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Synthesis method for spirally-epoxidized indole butenolide compound

A technology for indole croton lactone and compound is applied in the field of synthesizing spiro-epoxidized indole croton acid lactone compounds, and can solve the problems of less synthesis and research and the like

Inactive Publication Date: 2014-05-14
CHINA PHARM UNIV
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  • Abstract
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Problems solved by technology

[0003] Spiroepoxindole crotonolactone is an important type of spiroepoxindole derivatives, but its synthesis and research are less

Method used

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  • Synthesis method for spirally-epoxidized indole butenolide compound
  • Synthesis method for spirally-epoxidized indole butenolide compound
  • Synthesis method for spirally-epoxidized indole butenolide compound

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Experimental program
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Effect test

Embodiment 1

[0012] Embodiment 1: the reaction of 3-phenylpropional and 1-methyl isatin

[0013] 117mg (0.9mmol) of 3-phenylpropynaldehyde, 48.3mg (0.3mmol) of 1-methylisatin, 16mg (0.06mmol) of triazole salt as shown in formula III, and 38.1mg of diisopropylethylamine (0.3mmol), lithium chloride 14mg (0.33mmol) and dioxane 4mL were placed in a 25mL two-necked bottle, and reacted for 24h under nitrogen protection and 40°C. The reaction solution was cooled and concentrated. A mixed solvent with a ratio of 25:1 was used as the eluent for column chromatography to elute, and the eluate part of all detected products was collected, and 65 mg of the product was obtained after rotary evaporation to remove the solvent, with a yield of 75%.

[0014] White solid, MP: 194-195℃. 1 H NMR (300M, CDCl 3 ): δ7.46(m, 1H), 7.36(m, 1H), 7.24-7.29(m, 2H), 7.08-7.20(m, 4H), 6.99(d, J=7.8Hz, 1H), 6.66( s, 1H), 3.31(s, 3H). 13 C NMR (75M, CDCl 3 ): δ171.2, 169.9, 162.9, 144.4, 131.9, 131.5, 129.2, 128.9, 126...

Embodiment 2

[0015] Embodiment 2: the reaction of 3-(4-methylphenyl) propynaldehyde and 1-methyl isatin

[0016] 130mg (0.9mmol) of 3-(4-methylphenyl)propiolinal, 48.3mg (0.3mmol) of 1-methyl isatin, 16mg (0.06mmol) of triazole salt shown in formula III, diisopropyl 38.1mg (0.3mmol) of ethyl ethylamine, 14mg (0.33mmol) of lithium chloride and 4mL of dioxane were placed in a 25mL two-necked flask, and reacted for 24h under nitrogen protection and 65°C. A mixed solvent of petroleum ether: acetone with a volume ratio of 25:1 was used as an eluent for column chromatography, and the eluent part of all detected products was collected, and 65 mg of the product was obtained after rotary evaporation to remove the solvent, with a yield of 71%.

[0017] White solid, MP: 181-182℃. 1 H NMR (300M, CDCl3): δ7.44(t, J=7.8Hz, 1H), 7.15(d, J=7.5Hz, 1H), 6.96-7.09(m, 6H), 6.59(s, 1H), 3.27(s, 3H), 2.27(s, 3H). 13 C NMR (75M, CDCl 3 ): δ171.4, 170.0, 162.8, 144.3, 142.1, 131.8, 129.9, 126.9, 126.0, 124.9,...

Embodiment 3

[0018] Embodiment 3: the reaction of 3-(4-methoxyphenyl) propynaldehyde and 1-methyl isatin

[0019] 144mg (0.9mmol) of 3-(4-methoxyphenyl)propiolinal, 48.3mg (0.3mmol) of 1-methylisatin, 16mg (0.06mmol) of triazole salt shown in formula III, diiso 38.1mg (0.3mmol) of propylethylamine, 14mg (0.33mmol) of lithium chloride and 4mL of dioxane were placed in a 25mL two-neck flask, and reacted for 72h under nitrogen protection and 10°C, and the reaction solution was cooled and concentrated. After elution by column chromatography with a mixed solvent of petroleum ether: acetone volume ratio of 25:1 as the eluent, the eluent part of all the products detected was collected, and the product was obtained by rotary evaporation to remove the solvent 41mg, the yield was 42% .

[0020] White solid, MP: 200-201℃. 1 H NMR (300M, CDCl3): δ7.45(m, 1H), 6.98-7.17(m, 5H), 6.76(d, J=8.4Hz, 2H), 6.53(s, 1H), 3.75(s, 3H ), 3.30(s, 3H). 13 C NMR (75M, CDCl 3 ): δ171.5, 170.1, 162.3, 162.1, 144.3...

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Abstract

The invention relates to the technical field of organic chemistry and particularly relates to a synthesis method for a spirally-epoxidized indole butenolide compound which is shown as the formula IV. The method comprises takes alkynal shown as the formula I and N-methyl isatin shown as the formula II as raw materials, and takes dioxane as a solvent in the presence of a triazole salt shown as the formula III, lithium chloride and diisopropyl ethyl amine to react for 3-72 hours under the condition of nitrogen protection and at 10-65 DEG C; a reaction solution is cooled and concentrated and a mixed solvent of a petroleum ether and acetone in the volume ratio of 25:1 is used as an eluting agent to carry out column chromatography elution; detected eluting solution parts of all products are collected and rotary evaporation is carried out so as to remove the solvent to obtain a spirally-epoxidized indole butenolide product. The synthesis method provided by the invention has good yield, and the application range of primers is wide; the synthesis method has the advantages of simplicity and convenience for operation, moderate reaction, convenience for post-treatment and the like.

Description

(1) Technical field [0001] The invention relates to a synthesis method of a spiro-epoxy indole butenolide compound, belonging to the field of organic chemistry synthesis methodology. (2) Background technology [0002] Spiro-epoxindole is an important molecular module with various biological activities and widely present in medicines and natural products (Eur.J.Org.Chem.2003, 2209; Angew.Chem., Int.Ed.2007, 46, 8748.). Butenolide (Bioorg. Med. Chem. Lett. 2011, 21, 3074) is also an important molecular module in drugs with various biological activities. [0003] Spiroepoxindole crotonolactone is an important class of spiroepoxindole derivatives, but its synthesis and research are less. Therefore, it is very necessary to develop a general and convenient method for preparing such compounds. (3) Contents of the invention [0004] The object of the present invention is to provide a method for synthesizing a spiro-epoxy indole butenolide compound with simple operation, mild re...

Claims

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Application Information

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IPC IPC(8): C07D491/107
CPCC07D491/107
Inventor 杜鼎张瑜陆涛陆滢炎
Owner CHINA PHARM UNIV
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