C2 substituted 2H-benzothiazole aryl acylated derivative, and synthesis method and application thereof

A technology of benzothiazole aryl acylation and synthesis method, which is applied in the field of C2-substituted 2H-benzothiazole aryl acylation derivatives and synthesis thereof, can solve the problem of reduced yield, flammable and explosive organic peroxide oxidant, Problems such as the increase of reaction by-products

Active Publication Date: 2021-07-06
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method is milder than the above reaction, the flammable and explosive characteristics of the organic peroxide oxidant used make its use, especially the scale-up reaction, have certain limitations.
At t...

Method used

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  • C2 substituted 2H-benzothiazole aryl acylated derivative, and synthesis method and application thereof
  • C2 substituted 2H-benzothiazole aryl acylated derivative, and synthesis method and application thereof
  • C2 substituted 2H-benzothiazole aryl acylated derivative, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]Example 1 Synthesis of derivative Ia ((R)n=hydrogen, (R')m=hydrogen)

[0025] Weigh 2 H - Benzothiazole (0.3 mmol, 40.6 mg), toluene (7.5 mmol, 691.1 mg), Selectfluor (0.6 mmol, 212.6 mg) and trifluoroacetic acid (0.3 mmol, 34.2 mg) in a 25 mL reaction tube, and then added 2 mL of acetonitrile, reacted at 80 °C in air atmosphere, monitored by TLC, the reaction was completed after about 10 h, the reaction solution was extracted with dichloromethane, the organic layer was concentrated to remove the solvent, and the concentrated solution was separated by column chromatography (eluent: Volume ratio 1: 0.05 petroleum ether-ethyl acetate mixed solvent) to obtain a yellow solid, ie derivative Ia. The yield is 85%.

[0026] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0027] 1 H NMR (500 MHz, CDCl 3 ) δ 8.58 (dd, J = 8.5, 1.0 Hz, 2H), 8.28 – 8.25(m, 1H), 8.07 – 8.03 (m, 1H), 7.72 – 7.67 (m, 1H), 7.63 – 7.56 (m, 4H); 13 CNMR (125 MHz, CDCl...

Embodiment 2

[0031] Example 2 Synthesis of derivative Ib ((R)n=hydrogen, (R')m=4-methyl)

[0032] Weigh 2 H - Benzothiazole (0.3 mmol, 40.6 mg), p-xylene (8.0 mmol, 848.6 mg), Selectfluor (0.3 mmol, 106.3 mg) and trifluoroacetic acid (0.45 mmol, 51.3 mg) in a 25 mL reaction tube, and then Add 2 mL of acetonitrile, react at 70 °C in an air atmosphere, and monitor by TLC. After about 8 h, the reaction is completed. The reaction solution is extracted with dichloromethane, the organic layer is concentrated to remove the solvent, and the concentrated solution is separated by column chromatography (elution The solvent is petroleum ether-ethyl acetate mixed solvent with a volume ratio of 1:0.05) to obtain a yellow solid, i.e. derivative Ib. The yield is 96%.

[0033] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0034] 1 H NMR (500 MHz, CDCl 3 ) δ 8.50 (d, J = 8.5 Hz, 2H), 8.28 – 8.24 (m,1H), 8.05 – 8.02 (m, 1H), 7.62 – 7.54 (m, 2H), 7.38 (d, J = 8.0 Hz, 2...

Embodiment 3

[0036] Example 3 Synthesis of derivative Ic ((R)n=hydrogen, (R')m=3-methyl)

[0037] Weigh 2 H - Benzothiazole (0.3 mmol, 40.6 mg), m-xylene (8.0 mmol, 848.6 mg), Selectfluor (0.3 mmol, 106.3 mg) and trifluoroacetic acid (0.45 mmol, 51.3 mg) in a 25 mL reaction tube, and then Add 2 mL of acetonitrile, react at 70 °C in an air atmosphere, and monitor by TLC. After about 8 h, the reaction is completed. The reaction solution is extracted with dichloromethane, the organic layer is concentrated to remove the solvent, and the concentrated solution is separated by column chromatography (elution The solvent is petroleum ether-ethyl acetate mixed solvent with a volume ratio of 1:0.05) to obtain a yellow solid, namely the derivative Ic. Yield 88%.

[0038] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0039] 1 H NMR (500 MHz, CDCl 3 ) δ 8.40 (d, J = 7.5 Hz, 1H), 8.30 (s, 1H), 8.29– 8.26 (m, 1H), 8.05 – 8.03 (m, 1H), 7.63 – 7.57 (m, 2H), 7.51 – 7.45 ...

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Abstract

The invention discloses a C2 substituted 2H-benzothiazole aryl acylated derivative, and a synthesis method and application thereof. The preparation method of the derivative comprises the following steps: mixing substituted 2H-benzothiazole and substituted methyl benzene, adding into a solvent, in the presence of an oxidizing agent Selectfluor and an additive trifluoroacetic acid, carrying out a heating and stirring reaction in the air atmosphere, performing TLC monitoring is conducted till the reaction is finished, and separating and purifying the obtained reaction liquid to obtain the target product C2 substituted 2H-benzothiazole aryl acylated derivative. The substituted methyl benzene used in the invention is low in price, easy to obtain and good in chemical stability, the method has the advantages of being high in atom economy, simple in catalytic system, free of transition metal catalysts, good in product yield, wide in substrate range and the like, and the prepared compound structure can be further optimized as an anti-tumor drug lead.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a C2-substituted 2 H - Benzothiazole aryl acylated derivatives and their synthesis methods and applications. Background technique [0002] 2 replaced by C2 H - Benzothiazole derivatives have a high degree of structural diversity and a wide range of biological activities, and are widely found in natural products and synthetic compounds. They have broad application prospects in the fields of medicine, pesticides, and industry. In the field of pesticides, it has insecticidal (Chin. J. Org., Chem. 2012, 32, 957), bactericidal (J. Am. Chem.Soc., 2008, 130, 2900), antiviral (Chin. J. Org. , Chem. 2014, 34, 419) and other biological activities; in the field of medicine, it has antibacterial (Mini-Rev. Org. Chem., 2012, 9, 44), antitumor (Curr. Med.Chem., 2009, 16, 2430 ), anticancer (J. Clin. Endocr. Metab., 1998, 83, 4474) and other biological activities; in industry, it c...

Claims

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Application Information

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IPC IPC(8): C07D277/64A61P35/00
CPCC07D277/64A61P35/00
Inventor 翁建全孙晓彤孔瑶蕾刘幸海
Owner ZHEJIANG UNIV OF TECH
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