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Polycyclic aromatic selenide derivatives and preparation method thereof

A technology for polycyclic aromatic selenide and derivatives is applied in the field of polycyclic aromatic selenide derivatives and their preparation, which can solve problems such as group compatibility limitation, achieve high atom economy, complex and diverse structures, and cheap reagents Effect

Inactive Publication Date: 2019-03-22
YANCHENG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Copper and nickel catalysts also need to add ligands or other additives to play a catalytic role, and the addition of additional reagents must also limit the reaction conditions and the compatibility of the groups in the molecular structure of the raw materials.

Method used

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  • Polycyclic aromatic selenide derivatives and preparation method thereof
  • Polycyclic aromatic selenide derivatives and preparation method thereof
  • Polycyclic aromatic selenide derivatives and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0053] A polycyclic aromatic selenide derivative provided in this example has a structural formula as shown in formula (I).

[0054]

[0055] This embodiment also provides a method for preparing the above-mentioned polycyclic aromatic selenide derivatives:

[0056] Diethyl malonate bridged diyne compound (20mmol) and phenylacetylene bromide (48mmol) were added to the reaction flask, mixed in Pd(PPh 3 ) 2 Cl 2 and CuI as catalyst in the anhydrous oxygen-free catalytic system, wherein the amount of catalyst is 0.8mmol, Pd(PPh 3 ) 2 Cl 2 :CuI=3:1. With triethylamine (50mmol) as the base and anhydrous acetonitrile (40mL) as the solvent, the reaction was stirred at room temperature for 12 hours, and the reaction product was successively washed with 15% hydrochloric acid solution, 10% sodium bicarbonate solution, and saturated saline, respectively. Washing; then extracted with ethyl acetate, spin-dried under reduced pressure, column chromatography (the volume ratio of ethyl...

Embodiment 2

[0064] This embodiment provides a polycyclic aromatic selenide derivative, the structural formula of which is shown in formula (II).

[0065]

[0066] This embodiment also provides a method for preparing the above-mentioned polycyclic aromatic selenide derivatives:

[0067] Diethyl malonate bridged diyne compound (20mmol) and p-methylphenylacetylene bromide (40mmol) were added to the reaction flask, mixed in Pd(PPh 3 ) 2 Cl 2 and CuI as catalyst in the anhydrous oxygen-free catalytic system, wherein the amount of catalyst is 0.6mmol, Pd(PPh 3 ) 2 Cl 2 :CuI=3.2:1. With triethylamine (60mmol) as the base and anhydrous acetonitrile (25mL) as the solvent, the reaction was stirred at room temperature for 20 hours, and the reaction product was successively washed with 15% hydrochloric acid solution, 10% sodium bicarbonate solution, and saturated saline, respectively. Washing; then extracted with ethyl acetate, spin-dried under reduced pressure, column chromatography (the vo...

Embodiment 3

[0075] This embodiment provides a polycyclic aromatic selenide derivative, the structural formula of which is shown in formula (III).

[0076]

[0077] This embodiment also provides a method for preparing the above-mentioned polycyclic aromatic selenide derivatives:

[0078] Diisopropyl malonate bridged diyne compound (20mmol) and p-ethylphenylacetylene bromide (60mmol) were added to the reaction flask, mixed in Pd(PPh 3 ) 2 Cl 2 and CuI as catalyst in the anhydrous oxygen-free catalytic system, wherein the amount of catalyst is 1.0mmol, Pd(PPh 3 )2 Cl 2 :CuI=2.8:1. With triethylamine (100mmol) as the base and anhydrous acetonitrile (33mL) as the solvent, the reaction was stirred at room temperature for 16 hours, and the reaction product was successively washed with 15% hydrochloric acid solution, 10% sodium bicarbonate solution and saturated saline respectively Washing; then extracted with ethyl acetate, spin-dried under reduced pressure, column chromatography (the vo...

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Abstract

The invention relates to the field of organic synthesis, in particular to a polycyclic diaryliodonium type derivative and a preparation method thereof. Compared with a common selenide derivative, the polycyclic diaryliodonium type derivative, with the existence of polycyclic, is more complex and various in structure, and shows a wide use prospect in chemical engineering and clinical medicines. The preparation method for the polycyclic diaryliodonium type derivative comprises the following steps: mixing and reacting diyne compounds, arylethynylene bromine, anhydrous acetonitrile, a transition metal catalyst and organic alkali in an anhydrous oxygen-free system to obtain an intermediate; and mixing and reacting the intermediate, diphenyl diselenide and methylbenzene at a temperature of 115-125 DEG C. The preparation method overcomes the defects such as a too long route in conventional reaction, rigorous substrate and reaction condition requirements and limited substituent functional group expansion.

Description

technical field [0001] The invention relates to the field of organic synthesis, and in particular to a polycyclic aromatic selenide derivative and a preparation method thereof. Background technique [0002] Molecules containing aryl selenide structural units are widely used in medicine, agriculture and other fields. Some biologically active compounds containing aryl selenide fragments have demonstrated their unique pharmacological effects in the study of pharmaceutical molecules. As an antioxidant, selenium compound is an important compound for treating various cancers, heart disease, and inflammation. For example, selenide compound I as a retinoid (AtRA) can affect cell differentiation. [0003] [0004] With the wide application of organoselenium compounds in synthesis, the application of organoselenium compounds in organic synthesis has been paid more and more attention in recent years. The synthetic route of selenide compounds has aroused the active thinking of coun...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C391/02
CPCC07C391/02
Inventor 李立冬吴玉芹张奇于凉云许琦
Owner YANCHENG INST OF TECH
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