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3-ethylcyanobenzothiophene compound as well as synthesis and application method thereof

A technology of ethyl cyanobenzene and synthesis method, which is applied in the directions of biocide, organic chemistry, drug combination, etc., can solve the problems of high environmental harm of halogen-containing waste liquid, not conforming to green chemistry, poor reaction selectivity, etc., and achieves good expansion. performance, lower synthesis cost, and fewer reaction steps

Inactive Publication Date: 2020-09-18
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Wherein, the method for preparing benzothiophene compounds through intramolecular cyclization of o-alkynylthiophenol (thioether) mainly includes: 1. using Pd / Cu as a catalyst, through I 2 、Br 2 , NBS, p-O 2 NC 6 h 4 SCl or PhSeCl carry out electrophilic cyclization to prepare benzothiophene compound, and this method condition is mild, and yield is high, but the halogen-containing waste liquid that produces is bigger to environmental hazards, does not accord with the concept of green chemistry; ② with Au(I) -IPr is used as a catalyst to prepare benzothiophene compounds through cyclization reaction. This method has good substrate adaptability, but the catalyst is expensive and the reaction conditions are relatively harsh; Cyclization reaction to prepare benzothiophene compounds, this method can simultaneously build multiple chemical bonds to obtain benzothiophene derivatives with various structures, but this type of reaction has poor selectivity, many by-products, and low yield

Method used

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  • 3-ethylcyanobenzothiophene compound as well as synthesis and application method thereof
  • 3-ethylcyanobenzothiophene compound as well as synthesis and application method thereof
  • 3-ethylcyanobenzothiophene compound as well as synthesis and application method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Synthesis of 3-ethylcyano group substituted benzothiophene compound 1

[0040] Add 2-(4-methylphenylethynyl) anisole (50.9mg, 0.2mmol), DTPB (117.0mg, 0.8mmol), and disodium hydrogen phosphate (283.9mg, 0.2mmol) to a 25mL round bottom flask in sequence , Acetonitrile (2mL), heated to 130°C under nitrogen protection, stirred for 24h, extracted with 2x8mL dichloromethane, combined the organic phases, dried over anhydrous sodium sulfate or anhydrous magnesium sulfate overnight, spin-dried, and used petroleum ether: ethyl acetate = 2:1 through the column to obtain 29.0 mg of the target compound (compound 1), a white solid, with a yield of 55%.

[0041] Product structure verification (see attached Figure 1A-1B ):

[0042] 1 H NMR (δ, ppm, 400MHz, CDCl 3 ): δ7.85(dd,J=14.4,8.0Hz,2H), 7.50(td,J=7.8,1.3Hz,1H),7.44-7.40(m,3H),7.32(d,J=7.8Hz, 2H), 3.88(s, 2H), 2.44(s, 3H);

[0043] 13 C NMR(δ,ppm,100MHz,CDCl 3 ): δ143.0, 139.2, 138.8, 138.7, 129.9, 129.8, 129.5, 125.0, 122.5...

Embodiment 2

[0044] Example 2: Synthesis of 3-ethylcyano group substituted benzothiophene compound 3

[0045] Add 2-(4-chlorophenylethynyl) anisole (51.8 mg, 0.2 mmol), DTPB (117.0 mg, 0.8 mmol), and disodium hydrogen phosphate (283.9 mg, 0.2 mmol) to a 25 mL round bottom flask in sequence, Acetonitrile (2mL), heated to 130°C under nitrogen protection, stirred for 24h, extracted with 2x8mL dichloromethane, combined the organic phases, dried over anhydrous sodium sulfate or anhydrous magnesium sulfate overnight, spin-dried, and used petroleum ether: ethyl acetate = Pass the column 2:1 to obtain 34.0 mg of the target compound (compound 3), a white solid, with a yield of 60%.

[0046] Product structure verification (see attached Figure 3A-3B ):

[0047] 1 H NMR (δ, ppm, 400MHz, CDCl 3 ):δ7.98–7.77(m,2H), 7.59–7.32(m,6H), 3.86(s,2H);

[0048] 13 C NMR(δ,ppm,100MHz,CDCl 3 ): δ141.4, 138.8, 138.5, 135.4, 131.2, 130.9, 129.4, 125.4, 125.2, 122.5, 121.6, 119.6, 116.9, 15.8.

Embodiment 3

[0049] Example 3: Selection of the amount of free radical initiator

[0050] The experimental conditions and feeding amount of this example are the same as those of Example 1, and different amounts of free radical initiators are selected for the experiment, as shown in Table 1.

[0051] Table 1 Reaction results of different amounts of free radical initiators

[0052]

[0053]

[0054] It can be seen from Table 1 that the reaction effect and yield of DTPB with a dosage of 4 to 6 equiv are good to excellent, and the dosage of DTPB is preferably 4 equiv.

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Abstract

The invention provides a 3-ethylcyanobenzothiophene compound and a synthesis and application method thereof, and belongs to the technical field of heterocyclic compound synthesis. The 3-ethylcyanobenzothiophene compound has the following structure shown in the specification, wherein R1 is any one of H, methoxy, fluorine and bromine; and R2 is any one of phenyl, p-methoxyphenyl, p-methyl phenyl andp-chloro phenyl. The 3-ethylcyanobenzothiophene compound has the advantages of short synthesis steps, simple operation, low cost, and the like.

Description

Technical field [0001] The application relates to a 3-ethylcyanobenzothiophene compound and its synthesis and application methods, belonging to the technical field of heterocyclic compound synthesis. Background technique [0002] Benzothiophene and its derivatives are one of the aromatic heterocyclic compounds containing sulfur atoms, and its derivatives are widely used in medicine, dyes, new polymers and luminescent materials. In medicine, the drugs with benzothiophene as the pharmacophore include bripiprazole, iglipizin L-proline salt, sertaconazole nitrate, etc.; at the same time, benzothiophene derivatives can also be used for synthesis New materials such as liquid crystal polymers and superconductors are a new type of organic optoelectronic materials, which have good application prospects in the field of organic electronic materials such as new batteries. For example, S,S-dioxo-dibenzothiophene is a good Luminescent material. However, the reaction of benzothiophene is less...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/60A61P33/00A01P5/00A01P7/00
CPCA61P33/00C07D333/60
Inventor 沈润溥蔡涛徐慧婷吴春雷杜奎盛国栋吴永华
Owner SHAOXING UNIVERSITY