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Photocatalytic method for synthesizing alkaloids

A compound and photocatalytic technology, applied in the field of photocatalytic synthesis of alkaloids, synthesis of indole fused ring compounds or indole spiro compounds

Active Publication Date: 2022-05-17
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the strategy of synthesizing 3-functionalized 2-indolinones from nitrogen aryl acrylamides, there is still a lack of a very effective synthetic method for directly introducing formyl functional groups into 3-substituted 2-indolinones (While it should be pointed out that 3-substituted 2-indolones with formyl functional groups are important precursors for the synthesis of indole-fused ring alkaloids)
Therefore, it is of great significance to develop a mild and general method for the synthesis of 3-functionalized 2-indolones by introducing formyl functional groups, and further synthesis of alkaloids, especially indole fused ring compounds or indole spiro ring compounds, and there are also great challenges.

Method used

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  • Photocatalytic method for synthesizing alkaloids
  • Photocatalytic method for synthesizing alkaloids
  • Photocatalytic method for synthesizing alkaloids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112]

[0113] Add N-methyl-N-phenylacrylamide (88mg, 0.5mmol) and organic cyano-carbazole photocatalyst 4CzIPN (8mg, 0.01mmol) into the photoreactor, add 1,3-di Oxypentane (3mL), tert-butanol peroxide TBHP (1.0mmol, 0.13mL), irradiated with 5W blue light and stirred at room temperature for 12 hours, monitored by TLC, the reaction of raw materials was complete, concentrated under reduced pressure, added acetone (2mL), 2M HCl Aqueous solution (2 mL), stirred at room temperature for 12 hours. After carefully quenching the reaction by addition of sodium bicarbonate solution, it was extracted with ethyl acetate (3 x 20 mL). The organic phases were combined, washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified to obtain a colorless oily substance 2-(1,3-dimethyl-2-oxoindole (olin-3-yl)acetaldehyde (83 mg, 82%). 1 H NMR (600MHz, CDCl 3 )δ1.42(s,3H,CH 3 ), 2.94 (d, J=17.2Hz, 1H, CH 2 ), 2.99 (d,...

Embodiment 2

[0115]

[0116]In the photoreactor, add methyl 4-(N-methacrylamide) benzoate (117mg, 0.5mmol), organic cyano-carbazole photocatalyst 4CzIPN (8mg, 0.01mmol), add under nitrogen atmosphere 1,3-Dioxolane (3mL) and tert-butanol peroxy TBHP (1.0mmol, 0.13mL), irradiated with 5W blue light and stirred at room temperature for 12 hours, monitored by TLC, the reaction of raw materials was complete, concentrated under reduced pressure, added acetone ( 2 mL), 1M aqueous HCl (2 mL), and stirred at room temperature for 12 hours. After carefully quenching the reaction by addition of sodium bicarbonate solution, it was extracted with ethyl acetate (3 x 20 mL). The organic phases were combined, washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified to obtain a white solid methyl 1,3-dimethyl-2-oxo-3-(2 -Oxoethyl)indoline-5-carboxylate (82 mg, 63%). 1 H NMR (600MHz, CDCl 3 )δ1.41(s,3H,CH 3 ), 3.08 (d, J=18.2H...

Embodiment 3

[0118]

[0119] 2-(1,3-Dimethyl-2-oxoindol-3-yl)acetaldehyde (102mg, 0.5mmol) was dissolved in tetrahydrofuran (5mL) solvent, and 2.4 M tetrahydrofuran solution of lithium aluminum tetrahydrogen (0.85mL, 2.0mmol, 4.0equiv.), after stirring for five minutes at 0°C, add 10mL of ethyl acetate and continue the reaction at 0°C for 30 minutes to consume the remaining lithium aluminum tetrahydride. Then add 10 mL of saturated sodium chloride solution to quench the reaction, extract with ethyl acetate (3×20 mL), combine the organic phases, wash with saturated brine (20 mL), dry over anhydrous sodium sulfate, filter, concentrate under reduced pressure, and purify (3aS,8aS)-3a,8-dimethyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole (85mg, 90%) was obtained as a colorless oil . 1 H NMR (600MHz, CDCl 3 )δ1.46(s,3H,CH 3 ),2.02-2.07(m,1H,CH 2 ), 2.12 (ddd, J=1.1, 5.2, 11.9Hz, 1H, CH 2 ),2.92(s,3H,CH 3 ), 3.45 (ddd, J=5.2, 8.7, 11.2Hz, 1H, CH 2 ),3.93-3.96(m,1H,CH 2 ), 6.36(d, J=7.8H...

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Abstract

The invention provides a method for photocatalytically synthesizing alkaloids, the alkaloids include indole fused rings and indole spiro compounds, the process is as follows: nitrogen aryl acrylamide is used as raw material to react with peroxide under photocatalysis Synthesize 3-acetal 2-indolinone compounds, obtain 3-formyl-2-indolinone compounds through hydrolysis, and further reduce and synthesize alkaloids. This method has a mild route and high efficiency. The reaction can occur under light at room temperature, the conditions are mild, and it has good substrate versatility and functional group tolerance.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a method for photocatalytically synthesizing alkaloids, especially a method for synthesizing indole fused ring compounds or indole spiro compounds. Background technique [0002] The 2-indolinone skeleton is similar to the adenine structure, and its derivatives have inhibitory, regulatory receptor kinase and anti-tumor activities. The 3-functionalized 2-indolinone structure is a common intermediate for the synthesis of its derivatives. An important skeleton of natural products, such as indole spiro natural products (such as structural formula 1-7), or an important precursor of indole fused ring natural products (such as structural formula 8-12). This type of compound is also an important intermediate in the field of medicine. For example, drugs such as Ziprasid-one, Horsfiline, Paraherquamide, Rhyncophylline and Gelsemium alkaloids with 3-functionalized 2-indolinone as ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34C07D471/06C07D491/048C07D487/04C07D487/10C07D491/16C07D471/16
CPCC07D209/34C07D471/06C07D471/16C07D487/04C07D487/10C07D491/048C07D491/16
Inventor 苏陈良欧伟
Owner SHENZHEN UNIV
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