Thioetherified aromatic heterocyclic compound as well as preparation method and application thereof

A technology for aromatic heterocycles and compounds, which is applied in the field of thioetherified aromatic heterocycles and their preparation, can solve problems such as unfavorable industrial production, increase the difficulty and cost of obtaining reaction raw materials, and achieves low cost, easy industrialization, and substrates. Wide choice of effects

Inactive Publication Date: 2021-10-01
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Hostier et al. reported a method for constructing C-S without using organometallic or transition metal catalysts, which was achieved by prefunctionalization of reagents (Hostier, T., et al. (2015). "TFA- promoted direct C-H sulfenylation at the C 2 position of non-protected indoles."Chemical Communications 51(73):13898-13901.), although this method avoids the use of transition metals as catalysts, the introduction of pre-functionalized reagents increases the difficulty and difficulty of obtaining reaction raw materials cost, not conducive to industrial production

Method used

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  • Thioetherified aromatic heterocyclic compound as well as preparation method and application thereof
  • Thioetherified aromatic heterocyclic compound as well as preparation method and application thereof
  • Thioetherified aromatic heterocyclic compound as well as preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0036] A kind of thioetherification aromatic heterocyclic compound, its molecular structural formula is as follows figure 1 Chinese formula (a) shown.

[0037] The preparation method of the above-mentioned thioetherated aromatic heterocyclic compound comprises the following steps:

[0038] Take a 15mL pressure-resistant reaction tube, add PIFA 90mg, indole 24mg, 4-methylthiophenol 30mg, dichloromethane 2mL, open the reaction, and stir overnight at 30°C. After the reaction, add 10 mL of ethyl acetate to quench the reaction, add 10 mL of brine to wash, separate the organic phase, extract the aqueous phase with ethyl acetate three times, combine the organic phases, and separate by column chromatography to obtain 3-(p-tolylthio)- 38.4 mg of pure 1H-indole, yield 80%.

Embodiment 2

[0040] Different from Example 1, this example uses acetonitrile instead of dichloromethane. The yield of 3-(p-tolylthio)-1H-indole in this example was 50%.

Embodiment 3

[0042] Different from Example 1, this example uses Selectfluor fluorine reagent instead of PIFA. The yield of 3-(p-tolylthio)-1H-indole in this example was 45%.

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Abstract

The invention discloses a thioetherified aromatic heterocyclic compound as well as a preparation method and an application thereof, and the preparation method comprises the following steps: dissolving an aromatic heterocyclic compound (I), thiophenol (II) and an oxidizing agent in an organic solvent, and reacting at the reaction temperature of 0-100 DEG C to obtain the thioetherified aromatic heterocyclic compound, the molecular structural formulas of the aromatic heterocyclic compound (I) and the thiophenol (II) are shown in the specification, wherein R1 is selected from alkyl, alkoxy, halogen, aryl, cyano, nitro or hydroxyl; R2 is selected from alkyl, alkoxy, halogen, aryl, nitryl or hydroxyl; and the oxidizing agent is selected from one or more of a Selectfluor fluorine reagent, [bis (trifluoroacetoxy) iodine] benzene and iodobenzene diacetate. According to the method, transition metal does not need to be used as a catalyst, a pre-functionalization reaction reagent does not need to be used, the method can be carried out under mild conditions, and the method has the advantages of being environmentally friendly, low in cost, wide in substrate selectivity and easy to industrialize and is an environment-friendly method.

Description

technical field [0001] The present invention relates to the technical field of organic synthesis, and more specifically relates to a thioetherified aromatic heterocyclic compound and its preparation method and application. Background technique [0002] Heteroaryl compounds and their derivatives exhibit interesting biological activities, especially the heteroaryl sulfide structural motifs, which are found in many pharmaceutically active compounds and advanced materials. Therefore, the introduction of sulfinyl groups into aromatic heterocycles has great research significance. However, one of the most powerful reactions for C-S construction is the cross-coupling of thiols or disulfides with aryl halides or pseudohalides. This type of reaction often requires the catalysis of transition metals such as palladium, copper, and cobalt (Xu , X., et al. (2013). “Nickel-Mediated Inter-and Intramolecular C–S Coupling of Thiols and Thioacetates with Aryl Iodides at Room Temperature” Orga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B61/00C07D209/30C07D333/34
CPCC07B61/02C07D333/34C07D209/30
Inventor 李建基霍延平陈迁赵经纬
Owner GUANGDONG UNIV OF TECH
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