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Preparation method of C2-substituted 2H-benzothiazole hydroxyalkylated derivative

A technology of benzothiazole hydroxyalkyl and benzothiazole, which is applied in the field of preparation of C2-substituted 2H-benzothiazole hydroxyalkylated derivatives, can solve problems such as high price of Selectfluor, and achieves easy availability of catalyst and simple catalytic system. , the effect of mild reaction conditions

Active Publication Date: 2020-11-20
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method avoids the pollution of transition metal catalysts, the price of Selectfluor is relatively expensive

Method used

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  • Preparation method of C2-substituted 2H-benzothiazole hydroxyalkylated derivative
  • Preparation method of C2-substituted 2H-benzothiazole hydroxyalkylated derivative
  • Preparation method of C2-substituted 2H-benzothiazole hydroxyalkylated derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 Derivative Ia ((R)n=H, R 1 = H, R 2 = methyl) synthesis

[0024] Weigh 2 H - Benzothiazole (0.3 mmol, 40.6 mg), ethanol (6.0 mmol, 276.4 mg) and 1.5 mol% Eosin B were placed in a 25 mL reaction tube, then 2 mL of acetonitrile was added, and placed under a 20 W power LED white light reaction at room temperature, TLC monitoring, after about 16 h, the reaction was completed, the reaction solution was concentrated to remove the solvent, and the concentrated solution was separated by column chromatography (the eluent was a mixed solvent of sherwood oil-ethyl acetate with a volume ratio of 1: 1 ) to obtain a yellow solid, the derivative Ia. Yield 78%.

[0025] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0026] 1 H NMR (500 MHz, CDCl 3 ) δ 7.96 (d, J = 8.0 Hz, 1H), 7.86 (d, J = 8.0 Hz,1H), 7.45 (dd, J = 8.0, 7.0 Hz, 1H), 7.36 (t, J = 8.0 Hz, 1H), 5.25 (q, J =6.5 Hz, 1H), 3.81 (br, 1H), 1.70 (d, J = 6.5 Hz, 3H). 13...

Embodiment 2

[0027] Example 2 Derivative Ib ((R)n=H, R 1 = H, R 2 = ethyl) synthesis

[0028] Weigh 2 H - Benzothiazole (0.3 mmol, 40.6 mg), n-propanol (6.0 mmol, 360.6 mg) and 3.0 mol% Eosin B were placed in a 25 mL reaction tube, then 2 mL of acetonitrile was added, and placed under a 20 W power LED white light Reaction under light irradiation, stirring reaction at room temperature, TLC monitoring, after about 18 h, the reaction was completed, the reaction solution was concentrated to remove the solvent, and the concentrated solution was separated by column chromatography (the eluent was petroleum ether-ethyl acetate with a volume ratio of 1:1 mixed solvent) to obtain a white solid, namely derivative Ib. The yield is 70%.

[0029] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0030] 1 H NMR (500 MHz, CDCl 3 ) δ 7.98 (d, J = 8.5 Hz, 1H), 7.88 (d, J = 8.0 Hz,1H), 7.50 – 7.44 (m, 1H), 7.41 – 7.35 (m, 1H), 5.05 (dd, J = 7.5, 5.0 Hz,1H), 3.70 (br, ...

Embodiment 3

[0031] Example 3 Derivative Ic ((R)n=H, R 1 = methyl, R 2 = methyl) synthesis

[0032] Weigh 2 H - Benzothiazole (0.3 mmol, 40.6 mg), isopropanol (3.0 mmol, 180.3 mg) and 1.5 mol% Eosin B in a 25 mL reaction tube, then add 2 mL of acetonitrile, and place under a 20 W LED white light Reaction, stirring reaction at room temperature, TLC monitoring, after about 16 h, the reaction ends, the reaction solution is concentrated to remove the solvent, and the concentrated solution is separated by column chromatography (the eluent is a mixed solvent of petroleum ether-ethyl acetate with a volume ratio of 1: 1) A white solid, the derivative Ic, was obtained. The yield is 85%.

[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 8.00 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 8.0 Hz,1H), 7.48 (t, J = 7.5 Hz, 1H), 7.38 (t, J = 7.0 Hz, 1H), 3.35 (br, 1H), 1.77(s, 6H). 13 C NMR (125 MHz, CDCl 3 ) δ 180.10, 153.05, 13...

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Abstract

The invention discloses a preparation method of a C2-substituted 2H-benzothiazole hydroxyalkylated derivative. The preparation method comprises the following steps: mixing substituted 2H-benzothiazolewith fatty alcohol, taking an organic dye photosensitizer as a catalyst, carrying out a normal-temperature stirring reaction in a solvent under the protection of nitrogen and the irradiation of an LED white light lamp, carrying out TLC monitoring until the reaction is finished, and carrying out separation and purification on a reaction solution to obtain the C2-substituted 2H-benzothiazole hydroxyalkylated derivative. By adopting the technology, a cheap and readily available organic dye is used as the catalyst, the new method for synthesizing the 2H-benzothiazole C2 hydroxyalkylated derivative through visible light induction is simple in catalytic system, mild in reaction condition, cheap and readily available in catalyst and good in yield.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a C2-substituted 2 H - Process for the preparation of hydroxyalkylated derivatives of benzothiazoles. Background technique [0002] 2 replaced by C2 H - Benzothiazole derivatives are nitrogen-containing heterocyclic compounds that widely exist in nature. They have spectral biological activity and pharmacological activity. In addition to their high selectivity, they play an important role in many fields such as medicine and pesticides. For example, in the field of pesticides, there are herbicides (Bioorg. Med. Chem. Lett., 2016, 26, 1854), insecticides (Pharmazie, 2003, 58, 527), fungicides (Molecules, 1997, 2, 36), antiviral ( Chin. J. Org.Chem., 2007, 27, 279) and other biological activities; in the field of medicine, it has antibacterial (Eur. J. Med. Chem., 2010,45, 1323), antitumor (Brit. J. Cancer, 88, 470), anticancer (Eur. J. Med. Chem., 54, 447) and other bio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/64
CPCC07D277/64
Inventor 翁建全孔瑶蕾孙晓彤
Owner ZHEJIANG UNIV OF TECH
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