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Diaryl thioether derivatives, and preparation method thereof

A technology of diaryl sulfide and derivatives, which is applied in the field of diaryl sulfide derivatives and their preparation, can solve problems such as group compatibility limitations, and achieve high atom economy, complex and diverse structures, and substrate Composite simple effects

Inactive Publication Date: 2017-08-15
YANCHENG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Copper and nickel catalysts also need to add ligands and 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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  • Diaryl thioether derivatives, and preparation method thereof
  • Diaryl thioether derivatives, and preparation method thereof
  • Diaryl thioether derivatives, and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0055] A diaryl sulfide derivative provided in this embodiment has a structural formula as shown in formula (I).

[0056]

[0057] This embodiment also provides a method for preparing the above-mentioned diaryl sulfide derivatives:

[0058] Diethyl malonate bridged diacetylene compound (20mmol) and p-chlorophenylacetylene 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 acetate an...

Embodiment 2

[0066] A diaryl sulfide derivative provided in this example has a structural formula as shown in formula (II).

[0067]

[0068] This embodiment also provides a method for preparing the above-mentioned diaryl sulfide derivatives:

[0069] Add N,N-dipropargyl-p-toluenesulfonamide (20mmol) and 1-bromoheptyne (60mmol) into the reaction flask, mix in Pd(PPh 3 ) 2 Cl 2 and CuI as catalyst in anhydrous and 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 volume ratio of ethyl acetate and petroleum ether in the eluent w...

Embodiment 3

[0077] A diaryl sulfide derivative provided in this example has a structural formula as shown in formula (III).

[0078]

[0079] This embodiment also provides a method for preparing the above-mentioned diaryl sulfide derivatives:

[0080] Diisopropyl malonate bridged diyne compound (20mmol) and p-methoxyphenylacetylene bromide (40mmol) were added to the reaction flask, mixed in Pd(PPh 3 ) 2 Cl 2 and CuI as catalyst in anhydrous and oxygen-free catalytic system, wherein the amount of catalyst is 1.0mmol, Pd(PPh 3 ) 2 Cl 2 :CuI=3:1. With triethylamine (100mmol) as the base and anhydrous acetonitrile (29mL) 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 volume ratio of ethyl acetate and pe...

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Abstract

The invention belongs to the field of organic synthesis, and especially relates to diaryl thioether derivatives, and a preparation method thereof. Compared with common thioether derivatives, thediaryl thioether derivatives possess following characteristics: the diaryl thioether derivatives are polycyclic compounds; the structure is more complex and diverse; and application prospect is more promising. The preparation method comprises following steps: in a water-free oxygen-free system, a diyne compound, a hydrocarbyl alkyne bromide, anhydrous acetonitrile, a transition-metal catalyst, and an organic base are mixed and reacted so as to obtain an intermediate; at 90 to 115 DEG C, the intermediate, an aryl disulfide, and methylbenzene are mixed and reacted. According to the preparation method, substrate synthesis is simple; the reagents are relatively cheap; the target molecules are obtained with high atom economy; the preparation method is green, and is friendly to the environment; and a valuable approach is provided for industrialized production of the diaryl thioether derivatives.

Description

technical field [0001] The invention relates to the field of organic synthesis, and in particular to a diaryl sulfide derivative and a preparation method thereof. Background technique [0002] Diaryl sulfide derivatives are widely used in medicine, agriculture, dyes, light chemical products, high polymer materials and other fields. Some biologically active diaryl sulfide compounds have demonstrated their unique pharmacological effects in the study of medical molecules. For example, diaryl sulfide compound I is used as a leukocyte antidote (LFA-1), and compound II is used as a Tubulin inhibitors can significantly inhibit the growth of human MCF-7 breast cancer cells. [0003] [0004] With the wide application of organosulfur compounds in synthesis, the application of organosulfur compounds in organic synthesis has received widespread attention in recent years. The synthetic route of diaryl sulfide compounds has aroused the active thinking of countless organic synthesis ...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C321/30C07D209/44
CPCC07C319/14C07C67/28C07C321/30C07D209/44C07C69/38
Inventor 李立冬吴玉芹许琦于凉云张奇
Owner YANCHENG INST OF TECH
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