2-oxohexahydropyrimidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium hydrogen sulfate for 1h; Reflux;	Compounds 1a-1c. General procedure. General procedure: A mixture of 0.01 mol of methyl benzoylpyruvate, 0.01 molor aromatic aldehyde, and 0.015 mol of urea in 15 mL of methanol in the presence of 0.008 mol of sodium bisulfate was boiled for 1 h. The precipitate was washed with water and recrystallized from methanol. Methyl 5-benzoyl-4-methoxy-6-(4-chlorophenyl)-2-oxohexahydropyrimidine-4-carboxylate (1a).Yield 2.78 g (69%), mp 214-216°. IR spectrum, ν,cm-1: 3430, 3200 (NH), 1733 (COOCH3), 1687 (CO).1 NMR spectrum, δ, ppm: 3.10 s (3, COOCH3),3.19 s (3H, CH3O), 4.33 d (1H, H5, J 11 Hz), 5.01 d(1H, H6, J 11 Hz), 7.10-7.61 m (9, Ar), 6.88 br.s(1H, H1), 7.79 br.s (1H, H3). Found, %: 59.52,59.75; 4.67, 4.84; N 6.84, 7.08. 20H19ClN2O5.Calculated, %: 59.63; 4.75; N 6.95.

Reference： [1]Gein; Gorgopina; Zamaraeva; Dmitriev [Russian Journal of Organic Chemistry, 2017, vol. 53, # 11, p. 1675 - 1677][Zh. Org. Khim., 2017, vol. 53, # 11, p. 1639 - 1641,3]

30
[ 67-56-1 ]
[ 3132-99-8 ]
[ 57-13-6 ]
[ 20577-73-5 ]
methyl 5-benzoyl-6-(3-bromophenyl)-4-methoxy-2-oxohexahydropyrimidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium hydrogen sulfate for 1h; Reflux;	Compounds 1a-1c. General procedure. General procedure: A mixture of 0.01 mol of methyl benzoylpyruvate, 0.01 molor aromatic aldehyde, and 0.015 mol of urea in 15 mL of methanol in the presence of 0.008 mol of sodium bisulfate was boiled for 1 h. The precipitate was washed with water and recrystallized from methanol.

Reference： [1]Gein; Gorgopina; Zamaraeva; Dmitriev [Russian Journal of Organic Chemistry, 2017, vol. 53, # 11, p. 1675 - 1677][Zh. Org. Khim., 2017, vol. 53, # 11, p. 1639 - 1641,3]

31
[ 67-56-1 ]
[ 459-57-4 ]
[ 57-13-6 ]
[ 20577-73-5 ]
methyl 5-benzoyl-4-methoxy-6-(4-fluorophenyl)-2-oxohexahydropyrimidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium hydrogen sulfate for 1h; Reflux;	Compounds 1a-1c. General procedure. General procedure: A mixture of 0.01 mol of methyl benzoylpyruvate, 0.01 molor aromatic aldehyde, and 0.015 mol of urea in 15 mL of methanol in the presence of 0.008 mol of sodium bisulfate was boiled for 1 h. The precipitate was washed with water and recrystallized from methanol.

Reference： [1]Gein; Gorgopina; Zamaraeva; Dmitriev [Russian Journal of Organic Chemistry, 2017, vol. 53, # 11, p. 1675 - 1677][Zh. Org. Khim., 2017, vol. 53, # 11, p. 1639 - 1641,3]

32
[ 72-14-0 ]
[ 20577-73-5 ]
(2Z)-2-hydroxy-4-oxo-N-{4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}-4-phenylbut-2-eneamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium acetate In acetic acid for 0.333333h; Reflux;	General procedure: a. A solution of 2.40 g (0.01 mol) of methyl 4-chlorobenzoylpyruvateand 0.82 g (0.01 mol) of anhydroussodium acetate in 10 mL of glacial acetic acid wasadded to a solution of 2.55 g (0.01 mol) of 2-(4-aminobenzenesulfamido)thiazole in 15 mL of glacialacetic acid. The reaction mixture was refluxed for 20 min.

Reference： [1]Gein; Bobrovskaya; Russkikh; Petukhova [Russian Journal of General Chemistry, 2018, vol. 88, # 2, p. 334 - 337][Zh. Obshch. Khim., 2018, vol. 88, # 2, p. 338 - 341,4]

33
[ 617-89-0 ]
[ 100-52-7 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-phenyl-1-(2-furylmethyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With acetic acid In ethanol at 20℃; for 24h; Heating;	4-Acetyl-3-hydroxy-5-phenyl-1-(2-furylmethyl)-3-pyrrolin-2-one (1a). General procedure: Acetic acid (1.04 mL) was added to a mixture of acetylpyruvic acid methyl ester (1.44 g, 0.01 mol), bezaldehyde (1.06 g, 0.01 mol), and furfurylamine (0.97 g, 0.01 mol) in 10 mL of ethanol. The reaction mixture was heated for 15 min and kept at room temperature for 1 day. The precipitate was filtered off and recrystallized from acetonitrile.

Reference： [1]Gein; Nosova; Shishkin; Gein [Russian Journal of General Chemistry, 2018, vol. 88, # 3, p. 598 - 601][Zh. Obshch. Khim., 2018, vol. 88, # 3, p. 508 - 511,4]

34
[ 617-89-0 ]
[ 123-11-5 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(4-methoxyphenyl)-1-(2-furylmethyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With acetic acid In ethanol at 20℃; for 24h; Heating;	4-Acetyl-3-hydroxy-5-phenyl-1-(2-furylmethyl)-3-pyrrolin-2-one (1a). General procedure: Acetic acid (1.04 mL) was added to a mixture of acetylpyruvic acid methyl ester (1.44 g, 0.01 mol), bezaldehyde (1.06 g, 0.01 mol), and furfurylamine (0.97 g, 0.01 mol) in 10 mL of ethanol. The reaction mixture was heated for 15 min and kept at room temperature for 1 day. The precipitate was filtered off and recrystallized from acetonitrile.

Reference： [1]Gein; Nosova; Shishkin; Gein [Russian Journal of General Chemistry, 2018, vol. 88, # 3, p. 598 - 601][Zh. Obshch. Khim., 2018, vol. 88, # 3, p. 508 - 511,4]

35
[ 617-89-0 ]
[ 99-61-6 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(3-nitrophenyl)-1-(2-furylmethyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With acetic acid In ethanol at 20℃; for 24h; Heating;	4-Acetyl-3-hydroxy-5-phenyl-1-(2-furylmethyl)-3-pyrrolin-2-one (1a). General procedure: Acetic acid (1.04 mL) was added to a mixture of acetylpyruvic acid methyl ester (1.44 g, 0.01 mol), bezaldehyde (1.06 g, 0.01 mol), and furfurylamine (0.97 g, 0.01 mol) in 10 mL of ethanol. The reaction mixture was heated for 15 min and kept at room temperature for 1 day. The precipitate was filtered off and recrystallized from acetonitrile.

Reference： [1]Gein; Nosova; Shishkin; Gein [Russian Journal of General Chemistry, 2018, vol. 88, # 3, p. 598 - 601][Zh. Obshch. Khim., 2018, vol. 88, # 3, p. 508 - 511,4]

36
[ 617-89-0 ]
[ 104-88-1 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(4-chlorophenyl)-1-(2-furylmethyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With acetic acid In ethanol at 20℃; for 24h; Heating;	4-Acetyl-3-hydroxy-5-phenyl-1-(2-furylmethyl)-3-pyrrolin-2-one (1a). General procedure: Acetic acid (1.04 mL) was added to a mixture of acetylpyruvic acid methyl ester (1.44 g, 0.01 mol), bezaldehyde (1.06 g, 0.01 mol), and furfurylamine (0.97 g, 0.01 mol) in 10 mL of ethanol. The reaction mixture was heated for 15 min and kept at room temperature for 1 day. The precipitate was filtered off and recrystallized from acetonitrile.

Reference： [1]Gein; Nosova; Shishkin; Gein [Russian Journal of General Chemistry, 2018, vol. 88, # 3, p. 598 - 601][Zh. Obshch. Khim., 2018, vol. 88, # 3, p. 508 - 511,4]

37
[ 617-89-0 ]
[ 20577-73-5 ]
[ 552-89-6 ]
4-benzoyl-3-hydroxy-5-(2-nitrophenyl)-1-(2-furylmethyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With acetic acid In ethanol at 20℃; for 24h; Heating;	4-Acetyl-3-hydroxy-5-phenyl-1-(2-furylmethyl)-3-pyrrolin-2-one (1a). General procedure: Acetic acid (1.04 mL) was added to a mixture of acetylpyruvic acid methyl ester (1.44 g, 0.01 mol), bezaldehyde (1.06 g, 0.01 mol), and furfurylamine (0.97 g, 0.01 mol) in 10 mL of ethanol. The reaction mixture was heated for 15 min and kept at room temperature for 1 day. The precipitate was filtered off and recrystallized from acetonitrile.

Reference： [1]Gein; Nosova; Shishkin; Gein [Russian Journal of General Chemistry, 2018, vol. 88, # 3, p. 598 - 601][Zh. Obshch. Khim., 2018, vol. 88, # 3, p. 508 - 511,4]

38
[ 617-89-0 ]
[ 123-08-0 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(4-hydroxyphenyl)-1-(2-furylmethyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With acetic acid In ethanol at 20℃; for 24h; Heating;	4-Acetyl-3-hydroxy-5-phenyl-1-(2-furylmethyl)-3-pyrrolin-2-one (1a). General procedure: Acetic acid (1.04 mL) was added to a mixture of acetylpyruvic acid methyl ester (1.44 g, 0.01 mol), bezaldehyde (1.06 g, 0.01 mol), and furfurylamine (0.97 g, 0.01 mol) in 10 mL of ethanol. The reaction mixture was heated for 15 min and kept at room temperature for 1 day. The precipitate was filtered off and recrystallized from acetonitrile.

