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A kind of C2 substituted 2h-benzothiazole aryl acylation derivative and its synthetic method and application

A technology for the synthesis of benzothiazole aryl acyl derivatives, which is applied in the field of C2 substituted 2H-benzothiazole aryl acylate derivatives and their synthesis, can solve the problems of yield reduction, flammability and explosion of organic peroxide oxidants, The problems such as the increase of reaction by-products have been solved, and the catalytic system is simple, no transition metal catalyst is needed, and the product yield is good.

Active Publication Date: 2022-07-29
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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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 the same time, the above reactions all use aryl methyl ketone as the carbonyl source, but because the ketone is easily oxidized or reduced, it will lead to problems such as increased reaction by-products and reduced yield.

Method used

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  • A kind of C2 substituted 2h-benzothiazole aryl acylation derivative and its synthetic method and application
  • A kind of C2 substituted 2h-benzothiazole aryl acylation derivative and its synthetic method and application
  • A kind of C2 substituted 2h-benzothiazole aryl acylation derivative and its synthetic method and application

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, followed by 2 mL of acetonitrile was placed at 80 °C in an air atmosphere for the reaction, 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 of 1:0.05 petroleum ether-ethyl acetate mixed solvent) to obtain a yellow solid, namely derivative Ia. Yield 85%.

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

[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 (...

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 2 mL of acetonitrile was added, and the reaction was performed at 70 °C in an air atmosphere. TLC monitoring was performed. After about 8 h, the reaction was completed. 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 (eluting). The solvent is petroleum ether-ethyl acetate mixed solvent with a volume ratio of 1:0.05) to obtain a yellow solid, namely derivative Ib. Yield 96%.

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

[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 – ...

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 2 mL of acetonitrile was added, and the reaction was performed at 70 °C in an air atmosphere. TLC monitoring was performed. After about 8 h, the reaction was completed. 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 (eluting). The solvent is petroleum ether-ethyl acetate mixed solvent with a volume ratio of 1:0.05) to obtain a yellow solid, namely derivative Ic. The yield is 88%.

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

[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....

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Abstract

The invention discloses a C2 substitution 2 H Benzothiazole aryl acylation derivative and its synthetic method and application, described derivative preparation method is as follows: replace 2 H - Benzothiazole is mixed with substituted methylbenzene, added to a solvent, in the presence of oxidant Selectfluor and additive trifluoroacetic acid, heating and stirring reaction in air atmosphere, monitored by TLC until the end of the reaction, the obtained reaction solution is separated and purified to obtain the target product C2 replaces 2 H - Benzothiazole Arylated Derivatives. The substituted methylbenzene used in the present invention is cheap and easy to obtain, and has good chemical stability. The method has the advantages of high atom economy, simple catalytic system, no need for transition metal catalysts, good product yield, wide substrate range, and the like. The structure of the compound can be further optimized as an antitumor drug lead.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a kind of C2 substituted 2 H - Benzothiazole aryl acylated derivatives and synthetic methods and applications thereof. Background technique [0002] C2 substituted 2 H - Benzothiazole derivatives have a high degree of structural diversity and a wide range of biological activities, and widely exist in natural products and synthetic compounds. They have broad application prospects in the fields of medicine, pesticide, 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), anti-tumor (Curr. Med.Chem., 2009, 16, 2430 ), anticancer (J. Clin. Endocr. Metab., 1998, 83, 4474) and other biological activities; in industr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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