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A kind of preparation method of multi-substituted 1,3,5-triazine

A multi-substitution and substituent technology, which is applied in the field of preparation of multi-substituted 1,3,5-triazines, can solve problems such as environmentally unfriendly by-products

Active Publication Date: 2020-10-30
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the range of substrates is wide, catalysts and oxidants are used in the reaction, and a large number of by-products that are not friendly to the environment are produced

Method used

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  • A kind of preparation method of multi-substituted 1,3,5-triazine
  • A kind of preparation method of multi-substituted 1,3,5-triazine
  • A kind of preparation method of multi-substituted 1,3,5-triazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] Add 1a (4mmol), sodium difluorochloroacetate (4mmol), cesium carbonate (8mmol) and acetonitrile (10mL) into the reaction flask, then heat the reaction at 120°C for 24 hours. After the reaction was completed, it was first quenched with water, then extracted with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate. After concentration, the product 3a was obtained by column chromatography with a mixed solvent of petroleum ether and ethyl acetate. The yield was 96%. Pale yellow solid, Mp: 74-75℃; 1 H NMR (600MHz, CDCl 3 ):δ9.26(s,1H),8.66-8.63(m,4H),7.63-7.59(m,2H),7.57-7.54(m,4H); 13 C NMR (150MHz, CDCl 3 ): δ171.3, 166.7, 135.5, 132.8, 128.9, 128.7.

Embodiment 2

[0023]

[0024] Add 1a (4mmol), sodium difluorochloroacetate (4mmol), sodium carbonate (8mmol) and acetonitrile (10mL) into the reaction flask, then heat the reaction at 120°C for 24 hours. After the reaction was completed, it was first quenched with water, then extracted with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate. After concentration, the product 3a was obtained by column chromatography with a mixed solvent of petroleum ether and ethyl acetate. The yield was 83%. Pale yellow solid, Mp: 74-75℃; 1 H NMR (600MHz, CDCl 3 ):δ9.26(s,1H),8.66-8.63(m,4H),7.63-7.59(m,2H),7.57-7.54(m,4H); 13 C NMR (150MHz, CDCl 3 ): δ171.3, 166.7, 135.5, 132.8, 128.9, 128.7.

Embodiment 3

[0026]

[0027] Add 1a (4mmol), sodium difluorochloroacetate (4mmol), potassium carbonate (8mmol) and acetonitrile (10mL) into the reaction flask, then heat the reaction at 120°C for 24 hours. After the reaction was completed, it was first quenched with water, then extracted with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate. After concentration, the product 3a was obtained by column chromatography with a mixed solvent of petroleum ether and ethyl acetate. The yield was 78%. Pale yellow solid, Mp: 74-75℃; 1 H NMR (600MHz, CDCl 3 ):δ9.26(s,1H),8.66-8.63(m,4H),7.63-7.59(m,2H),7.57-7.54(m,4H); 13 C NMR (150MHz, CDCl 3 ): δ171.3, 166.7, 135.5, 132.8, 128.9, 128.7.

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Abstract

The invention discloses a preparation method of polysubstituent 1,3,5-triazine. Specifically, substituen formamidine hydrochloride is used as a reactive substrate, chlorodifluoroacetic acid sodium salt is used as a carbon synthon, and the symmetrical or asymmetrical polysubstituent 1,3,5-triazine is obtained through fracture of carbon-chlorine, carbon-carbon and carbon-fluorine bonds under the action of equivalent inorganic base. The chemical structural general formula of the substituen formamidine hydrochloride is as shown in specification, and the inorganic is one selected from potassium carbonate, sodium carbonate, cesium carbonate. The preparation method disclosed by the invention has the advantages of easily available raw materials, no need for catalyst or oxidant, a wide variety of substrates, simple and convenient operation and environmental friendliness.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of multi-substituted 1,3,5-triazines. Background technique [0002] 1,3,5-Triazine is a very important class of nitrogen-containing heterocyclic compounds, which not only exhibit excellent biological activity, but also can be used as ligands for metal catalysis and organometallic materials. The traditional method generally all is to synthesize 2,4-diphenyl-1,3,5-triazine (Angew.Chem.1960,72,956; Chem.Ber.1963,96,3265; Monatsh.Chem.1995,126,99; Zhurnal Organiccheskoi Khimii,1987,23,2443), however, the substrate range is narrow, the yield is generally low and the reaction conditions are harsh. In recent years, some research groups have used substituted formamidine hydrochloride as substrate, N,N-dimethylformamide, dimethyl sulfoxide, fatty ether, tertiary amine, dichloromethane and other reagents as new carbon synthons , synthesized poly...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D251/22
Inventor 闫溢哲牛斌张艳艳崔畅李绍青刘延奇史苗苗
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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