Reference： [1]Gein; Nosova; Shishkin; Gein [Russian Journal of General Chemistry, 2018, vol. 88, # 3, p. 598 - 601][Zh. Obshch. Khim., 2018, vol. 88, # 3, p. 508 - 511,4]

39
[ 617-89-0 ]
[ 122-03-2 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(4-isopropylphenyl)-1-(2-furylmethyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With acetic acid In ethanol at 20℃; for 24h; Heating;	4-Acetyl-3-hydroxy-5-phenyl-1-(2-furylmethyl)-3-pyrrolin-2-one (1a). General procedure: Acetic acid (1.04 mL) was added to a mixture of acetylpyruvic acid methyl ester (1.44 g, 0.01 mol), bezaldehyde (1.06 g, 0.01 mol), and furfurylamine (0.97 g, 0.01 mol) in 10 mL of ethanol. The reaction mixture was heated for 15 min and kept at room temperature for 1 day. The precipitate was filtered off and recrystallized from acetonitrile.

Reference： [1]Gein; Nosova; Shishkin; Gein [Russian Journal of General Chemistry, 2018, vol. 88, # 3, p. 598 - 601][Zh. Obshch. Khim., 2018, vol. 88, # 3, p. 508 - 511,4]

40
[ 617-89-0 ]
[ 100-83-4 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(3-hydroxyphenyl)-1-(2-furylmethyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With acetic acid In ethanol at 20℃; for 24h; Heating;	4-Acetyl-3-hydroxy-5-phenyl-1-(2-furylmethyl)-3-pyrrolin-2-one (1a). General procedure: Acetic acid (1.04 mL) was added to a mixture of acetylpyruvic acid methyl ester (1.44 g, 0.01 mol), bezaldehyde (1.06 g, 0.01 mol), and furfurylamine (0.97 g, 0.01 mol) in 10 mL of ethanol. The reaction mixture was heated for 15 min and kept at room temperature for 1 day. The precipitate was filtered off and recrystallized from acetonitrile.

Reference： [1]Gein; Nosova; Shishkin; Gein [Russian Journal of General Chemistry, 2018, vol. 88, # 3, p. 598 - 601][Zh. Obshch. Khim., 2018, vol. 88, # 3, p. 508 - 511,4]

41
[ 62-53-3 ]
[ 20577-73-5 ]
[ 85635-61-6 ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium acetate In acetic acid Reflux;	(Z)-2-Hydroxy-4-oxo-N,4-diphenylbut-2-enamide (1). a. To 1.0 g (0.0057 mol) of 5-phenyl-2,3-dihydrofuran-2,3-dione in 20 mL of anhydrous dioxane was added 0.52 mL (0.0057 mol) of aniline in 2 mL of anhydrous dioxane. Then the solvent was distilled off, the precipitate was washed with ethyl alcohol. b. A mixture of 8.24 g (0.04 mol) of methyl benzoylpyruvate and 3.28 g (0.04 mol) of anhydrous sodium acetate in 10 mL of glacial acetic acid was added to 3.65 mL (0.04 mol) of aniline dissolved in glacial acetic acid. The reaction mixture was refluxed for 20-30 min. The residue was filtered off and recrystallized from acetic acid. Yield 1.09 g (72%, method a), 6.74 g (63%, method b), mp 90-92 °C. 1H NMR spectrum (DMSO-d6), δ, ppm: 4.63 s (2H, COCH2CO), 7.02 s (1H, CH=), 7.12 t (1H, ArH, J =7.5 Hz), 7.35 t (2H, ArH, J = 7.5 Hz), 7.52 t (1H, ArH, J = 6.9 Hz), 7.59 t (2H, ArH, J = 6.9 Hz), 7.79 d (2H, ArH, J = 7.5 Hz), 7.98 d (2H, ArH, J = 6.9 Hz), 10.37 s (1H, CONH). Found, %: C 70.98, 72.02; H 4.82, 4.99; N 5.12, 5.37. C16H13NO3. Calculated, %: C 71.90; H 4.90; N 5.24.

Reference： [1]Gein; Zamaraeva; Gorgopina; Igidov; Bobrovskaya; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 4, p. 832 - 835][Zh. Obshch. Khim., 2018, vol. 88, # 4, p. -686 - -689,4]

42
[ 20577-73-5 ]
[ 106-40-1 ]
[ 85635-65-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium acetate In acetic acid Reflux;	(Z)-2-Hydroxy-4-oxo-N,4-diphenylbut-2-enamide (1). General procedure: a. To 1.0 g (0.0057 mol) of 5-phenyl-2,3-dihydrofuran-2,3-dione in 20 mL of anhydrous dioxane was added 0.52 mL (0.0057 mol) of aniline in 2 mL of anhydrous dioxane. Then the solvent was distilled off, the precipitate was washed with ethyl alcohol. b. A mixture of 8.24 g (0.04 mol) of methyl benzoylpyruvate and 3.28 g (0.04 mol) of anhydrous sodium acetate in 10 mL of glacial acetic acid was added to 3.65 mL (0.04 mol) of aniline dissolved in glacial acetic acid. The reaction mixture was refluxed for 20-30 min. The residue was filtered off and recrystallized from acetic acid. Yield 1.09 g (72%, method a), 6.74 g (63%, method b), mp 90-92 °C.

Reference： [1]Gein; Zamaraeva; Gorgopina; Igidov; Bobrovskaya; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 4, p. 832 - 835][Zh. Obshch. Khim., 2018, vol. 88, # 4, p. -686 - -689,4]

43
[ 20577-73-5 ]
[ 540-37-4 ]
(Z)-N-(4-iodophenyl)-2-hydroxy-4-oxo-4-phenylbut-2-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium acetate In acetic acid Reflux;	(Z)-2-Hydroxy-4-oxo-N,4-diphenylbut-2-enamide (1). General procedure: a. To 1.0 g (0.0057 mol) of 5-phenyl-2,3-dihydrofuran-2,3-dione in 20 mL of anhydrous dioxane was added 0.52 mL (0.0057 mol) of aniline in 2 mL of anhydrous dioxane. Then the solvent was distilled off, the precipitate was washed with ethyl alcohol. b. A mixture of 8.24 g (0.04 mol) of methyl benzoylpyruvate and 3.28 g (0.04 mol) of anhydrous sodium acetate in 10 mL of glacial acetic acid was added to 3.65 mL (0.04 mol) of aniline dissolved in glacial acetic acid. The reaction mixture was refluxed for 20-30 min. The residue was filtered off and recrystallized from acetic acid. Yield 1.09 g (72%, method a), 6.74 g (63%, method b), mp 90-92 °C.

Reference： [1]Gein; Zamaraeva; Gorgopina; Igidov; Bobrovskaya; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 4, p. 832 - 835][Zh. Obshch. Khim., 2018, vol. 88, # 4, p. -686 - -689,4]

44
[ 108-42-9 ]
[ 20577-73-5 ]
(Z)-N-(3-chlorophenyl)-2-hydroxy-4-oxo-4-phenylbut-2-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium acetate In acetic acid Reflux;	(Z)-2-Hydroxy-4-oxo-N,4-diphenylbut-2-enamide (1). General procedure: a. To 1.0 g (0.0057 mol) of 5-phenyl-2,3-dihydrofuran-2,3-dione in 20 mL of anhydrous dioxane was added 0.52 mL (0.0057 mol) of aniline in 2 mL of anhydrous dioxane. Then the solvent was distilled off, the precipitate was washed with ethyl alcohol. b. A mixture of 8.24 g (0.04 mol) of methyl benzoylpyruvate and 3.28 g (0.04 mol) of anhydrous sodium acetate in 10 mL of glacial acetic acid was added to 3.65 mL (0.04 mol) of aniline dissolved in glacial acetic acid. The reaction mixture was refluxed for 20-30 min. The residue was filtered off and recrystallized from acetic acid. Yield 1.09 g (72%, method a), 6.74 g (63%, method b), mp 90-92 °C.

Reference： [1]Gein; Zamaraeva; Gorgopina; Igidov; Bobrovskaya; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 4, p. 832 - 835][Zh. Obshch. Khim., 2018, vol. 88, # 4, p. -686 - -689,4]

45
[ 94-09-7 ]
[ 20577-73-5 ]
(Z)-ethyl 4-[2-hydroxy-4-oxo-4-phenylbut-2-enoyl]amino}benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium acetate In acetic acid Reflux;	(Z)-2-Hydroxy-4-oxo-N,4-diphenylbut-2-enamide (1). General procedure: a. To 1.0 g (0.0057 mol) of 5-phenyl-2,3-dihydrofuran-2,3-dione in 20 mL of anhydrous dioxane was added 0.52 mL (0.0057 mol) of aniline in 2 mL of anhydrous dioxane. Then the solvent was distilled off, the precipitate was washed with ethyl alcohol. b. A mixture of 8.24 g (0.04 mol) of methyl benzoylpyruvate and 3.28 g (0.04 mol) of anhydrous sodium acetate in 10 mL of glacial acetic acid was added to 3.65 mL (0.04 mol) of aniline dissolved in glacial acetic acid. The reaction mixture was refluxed for 20-30 min. The residue was filtered off and recrystallized from acetic acid. Yield 1.09 g (72%, method a), 6.74 g (63%, method b), mp 90-92 °C.

