一二三四区视频,亚洲少妇熟女色,日本久热无码视频网,欧美国产日韩大尺度,亚洲a视频,久久少妇一区二区,日韩999无码视频,刺激久久久久久久,啊啊啊啊不要啊在线

Methyl 4-methoxyacetoacetate - application on synthetic works

Dec 24,2019

Methyl 4-methoxyacetoacetate has been used in generation of a small focused library of diversely functionalized dihydropyrimidine derivatives via one-pot three-component Biginelli cyclocondensation of β-ketoesters, aldehydes and (thio)ureas. Methyl 4-Methoxyacetoacetate is also a reactant in the formation of an abiotic poorphyrinogen in aqueous solution.

Application on synthetic works

The following example is about its application on the synthesis of N-hydroxyamidinoheterocycles [1]

Methyl 4-methoxy-3-oxobutanoate (4.28 g, 0.029 mol) was dissolved in ether (20 mL). The solution was cooled in an ice bath. To the solution was added p-toluenesulfonyl azide (5.78 g, 0.029 mol) followed by N-ethylethanamine (2.0 mL, 0.019 mol). The solution was stirred at 0° C. for 15 minutes, then at rt for 30 minutes.
Upon evaporation, the tosyl amide bi-product solidified. This was filtered off and the filtrate was purified by flash chromatography to give the desired product (4.5 g, 89 percent) as a light oil.

 

The following example is about its application on the synthesis of pyridazinone compounds [2]

A solution of NaNO2 (1.66 g, 24 mmol) in H2O (5 mL) was added dropwise at 0° C. to a mixture of 2-fluoroaniline (1.93 mL, 20 mmol) and 6 M HCl aqueous solution (20 mL, 120 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (2.59 mL, 20 mmol) and NaOAc (9.84 g, 120 mmol) in MeOH (40 mL) pre-cooled at 0° C. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with saturated NaHCO3 aqueous solution and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from hexane/AcOEt to give the title compound (5.03 g, 94percent yield) as pale yellow crystals

The following example is about its application on the synthesis of pyrimidinyl indole compounds  [3]

To a solution of 4-methoxy-3-oxo-butyric acid methylester (1 g, 6.88 mmol) in anhydrous isopropanol (10 mL) were added lH-indole-4-carbaldehyde (0.3 g, 4.39 mmol) followed by catalytic amount of piperidine acetate (0.1 g, 0.68 mmol) and the reaction mixture was stirred at ambient temperature for 6 hours. The separated yellow solid was filtered to get 2-(lH-indol-4-ylmethylene)-4-methoxy-3-oxo-butyric acid methyl ester in 75 percent yield (1.41 g).

The following example is about its application on the synthesis of novel 2-oxindole scaffold as a highly potent and brain-penetrant phosphodiesterase 10A inhibitor [4]

A solution of sodium nitrite (0.081 g, 1.17 mmol) in water (1 mL) was added dropwise to a solution of staring material (0.19 g, 0.978 mmol) in 6 M HCl aq (2 mL) at 0°C. After stirring at 0°C for 15 min, the mixture was added to a suspension of methyl 4-methoxyacetoacetate (0.127 mL, 0.978 mmol) and sodium acetate (1.0 g, 12.19 mmol) in MeOH (5 mL) at 0°C. The formed precipitate was dissolved in EtOAc, and the solution was washed with water and saturated NaHCO3 aqueous solution. The organic layer was dried over MgSO4, and concentrated under reduced pressure to give the product (0.25 g, 73 percent) as a yellow solid.

References

1.Combs AP,Takvorian A, Zhu W. Sparks R. N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase. US2007/185165[P], 2007, A1, Page column 57.

2.Taniguchi T, Kawada A, Kondo M, Quinn JF, Kunitomo J, Yoshikawa MF. Pyridazinone compounds. MakotoUS2010/197651[P], 2010, A1, Page column 60.

3.CHEMOCENTRYX. Substituted dihydropyridines and methods of use, NC.WO2007/51062[P], 2007, A2, Page column 155-156.

4.Yoshikawa M, Kamisaki H, Kunitomo J, Oki H, Kokubo H, Suzuki A, Ikemoto T, Kimura H, Taniguchi T. Design and synthesis of a novel 2-oxindole scaffold as a highly potent and brain-penetrant phosphodiesterase 10A inhibitor. Bioorganic and Medicinal Chemistry, 2015, 23(22):7138-7149.

5.https://iaspub.epa.gov/sor_internet/registry/substreg/searchandretrieve/advancedsearch/externalSearch.do?p_type=CASNO&p_value=41051-15-4

6.https://pubchem.ncbi.nlm.nih.gov/compound/123500

  • Related articles
  • Related Qustion
See also
4

Cefditoren pivoxil is belong to cephalosporin drugs and is widely used for the treatment and prevention of various infectious diseases caused by pathogenic bacteria. Cefpodoxime proxetil is the third-generation cephalosporin antibiotic for....

Dec 24,2019Analytical Chemistry
4

4-Iodobenzaldehyde is an important organic building block, which has been used in the preparation of benzaldimine monolayers, 4-[2-(trimethylsilyl)ethynyl] benzaldehyde, and other substituted benzene products.....

Dec 24,2019Chemical Reagents

Methyl 4-methoxyacetoacetate manufacturers


万州区| 饶河县| 土默特左旗| 陆川县| 和田县| 望城县| 前郭尔| 萝北县| 石屏县| 仁怀市| 新巴尔虎左旗| 加查县| 开江县| 内黄县| 鹤峰县| 腾冲县| 新巴尔虎右旗| 英吉沙县| 宁化县| 元氏县| 德江县| 嘉义县| 类乌齐县| 新沂市| 桂林市| 奉新县| 手机| 宁陵县| 抚顺县| 西华县| 石河子市| 绥滨县| 宁陕县| 泾源县| 岳阳市| 云安县| 静乐县| 龙州县| 三河市| 乌拉特后旗| 东乌|