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Synthetic method of 2-aryl benzothiazole compounds

A technology for the synthesis of benzothiazoles and methods, applied in the field of synthesis of 2-arylbenzothiazoles, achieving the effects of low temperature, good research value and potential, good reactivity and easy operation

Active Publication Date: 2014-05-14
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] As mentioned above, although multiple methods for the synthesis of 2-substituted benzothiazoles have been disclosed in the prior art, there is still a need and demand for continuous improvement and an attempt to establish a simpler and more efficient synthetic method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the synthesis of 2-phenylbenzothiazole

[0052]

[0053] To 50mL solvent water, add 10mmol o-aminothiophenol and 10mmol benzoylformic acid, mix well, then add 0.5mmol catalyst Cu(OTf) 2 and 10 mmol NaOH, heated to 100° C. and reacted at this temperature for 3 hours. After the reaction, the reaction system was cooled to room temperature, the solvent was evaporated under negative pressure, and the residue was purified by flash column chromatography (n-hexane / ethyl acetate, the volume ratio of the two was 1:1) to obtain the target product 2-phenyl Benzothiazole, yield 94.3%, purity 98.3% (HPLC).

[0054] Melting point: 115-116°C;

[0055] NMR: 1 H NMR (500MHz, CDCl 3 )δ8.11-8.08(m,3H),7.91(d,J=8.0Hz,1H),7.52-7.49(m,4H),7.41-7.38(m,1H);

[0056] 13 C NMR (125MHz, CDCl 3 ) δ 168.0, 154.1, 135.0, 133.6, 130.9, 129.0 (2C), 127.5 (2C), 126.3, 125.2, 123.2, 121.6.

Embodiment 2

[0057] Embodiment 2: the synthesis of 2-p-tolylbenzothiazole

[0058]

[0059] To 50mL solvent water, add 10mmol o-aminothiophenol and 20mmol p-toluoylformic acid, mix well, then add 1mmol catalyst Cu(OTf) 2 and 20mmol NaOH, heated to 90°C and reacted at this temperature for 5 hours. After the reaction, the reaction system was cooled to room temperature, and the solvent was evaporated under negative pressure, and the residue was purified by flash column chromatography (n-hexane / ethyl acetate, the volume ratio of the two was 2:1) to obtain the target product 2-p-toluene Base benzothiazole, yield 95.9%, purity 98.7% (HPLC).

[0060] Melting point: 86-87°C;

[0061] NMR: 1 H NMR (500MHz, CDCl 3 )δ8.07(d,J=8.5Hz,1H),7.99(d,J=8.5Hz,2H),7.89(d,J=8.0Hz,1H),7.50-7.47(m,1H),7.39- 7.30(m,1H),7.30(d,J=8.0Hz,2H),2.43(s,3H);

[0062] 13 C NMR (125MHz, CDCl 3 ) δ 168.2, 154.1, 141.4, 134.9, 130.9, 129.7 (2C), 127.4 (2C), 126.2, 124.9, 123.0, 121.5, 21.5.

Embodiment 3

[0063] Embodiment 3: the synthesis of 2-p-methoxyphenylbenzothiazole

[0064]

[0065] To 50mL solvent water, add 10mmol o-aminothiophenol and 30mmol p-methoxybenzoylformic acid, mix well, then add 1.5mmol catalyst Cu(OTf) 2 and 30mmol NaOH, heated to 80°C and reacted at this temperature for 7 hours. After the reaction, the reaction system was cooled to room temperature, and the solvent was evaporated under negative pressure, and the residue was purified by flash column chromatography (n-hexane / ethyl acetate, the volume ratio of the two was 3:1) to obtain the target product 2-p-methanol Oxyphenylbenzothiazole, yield 84.6%, purity 99.1% (HPLC).

[0066] Melting point: 121-123°C;

[0067] NMR: 1 H NMR (500MHz, CDCl 3 )δ8.05-8.02(m,3H),7.87(d,J=8.5Hz,1H),7.47(t,J=7.0Hz,1H),7.35(t,J=7.0Hz,1H),6.99( d,J=9.0Hz,2H),3.87(s,3H);

[0068] 13 C NMR (125MHz, CDCl 3 ) δ 167.8, 161.8, 154.1, 134.8, 129.0 (2C), 126.3, 126.1, 124.7, 122.7, 121.5, 114.3 (2C), 55.4.

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Abstract

The invention relates to a synthetic method of 2-aryl benzothiazole compounds. The method comprises the steps of reacting o-aminothiophenol type compounds with aryl glyoxalic acid type compounds in a solvent in the presence of a catalyst and additives to obtain the 2-aryl benzothiazole compounds. The method has many advantages such has high yield, high purity and simple operation, and provides a brand-new method for synthesizing the compounds.

Description

technical field [0001] The invention relates to a synthesis method of heterocyclic compounds, more particularly to a synthesis method of 2-arylbenzothiazole, belonging to the field of synthesis of heterocyclic compounds. Background technique [0002] Benzothiazole compounds are an important class of heterocyclic and bicyclic compounds, which widely exist in a variety of plants in nature. Scientists have found that benzothiazole compounds have certain physiological and pharmaceutical activities. They are widely used in medicinal chemistry and pesticides. Chemical methods have been widely used and intensively studied. [0003] In agricultural production, benzothiazole compounds have been found to have various activities such as antibacterial, herbicide and insect resistance, anti-plant virus and plant growth regulation; in drug development and pharmacological research, they have antibacterial, anti-allergic, anti-inflammatory, anti-tumor, anti-convulsant , immune regulation a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66
CPCC07D277/66
Inventor 刘妙昌陈久喜吴华悦严绍熙高文霞黄小波
Owner WENZHOU UNIVERSITY
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