Reference： [1]Gein; Zamaraeva; Gorgopina; Igidov; Bobrovskaya; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 4, p. 832 - 835][Zh. Obshch. Khim., 2018, vol. 88, # 4, p. -686 - -689,4]

46
aminoacetonitrile neutral sulfate [ No CAS ]
[ 100-52-7 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium acetate In acetic acid at 20℃; for 24h; Heating;	4-Benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one (1). To a solution of 0.005 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added 0.005 mol of benzoylpyruvic acid methyl ester, 0.005 mol of benzaldehyde, and 0.0025 mol of aminoacetonitrile sulfate. The reaction mixture was heated until all the reagents were completely dissolved and stirred at room temperature for 1 day. The precipitate was filtered off and recrystallized from ethyl alcohol. Yield 1.35 g (85%), mp 235-240°C. IR spectrum, ν, cm-1: 3160 (OH), 1700 (CON), 1624(CO). 1 NMR spectrum, δ, ppm: 4.26 d (1, HAHB,2N, J = 18.0 Hz), 4.45 d (1, HAHB, 2N, J =18.0 Hz), 5.52 s (1, 5), 7.30-7.75 m (10H, CHAr),12.0 s (1, ). 13 NMR spectrum, δ, ppm: 192.08,188.74, 178.60, 176.41, 165.45, 150.52, 145.35, 144.23,142.84, 137.78, 134.81, 132.39, 128.57, 120.37, 128.54,114.99, 61.74, 61.72, 29.26. Mass spectrum, m/z: 318[]+. Found, %: 71.51, 71.85; H 4.23, 4.61; N 8.63,8.90. C19H14N2O3. Calculated, %: 71.69; H 4.43; N 8.80

Reference： [1]Gein; Buldakova; Korol; Veikhman; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 908 - 911][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 764 - 768,5]

47
aminoacetonitrile neutral sulfate [ No CAS ]
[ 123-11-5 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(4-methoxyphenyl)-1-cyanomethyl-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium acetate In acetic acid at 20℃; for 24h; Heating;	4-Benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one (1). General procedure: To a solution of 0.005 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added 0.005 mol of benzoylpyruvic acid methyl ester, 0.005 mol of benzaldehyde, and 0.0025 mol of aminoacetonitrile sulfate. The reaction mixture was heated until all the reagents were completely dissolved and stirred at room temperature for 1 day. The precipitate was filtered off and recrystallized from ethyl alcohol.

Reference： [1]Gein; Buldakova; Korol; Veikhman; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 908 - 911][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 764 - 768,5]

48
[ 10031-82-0 ]
aminoacetonitrile neutral sulfate [ No CAS ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-1-cyanomethyl-5-(4-ethoxyphenyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium acetate In acetic acid at 20℃; for 24h; Heating;	4-Benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one (1). General procedure: To a solution of 0.005 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added 0.005 mol of benzoylpyruvic acid methyl ester, 0.005 mol of benzaldehyde, and 0.0025 mol of aminoacetonitrile sulfate. The reaction mixture was heated until all the reagents were completely dissolved and stirred at room temperature for 1 day. The precipitate was filtered off and recrystallized from ethyl alcohol.

Reference： [1]Gein; Buldakova; Korol; Veikhman; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 908 - 911][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 764 - 768,5]

49
aminoacetonitrile neutral sulfate [ No CAS ]
[ 613-45-6 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(2,4-dimethoxyphenyl)-1-cyanomethyl-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With sodium acetate In acetic acid at 20℃; for 24h; Heating;	4-Benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one (1). General procedure: To a solution of 0.005 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added 0.005 mol of benzoylpyruvic acid methyl ester, 0.005 mol of benzaldehyde, and 0.0025 mol of aminoacetonitrile sulfate. The reaction mixture was heated until all the reagents were completely dissolved and stirred at room temperature for 1 day. The precipitate was filtered off and recrystallized from ethyl alcohol.

Reference： [1]Gein; Buldakova; Korol; Veikhman; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 908 - 911][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 764 - 768,5]

50
aminoacetonitrile neutral sulfate [ No CAS ]
[ 120-14-9 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(3,4-dimethoxyphenyl)-1-cyanomethyl-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium acetate In acetic acid at 20℃; for 24h; Heating;	4-Benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one (1). General procedure: To a solution of 0.005 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added 0.005 mol of benzoylpyruvic acid methyl ester, 0.005 mol of benzaldehyde, and 0.0025 mol of aminoacetonitrile sulfate. The reaction mixture was heated until all the reagents were completely dissolved and stirred at room temperature for 1 day. The precipitate was filtered off and recrystallized from ethyl alcohol.

Reference： [1]Gein; Buldakova; Korol; Veikhman; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 908 - 911][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 764 - 768,5]

51
[ 459-57-4 ]
aminoacetonitrile neutral sulfate [ No CAS ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(4-fluorophenyl)-1-cyanomethyl-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium acetate In acetic acid at 20℃; for 24h; Heating;	4-Benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one (1). General procedure: To a solution of 0.005 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added 0.005 mol of benzoylpyruvic acid methyl ester, 0.005 mol of benzaldehyde, and 0.0025 mol of aminoacetonitrile sulfate. The reaction mixture was heated until all the reagents were completely dissolved and stirred at room temperature for 1 day. The precipitate was filtered off and recrystallized from ethyl alcohol.

Reference： [1]Gein; Buldakova; Korol; Veikhman; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 908 - 911][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 764 - 768,5]

52
[ 104-88-1 ]
aminoacetonitrile neutral sulfate [ No CAS ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(4-chlorophenyl)-1-cyanomethyl-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium acetate In acetic acid at 20℃; for 24h; Heating;	4-Benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one (1). General procedure: To a solution of 0.005 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added 0.005 mol of benzoylpyruvic acid methyl ester, 0.005 mol of benzaldehyde, and 0.0025 mol of aminoacetonitrile sulfate. The reaction mixture was heated until all the reagents were completely dissolved and stirred at room temperature for 1 day. The precipitate was filtered off and recrystallized from ethyl alcohol.

Reference： [1]Gein; Buldakova; Korol; Veikhman; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 908 - 911][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 764 - 768,5]

53
aminoacetonitrile neutral sulfate [ No CAS ]
[ 93-02-7 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(2,5-dimethoxyphenyl)-1-cyanomethyl-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium acetate In acetic acid at 20℃; for 24h; Heating;	4-Benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one (1). General procedure: To a solution of 0.005 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added 0.005 mol of benzoylpyruvic acid methyl ester, 0.005 mol of benzaldehyde, and 0.0025 mol of aminoacetonitrile sulfate. The reaction mixture was heated until all the reagents were completely dissolved and stirred at room temperature for 1 day. The precipitate was filtered off and recrystallized from ethyl alcohol.

Reference： [1]Gein; Buldakova; Korol; Veikhman; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 908 - 911][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 764 - 768,5]

54
[ 22924-15-8 ]
aminoacetonitrile neutral sulfate [ No CAS ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-1-cyanomethyl-5-(3-ethoxyphenyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium acetate In acetic acid at 20℃; for 24h; Heating;	4-Benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one (1). General procedure: To a solution of 0.005 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added 0.005 mol of benzoylpyruvic acid methyl ester, 0.005 mol of benzaldehyde, and 0.0025 mol of aminoacetonitrile sulfate. The reaction mixture was heated until all the reagents were completely dissolved and stirred at room temperature for 1 day. The precipitate was filtered off and recrystallized from ethyl alcohol.

Reference： [1]Gein; Buldakova; Korol; Veikhman; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 908 - 911][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 764 - 768,5]

55
aminoacetonitrile neutral sulfate [ No CAS ]
[ 100-10-7 ]
[ 20577-73-5 ]
4-benzoyl-3-hydroxy-5-(4-dimethylaminophenyl)-1-cyanomethyl-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium acetate In acetic acid at 20℃; for 24h; Heating;	4-Benzoyl-3-hydroxy-5-phenyl-1-cyanomethyl-3-pyrrolin-2-one (1). General procedure: To a solution of 0.005 mol of anhydrous sodium acetate in 10 mL of glacial acetic acid were added 0.005 mol of benzoylpyruvic acid methyl ester, 0.005 mol of benzaldehyde, and 0.0025 mol of aminoacetonitrile sulfate. The reaction mixture was heated until all the reagents were completely dissolved and stirred at room temperature for 1 day. The precipitate was filtered off and recrystallized from ethyl alcohol.

Reference： [1]Gein; Buldakova; Korol; Veikhman; Dmitriev [Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 908 - 911][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 764 - 768,5]

56
[ 122-51-0 ]
[ 57-13-6 ]
[ 20577-73-5 ]
C₁₃H₁₂N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In methanol at 50℃; for 4h;	2.2 (2) In a 50 ml single-necked flask, 5.16 g (0.025 mol) of methyl ester intermediate I and trimethyl orthoformate 6 mL were added.(0.05 mol), 1.44 g (0.024 mol) of urea and 20 mL of anhydrous methanol, stirred, heated to 50 ° C, and kept at 4 h. Cool down toThe mixture was filtered at room temperature, and the cake was recrystallized from 95% ethanol to obtain 6.2 g of pure Intermediate II (purity: 99.5%), yield 93%.

