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

A kind of indole [3,2-c] coumarin compound and its derivative and synthetic method

A technology for coumarins and synthesis methods, which is applied in the directions of steroids, organic chemistry, organic chemistry, etc., can solve the problems of high temperature required for reaction conditions, low reaction efficiency of toxic and dangerous reagents, etc., and achieves high reaction efficiency and suitable substrates. Wide-ranging, high-yield effects

Active Publication Date: 2022-04-05
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
  • A kind of indole [3,2-c] coumarin compound and its derivative and synthetic method
  • A kind of indole [3,2-c] coumarin compound and its derivative and synthetic method
  • A kind of indole [3,2-c] coumarin compound and its derivative and synthetic method

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 method for synthesizing indole[3,2-c]coumarin compounds and their derivatives, which are prepared by palladium-catalyzed intramolecular alkyne cyclization and series inter-molecular carbon monoxide intercalation reaction of the compound of formula (1) Indo[3,2-c]coumarin compounds represented by formula (2) and derivatives thereof are obtained. The invention has mild reaction conditions, simple reaction operation, high atom economy, wide application range of substrates, and can quickly and efficiently prepare a series of indole[3,2-c]coumarin compounds substituted by 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 Application [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 Patents(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