Unlock instant, AI-driven research and patent intelligence for your innovation.

Indolo[3,2-c] coumarin compounds, derivatives thereof and synthesis method thereof

A technology of coumarins and synthetic methods, applied in the direction of steroids, organic chemistry methods, organic chemistry, etc., can solve the problems of low reaction efficiency of toxic and dangerous reagents, high temperature required for reaction conditions, etc., and achieve a wide range of substrates , simple reaction operation and high atom economy

Active Publication Date: 2019-11-01
EAST CHINA NORMAL UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, most of the methods for synthesizing indole[3,2-c]coumarin compounds have certain limitations, such as the need for pre-functionalization of the reaction substrate, high temperature for reaction conditions, use of toxic and dangerous reagents and The reaction efficiency is not high

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
  • Indolo[3,2-c] coumarin compounds, derivatives thereof and synthesis method thereof
  • Indolo[3,2-c] coumarin compounds, derivatives thereof and synthesis method thereof
  • Indolo[3,2-c] coumarin compounds, derivatives thereof and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Synthesis of Compound 2a:

[0058]

[0059] Under a nitrogen atmosphere, bis(acetonitrile)palladium dichloride (2.6mg, 0.01mmol), silver trifluoromethanesulfonate (5.1mg, 0.02mmol), dppm (3.8mg, 0.01mmol), acetonitrile (0.5 mL), stirred at room temperature for 10 minutes. Then add alkyne substrate 1a (32.9mg, 0.1mmol), p-benzoquinone (16.2mg, 0.15mmol), acetonitrile (0.5mL), then use CO balloon to pump three times, the reaction system was stirred at room temperature for 3 hours, and the reaction After completion, the solvent was spin-dried, and the compound 2a was separated by column chromatography with a yield of 71% (25.2 mg) as a white solid. 1 H NMR (400MHz, CDCl 3 )δ8.38(m,1H),7.82(d,J=8.0Hz,1H),7.53–7.33(m,5H),7.20(m,1H),7.05(d,J=8.5Hz,2H), 6.85(d, J=8.6Hz, 2H), 5.80(s, 2H), 3.75(s, 3H). 13 C NMR (100MHz, CDCl 3 )δ159.4, 158.7, 153.5, 141.0, 139.7, 130.1, 127.2, 126.9, 125.3, 124.4, 124.1, 123.3, 122.6, 121.8, 118.4, 114.8, 113.6, 109.8, 102.8, 55.3, 2KBr ...

Embodiment 2

[0061] Synthesis of compound 2b:

[0062]

[0063]Under a nitrogen atmosphere, bis(acetonitrile)palladium dichloride (2.6mg, 0.01mmol), silver trifluoromethanesulfonate (5.1mg, 0.02mmol), dppm (3.8mg, 0.01mmol), acetonitrile (0.5 mL), stirred at room temperature for 10 minutes. Then add alkyne substrate 1b (37.8mg, 0.1mmol), p-benzoquinone (16.2mg, 0.15mmol), acetonitrile (0.5mL), and then use CO balloon to pump three times, and the reaction system was stirred at room temperature for 3 hours. After the completion, the solvent was spin-dried, and the compound 2b was separated by column chromatography with a yield of 70% (28.3 mg) as a white solid. 1 H NMR (400MHz, CDCl 3 )δ8.38(dd, J=6.6,1.7Hz,1H),7.92(d,J=2.1Hz,1H),7.57–7.28(m,8H),7.13(d,J=7.0Hz,2H), 5.82(s,2H). 13 C NMR (100MHz, CDCl 3 )δ158.0, 152.2, 140.0, 139.4, 135.1, 132.8, 129.5, 128.4, 125.9, 125.7, 125.3, 124.1, 123.6, 121.9, 119.8, 116.7, 115.1, 109.8, 105.0, 70.0, 72, 42 (KBr)1 ,1428,971,778,754,732. HRMS (...

Embodiment 3

[0065] Synthesis of compound 2c:

[0066]

[0067] Under a nitrogen atmosphere, bis(acetonitrile)palladium dichloride (2.6mg, 0.01mmol), silver trifluoromethanesulfonate (5.1mg, 0.02mmol), dppm (3.8mg, 0.01mmol), acetonitrile (0.5 mL), stirred at room temperature for 10 minutes. Then add alkyne substrate 1c (32.9mg, 0.1mmol), p-benzoquinone (16.2mg, 0.15mmol), acetonitrile (0.5mL), and then use CO balloon to pump three times, and the reaction system was stirred at room temperature for 3 hours. After completion, the solvent was spin-dried, and compound 2c was separated by column chromatography with a yield of 61% (21.7 mg) as a white solid. 1 H NMR (400MHz, CDCl 3 )δ8.47–8.35(m,1H),7.48–7.27(m,7H),7.16(m,3H),7.01(dd,J=9.1,2.7Hz,1H),5.85(s,2H),3.59 (s,3H). 13 C NMR (100MHz, CDCl 3 )δ 158.9, 155.7, 147.9, 141.0, 139.9, 135.6, 129.4, 128.2, 125.5, 125.4, 124.4, 123.3, 121.9, 119.2, 117.6, 113.6, 109.6, 105.8, 102.9, 55.7, 4KBr ,1457,1446,1385,1198,975,777,746,734.HRMS(EI)...

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 a synthesis method of indolo[3,2-c] coumarin compounds and derivatives thereof. The indolo[3,2-c] coumarin compounds and derivatives thereof, shown as a formula (2), are prepared by catalyzing, with palladium, intramolecular alkyne cyclization and intermolecular carbon monoxide carbonyl insertion in series of compounds shown as a formula (1). The method has advantages of mild reaction conditions, simple reaction operation, high atomic economy and a wide application range of substrates, and can rapidly and efficiently prepare a series of indolo[3,2-c] coumarin compoundssubstituted with different functional groups.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to indole[3,2-c]coumarin compounds and a synthesis method thereof. Background technique [0002] Compounds containing indole[3,2-c]coumarin structure have biological and physiological activities, such as antifungal, anticoagulant, anti-HIV and anti-angiogenic activities, so they are widely used in the pharmaceutical industry, perfume industry , food industry and agriculture. In particular, certain indole[3,2-c]coumarin compounds have some important activities such as unique anti-HIV, anti-tumor and anti-hepatitis C. Therefore, it is particularly important to find a method with mild conditions, simple operation and wide substrate range to prepare indole[3,2-c]coumarin compounds. [0003] [0004] Compounds Containing Indole [3,2-c] Coumarin Structure and Their Applications [0005] In the prior art, most of the methods for synthesizing...

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 Applications(China)
IPC IPC(8): C07D491/052C07D491/16C07D491/08C07J71/00
CPCC07D491/052C07D491/16C07D491/08C07J71/0036C07B2200/07
Inventor 姜雪峰丁冬朱国浩
Owner EAST CHINA NORMAL UNIV