Reference： [1]Current Patent Assignee: BAYNOE CHEM (SUZHOU) CO LTD - CN108148003, 2018, A Location in patent: Paragraph 0090; 0092

57
[ 120-92-3 ]
[ 20577-73-5 ]
methyl 2-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: cyclopentanone With ammonium acetate In 1,4-dioxane at 20℃; for 0.75h; Inert atmosphere; Green chemistry; Stage #2: methyl 4-phenyl-2,4-dioxobutanoate With chitosan In 1,4-dioxane at 80℃; for 10h; Inert atmosphere; Green chemistry; regioselective reaction;

Reference： [1]Jaiswal, Pradeep K.; Sharma, Vashundhra; Mathur, Manas; Chaudhary, Sandeep [Organic Letters, 2018, vol. 20, # 19, p. 6059 - 6063]

58
[ 20577-73-5 ]
[ 502-42-1 ]
methyl 2-phenyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: cycloheptanone With ammonium acetate In 1,4-dioxane at 20℃; for 0.75h; Inert atmosphere; Green chemistry; Stage #2: methyl 4-phenyl-2,4-dioxobutanoate With chitosan In 1,4-dioxane at 80℃; for 10h; Inert atmosphere; Green chemistry; regioselective reaction;

Reference： [1]Jaiswal, Pradeep K.; Sharma, Vashundhra; Mathur, Manas; Chaudhary, Sandeep [Organic Letters, 2018, vol. 20, # 19, p. 6059 - 6063]

59
[ 502-49-8 ]
[ 20577-73-5 ]
methyl 2-phenyl-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: cycloactanone With ammonium acetate In 1,4-dioxane at 20℃; for 0.75h; Inert atmosphere; Green chemistry; Stage #2: methyl 4-phenyl-2,4-dioxobutanoate With chitosan In 1,4-dioxane at 80℃; for 10h; Inert atmosphere; Green chemistry; regioselective reaction;

Reference： [1]Jaiswal, Pradeep K.; Sharma, Vashundhra; Mathur, Manas; Chaudhary, Sandeep [Organic Letters, 2018, vol. 20, # 19, p. 6059 - 6063]

60
[ 20577-73-5 ]
[ 10199-53-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ethanol / 3 h / Heating / reflux 2: sodium hydroxide / ethanol; water / 0.5 h / Heating / reflux

Reference： [1]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - EP1176140, 2002, A1

61
[ 20577-73-5 ]
[ 10250-64-3 ]

Reference： [1]Patent: EP1176140,2002,A1

62
3-benzyl-2-(2-hydrazinyl-2-oxoethylthio)-5-methyl-4-oxo-3,4-dihydrothieno [2,3-d]pyrimidine-6-carboxamide [ No CAS ]
[ 20577-73-5 ]
methyl 1-[2-(3-benzyl-6-carbamoyl-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-ylthio)acetyl]-5-phenyl-1H-pyrazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With acetic acid In ethanol Reflux;	4.1.3. Methyl 1-[2-(3-benzyl-6-carbamoyl-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-ylthio)acetyl]-5-(4-substituted phenyl)-1H-pyrazole-3-carboxylates (5a,b) General procedure: A mixture of acid hydrazide 4 (1 mmol, 0.4 g) and methyl 2,4-dioxo-4-(4-substituted phenyl) butyrate (1 mmol) in absolute ethanol (10 ml)and 0.5 ml glacial acetic was heated under reflux for 5-7 h. The reactionmixture was evaporated to dryness under vacuum; the residue wastriturated with cold ethanol and the precipitate obtained was filtered,washed with cold ethanol, dried and crystallized from ethanol/water 4.1.3.1. Methyl 1-[2-(3-benzyl-6-carbamoyl-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-ylthio)acetyl]-5-phenyl-1H-pyrazole-3-carboxylates(5a). Yield: 55%, m.p. 152-154 °C. IR (cm-1): 3345, 3216 (NH2); 1720(C]O ester); 1665 (C]O amide); 1590 (C]N); 1513 (C]C); 1215(CeSeC); 1168 (CeOeC). 1H NMR (300 MHz, DMSO-d6) (δ ppm): 2.71(s, 3H, CH3); 3.83 (s, 3H, COOCH3); 4.21 (s, 2H, SeCH2); 5.33 (s, 2H,NeCH2); 7.12 (s, 1H, pyrazolyl-C4-H); 7.25-7.29 (m, 5H, phenyl-H);7.31-7.38 (m, 5H, phenyl-H); 7.61 (s, 2H, CONH2, D2O exchangeable).MS(EI) m/z (%): 574 [M+%+1] (14.84); 573 [M+%] (28.02). Anal. Calcd. for(C28H23N5O5S2) (573.64): C, 58.63; H, 4.04; N, 12.21. Found: C, 58.75; H,3.98; N, 12.40.

Reference： [1]Shaaban, Omaima G.; Issa, Doaa A.E.; El-Tombary, Alaa A.; Abd El Wahab, Shrouk M.; Abdel Wahab, Abeer E.; Abdelwahab, Ibrahim A. [Bioorganic Chemistry, 2019, vol. 88]

63
[ 72-14-0 ]
[ 20577-73-5 ]
methyl (2E)-4-oxo-4-phenyl-2-{4-[(1,3-thiazol-2-yl)sulfamoyl]phenylamino}but-2-enoate [ No CAS ]
methyl (2Z)-4-oxo-4-phenyl-2-{4-[(1,3-thiazol-2-yl)sulfamoyl]phenylamino}but-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In ethanol; acetic acid for 0.166667h; Reflux;	Methyl (2Z)-4-(4-chlorophenyl)-4-oxo-2-{4-[(1,3-thiazol-2-yl)sulfamoyl]phenylamino}but-2-enoate(1a) General procedure: A solution of 2.40 g (0.01 mol) of methyl (4-chlorobenzoyl)pyruvate in 15 mL of ethanol was added to a 2.55 g (0.01 mol) of 2-(4-aminobenzenesulfonamido)thiazole dissolved under heating in 15 mLof glacial acetic acid. The reaction mixture was refluxed for 10 min. After cooling, a precipiate formed and was filtered off and recrystallized from ethanol. Yield 3.97 g (83%)

Reference： [1]Gein; Bobrovskaya; Russkikh; Dmitriev; Yankin [Russian Journal of Organic Chemistry, 2019, vol. 55, # 5, p. 602 - 607][Zh. Org. Khim., 2019, vol. 55, # 5, p. 694 - 700,7]

64
[ 67-56-1 ]
[ 98-86-2 ]
[ 95-92-1 ]
[ 20577-73-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium In methanol at 0 - 10℃; for 1h;	Synthesis of methyl 2,4-dioxo-4-phenylbutanoate (2) For the synthesis of compound 2, the procedure of Veeraswamyet al. (2012) was followed with some modifications.Sliced sodium metal (1.15 g) was added to methanol(25 mL) maintained at 0-10 °C in an ice bath and was keptstirring. Acetophenone (6.0 mL, 0.05 mol) was addedslowly and then the diethyl oxalate (8.0 mL, 0.06 mol) wasadded drop-wise and stirred for an hour while maintainingthe temperature as stated above till the product separated.The solid was dissolved in distilled water and then extractedwith diethyl ether to remove unreacted acetophenone, ifany. Then dilute acetic acid was added to precipitate out theproduct which was separated and the recrystallization was done using ethanol to give compound 2 (6.69 g; 65.0%; m.p.: 60-61 °C, lit. 61 °C) (Veeraswamy et al. 2012).

Reference： [1]Agrawal, Neetu; Mishra, Pradeep [Medicinal Chemistry Research, 2019, vol. 28, # 9, p. 1488 - 1501]

65
[ 89-98-5 ]
aminoacetonitrile neutral sulfate [ No CAS ]
[ 20577-73-5 ]
[3-benzoyl-2-(2-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium acetate In acetic acid at 24℃; for 20h;	[3-Benzoyl-2-(2-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetonitrile (1a). Anhydrous sodium acetate, 0.41 g (5 mmol), was dissolved in 5 mL of glacial acetic acid, and 1.03 g (5 mmol) of methyl 4-phenyl-2,4-dioxobutanoate, 0.56 mL (5 mmol) of 2-chlorobenzaldehyde, and 0.53 g (2.5 mmol) of aminoacetonitrile sulfate were added. The mixture was heated until it became homogeneous and was kept for 24 h at room temperature. The precipitate was filtered off and recrystallized from ethanol. Yield 1.54 g (85%), white crystals, mp 230-232°C. IR spectrum, ν, cm -1 : 3152 (OH), 1704 (C 5 =O), 1624 (3-C=O). 1 H NMR spectrum, δ, ppm: 4.17 d and 4.45 d (1H each, CH 2 CN, J = 18.0 Hz), 5.67 s (1H, 2-H), 7.31-7.75 m (9H, H arom ). Found, %: C 64.55; H 3.83; N 8.08. C19H13CIN2O3. Calculated, %: C 64.69; H 3.71; N 7.94.

Reference： [1]Gein; Buldakova; Dmitriev [Russian Journal of Organic Chemistry, 2019, vol. 55, # 7, p. 951 - 957][Zh. Org. Khim., 2019, vol. 55, # 7, p. 1046 - 1054,7]

66
aminoacetonitrile neutral sulfate [ No CAS ]
[ 135-02-4 ]
[ 20577-73-5 ]
[3-benzoyl-4-hydroxy-2-(2-methoxyphenyl)- 5-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With sodium acetate In acetic acid at 24℃; for 20h;	[3-Benzoyl-2-(2-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetonitrile (1a). General procedure: Anhydrous sodium acetate, 0.41 g (5 mmol), was dissolved in 5 mL of glacial acetic acid, and 1.03 g (5 mmol) of methyl 4-phenyl-2,4-dioxobutanoate, 0.56 mL (5 mmol) of 2-chlorobenzaldehyde, and 0.53 g (2.5 mmol) of aminoacetonitrile sulfate were added. The mixture was heated until it became homogeneous and was kept for 24 h at room temperature. The precipitate was filtered off and recrystallized from ethanol. Yield 1.54 g (85%), white crystals, mp 230-232°C. IR spectrum, ν, cm -1 : 3152 (OH), 1704 (C 5 =O), 1624 (3-C=O). 1 H NMR spectrum, δ, ppm: 4.17 d and 4.45 d (1H each, CH 2 CN, J = 18.0 Hz), 5.67 s (1H, 2-H), 7.31-7.75 m (9H, H arom ). Found, %: C 64.55; H 3.83; N 8.08. C19H13CIN2O3. Calculated, %: C 64.69; H 3.71; N 7.94.

