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Aryl alkyl thioether derivatives, and preparation method thereof

A technology for aryl alkyl sulfides and derivatives, which is applied in the field of aryl alkyl sulfide derivatives and their preparation, can solve problems such as group compatibility limitations, achieve high atom economy, complex and diverse structures, Simple effect of substrate synthesis

Inactive Publication Date: 2017-08-15
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 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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  • Aryl alkyl thioether derivatives, and preparation method thereof
  • Aryl alkyl thioether derivatives, and preparation method thereof
  • Aryl alkyl thioether derivatives, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] An aryl alkyl sulfide derivative provided in this example has a structural formula as shown in formula (I).

[0058]

[0059] 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 acetate and petroleum ether in the eluent was 1:40) to obtain a light brown solid product.

[0060] Under the condition of 95° C., t...

Embodiment 2

[0067] An aryl alkyl sulfide derivative provided in this example has a structural formula as shown in formula (II).

[0068]

[0069] This embodiment also provides a method for preparing the above-mentioned aryl alkyl sulfide derivatives:

[0070] 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 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 ac...

Embodiment 3

[0078] An aryl alkyl sulfide derivative provided in this example has a structural formula as shown in formula (III).

[0079]

[0080] Diisopropyl malonate bridged diyne compound (20mmol) and p-fluorophenylacetylene bromide (60mmol) 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=2.8:1. With triethylamine (40mmol) 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 volume ratio of ethyl acetate and petroleum ether in the eluent was 1:60) to obtain a light brown solid product.

[0081] Under the condit...

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Abstract

The invention belongs to the field of organic synthesis, and especially relates to aryl alkyl thioether derivatives, and a preparation method thereof. Compared with common thioether derivatives, the aryl alkyl thioether derivatives possess following characteristics: the aryl alkyl thioether derivatives are polycyclic compounds; the structure is more complex and diverse; application prospect in the field of chemical production and clinical medicine 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 100 DEG C, the intermediate, alkyl disulfide, and methylbenzene are mixed and reacted. The preparation method is capable of solving problems in the prior art that reaction route is too long; requirements on substrates and reaction conditions are strict; and expansion of replaced function groups is limited.

Description

technical field [0001] The invention relates to the field of organic synthesis, and in particular to an aryl alkyl sulfide derivative and a preparation method thereof. Background technique [0002] Aryl alkyl sulfide derivatives are widely used in medicine, dyes, light chemical products, agriculture, high polymer materials and other fields. Some biologically active aryl alkyl sulfide compounds have demonstrated their unique pharmacological effects in the study of medical molecules. For example, compound I containing aryl alkyl sulfide structural units can effectively inhibit the viral protease ( HIVPr) is an important drug for the treatment of AIDS. [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 aryl alkyl sulfide compounds has aroused the active thinking of many organic chemists, and some effective...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/62C07C319/14
CPCC07C323/62
Inventor 吴玉芹李立冬王玉琴严新许琦
Owner YANCHENG INST OF TECH
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