Polysubstituted benzothiophene thiazole and derivative and synthetic method thereof

A technology of benzothiophene and a synthesis method is applied in the field of organic compound synthesis to achieve the effects of simple reaction system, reduced environmental pollution and mild reaction conditions

Active Publication Date: 2018-09-21
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

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  • Polysubstituted benzothiophene thiazole and derivative and synthetic method thereof
  • Polysubstituted benzothiophene thiazole and derivative and synthetic method thereof
  • Polysubstituted benzothiophene thiazole and derivative and synthetic method thereof

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Experimental program
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Effect test

Embodiment 1-45

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

[0062] Step 1: Add ketoxime ester compound (see Table 1 for specific substance), formaldehyde 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) and organic solvent (see table 1 for specific substances) add in the reaction vessel and mix uniformly;

[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, benzaldehyde compound and sulfur powder are reacted in a solvent, and continue the reaction described in Table 1. the time stated;

[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 alkal...

Embodiment 1

[0072] The nuclear magnetic data of embodiment 1 product is as follows:

[0073] 1 H NMR (400MHz, CDCl 3 , ppm): δ8.29(d, J=7.8Hz, 1H), 8.10-8.01(m, 2H), 7.84(d, J=8.1Hz, 1H), 7.54-7.39(m, 5H).; 13 C NMR (100MHz, CDCl 3 , ppm): δ170.6, 156.1, 142.8, 134.0, 130.8, 130.6, 130.3, 129.1, 126.6, 125.1, 125.1, 123.4, 121.9

[0074] The nuclear magnetic data of embodiment 2 product is as follows:

[0075] 1 H NMR (100MHz, CDCl 3 , ppm): δ8.15(d, J=8.1Hz, 1H), 8.03(dd, J=7.8, 1.3Hz, 2H), 7.62(s, 1H), 7.47(d, J=7.5Hz, 3H) , 7.31(d, J=7.9Hz, 1H), 2.50(s, 3H); 13 C NMR (100MHz, CDCl 3 , ppm): δ170.4, 155.9, 143.1, 135.2, 134.0, 130.2, 129.8, 129.0, 128.2, 126.6, 126.5, 123.3, 121.4, 21.6.

Embodiment 3

[0076] The NMR data of embodiment 3 product are as follows:

[0077] 1 H NMR (400MHz, CDCl 3 , ppm): δ8.11(d, J=8.7Hz, 1H), 8.02-7.96(m, 2H), 7.47-7.40(m, 3H), 7.27(d, J=2.0Hz, 1H), 7.07( dd, J=8.7, 2.1Hz, 1H), 3.85(s, 3H); 13 C NMR (100MHz, CDCl 3 , ppm): δ170.3, 157.8, 155.7, 144.2, 134.0, 130.1, 129.0, 128.1, 126.4, 124.4, 122.2, 114.1, 106.6, 55.6.

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Abstract

The invention relates to a polysubstituted benzothiophene thiazole and a derivative and a synthetic method thereof. The method comprises the steps that ketoxime ester compounds, formaldehyde compoundsand powdered sulfur are converted into 2-polysubstituted benzothiophene-[3,2-d] thiazole and the derivative in the air atmosphere under Cu catalysis for the first time, and the obtained product is stable in molecular structure and good in chemical property. According to the synthesis method, reaction raw materials are cheap and easy to obtain, no preprocessing is needed, and the atom economy of the reaction is high; only cheap copper catalyst needs to be adopted in the reaction, environment contaminations are reduced, raw materials are saved, and the reaction cost is lowered; the whole reaction system is simple, reaction conditions are mild, a small amount of reaction equipment is needed, the experiment operation is easy and convenient, and the adopted materials are wide in source.

Description

technical field [0001] The invention relates to a multi-substituted benzothienothiazole and its derivatives and a synthesis method thereof, belonging to the technical field of organic compound synthesis. Background technique [0002] Benzothieno[3,2-d]thiazole and its derivatives are an important class of aromatic heterocyclic compounds, and various derivatives of thiazole 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 benzothienothiazole and its derivatives with stable molecular structure and excellent chemical properties. [0004] The invention also provides a method for synthesizing multi-substituted benzothienothiazoles and derivatives. [0005] The technical scheme adopted by the pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04C07D513/14
CPCC07D513/04C07D513/14Y02P20/584
Inventor 黄华文徐振华邓国军肖福红
Owner XIANGTAN UNIV
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