Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

3-Sulfonylcoumarin and preparation method thereof

A technology for coumarin and coumarin derivatives, applied in the field of coumarin, can solve problems such as unfavorable operation and use, odor, etc., and achieve the effects of avoiding the use of sulfonyl chloride, simple and easy-to-obtain raw materials, and good application prospects.

Inactive Publication Date: 2017-09-12
JIANGXI NORMAL UNIV
View PDF1 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The oxidation method requires the use of some strong oxidants, and the sulfur-containing reagents have a foul smell, which is not conducive to operation and use

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
  • 3-Sulfonylcoumarin and preparation method thereof
  • 3-Sulfonylcoumarin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] A 3-sulfone coumarin, the structural formula is:

[0021] The preparation method is: add 1.5 equivalents of aromatic amine, 1.5 mL of 1,2-dichloroethane, 1.8 equivalents of tBuONO, 1.5 equivalents of boron trifluoride ether solution into the reaction tube, and under the protection of inert gas nitrogen or argon, Stir at 0°C for 10 minutes; then add 0.2mmol of phenyl phenylpropiolate, 1.6 equivalents of white block and 2.0mL of 1,2-dichloroethane, stir at 70~80°C for 5.0-6.0 hours, until TLC detection is complete reaction. After the reaction liquid was washed with water, extracted with ethyl acetate, the extract was concentrated and separated by column chromatography to obtain the corresponding 3-sulfone coumarin Ia with a reaction yield of 83%.

[0022] The structure of the compound 1 H NMR, 13 C NMR, HRMS and other methods are characterized and confirmed: 1 H NMR(400MHz, CDCl 3 )δ7.95(d,J=8.9Hz,2H),7.56-7.58(m,3H),7.32-7.34(m,2H),7.14(s,1H),6.95-7.00(m,3H),6.88 (d,J=8.3,...

Embodiment 2

[0024] A 3-sulfone coumarin with the structural formula

[0025] The preparation method is as follows: add aromatic amine (1.5 equivalents), 1,2-dichloroethane (1.5mL), tBuONO (1.8 equivalents), boron trifluoride ether solution (1.5 equivalents) in order in the reaction tube, Under the protection of nitrogen or argon, stir at 0°C for 10 minutes; then add phenyl phenylpropiolate (0.2mmol), white cubes (1.6 equivalent) and 1,2-dichloroethane (2.0mL), at 70 Stir at ~80°C for 5.0-6.0 hours until TLC detects complete reaction. After the reaction liquid was washed with water, extracted with ethyl acetate, the extract was concentrated and separated by column chromatography to obtain the corresponding 3-sulfone coumarin Ib, with a reaction yield of 84.5%.

[0026] The structure of the compound 1 H NMR, 13 C NMR, HRMS and other methods are characterized and confirmed: 1 H NMR(400MHz, CDCl 3 )δ7.94(d,J=8.6Hz,2H),7.58-7.89(m,3H),7.47(d,J=8.6Hz,2H),7.32-7.34(m,2H),7.16(s,1H) ), 7.02 (d, J =...

Embodiment 3

[0028] A 3-sulfone coumarin with the structural formula

[0029] The preparation method is as follows: add aromatic amine (1.5 equivalents), 1,2-dichloroethane (1.5mL), tBuONO (1.8 equivalents), boron trifluoride ether solution (1.5 equivalents) in order in the reaction tube, Under the protection of nitrogen or argon, stir at 0°C for 10 minutes; then add phenyl phenylpropiolate (0.2mmol), white cubes (1.6 equivalent) and 1,2-dichloroethane (2.0mL), at 70 Stir at ~80°C for 5.0-6.0 hours until TLC detects complete reaction. After the reaction liquid was washed with water, extracted with ethyl acetate, the extract was concentrated and separated by column chromatography to obtain the corresponding 3-sulfone coumarin Ic with a reaction yield of 85%.

[0030] The structure of the compound 1 H NMR, 13 C NMR, HRMS and other methods are characterized and confirmed: 1 H NMR(400MHz, CDCl 3 )δ7.87(d,J=8.7Hz,2H),7.64(d,J=8.7Hz,2H),7.58-7.59(m,3H),7.32-7.34(m,2H),7.17(s,1H) ), 7.02 (d, J = 8....

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 invention discloses 3-sulfonylcoumarin and a preparation method thereof. The preparation method includes: in an organic solvent, allowing arylamine and phenyl phenylpropiolate to react with rongalite to obtain 3-sulfonylcoumarin compound. The structure of the 3-sulfonylcoumarin compound is confirmed by characterization via 1H NMR (nuclear magnetic resonance), 13C NMR, HRMS (high resolution mass spectrometry) and other processes. The preparation method has the advantages that the reaction herein is performed under mild conditions, rongalite is used as a sulfur dioxide source, sulfonyl reaction is achieved directly, and the 3-sulfonylcoumarin compound is constructed; the raw materials for the reaction are simple and easily accessible, the usage of sulfonyl chloride in traditional synthetic processes is avoided, and the preparation method is suitable for large-scale preparation and has a promising application prospect.

Description

Technical field [0001] The invention belongs to the technical field of coumarin, and particularly relates to a 3-sulfone coumarin and a preparation method thereof. Background technique [0002] Coumarin compounds play an important role in the fields of medicine, dyes, and materials. The coumarin skeleton is one of the common heterocyclic structures, which is widely present in a variety of natural products and drug molecules with significant biological activity. For example, Calanolide A extracted from the plant Populus euphratica shows very good HIV-1 reverse transcriptase inhibitory activity and is a potential anti-AIDS drug; the coumarin-based compound Warfarin (Wafarin) is a widely used Anticoagulant used in clinical medicine; Umbelliferolide in ruta, esculetin in Qin bark, and Angelica lactone in sylvestris, etc., all have a coumarin skeleton; industrialized coumarin fluorescent dyes include disperse yellow 184, Disperse Yellow 232, Solvent Red 196 and Disperse Red 277, etc...

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
IPC IPC(8): C07D311/58
CPCC07D311/58
Inventor 钟前陈知远吴劼
Owner JIANGXI NORMAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com