Reference： [1]Gein; Buldakova; Dmitriev [Russian Journal of Organic Chemistry, 2019, vol. 55, # 7, p. 951 - 957][Zh. Org. Khim., 2019, vol. 55, # 7, p. 1046 - 1054,7]

67
aminoacetonitrile neutral sulfate [ No CAS ]
[ 874-42-0 ]
[ 20577-73-5 ]
[3-benzoyl-2-(2,4-dichlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium acetate In acetic acid at 24℃; for 20h;	[3-Benzoyl-2-(2-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetonitrile (1a). General procedure: Anhydrous sodium acetate, 0.41 g (5 mmol), was dissolved in 5 mL of glacial acetic acid, and 1.03 g (5 mmol) of methyl 4-phenyl-2,4-dioxobutanoate, 0.56 mL (5 mmol) of 2-chlorobenzaldehyde, and 0.53 g (2.5 mmol) of aminoacetonitrile sulfate were added. The mixture was heated until it became homogeneous and was kept for 24 h at room temperature. The precipitate was filtered off and recrystallized from ethanol. Yield 1.54 g (85%), white crystals, mp 230-232°C. IR spectrum, ν, cm -1 : 3152 (OH), 1704 (C 5 =O), 1624 (3-C=O). 1 H NMR spectrum, δ, ppm: 4.17 d and 4.45 d (1H each, CH 2 CN, J = 18.0 Hz), 5.67 s (1H, 2-H), 7.31-7.75 m (9H, H arom ). Found, %: C 64.55; H 3.83; N 8.08. C19H13CIN2O3. Calculated, %: C 64.69; H 3.71; N 7.94.

Reference： [1]Gein; Buldakova; Dmitriev [Russian Journal of Organic Chemistry, 2019, vol. 55, # 7, p. 951 - 957][Zh. Org. Khim., 2019, vol. 55, # 7, p. 1046 - 1054,7]

68
[ 99-61-6 ]
aminoacetonitrile neutral sulfate [ No CAS ]
[ 20577-73-5 ]
[3-benzoyl-4-hydroxy-2-(3-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium acetate In acetic acid at 24℃; for 20h;	[3-Benzoyl-2-(2-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetonitrile (1a). General procedure: Anhydrous sodium acetate, 0.41 g (5 mmol), was dissolved in 5 mL of glacial acetic acid, and 1.03 g (5 mmol) of methyl 4-phenyl-2,4-dioxobutanoate, 0.56 mL (5 mmol) of 2-chlorobenzaldehyde, and 0.53 g (2.5 mmol) of aminoacetonitrile sulfate were added. The mixture was heated until it became homogeneous and was kept for 24 h at room temperature. The precipitate was filtered off and recrystallized from ethanol. Yield 1.54 g (85%), white crystals, mp 230-232°C. IR spectrum, ν, cm -1 : 3152 (OH), 1704 (C 5 =O), 1624 (3-C=O). 1 H NMR spectrum, δ, ppm: 4.17 d and 4.45 d (1H each, CH 2 CN, J = 18.0 Hz), 5.67 s (1H, 2-H), 7.31-7.75 m (9H, H arom ). Found, %: C 64.55; H 3.83; N 8.08. C19H13CIN2O3. Calculated, %: C 64.69; H 3.71; N 7.94.

Reference： [1]Gein; Buldakova; Dmitriev [Russian Journal of Organic Chemistry, 2019, vol. 55, # 7, p. 951 - 957][Zh. Org. Khim., 2019, vol. 55, # 7, p. 1046 - 1054,7]

69
aminoacetonitrile neutral sulfate [ No CAS ]
[ 20577-73-5 ]
[ 552-89-6 ]
[3-benzoyl-4-hydroxy-2-(2-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium acetate In acetic acid at 24℃; for 20h;	[3-Benzoyl-2-(2-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]acetonitrile (1a). General procedure: Anhydrous sodium acetate, 0.41 g (5 mmol), was dissolved in 5 mL of glacial acetic acid, and 1.03 g (5 mmol) of methyl 4-phenyl-2,4-dioxobutanoate, 0.56 mL (5 mmol) of 2-chlorobenzaldehyde, and 0.53 g (2.5 mmol) of aminoacetonitrile sulfate were added. The mixture was heated until it became homogeneous and was kept for 24 h at room temperature. The precipitate was filtered off and recrystallized from ethanol. Yield 1.54 g (85%), white crystals, mp 230-232°C. IR spectrum, ν, cm -1 : 3152 (OH), 1704 (C 5 =O), 1624 (3-C=O). 1 H NMR spectrum, δ, ppm: 4.17 d and 4.45 d (1H each, CH 2 CN, J = 18.0 Hz), 5.67 s (1H, 2-H), 7.31-7.75 m (9H, H arom ). Found, %: C 64.55; H 3.83; N 8.08. C19H13CIN2O3. Calculated, %: C 64.69; H 3.71; N 7.94.

Reference： [1]Gein; Buldakova; Dmitriev [Russian Journal of Organic Chemistry, 2019, vol. 55, # 7, p. 951 - 957][Zh. Org. Khim., 2019, vol. 55, # 7, p. 1046 - 1054,7]

70
[ 2231-57-4 ]
[ 20577-73-5 ]
4-amino-6-(2-oxo-2-phenylethyl)-3-sulfanylidene-3,4-dihydro-1,2,4-triazin-5(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol for 1.5h; Reflux;	4-Amino-6-(2-oxo-2-phenylethyl)-3-sulfanylidene-3,4-dihydro-1,2,4-triazin-5(2H)-one (3a). a. Thiocarbonohydrazide, 0.106 g (1.0 mmol), was added to a solution of 0.319 g (1.0 mmol) of 1a in15 mL of anhydrous dioxane, and the mixture was refluxed for 1-3 min until the violet color typical of 1a disappeared. The mixture was cooled and partly evaporated until a solid began to precipitate, and the precipitate of 3a was filtered off. Yield 0.191 g (73%), yellow powder, mp 178-180°C (decomp., from EtOH). b. A solution of 0.106 g (1.0 mmol) of thiocarbonohydrazide was added to a solution of 0.206 g (1.0 mmol) of methyl 4-phenyl-2,4-dioxobutanoate (4a) in 15 mL of ethanol. The mixture was refluxed for 1.5 h and cooled, and the precipitate was filtered off. Yield 0.197 g (75%), mp 178-180°C (decomp., from EtOH). IR spectrum, ν, cm-1: 3196 br (N-H), 1698 (C=S, C5=O), 1677 (PhC=O). 1H NMR spectrum, δ, ppm: 4.41 s (2H, CH2), 6.52 br.s (2H, NH2), 7.58 m (2H, Harom), 7.70 m (1H, Harom), 8.04 m (2H, Harom), 14.01 br.s (1H, N2H). 13C NMR spectrum, δC, ppm: 40.4 (CH2), 128.3 (2C), 128.8 (2C), 133.7, 135.9 (Carom), 143.9 (C6), 148.4 (C5), 168.3 (C3), 195.2 (PhCO). Found, %: C 50.39; H 3.87; N 21.34. C11H10N4O2S. Calculated, %: C 50.37; H 3.84; N 21.36.

Reference： [1]Kobelev; Stepanova; Dmitriev; Maslivets [Russian Journal of Organic Chemistry, 2019, vol. 55, # 7, p. 1013 - 1018][Zh. Org. Khim., 2019, vol. 55, # 7, p. -1120 - -1126,7]

71
[ 61-54-1 ]
[ 89-98-5 ]
[ 20577-73-5 ]
4-[hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl]-5-(2-chlorophenyl)pyrrolidin-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In 1,4-dioxane at 20℃; for 24h;	4-[Hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl-5-(2-chlorophenyl)pyrrolidin-2,3-dione (1a). General procedure: To a mixture of 1.11 g (0.01 mol) of aromatic aldehyde and 1.60 g (0.01 mol) of tryptamine in 50 mL of dioxane was added 2.06 g (0.01 mol) of benzoylpyruvic acid methyl ester. The resulting mixture was heated until the reagents were dissolved and kept for 1 day at room temperature. The precipitate was fi ltered off and recrystallized from ethanol. Yield 2.7 g (60%), mp 204-206°C.IR spectrum, ν, cm-1: 1621 (=), 1664 (=), 1689(ON), 3082 (OH), 3498 (N). 1H NMR spectrum, δ,ppm: 2.71-2.85 m (1H, CHAHBC), 2.89-3.07 m (2H,CHAHBC, CHAHBN), 3.78-3.99 m (1H, CHAHBN), 6.00 s (1H, C5H), 6.88-6.98 m (1H, Ar), 7.06 t (1H, Ar,JHH = 7.5 Hz), 7.12 d (1H, indole-C2H, JHH = 1.5 Hz),7.19-7.37 m (5H, Ar), 7.45 t (2H, Ar, JHH = 7.6 Hz),7.50-7.59 m (2H, Ar), 7.69 t (2H, Ar, JHH = 8.0 Hz),10.84 s (1H, indole-NH), 11.94 br. s (1H, C4COH). 13CNMR spectrum, δ, ppm: 24.1 (CH2C), 41.9 (CH2N),57.0 (C5), 111.0 (indole-C3), 111.2, 111.9, 118.3, 118.8(C-Ar), 121.5 (C4), 123.2 (indole-C2H), 127.8, 128.3,128.4 128.5, 129.1, 130.0, 130.4, 132.8, 134.3, 135.0,135.5, 136.7 (C-Ar), 138.6 (C2O), 165.7 (C3O), 189.3(C4COH). Mass spectrum (ESI), m/z: 457.1324 [M + H]+(calcd. C27H22ClN2O3: 457.1313). Found, %: 70.77; 6.36; N 6.44. 2721ClN2O3. Calculated, %: 70.97; 4.63; N 6.10.

