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Synthesis method of aryl selenocyanate compounds

A synthesis method and aryl selenium technology, applied in organic chemistry and other directions, can solve problems such as limiting reaction expansion, and achieve the effects of good tolerance, high yield and low environmental pollution

Active Publication Date: 2020-01-24
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] The problem of this method is the same as the above method four, the reaction substrates are limited to electron-rich arenes, which limits the expansion of the reaction

Method used

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  • Synthesis method of aryl selenocyanate compounds
  • Synthesis method of aryl selenocyanate compounds
  • Synthesis method of aryl selenocyanate compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1. Synthesis of 2-methylbenzeneselenocyanine.

[0048] Add 27.2 mg of o-tolueneboronic acid, 115.3 mg of potassium selenocyanate, 30.2 mg of tetrabutylammonium acetate and 10 mL of acetonitrile into a three-port reaction tube equipped with a magnetic stirring bar. Under the conditions of air and room temperature, the reaction was carried out by electricity for 3 hours, and the constant current was 10mA. After the reaction was completed, it was simply filtered, concentrated by rotary evaporation, and put on the column. Using pure petroleum ether and 2% ethyl acetate as mobile phases in turn, 31.4 mg of 2-methylbenzeneselenocyanate was obtained with a yield of 80%.

[0049] Product 2-methylphenylselencyanide: 1 H NMR (400MHz, CDCl 3 ): δ7.72(d, J=7.6Hz, 1H), 7.22(t, J=7.6Hz, 1H), 2.49(s, 3H); 13 C NMR (100MHz, CDCl 3 ): δ139.9, 134.0, 131.2, 130.3, 127.8, 123.0, 101.2, 22.3.

Embodiment 2

[0050] Example 2. Synthesis of 4-methylphenylselencyanide.

[0051] Add 27.2 mg of p-tolueneboronic acid, 115.3 mg of potassium selenocyanate and 10 mL of acetonitrile into a three-port reaction tube equipped with a magnetic stirring bar. Under the conditions of air and room temperature, electricity was reacted for 5 hours, and the constant current was 10mA. After the reaction was completed, it was simply filtered, concentrated by rotary evaporation, and put on the column. Using pure petroleum ether and 2% ethyl acetate as mobile phases in turn, 25.9 mg of 4-methylphenylselenocyanate was obtained with a yield of 66%.

[0052] Product 4-methylphenylselencyanide: 1 H NMR (400MHz, CDCl 3): δ7.53(d, J=8.0Hz, 2H), 7.21(d, J=8.0Hz), 2.38(s, 3H); 13 C NMR (100MHz, CDCl 3 ): δ140.4, 133.3, 131.1, 117.9, 101.7, 21.2.

Embodiment 3

[0053] Example 3. Synthesis of 2,6-dimethylbenzenselencyanide.

[0054] Add 30.0 mg of 2,6-dimethylphenylboronic acid, 115.3 mg of potassium selenocyanate, 8.2 mg of sodium acetate and 10 mL of acetonitrile into a three-port reaction tube equipped with a magnetic stirring bar. Under the conditions of air and room temperature, electricity was reacted for 5 hours, and the constant current was 15mA. After the reaction was completed, it was simply filtered, concentrated by rotary evaporation and put on the column. Using pure petroleum ether and 2% ethyl acetate as the mobile phase in turn, 17.7 mg of 2,6-dimethylbenzenselencyanide was obtained with a yield of 42%.

[0055] Product 2,6-dimethylbenzenselencyanide: 1 H NMR (400MHz, CDCl 3 ): δ7.23(t, J=7.6Hz, 1H), 7.16(d, J=7.6Hz, 2H); 13 C NMR (100MHz, CDCl 3 ): δ143.1, 130.9, 128.8, 123.9, 101.1, 24.5.

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Abstract

The invention relates to the field of synthesis of chemical products, in particular to a synthesis method of aryl selenocyanate compounds. The method starts from arylboronic acid which is easy to obtain, KSeCN which is the cheapest is used as a selenocyanate source, environment-friendly pollution-free current is adopted as a reaction driver, and under conditions of air and a room temperature, arylselenocyanates are efficiently synthesized. Compared with a conventional aryl selenocyanate synthesis method, the method has the obvious advantages that reaction raw materials (including the arylboronic acid) are cheap and easy to obtain, the current causes the lowest pollution to the environment, multiple kinds of functional groups of aromatic rings have good tolerance, yields are high, and thelike. The method can be applied to synthesis of a wide variety of fields of medicines, materials, natural products and the like of the industrial circles and the academic circles.

Description

technical field [0001] The invention relates to the synthesis and preparation of a class of chemical products, more specifically to the synthesis method of aryl selenocyanide. Background technique [0002] The introduction of selenocyanine group (-SeCN) on aromatic compounds can significantly change the physical, chemical and biological properties of aromatic compounds. Aryl selenocyanides not only have excellent biological activities, such as antioxidant and antitumor activities, but also are often used as synthons in organic synthesis reactions to further construct aryl selenides and selenium nitrogen heterocyclic compounds. Therefore, the synthesis of related aryl selenocyanides has important theoretical significance and industrial practical value. At present, the method for synthesizing aryl selenocyanide has: [0003] Method 1, using aryl diazonium salt and potassium selenocyanate to prepare aryl selenocyanide. [0004] [0005] The problem of this method is that ...

Claims

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Application Information

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IPC IPC(8): C07C391/02
CPCC07C391/02
Inventor 蔡琥付拯江何冬冬郝广果
Owner NANCHANG UNIV
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