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Maleimide carbazole compound and synthesis method thereof

A technology of maleimide and maleimide, applied in organic chemistry and other directions, can solve problems such as complex synthesis steps, and achieve the effects of good group positioning and selectivity, scientific process and wide source of materials

Pending Publication Date: 2022-05-27
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing synthetic methods of maleimidocarbazole compounds have complex synthetic steps, need to take multi-step synthetic processes to complete, or need to use metal catalysts and equivalent metal oxidants and other shortcomings

Method used

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  • Maleimide carbazole compound and synthesis method thereof
  • Maleimide carbazole compound and synthesis method thereof
  • Maleimide carbazole compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] The nuclear magnetic data of the product of Example 1 are as follows:

[0105] 1 H NMR (400MHz, Pyridine-d 5 )δ13.43(s, 1H), 12.91(s, 1H), 9.71(d, J=8.0Hz, 1H), 7.87(d, J=8.0Hz, 1H), 7.68(t, J=7.6Hz, 1H), 7.45(t, J=7.8Hz, 1H), 3.65(t, J=6.2Hz, 2H), 2.89(t, J=6.6Hz, 2H), 2.11–2.05(m, 2H); 13 C NMR (100MHz, Pyridine-d 5 )δ198.9,171.1,169.5,144.9,134.1,133.1,129.2,128.5,128.1,126.0,123.5,122.1,120.1,118.4,111.9,40.7,25.6,22.8.

Embodiment 2

[0106] The nuclear magnetic data of the product of Example 2 are as follows:

[0107] 1 H NMR (400MHz, CDCl 3 )δ9.95(s,1H),8.83(s,1H),7.32(d,J=4.2Hz,2H),3.65(t,J=7.6Hz,2H),3.41(s,2H),2.88( t, J=6.6Hz, 2H), 2.55(s, 3H), 2.23(t, J=6.4Hz, 2H), 1.65(t, J=7.6Hz, 2H), 1.10(s, 10H), 0.80( t, J=7.2Hz, 3H); 13 C NMR (100MHz, CDCl 3)δ199.1,168.8,168.7,141.4,135.7,133.3,132.4,130.9,129.8,127.9,127.3,123.3,121.2,115.7,110.4,40.6,38.1,31.7,29.1,225.5,26.9 ,21.7,14.0.

Embodiment 3

[0108] The nuclear magnetic data of the product of Example 3 are as follows:

[0109] 1 H NMR (400MHz, CDCl 3 )δ9.50(s, 1H), 8.64(s, 1H), 7.36(d, J=8.8Hz, 1H), 7.21–7.18(m, 1H), 3.98(s, 3H), 3.68(t, J =7.4Hz,2H),3.50(t,J=6.2Hz,2H),2.92-2.84(m,2H),2.26-2.20(m,2H),1.67(d,J=7.4Hz,2H),1.35 –1.16(m,10H),0.84(t,J=6.8Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ199.3, 169.1, 168.6, 154.1, 138.1, 135.8, 133.8, 132.6, 128.3, 123.7, 121.8, 120.1, 116.2, 111.5, 109.1, 55.9, 40.7, 38.1, 31.8, 29.2, 2, 9.2, 28.8 , 22.5, 14.1.

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Abstract

The invention mainly relates to a synthesis method of maleimide carbazole and derivatives thereof, and adopts the technical scheme that maleimide carbazole and derivatives thereof are prepared from 2-(3-indolyl) cyclohexanone compounds and maleic imide compounds as raw materials in an oxygen atmosphere under the action of an iodine catalyst and acid. The synthesis method overcomes the defects that the existing synthesis method of the maleimide and carbazole compound has complex synthesis steps, can be completed by adopting a multi-step synthesis process, or needs to use a metal catalyst and an equivalent metal oxidant, and the like. The method has the advantages of simple and mild reaction conditions, no need of adding a transition metal catalyst or a reaction solvent, simplicity and convenience in operation, wide raw material source, wide substrate range, good atom economy, high yield and the like. The maleimide carbazole derivative and the synthesis method thereof can be used in a plurality of industrial production fields such as medicines, pesticides, dyes, organic functional materials and the like.

Description

technical field [0001] The invention relates to a maleimidocarbazole compound and a synthesis method thereof, belonging to the field of organic synthesis. Background technique [0002] Maleimidocarbazoles are an important class of nitrogen-containing polycyclic aromatic hydrocarbons (NPAHs), widely distributed in a variety of pharmaceutical ingredients and bioactive molecules, with potent and broad-spectrum pharmacological activities, such as kinase inhibitors, Antibacterial, angiogenesis inhibitor, anticancer and antiproliferative. The existing methods for synthesizing maleimidocarbazole compounds have the disadvantages of complex synthesis steps, requiring multi-step synthesis processes, or requiring the use of metal catalysts and equivalent metal oxidants. SUMMARY OF THE INVENTION [0003] Therefore, the object of the present invention is to provide a maleimidocarbazole and its derivatives. Under the action of an iodine catalyst and an acid, in an oxygen atmosphere, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 邓国军方芳陈善平
Owner XIANGTAN UNIV