Reference： [1]Gein; Varkentin; Kazantseva; Dmitriev; Yankin [Russian Journal of General Chemistry, 2019, vol. 89, # 11, p. 2196 - 2200][Zh. Obshch. Khim., 2019, vol. 89, # 11, p. 1673 - 1678,6]

72
[ 61-54-1 ]
[ 123-08-0 ]
[ 20577-73-5 ]
5-(4-hydroxyphenyl)-4-[hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl]pyrrolidine-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	In 1,4-dioxane at 20℃; for 24h;	4-[Hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl-5-(2-chlorophenyl)pyrrolidin-2,3-dione (1a). General procedure: To a mixture of 1.11 g (0.01 mol) of aromatic aldehyde and 1.60 g (0.01 mol) of tryptamine in 50 mL of dioxane was added 2.06 g (0.01 mol) of benzoylpyruvic acid methyl ester. The resulting mixture was heated until the reagents were dissolved and kept for 1 day at room temperature. The precipitate was fi ltered off and recrystallized from ethanol.

Reference： [1]Gein; Varkentin; Kazantseva; Dmitriev; Yankin [Russian Journal of General Chemistry, 2019, vol. 89, # 11, p. 2196 - 2200][Zh. Obshch. Khim., 2019, vol. 89, # 11, p. 1673 - 1678,6]

73
[ 61-54-1 ]
[ 591-31-1 ]
[ 20577-73-5 ]
4-[hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl]-5-(3-methoxyphenyl)pyrrolidine-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	In 1,4-dioxane at 20℃; for 24h;	4-[Hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl-5-(2-chlorophenyl)pyrrolidin-2,3-dione (1a). General procedure: To a mixture of 1.11 g (0.01 mol) of aromatic aldehyde and 1.60 g (0.01 mol) of tryptamine in 50 mL of dioxane was added 2.06 g (0.01 mol) of benzoylpyruvic acid methyl ester. The resulting mixture was heated until the reagents were dissolved and kept for 1 day at room temperature. The precipitate was fi ltered off and recrystallized from ethanol.

Reference： [1]Gein; Varkentin; Kazantseva; Dmitriev; Yankin [Russian Journal of General Chemistry, 2019, vol. 89, # 11, p. 2196 - 2200][Zh. Obshch. Khim., 2019, vol. 89, # 11, p. 1673 - 1678,6]

74
[ 1121-60-4 ]
[ 61-54-1 ]
[ 20577-73-5 ]
4-[hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl]-5-(pyridin-2-yl)pyrrolidine-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	In 1,4-dioxane at 20℃; for 24h;	4-[Hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl-5-(2-chlorophenyl)pyrrolidin-2,3-dione (1a). General procedure: To a mixture of 1.11 g (0.01 mol) of aromatic aldehyde and 1.60 g (0.01 mol) of tryptamine in 50 mL of dioxane was added 2.06 g (0.01 mol) of benzoylpyruvic acid methyl ester. The resulting mixture was heated until the reagents were dissolved and kept for 1 day at room temperature. The precipitate was fi ltered off and recrystallized from ethanol.

Reference： [1]Gein; Varkentin; Kazantseva; Dmitriev; Yankin [Russian Journal of General Chemistry, 2019, vol. 89, # 11, p. 2196 - 2200][Zh. Obshch. Khim., 2019, vol. 89, # 11, p. 1673 - 1678,6]

75
[ 500-22-1 ]
[ 61-54-1 ]
[ 20577-73-5 ]
4-[hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl]-5-(pyridin-3-yl)pyrrolidine-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	In 1,4-dioxane at 20℃; for 24h;	4-[Hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl-5-(2-chlorophenyl)pyrrolidin-2,3-dione (1a). General procedure: To a mixture of 1.11 g (0.01 mol) of aromatic aldehyde and 1.60 g (0.01 mol) of tryptamine in 50 mL of dioxane was added 2.06 g (0.01 mol) of benzoylpyruvic acid methyl ester. The resulting mixture was heated until the reagents were dissolved and kept for 1 day at room temperature. The precipitate was fi ltered off and recrystallized from ethanol.

Reference： [1]Gein; Varkentin; Kazantseva; Dmitriev; Yankin [Russian Journal of General Chemistry, 2019, vol. 89, # 11, p. 2196 - 2200][Zh. Obshch. Khim., 2019, vol. 89, # 11, p. 1673 - 1678,6]

76
[ 61-54-1 ]
[ 20577-73-5 ]
[ 456-48-4 ]
4-[hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl]-5-(3-fl uorophenyl)pyrrolidine-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	In 1,4-dioxane at 20℃; for 24h;	4-[Hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl-5-(2-chlorophenyl)pyrrolidin-2,3-dione (1a). General procedure: To a mixture of 1.11 g (0.01 mol) of aromatic aldehyde and 1.60 g (0.01 mol) of tryptamine in 50 mL of dioxane was added 2.06 g (0.01 mol) of benzoylpyruvic acid methyl ester. The resulting mixture was heated until the reagents were dissolved and kept for 1 day at room temperature. The precipitate was fi ltered off and recrystallized from ethanol.

Reference： [1]Gein; Varkentin; Kazantseva; Dmitriev; Yankin [Russian Journal of General Chemistry, 2019, vol. 89, # 11, p. 2196 - 2200][Zh. Obshch. Khim., 2019, vol. 89, # 11, p. 1673 - 1678,6]

77
[ 61-54-1 ]
[ 874-42-0 ]
[ 20577-73-5 ]
4-[hydroxy(phenyl)methylene]-5-(2,4-dichlorophenyl)-1-[2-(1H-indol-3-yl)ethyl]pyrrolidine-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	In 1,4-dioxane at 20℃; for 24h;	4-[Hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl-5-(2-chlorophenyl)pyrrolidin-2,3-dione (1a). General procedure: To a mixture of 1.11 g (0.01 mol) of aromatic aldehyde and 1.60 g (0.01 mol) of tryptamine in 50 mL of dioxane was added 2.06 g (0.01 mol) of benzoylpyruvic acid methyl ester. The resulting mixture was heated until the reagents were dissolved and kept for 1 day at room temperature. The precipitate was fi ltered off and recrystallized from ethanol.

Reference： [1]Gein; Varkentin; Kazantseva; Dmitriev; Yankin [Russian Journal of General Chemistry, 2019, vol. 89, # 11, p. 2196 - 2200][Zh. Obshch. Khim., 2019, vol. 89, # 11, p. 1673 - 1678,6]

78
[ 61-54-1 ]
[ 120-14-9 ]
[ 20577-73-5 ]
4-[hydroxy(phenyl)methylene]-5-(2,4-dimethoxyphenyl)-1-[2-(1H-indol-3-yl)ethyl]pyrrolidine-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In 1,4-dioxane at 20℃; for 24h;	4-[Hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl-5-(2-chlorophenyl)pyrrolidin-2,3-dione (1a). General procedure: To a mixture of 1.11 g (0.01 mol) of aromatic aldehyde and 1.60 g (0.01 mol) of tryptamine in 50 mL of dioxane was added 2.06 g (0.01 mol) of benzoylpyruvic acid methyl ester. The resulting mixture was heated until the reagents were dissolved and kept for 1 day at room temperature. The precipitate was fi ltered off and recrystallized from ethanol.

Reference： [1]Gein; Varkentin; Kazantseva; Dmitriev; Yankin [Russian Journal of General Chemistry, 2019, vol. 89, # 11, p. 2196 - 2200][Zh. Obshch. Khim., 2019, vol. 89, # 11, p. 1673 - 1678,6]

79
[ 61-54-1 ]
[ 4748-78-1 ]
[ 20577-73-5 ]
4-[hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl]-5-(4-ethylphenyl)pyrrolidine-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	In 1,4-dioxane at 20℃; for 24h;	4-[Hydroxy(phenyl)methylene]-1-[2-(1H-indol-3-yl)ethyl-5-(2-chlorophenyl)pyrrolidin-2,3-dione (1a). General procedure: To a mixture of 1.11 g (0.01 mol) of aromatic aldehyde and 1.60 g (0.01 mol) of tryptamine in 50 mL of dioxane was added 2.06 g (0.01 mol) of benzoylpyruvic acid methyl ester. The resulting mixture was heated until the reagents were dissolved and kept for 1 day at room temperature. The precipitate was fi ltered off and recrystallized from ethanol.

Reference： [1]Gein; Varkentin; Kazantseva; Dmitriev; Yankin [Russian Journal of General Chemistry, 2019, vol. 89, # 11, p. 2196 - 2200][Zh. Obshch. Khim., 2019, vol. 89, # 11, p. 1673 - 1678,6]

80
[ 67-56-1 ]
[ 591-31-1 ]
[ 57-13-6 ]
[ 20577-73-5 ]
methyl 5-benzoyl-4-methoxy-6-(3-methoxyphenyl)-2-oxohexahydropyrimidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium hydrogen sulfate Reflux;	Synthesis of methyl 5-aroyl-6-aryl-4-methoxy(hydroxy)-2-oxo(thioxo)hexahydropyrimidine-4-carboxylates 1a-i, 2b (General method). General procedure: A mixture of methyl 3-aroylpyruvate(0.01 mol), aromatic aldehyde (0.01 mol), urea or thiourea(0.015 mol), and NaHSO4 (0.012 mol, 1.44 g) in MeOH(10 ml) was heated at reflux for 0.5-1 h. After the reactionwas run to completion, the resulting precipitate wascollected by filtration and washed with H2O. The crudeproduct was recrystallized from MeOH.

