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Polysubstituted benzothienoisoquinoline, derivative and synthesis method thereof

A technology of benzothiophene and a synthesis method is applied in the field of organic compound synthesis, and achieves the effects of simple reaction system, convenient experimental operation and scientific process

Active Publication Date: 2019-12-24
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

To date there is no method for the synthesis of such compounds

Method used

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  • Polysubstituted benzothienoisoquinoline, derivative and synthesis method thereof
  • Polysubstituted benzothienoisoquinoline, derivative and synthesis method thereof
  • Polysubstituted benzothienoisoquinoline, derivative and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1-45

[0061] The synthetic method of multi-substituted benzothienoisoquinolines and derivatives comprises the following steps:

[0062] Step 1: Add ketoxime ester compound (see Table 1 for specific substance), o-chlorobenzaldehyde compound (see Table 1 for specific substance) and sulfur powder and alkali into the reaction vessel, add copper catalyst (see Table 1 for specific substance) Add organic solvent (see Table 1 for specific substances) and mix in the reaction vessel;

[0063] Step 2: The reaction vessel is evenly heated (such as oil bath heating) to the temperature described in Table 1, and the acetophenone oxime ester compound, o-chlorobenzaldehyde compound and sulfur powder are reacted in the solvent, and continue Table 1 the time stated in;

[0064] Step 3: Purify after the reaction is completed.

[0065] Table 1: Molar ratio, reaction temperature and reaction time of formaldehyde compound, ketoxime ester compound, sulfur powder, copper catalyst and alkali in embodiment 1-...

Embodiment 1

[0071] The nuclear magnetic data of embodiment 1 product is as follows:

[0072] 1H NMR (400MHz, CDCl3, ppm) δ9.28(s, 1H), 8.58-8.51(m, 1H), 8.11(d, J=8.1Hz, 1H), 8.06(d, J=8.2Hz, 1H) , 7.94(dd, J=6.9, 1.4Hz, 1H), 7.83-7.77(m, 1H), 7.66(t, J=7.6Hz, 1H), 7.56(pd, J=7.1, 1.4Hz, 2H). 13C NMR (100MHz, CDCl3, ppm) δ150.5, 146.1, 138.3, 135.9, 131.8, 131.1, 129.9, 128.9, 127.3, 127.3, 126.9, 125.1, 123.6, 123.0, 122.7.

[0073] The nuclear magnetic data of embodiment 2 product is as follows:

[0074] 1H NMR (400MHz, CDCl3, ppm) δ9.27(s, 1H), 8.43(d, J=8.1Hz, 1H), 8.11(d, J=8.2Hz, 1H), 8.05(d, J=8.2Hz , 1H), 7.83-7.77(m, 1H), 7.73(s, 1H), 7.65(t, J=7.3Hz, 1H), 7.39(d, J=8.1Hz, 1H), 2.55(s, 3H) .13C NMR (100MHz, CDCl3, ppm) δ150.1, 145.9, 138.6, 137.7, 133.4, 131.9, 131.1, 129.4, 128.9, 127.0, 126.8, 126.6, 123.5, 122.9, 122.3, 21.8.

Embodiment 3

[0075] The NMR data of embodiment 3 product are as follows:

[0076] 1H NMR (400MHz, CDCl3, ppm) δ9.25(s, 1H), 8.43(d, J=8.7Hz, 1H), 8.09(d, J=8.2Hz, 1H), 8.01(d, J=8.2Hz , 1H), 7.79(dd, J=11.2, 4.0Hz, 1H), 7.62(t, J=7.6Hz, 1H), 7.39(d, J=2.2Hz, 1H), 7.17(dd, J=8.7, 2.3Hz, 1H), 3.94(s, 3H).13C NMR (100MHz, CDCl3, ppm) δ159.7, 150.1, 145.7, 140.0, 131.9, 131.1, 129.3, 129.0, 128.5, 126.8, 126.3, 123.4, 123.3, 114.4, 106.0, 55.7.

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Abstract

The invention relates to a polysubstituted benzothienoisoquinoline, a derivative and a synthesis method thereof. According to the method, a ketoxime ester compound, an o-chlorobenzaldehyde compound and sulfur powder are converted into benzo[4,5]thieno[3, 2-C]isoquinoline and derivatives thereof for the first time under the catalysis of Cu in the air atmosphere, wherein the prepared benzo[4,5]thieno[3, 2-C]isoquinoline is stable in molecular structure and excellent in chemical property. Reaction raw materials of the synthesis method are cheap and easy to obtain, pretreatment is not needed, andthe atom economy of the reaction is high; only a cheap copper catalyst is used in the reaction, environmental pollution is reduced, raw materials are saved, and reaction cost is reduced; the whole reaction system is simple, reaction conditions are mild, reaction equipment is less, experimental operation is simple and convenient, and material sources are wide.

Description

technical field [0001] The invention relates to a multi-substituted benzothienoisoquinoline and its derivatives and a synthesis method thereof, belonging to the technical field of organic compound synthesis. Background technique [0002] Benzothienoisoquinoline and its derivatives are an important class of aromatic heterocyclic compounds, and various derivatives of thiophene are important drugs or physiologically active substances. It may have potential applications in many fields such as optoelectronic materials. To date there is no method for the synthesis of such compounds. Contents of the invention [0003] In order to fill the gap in the prior art, the present invention provides a multi-substituted benzothienoisoquinoline and its derivatives with stable molecular structure and excellent chemical properties. [0004] The invention also provides a method for synthesizing multi-substituted benzothienoisoquinolines and derivatives. [0005] The technical scheme adopted...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D495/20
CPCC07D495/04C07D495/20
Inventor 黄华文徐振华邓国军肖福红陈善平
Owner XIANGTAN UNIV