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A kind of preparation method of 3-peroxy-2-indolone compound in water phase

A technology of indolinone and peroxy, which is applied in the field of preparing 3-peroxy-2-indolinone compounds, can solve problems such as unsatisfactory reaction yields, and achieve the effect of simple operation and easy purification

Active Publication Date: 2022-04-05
NINGBO UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The inventors (Synlett, 29(2018), 663-667) reported a 2-indolinone derivative C(sp 3 )-H bond free radical peroxidation reaction, this reaction also needs to use organic solvent 1,2-dichloroethane (DCE) as reaction solvent and unsatisfactory reaction yield (61%-92%)

Method used

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  • A kind of preparation method of 3-peroxy-2-indolone compound in water phase
  • A kind of preparation method of 3-peroxy-2-indolone compound in water phase
  • A kind of preparation method of 3-peroxy-2-indolone compound in water phase

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Experimental program
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Effect test

Embodiment 1

[0031]

[0032] In the Schlenk bottle, add 2-indolinone derivatives (41.8 mg, 0.2 mmol) shown in formula 1a, tert-butanol peroxide (t-BuOOH, 43.2 mg, 0.48 mmol), then add solvent water (2 mL), Then the reactor was stirred and reacted in an air atmosphere at 60°C, and the reaction process was monitored by TLC until the raw materials disappeared (reaction time was 24 hours). After the reaction was completed, the reaction solution was extracted three times with ethyl acetate, and the organic phase was extracted with anhydrous Dry over sodium sulfate, filter and concentrate under reduced pressure to remove the solvent, and the residue is separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain the target product I-1. (42% yield); 1 H NMR (400MHz, CDCl 3 )δ: 8.62(s, 1H), 7.45-7.43(m, 2H), 7.34-7.25(m, 5H), 7.08(t, J=8.0Hz, 1H), 6.90(d, J=7.6Hz, 1H ), 1.19(s, 9H); 13 C NMR (100MHz, CDCl 3 )δ: 176.3, 141.7, 136.0, 129.8, 129.0, 128.9, 128.5, 127.0...

Embodiment 2

[0034] The reaction temperature was increased to 80° C., and the other conditions were the same as in Example 1. The yield of the target product I-1 was 94%.

Embodiment 3

[0036] The reaction temperature was raised to 100° C., and the rest of the conditions were the same as in Example 1. The yield of the target product I-1 was 92%.

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Abstract

The present invention relates to a kind of preparation technology of 3-peroxy-2-indolone compound, this method takes 2-indolinone derivative as raw material, water is reaction solvent, and peroxide tert-butanol at a certain temperature and Under air conditions, the 3-peroxy-2-indolinone compounds were prepared in high yield. The inventive method does not use any additive, realizes C (sp in green solvent) 3 The peroxidation reaction of )-H bond has the advantages of simple synthesis and post-treatment process, low cost and environmental friendliness.

Description

technical field [0001] This application belongs to the field of organic synthesis, and specifically relates to a method for preparing 3-peroxy-2-indolinone compounds in an aqueous phase using 2-indolinone derivatives as raw materials, with simple process, low cost and environmental friendliness . Background technique [0002] 3-Peroxy-2-indolone compounds are molecules with biological activity and pharmacodynamic activity. Therefore, the synthesis of compounds containing such skeletons has attracted more and more attention from chemists. C(sp 3 The direct functionalization of )-H bonds has been a research hotspot in organic synthesis, especially through metal-free catalytic strategies to achieve such transformations. So far, 2-indolinone derivatives C(sp 3 There are not many examples of free radical peroxidation of )-H bonds. [0003] Klare et al. (Organic Letters, 19(2017), 988-991) developed a 2-indolinone derivative C(sp 3 )-H bond free radical peroxidation, the rea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/38
Inventor 宋思哲魏文廷包雯慧孟亚楠孟潇潇
Owner NINGBO UNIV
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