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Synthesis method for aromatic ring diindyl-5-alcohol compound

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of complicated operation steps, harsh reaction conditions, low atom economy, etc., and achieve the effects of high atom economy, simple operation and high efficiency.

Active Publication Date: 2019-06-28
HENAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these methods can effectively synthesize benzindol-5-alcohol compounds, there are still some problems that need to be solved urgently, such as: low atom economy of reaction, harsh reaction conditions and cumbersome operation steps, etc. These deficiencies also The practicability of the above method is greatly limited

Method used

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  • Synthesis method for aromatic ring diindyl-5-alcohol compound
  • Synthesis method for aromatic ring diindyl-5-alcohol compound
  • Synthesis method for aromatic ring diindyl-5-alcohol compound

Examples

Experimental program
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Embodiment 1

[0015]

[0016] 1a (0.5mmol, 160mg), solvent acetic acid (500μL) and zinc powder (2.5mmol, 163mg) were successively added into the reaction tube, and the reaction was stirred at room temperature under an air atmosphere for 4h. Then 10 mL of ethyl acetate was added to the reaction system and suction filtered. The filtrate was extracted with ethyl acetate (15 mL×3) and saturated sodium carbonate solution (20 mL), and the organic phases were combined and dried over anhydrous magnesium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=10:1) to obtain brown solid product 2a (116 mg, 90%). The characterization data of this compound are as follows: mp:63-64°C. 1 H NMR (400MHz, DMSO-d 6 )δ: 6.88(d, J=2.0Hz, 1H), 6.99(s, 1H), 7.28(t, J=7.6Hz, 1H), 7.36-7.40(m, 1H), 7.46(t, J=7.6 Hz, 2H), 7.52-7.56(m, 1H), 7.92-7.94(m, 2H), 8.16(d, J=8.0Hz, 1H), 8.52(d, J=8.4Hz, 1H), 9.42(s ,1H),11.73(s,1H). 13 C NMR (100MHz, DMSO-d 6 )δ: 100.6, 10...

Embodiment 2

[0018] 1a (0.5mmol, 160mg), solvent acetic acid (500μL) and zinc powder (1.5mmol, 98mg) were sequentially added into the reaction tube, and the reaction was stirred at room temperature under an air atmosphere for 4h. Then 10 mL of ethyl acetate was added to the reaction system and suction filtered. The filtrate was extracted with ethyl acetate (15 mL×3) and saturated sodium carbonate solution (20 mL), and the organic phases were combined and dried over anhydrous magnesium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=10:1) to obtain brown solid product 2a (93 mg, 72%).

Embodiment 3

[0020] 1a (0.5mmol, 160mg), solvent acetic acid (500μL) and zinc powder (5mmol, 327mg) were successively added into the reaction tube, and the reaction was stirred at room temperature under an air atmosphere for 4h. Then 10 mL of ethyl acetate was added to the reaction system and suction filtered. The filtrate was extracted with ethyl acetate (15 mL×3) and saturated sodium carbonate solution (20 mL), and the organic phases were combined and dried over anhydrous magnesium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=10:1) to obtain brown solid product 2a (106 mg, 82%).

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Abstract

The invention discloses a synthesis method for an aromatic ring diindyl-5-alcohol compound and belongs to the technical field of organic synthesis. The method is characterized in that zinc powder is used for promoting a cascade reaction of 5-oxo-benzoindoles-1-oxide or 5-oxo-thiophene diindyl-1-oxide, the aromatic ring diindyl-5-alcohol compound is directly synthesized, and in the whole process, operation is simple, and the efficiency is high; in the synthesis process, a noble metal catalyst does not need to be used, and the method has the advantages of being economical and environmentally friendly; the atom economy of the reaction is high, and the demand of environment-friendly chemistry is met; the application range of a substrate is wide.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing aromatic ring indole-5-alcohol compounds. Background technique [0002] Benzindole-5-ols not only have remarkable biological activity, but also have been widely used as intermediates in the synthesis of many fine chemicals. Based on its importance, research on new synthetic methods of this type of compound has always attracted the attention of chemists. At present, such compounds are mainly obtained through the following routes: 1) demethylation reaction of benzindole-5-methoxy; 2) 1-(2-oxo-2-phenylethyl)pyridinium salt and 1 - Condensation-demethylation reaction of amino-4-methoxynaphthalene; 3) Condensation reaction of 1,4-naphthoquinone and ethyl acetoacetate containing active methylene compounds, etc. Although these methods can effectively synthesize benzindol-5-alcohol compounds, there are still some problems that need to be ...

Claims

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Application Information

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IPC IPC(8): C07D209/60C07D495/04
Inventor 何艳丰田范学森
Owner HENAN NORMAL UNIV
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