Reference： [1]Gein, Vladimir L.; Zamaraeva, Tatiana M.; Gorgopina, Ekaterina V.; Dmitriev, Maksim V. [Chemistry of Heterocyclic Compounds, 2020, vol. 56, # 3, p. 339 - 346][Khim. Geterotsikl. Soedin., 2020, vol. 56, # 3, p. 339 - 346,8]

81
[ 104-88-1 ]
[ 17356-08-0 ]
[ 20577-73-5 ]
methyl 5-benzoyl-6-(4-chlorophenyl)-4-hydroxy-2-thioxohexahydropyrimidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	In methanol at 78℃; for 1h;	Methyl 5-benzoyl-6-(4-chlorophenyl)-4-hydroxy-2-thioxohexahydropyrimidine-4-carboxylate (2a). Amixture of methyl 3-benzoylpyruvate (2.06 g, 0.01 mol),4-chlorobenzaldehyde (1.41 g, 0.01 mol), thiourea (1.14 g,0.015 mol) in MeOH (10 ml) was heated at 78°C for 1 h.After reaction completion, the resulting precipitate wascollected by filtration and washed with H2O, the crudeproduct was recrystallized from MeOH. Yield 1.77 g(44%), white crystals, mp 179-181°C. 1H NMR spectrum,δ, ppm (J, Hz): 3.19 (3H, s, COOCH3); 4.41 (1H, d,J = 12.0, 5-CH); 5.00 (1H, d, J = 12.0, 6-CH); 6.72 (1H, s,OH); 7.29 (2H, d, J = 8.4, H Ar); 7.65 (2H, d, J = 8.4,H Ar); 7.53 (1H, t, J = 8.4, H Ar); 7.37-7.43 (4H, m, HAr); 8.66 (1H, s, 1-NH); 8.81 (1H, s, 3-NH). 13 NMR spectrum, δ, ppm: 52.0 (2C); 53.3; 81.4; 127.7; 128.1;128.4; 130.0; 132.3; 133.1; 137.5; 138.8; 153.7; 169.4;196.3. Found, %: 56.60; 4.33; N 6.64. 19H17ClN2O4S.Calculated, %: 56.37; 4.23; N 6.92.

Reference： [1]Gein, Vladimir L.; Zamaraeva, Tatiana M.; Gorgopina, Ekaterina V.; Dmitriev, Maksim V. [Chemistry of Heterocyclic Compounds, 2020, vol. 56, # 3, p. 339 - 346][Khim. Geterotsikl. Soedin., 2020, vol. 56, # 3, p. 339 - 346,8]

82
[ 67-56-1 ]
[ 104-88-1 ]
[ 17356-08-0 ]
[ 20577-73-5 ]
methyl (4RS,5SR,6RS)-5-benzoyl-6-(4-chlorophenyl)-4-methoxy-2-thioxohexahydropyrimidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydrogen sulfate Reflux;	Synthesis of methyl 5-aroyl-6-aryl-4-methoxy(hydroxy)-2-oxo(thioxo)hexahydropyrimidine-4-carboxylates 1a-i, 2b (General method). General procedure: A mixture of methyl 3-aroylpyruvate(0.01 mol), aromatic aldehyde (0.01 mol), urea or thiourea(0.015 mol), and NaHSO4 (0.012 mol, 1.44 g) in MeOH(10 ml) was heated at reflux for 0.5-1 h. After the reactionwas run to completion, the resulting precipitate wascollected by filtration and washed with H2O. The crudeproduct was recrystallized from MeOH.

Reference： [1]Gein, Vladimir L.; Zamaraeva, Tatiana M.; Gorgopina, Ekaterina V.; Dmitriev, Maksim V. [Chemistry of Heterocyclic Compounds, 2020, vol. 56, # 3, p. 339 - 346][Khim. Geterotsikl. Soedin., 2020, vol. 56, # 3, p. 339 - 346,8]

83
[ 67-56-1 ]
[ 459-57-4 ]
[ 17356-08-0 ]
[ 20577-73-5 ]
methyl 5-benzoyl-6-(4-fluorophenyl)-4-methoxy-2-thioxohexahydropyrimidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydrogen sulfate Reflux;	Synthesis of methyl 5-aroyl-6-aryl-4-methoxy(hydroxy)-2-oxo(thioxo)hexahydropyrimidine-4-carboxylates 1a-i, 2b (General method). General procedure: A mixture of methyl 3-aroylpyruvate(0.01 mol), aromatic aldehyde (0.01 mol), urea or thiourea(0.015 mol), and NaHSO4 (0.012 mol, 1.44 g) in MeOH(10 ml) was heated at reflux for 0.5-1 h. After the reactionwas run to completion, the resulting precipitate wascollected by filtration and washed with H2O. The crudeproduct was recrystallized from MeOH.

Reference： [1]Gein, Vladimir L.; Zamaraeva, Tatiana M.; Gorgopina, Ekaterina V.; Dmitriev, Maksim V. [Chemistry of Heterocyclic Compounds, 2020, vol. 56, # 3, p. 339 - 346][Khim. Geterotsikl. Soedin., 2020, vol. 56, # 3, p. 339 - 346,8]

84
[ 3132-99-8 ]
[ 57-13-6 ]
[ 20577-73-5 ]
methyl 5-benzoyl-6-(3-bromophenyl)-4-hydroxy-2-oxohexahydropyrimidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium hydrogen sulfate In isopropyl alcohol for 1h; Reflux; diastereoselective reaction;	Methyl 5-benzoyl-6-(3-bromophenyl)-4-hydroxy-2-oxohexahydropyrimidine-4-carboxylate (2c). A mixture of methyl 3-benzoylpyruvate (1.03 g, 0.005 mol), 3-bromobenzaldehyde (0.6 ml, 0.005 mol), urea (0.45 g, 0.007 mol),and NaHSO4 (0.84 g, 0.007 mol) in i-PrOH (10 ml) washeated at reflux for 1 h. After reaction completion, the resulting precipitate was collected by filtration and washedwith H2O, the crude product was recrystallized fromi-PrOH. Yield 0.82 g (35%), white crystals, mp 172-174°C.1H NMR spectrum, δ, ppm (J, Hz): 3.09 (3H, s, COOCH3);4.64 (1H, d, J = 11.4, 5-CH); 4.89 (1H, d, J = 11.1, 6-CH);7.05 (1H, s, 1-NH); 7.22 (1H, t, J = 7.8, H Ar); 7.39 (2H, d,J = 7.5, H Ar); 7.46 (2H, t, J = 7.8, H Ar); 7.60 (1H, t, J = 7.2,H Ar); 7.64 (1H, s, H Ar); 7.75 (2H, d, J = 7.2, H Ar); 8.23(1H, s, 3-NH). Found, %: 52.96; 4.07; N 6.13.19H17BrN2O5. Calculated, %: 52.67; 3.96; N 6.47.

Reference： [1]Gein, Vladimir L.; Zamaraeva, Tatiana M.; Gorgopina, Ekaterina V.; Dmitriev, Maksim V. [Chemistry of Heterocyclic Compounds, 2020, vol. 56, # 3, p. 339 - 346][Khim. Geterotsikl. Soedin., 2020, vol. 56, # 3, p. 339 - 346,8]

85
[ 17356-08-0 ]
[ 100-10-7 ]
[ 20577-73-5 ]
methyl (4RS,5SR,6RS)-5-benzoyl-6-[4-(dimethylamino)phenyl]-4-hydroxy-2-thioxohexahydropyrimidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With sodium hydrogen sulfate In methanol Reflux;	Synthesis of methyl 5-aroyl-6-aryl-4-methoxy(hydroxy)-2-oxo(thioxo)hexahydropyrimidine-4-carboxylates 1a-i, 2b (General method). General procedure: A mixture of methyl 3-aroylpyruvate(0.01 mol), aromatic aldehyde (0.01 mol), urea or thiourea(0.015 mol), and NaHSO4 (0.012 mol, 1.44 g) in MeOH(10 ml) was heated at reflux for 0.5-1 h. After the reactionwas run to completion, the resulting precipitate wascollected by filtration and washed with H2O. The crudeproduct was recrystallized from MeOH.

Reference： [1]Gein, Vladimir L.; Zamaraeva, Tatiana M.; Gorgopina, Ekaterina V.; Dmitriev, Maksim V. [Chemistry of Heterocyclic Compounds, 2020, vol. 56, # 3, p. 339 - 346][Khim. Geterotsikl. Soedin., 2020, vol. 56, # 3, p. 339 - 346,8]

86
[ 4919-03-3 ]
[ 20577-73-5 ]
methyl 4-phenylimidazo[1,5-a]pyrimidine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.25 g	With trifluoroacetic acid In dichloromethane at 60℃; for 7h;	Synthesis of imidazo[1,5-a]pyrimidines 3a-f, 5, 6, 8,9, and 15-17 (General method). General procedure: tert-Butyl (1H-imidazol-4-yl)carbamate (1) (1.83 g, 10 mmol) was added in portionsto TFA (12 ml) at 10°C, and the mixture was stirred at 25°Cfor 0.2 h. A solution of 1,3-dicarbonyl compound 2a-f, 4,7, or 12-14 (10 mmol) in CH2Cl2 (10 ml) was added, andthe resulting mixture was stirred at 60°C for 7 h. Aftercompletion of the reaction, TFA was evaporated underreduced pressure. The residue was diluted with 0.5 NNaHCO3 (50 ml) and extracted with CH2Cl2 (100 ml). Theorganic layer was separated, washed with H2O (50 ml), anddried with anhydrous Na2SO4. The obtained crude productwas purified by crystallization or by flash column chromatography.

