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Selenized/sulfurized sulfuryl arylamine compound and selenylation/sulfurization method thereof

A technology for sulfurizing sulfonyl arylamine and sulfonyl arylamine, which is applied in the fields of sulfide preparation, organic chemistry, antibacterial drugs, etc., can solve the problems of complex reaction system, cumbersome post-processing, long reaction time, etc., and achieves easy preparation conditions. The effect of obtaining, wide derivation and strong antibacterial activity

Active Publication Date: 2020-05-19
CHENGDU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods can synthesize organic selenium (sulfur) compounds with high chemical and site selectivity, but there are still shortcomings such as complex reaction system, long reaction time, and cumbersome post-treatment.

Method used

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  • Selenized/sulfurized sulfuryl arylamine compound and selenylation/sulfurization method thereof
  • Selenized/sulfurized sulfuryl arylamine compound and selenylation/sulfurization method thereof
  • Selenized/sulfurized sulfuryl arylamine compound and selenylation/sulfurization method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Mix 0.25 mmol of sulfonyl arylamine substrate 1 and 2 times the molar amount of diaryl diselenide 2, and add catalyst Pd(TFA) in a molar amount of 10% of the molar amount of the sulfonyl aryl amine substrate 2 and oxidant Cu(OAc) of 2 times the molar amount of sulfonyl arylamine substrate 2 Add 3 mL of dry toluene to the reaction tube under the protection of argon, and react at 125°C for 12 hours to obtain a mixed liquid. After the reaction, add water and ethyl acetate to extract three times, combine the organic layers, and anhydrous Na 2 SO 4 The organic layer was dried, filtered, concentrated, separated and purified by silica gel column chromatography (mobile phase: petroleum ether / ethyl acetate=30 / 1-5 / 1) to obtain selenide sulfonyl arylamine compound 3.

[0049]

[0050] R 1 for H, -CH 3 , -Cl, -F, -Br, -CF 3 ,-Et,-OCH 3 , 1,3 dioxane, 1,4 dioxane, benzene ring, one of bromobenzene, R 1 is a para and / or meta substitution;

[0051] When it is 1,3-dioxane or ...

Embodiment 2

[0062] Add the catalyst Pd (TFA) of 10% molar quantity of sulfonyl arylamine substrate molar quantity 2 and oxidant Cu(OAc) of 2 times the molar amount of sulfonyl arylamine substrate 2 Add 3 mL of dry toluene to the reaction tube under the protection of argon, and react at 125°C for 12 hours to obtain a mixed liquid. After the reaction, add water and ethyl acetate to extract three times, combine the organic layers, and anhydrous Na 2 SO 4 The organic layer was dried, filtered, concentrated, separated and purified by silica gel column chromatography (mobile phase: petroleum ether / ethyl acetate=30 / 1-5 / 1) to obtain sulfonyl arylamine compound 5.

[0063]

[0064] R 1 for -CH 3 , -Cl, -CF 3 ,-Et,-OCH 3 , 1,3 dioxane;

[0065] R 2 for -CH 3 ;

[0066] R 3 is -Ph(phenyl), One of them, where R 4 It is one of -Cl, methyl, and methoxy.

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Abstract

The invention provides a selenized / sulfurized sulfonyl arylamine compound and a selenylation / sulfurization method thereof, wherein sulfamide is used as a guide group, and a transition metal palladiumcatalytic ortho-position C (sp<2>)-H selective selenylation / sulfurization reaction is constructed through a weak coordination effect to synthesize a series of selenized / sulfurized sulfonyl arylamine derivatives.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a transition metal catalyzed C(sp) assisted by a directing group. 2 )—H selenium (sulfurization) reaction. Background technique [0002] In recent years, organic selenium (sulfur) compounds have been widely used in organic synthesis, functional materials, fluorescent probes and other fields. In addition, such compounds exhibit anti-tumor, anti-oxidation, anti-inflammatory, anti-bacterial, anti-viral and other biological activities, so they are also of great significance in the field of drug development. [0003] Using traditional synthesis methods, organic selenium (sulfur) compounds are mainly obtained through the reverse coupling reaction of aryl halides, aryl amines or aryl borates with selenium (sulfur) ethers (alcohols). This method has the disadvantages of substrate limitations, cumbersome steps, and the need for pre-functionalization of the substrate. [0004] Transiti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/02C07D317/66C07D319/18C07D333/34C07C319/14C07C323/37A61P31/04
CPCC07C391/02C07D317/66C07D319/18C07D333/34C07C319/14C07C323/37A61P31/04C07C2601/02
Inventor 辜玲慧马文博方新月翁正云
Owner CHENGDU UNIV
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