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Synthesis method of 3-arylisoindol derivatives

A technology for aryl isoindolinone and its derivatives, which is applied in the field of synthesis technology for preparing 3-aryl isoindolinone, can solve the problems of harsh conditions and low yield, and achieve good reaction universality, Easily extendable effects

Active Publication Date: 2017-11-24
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the methods reported in the literature have the disadvantages that the reaction needs to synthesize the starting materials step by step, the yield is not high, the conditions are harsh, and toxic or flammable reagents need to be used in the preparation process. Therefore, the development of simple, efficient and green isoindole Synthetic methods of phenone derivatives are still of great importance

Method used

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  • Synthesis method of 3-arylisoindol derivatives
  • Synthesis method of 3-arylisoindol derivatives
  • Synthesis method of 3-arylisoindol derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] O-cyanobenzaldehyde (1mmol), 1,3,5-trimethylbenzene (1mmol), bis(4-bromophenyl)iodonium trifluoromethanesulfonate (1.2mmol), copper acetate (5mmol%) and 2mL Add o-dichloroethane into a 15mL pressure-resistant tube, stir at 110°C, react for 2.5 hours, and separate by silica gel column chromatography to obtain 4a with a yield of 99%. 1 H NMR (300MHz, CDCl 3 )δ7.94-7.92(m,1H),7.48-7.43(m,4H),7.37-7.34(m,2H),7.16-7.13(m,1H),6.93(s,1H),6.57(s, 1H),6.44(s,1H),2.66(s,3H),2.18(s,3H),1.61(s,3H). 13 C NMR (75MHz, CDCl 3 )δ167.8, 143.8, 138.1, 136.9, 132.8, 131.8, 129.9, 129.1, 128.5, 123.9, 122.9, 122.4, 117.8, 61.4, 21.3, 20.8, 18.9.

Embodiment 2

[0018] O-cyanobenzaldehyde (1mmol), 1,3,5-trimethylbenzene (1mmol), bis(4-fluorophenyl)iodonium trifluoromethanesulfonate (1.2mmol), copper acetate (5mmol%) and 2mL Add o-dichloroethane into a 15mL pressure-resistant tube, stir at 110°C, react for 2.5 hours, and separate by silica gel column chromatography to obtain 4b with a yield of 72%. 1 H NMR (300MHz, CDCl 3 )δ7.97-7.94(m,1H),7.51-7.44(m,4H),7.18-7.15(m,1H), 6.99-6.91(m,3H),6.60(s,1H),6.47(s, 1H), 2.62(s,3H), 2.19(s,3H), 1.64(s,3H). 13 C NMR (75MHz, CDCl 3 )δ167.9, 159.9 (d, J = 242.8Hz), 144.1, 138.0, 136.9 (d, J = 18.7Hz), 133.8, 132.6, 131.7, 129.8, 128.5, 123.8 (d, J = 7.5Hz), 122.4, 115.7 (d, J=22.5Hz), 61.9, 21.3, 20.8, 18.9. 19 F NMR (282MHz, CDCl 3 )δ-116.7.

Embodiment 3

[0020] O-cyanobenzaldehyde (1mmol), 1,3,5-trimethylbenzene (1mmol), bis(4-trifluoromethylbenzene)iodonium trifluoromethanesulfonate (1.2mmol), copper acetate (5mmol%) ) and 2 mL of o-dichloroethane were added to a 15 mL pressure-resistant tube, stirred at 110° C., reacted for 2.5 hours, and separated by silica gel column chromatography to obtain 4c with a yield of 76%. 1 H NMR (300MHz, CDCl 3 )δ7.98-7.95(m,1H),7.74-7.71(m,2H),7.55-7.52(m,4H),7.19-7.17(m,1H),6.96(s,1H),6.59-6.54( m,2H),2.72(s,3H),2.21(s,3H),1.63(s,3H). 13 C NMR (75MHz, CDCl 3 )δ168.2, 143.7, 138.2, 136.8, 136.2, 133.1, 131.9, 129.9, 128.7, 126.0, 124.0, 122.5, 120.6, 61.4, 21.3, 20.8, 18.9. 19 F NMR (282MHz, CDCl 3 )δ-62.2.

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Abstract

The invention belongs to a synthesis method of 3-aryl isoindoline derivatives, and relates to the field of natural products and medicine with bioactivity. Used raw materials are o-cyanobenzaldehyde derivatives; electron-rich aryls and diphenyliodonium trifluoromethanesulfonate are used as raw materials; copper acetate is used as a catalyst; reaction is performed in an o-dichloromethane solution at 110 DEG C to obtain the 3-aryl isoindoline derivatives. By using the method provided by the invention, the reaction is performed for 2 to 3 hours at 110 DEG C; the 3-aryl isoindoline derivatives can be obtained; the yield is 69 to 99 percent. The simple and easy-to-obtain raw materials are used; the 3-aryl isoindoline derivatives are synthesized by a one-pot method; a simple, convenient, efficient and green synthesis method is provided for the synthesis of the derivatives.

Description

technical field [0001] The invention relates to a synthesis process for preparing 3-arylisoindolinone, which belongs to the technical field of medicine synthesis and active natural products. Background technique [0002] Nitrogen-containing heterocyclic skeletons are widely found in biologically active natural products and medicinal chemistry. Among various nitrogen-containing compounds, 3-arylisoindolinones serve as a class of important biologically active and therapeutic potential building blocks, such as TACE inhibitors, antihypertensive, HIV-1 inhibitors, and antivirals. . At present, the methods reported in the literature have the disadvantages that the reaction needs to synthesize the starting materials step by step, the yield is not high, the conditions are harsh, and toxic or flammable reagents need to be used in the preparation process. Therefore, the development of simple, efficient and green isoindole Synthetic methods of phenone derivatives are still of great s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/46
CPCC07D209/46
Inventor 刘莉柏淑华李剑
Owner CHANGZHOU UNIV
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