Reference： [1]Smirnova, Olga V.; Tolkunov, Andrew S.; Tolkunov, Sergei V.; Tolkunov, Valery S. [Chemistry of Heterocyclic Compounds, 2021, vol. 57, # 5, p. 554 - 559][Khim. Geterotsikl. Soedin., 2021, vol. 57, # 5, p. 554 - 559,6]

87
[ 20577-73-5 ]
4-Hydrazino-N-methylbenzenemethanesulphonamide hydrochloride [ No CAS ]
1-(4-((N-methylsulfamoyl)methyl)phenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 2,4-dioxo-4-phenylbutanoate; 4-Hydrazino-N-methylbenzenemethanesulphonamide hydrochloride In ethanol at 85℃; for 12h; Stage #2: With lithium hydroxide monohydrate; lithium hydroxide monohydrate In tetrahydrofuran; methanol at 20℃; for 2h;	4.1.1. 5-methyl-1-(4-((N-methylsulfiiamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid (12a) General procedure: Step 1. To a solution of acetone (6a, 580 mg, 10 mmol) and dimethyloxalate (7, 1.18 g, 10 mmol) in anhydrous methanol (50 mL) was degassed with argon and cooled to 0 °C in an ice bath. 30% sodium methanolate in methanol (20 mmol) was added dropwise into the coldsolution and the mixture was allowed to warm to room temperature. After 12 h, the resultant mixture was quenched with conc. HCl (5 mL)and concentrated in vacuo. The residue was then diluted with water (50 mL) and extracted with EA (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated to give methyl acetopyruvate (8a) which was directly used in the next step without further purification. Step 2. To a solution of 8a (118 mg, 1 mmol) and 4-hydrazino-N-methylbenzenemethanesulfonamide hydrochloride (9, 252 mg, 1 mmol)in anhydrous ethanol (10 mL) was stirred at 85 °C overnight. The reaction was allowed to cool to room temperature and concentrated. The crude material was purified by Isolera Biotage LPLC (PE/EA = 30%) to give a mixture of methyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (10a) and ethyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (11a) as a white solid. Step 3. To a solution of 10a and 11a (100mg) in 2:2:1 MeOH/THF/H2O (5mL) was added 1M LiOH (1mL) and stirred at room temperature. After 2h, the mixture was concentrated, diluted with water (5mL), acidified with 2M HCl (1mL) and filtered. The filtrate cake was washed with water and dried under vacuum to give the 12a (73mg) as a white solid.
	Stage #1: methyl 2,4-dioxo-4-phenylbutanoate; 4-Hydrazino-N-methylbenzenemethanesulphonamide hydrochloride In ethanol at 85℃; for 12h; Stage #2: With lithium hydroxide monohydrate; lithium hydroxide monohydrate In tetrahydrofuran; methanol at 20℃; for 2h;	4.1.1. 5-methyl-1-(4-((N-methylsulfiiamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylic acid (12a) General procedure: Step 1. To a solution of acetone (6a, 580 mg, 10 mmol) and dimethyloxalate (7, 1.18 g, 10 mmol) in anhydrous methanol (50 mL) was degassed with argon and cooled to 0 °C in an ice bath. 30% sodium methanolate in methanol (20 mmol) was added dropwise into the coldsolution and the mixture was allowed to warm to room temperature. After 12 h, the resultant mixture was quenched with conc. HCl (5 mL)and concentrated in vacuo. The residue was then diluted with water (50 mL) and extracted with EA (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated to give methyl acetopyruvate (8a) which was directly used in the next step without further purification. Step 2. To a solution of 8a (118 mg, 1 mmol) and 4-hydrazino-N-methylbenzenemethanesulfonamide hydrochloride (9, 252 mg, 1 mmol)in anhydrous ethanol (10 mL) was stirred at 85 °C overnight. The reaction was allowed to cool to room temperature and concentrated. The crude material was purified by Isolera Biotage LPLC (PE/EA = 30%) to give a mixture of methyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (10a) and ethyl 5-methyl-1-(4-((N-methylsulflamoyl)methyl)phenyl)-1H-pyrazole-3-carboxylate (11a) as a white solid. Step 3. To a solution of 10a and 11a (100mg) in 2:2:1 MeOH/THF/H2O (5mL) was added 1M LiOH (1mL) and stirred at room temperature. After 2h, the mixture was concentrated, diluted with water (5mL), acidified with 2M HCl (1mL) and filtered. The filtrate cake was washed with water and dried under vacuum to give the 12a (73mg) as a white solid.

Reference： [1]Fan, Yan; Fang, Zhen; Guo, Nihong; Guo, Yinping; Li, Linli; Liu, Yang; Mu, Bo; Xia, Anjie; Xiang, Rong; Xiong, Liang; Yang, Shengyong; Yao, Rui; Zhang, Hailin; Zhang, Rong [European Journal of Medicinal Chemistry, 2022, vol. 238]
[2]Fan, Yan; Fang, Zhen; Guo, Nihong; Guo, Yinping; Li, Linli; Liu, Yang; Mu, Bo; Xia, Anjie; Xiang, Rong; Xiong, Liang; Yang, Shengyong; Yao, Rui; Zhang, Hailin; Zhang, Rong [European Journal of Medicinal Chemistry, 2022, vol. 238]

88
[ 143504-99-8 ]
[ 20577-73-5 ]
methyl 2-amino-4-oxo-7-phenyl-3H-pyrido[2,3-d]pyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With glacial acetic acid for 0.0166667h; Heating;	Methyl 2-amino-4-oxo-7-phenyl-3H-pyrido[2,3-d]- pyrimidine-5-carboxylate (5a) a. A mixture of 0.63 g (0.005 mol) of amine 1, 1.03 g (0.005 mol) of ester 2 and 0.6 mL (0.005 mol) of aldehyde 3 was dissolved at heating in 30 mL of glacial acetic acid. After one minute, the formed precipitate was filtered off, washed with acetic acid and dried. Yield 0.55 g (38%), pale yellow powder, mp 277-279°C (AcOH). IR spectrum, ν, cm-1: 3420 and 3470 br (NH2), 1750 s (CO3), 1650 s (=O). 1 NMR spectrum, δ, ppm: 3.80 s (3, 3), 6.79 br. s (2, NH2), 7.45 m (3, Ar), 7.64 s (1, ), 8.12 m (2, Ar), 11.26 br. s (1, NH). Found, %: 60.75; 3.99; N 18.98. C15H12N4O3. Calculated, %: C 60.81; 4.08; N 18.91. b. To 15 mL of a hot solution of 1.26 g (0.01 mol) of amine 1 in glacial acetic acid was added 10 mL of a hot solution of 2.06 g (0.01 mol) of ester 2 in glacial acetic acid with stirring. After one minute, the formed precipitate was filtered off, washed with acetic acid and dried. Yield 2.0 g (68%).

Reference： [1]Dmitriev, M. V.; Gein, V. L.; Lomakina, N. N.; Prudnikova, A. N. [Russian Journal of General Chemistry, 2022, vol. 92, # 5, p. 766 - 770][Zh. Obshch. Khim., 2022, vol. 92, # 5, p. 696 - 701]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	20577-73-5	MDL No. :	MFCD00225528
Formula :	C₁₁H₁₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AQYAHPDSJAFBOS-UHFFFAOYSA-N
M.W :	206.20	Pubchem ID :	308117
Synonyms :

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

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P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 20577-73-5 ] {[proInfo.proName]}

Quality Control of [ 20577-73-5 ]

Related Doc. of [ 20577-73-5 ]

Product Details of [ 20577-73-5 ]

Safety of [ 20577-73-5 ]

Application In Synthesis of [ 20577-73-5 ]

[ 20577-73-5 ] Synthesis Path-Upstream 1~7

[ 20577-73-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 20577-73-5 ]

Aryls

Esters

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Yield	Reaction Conditions	Operation in experiment
69%	at 118℃; for 2 h;	Methyl 2,4-dioxo-4-phenylbutanoate (470mg, 2.28mmol) was dissolved in AcOH (5mL), hydrazine hydrate (122uL, 2.51mmol) was added and the reaction mixture was heated under reflux at 118°C for 2h. The reaction mixture was concentrated in vacuo to give the title compound (320mg, 69percent) as a yellow solid. LCMS: ES⁺ 203.0 [MH]⁺.
69%	at 118℃; for 2 h;	Methyl 2,4-dioxo-4-phenylbutanoate (470mg, 2.28mmol) was dissolved in AcOH (5mL), hydrazine hydrate (122uL, 2.Slmmol) was added and the reaction mixture was heated under reflux at 118°C for 2h. The reaction mixture was concentrated in vacuo to0 . + +give the title compound (320mg, 69/o) as a yellow solid. LCMS: ES 203.0 [IVIH]
1.3 g	at 20℃;	6.02.02.39 5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester 983 mg hydrazine acetate was added to 2 g 2,4-Dioxo-4-phenyl-butyric acid methyl ester in 10 mL concentrated acetic acid. The mixture was stirred over night at RT. Then water was added. The precipitate was filtered, stirred with diisopropylether and again filtered to give 1.3 g desired product. R_t: 1.39 min (method O), (M+H)⁺: 203

[ CAS No. 20577-73-5 ] {[proInfo.proName]}

Quality Control of [ 20577-73-5 ]

Related Doc. of [ 20577-73-5 ]

Product Details of [ 20577-73-5 ]

Safety of [ 20577-73-5 ]

Application In Synthesis of [ 20577-73-5 ]

[ 20577-73-5 ] Synthesis Path-Upstream 1~7

[ 20577-73-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 20577-73-5 ]

Aryls

Esters

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 20577-73-5 ]