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
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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

Examples

Experimental program
Comparison scheme
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%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap