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Synthesis method of pyrano [3, 2-b] indole-2-ketone compound

A technology of ketone compounds and synthetic methods, which is applied in the field of chemical synthesis, can solve the problems of difficult preparation of raw materials and long synthetic routes, and achieve the effects of simple operation, mild reaction, and simple and easy-to-obtain raw materials

Pending Publication Date: 2021-12-03
NORTHWESTERN POLYTECHNICAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The above methods usually need the disadvantages of high temperature, vacuum, long synthesis route, and difficult preparation of raw materials.

Method used

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  • Synthesis method of pyrano [3, 2-b] indole-2-ketone compound
  • Synthesis method of pyrano [3, 2-b] indole-2-ketone compound
  • Synthesis method of pyrano [3, 2-b] indole-2-ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Under nitrogen atmosphere, add 42mg N-tosylindol-3-one, 36mg o-methoxyphenylpropynaldehyde, 6.4mg carbene salt, 21μL N,N-diethylpropylamine, 3, 3',5,5'-tetra-tert-butyl-4,4'-diphenoquinone 90 mg, 1,2-dichloroethane 1 mL. The mixed system was reacted at 30°C for 20h. After the reaction, the reaction system was cooled to room temperature, 5 mL of dichloromethane was added to the system, filtered, and the filter cake was washed 3 times with dichloromethane. The solvent was removed under reduced pressure and separated by column chromatography to obtain the target product 1 (49 mg, yield 73%).

[0051] The hydrogen spectrum and carbon spectrum data are as follows:

[0052] 1 H NMR (500MHz, CDCl 3 )δ8.24(d,J=8.5Hz,1H),7.66(d,J=7.8Hz,1H),7.54–7.46(m,2H),7.43(dd,J=7.6,1.7Hz,1H), 7.37(t, J=7.6Hz, 1H), 7.16(d, J=8.4Hz, 2H), 7.11(t, J=7.5Hz, 1H), 7.03(d, J=8.3Hz, 1H), 6.98( d,J=8.1Hz,2H),6.29(s,1H),3.89(s,3H),2.25(s,3H).

[0053] 13 C NMR (125MHz, CDCl 3 )δ160.90,156.68,1...

Embodiment 2

[0055] Under nitrogen atmosphere, add 42mg N-tosylindol-3-one, 36mg m-methoxyphenylpropynaldehyde, 6.4mg carbene salt, 21μL N,N-diethylpropylamine, 3, 3',5,5'-tetra-tert-butyl-4,4'-diphenoquinone 90 mg, 1,2-dichloroethane 1 mL. The mixed system was reacted at 30°C for 20h. After the reaction, the reaction system was cooled to room temperature, 5 mL of dichloromethane was added to the system, filtered, and the filter cake was washed 3 times with dichloromethane. The solvent was removed under reduced pressure and separated by column chromatography to obtain the target product 2 (42 mg, yield 63%).

[0056] The hydrogen spectrum and carbon spectrum data are as follows:

[0057] 1 H NMR (500MHz, CDCl 3 )δ8.22(d,J=8.4Hz,1H),7.65–7.58(d,1H),7.54(m,J=8.5,7.3,1.2Hz,1H),7.45(t,J=7.9Hz,1H ),7.39–7.34(m,1H),7.34–7.30(m,1H),7.25(t,J=2.0Hz,1H),7.10(d,J=8.2Hz,2H),7.05(ddd,J= 8.4,2.6,1.1Hz,1H),6.96(d,J=8.1Hz,2H),6.30(s,1H),3.89(s,J=1.3Hz,3H),2.25(s,3H).

[0058] 13 C NMR (125MHz, CDC...

Embodiment 3

[0060] Under a nitrogen atmosphere, add 42mg N-p-toluenesulfonylindol-3-one, 36mg p-methoxyphenylpropynaldehyde, 6.4mg carbene salt, 21μL N,N-diethylpropylamine, 3, 3',5,5'-tetra-tert-butyl-4,4'-diphenoquinone 90 mg, 1,2-dichloroethane 1 mL. The mixed system was reacted at 30°C for 20h. After the reaction, the reaction system was cooled to room temperature, 5 mL of dichloromethane was added to the system, filtered, and the filter cake was washed 3 times with dichloromethane. The solvent was removed under reduced pressure and separated by column chromatography to obtain the target product 3 (51 mg, yield 76%).

[0061] The hydrogen spectrum and carbon spectrum data are as follows:

[0062] 1 H NMR (500MHz, CDCl 3 )δ8.23(d, J=8.4Hz, 1H), 7.74(d, J=8.7Hz, 2H), 7.59(d, J=7.8Hz, 1H), 7.57–7.50(m, 1H), 7.37( t,J=7.6Hz,1H),7.12–7.00(m,4H),6.95(d,J=8.1Hz,2H),6.25(s,1H),3.90(s,3H),2.24(s,3H ).

[0063] 13 C NMR (125MHz, CDCl 3 )δ161.23, 161.17, 151.63, 151.61, 145.30, 140.84, ...

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Abstract

The present invention discloses a synthesis method of a pyrano [3, 2-b] indole-2-ketone compound. The method comprises: under a nitrogen atmosphere, mixing an N-p-toluenesulfonyl indole-3-ketone derivative, substituted phenylpropargyl aldehyde, an N-heterocyclic carbene salt, an oxidizing agent, an alkali and an organic solvent, and uniformly stirring to obtain a mixed system; fully reacting the mixed system at 25-35 DEG C for 12-36 hours; and after the reaction, cooling to room temperature, and carrying out post-treatment to obtain a target product. The method is simple and convenient to operate, mild in reaction and high in regioselectivity, is a cheap method with a good application prospect, and can be applied to efficient synthesis of natural products, medicines and materials.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of pyrano[3,2-b]indol-2-one compounds. Background technique [0002] In recent years, nitrogen-heterocyclic carbene (NHC) catalysis has become an efficient synthetic method for the synthesis of important biological substances (S. Mondal, S. R. Yetra, S. Mukherjee, A. T. Biju, Acc. Chem. Res., 2019, 52, 425; C.-H. Zhang, J.F. Hooper, D.W. Lupton, ACS Catal., 2017, 7, 2583). It is a new type of nucleophilic organic small molecule catalyst developed in recent years. It forms Breslow intermediates with α, β unsaturated enaldehydes. According to NHC, species structure skeleton, proton migration ability and isomerization ability, Breslow Intermediates can form acyl anion intermediates (acyl anion), enol intermediates (enolate), high enol intermediates (homoenolate) and the like. Efficiently catalyzes the polarity reversal of aldehydes to reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052
CPCC07D491/052
Inventor 鲁神赐王霞刘世飞张司辰蒋建锋胡丹范子翔
Owner NORTHWESTERN POLYTECHNICAL UNIV
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