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Isoindoline derivative and preparation method thereof

A technology of isoindolines and indolines, which is applied in the field of isoindoline derivatives and their preparation, can solve the problems of many by-products and poor compatibility, and achieve the effect of increasing complexity and good application prospects

Active Publication Date: 2019-08-23
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of this, the present invention provides a kind of isoindoline derivatives and preparation method thereof, which can effectively solve the technical problems of poor compatibility and more by-products in existing preparation methods of isoindoline derivatives

Method used

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  • Isoindoline derivative and preparation method thereof
  • Isoindoline derivative and preparation method thereof
  • Isoindoline derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0051] This example carries out the preparation of 1-((1E,3Z)-2-phenyl-3-(phenylamino)isoindoline-1-enyl-2-propanone (1a), and its reaction formula is as follows :

[0052]

[0053] Under the air atmosphere, the aromatic aldehyde compound 2a (25 mg, 0.2 mmol) shown in the formula II was sequentially added to the reactor, and the amine compound 3a (46 mg, 0.5 mmol) shown in the formula III was dissolved in 1,2-dichloroethane ( 0.5mL) was stirred at room temperature for one hour, and then 2mg of pentamethylcyclopentadienyl rhodium(III) chloride dimer, 5mg of bistrifluoromethanesulfonimide silver salt, 10mg of sodium acetate and 30mg of acetic acid were added successively Copper, use a syringe to inject a solution of terminal olefin 4a (20 μL, 0.20 mmol) in 1,2-dichloroethane (0.5 mL) into the reactor, place the reactor on the reaction device and adjust the temperature to 100 ° C, carry out After 12 hours of reaction, the end of the reaction was confirmed by thin-layer chroma...

Embodiment 2

[0059] This embodiment carries out the preparation of 1-((1E,3Z)-6-bromo-2-phenyl-3-(phenylamino)isoindoline-1-enyl-2-propanone (1b), and its reaction The formula is as follows:

[0060]

[0061] Under the air atmosphere, the aromatic aldehyde compound 2b (37mg, 0.2mmol) shown in the formula II was sequentially added to the reactor, and the amine compound 3a (46mg, 0.5mmol) shown in the formula III was dissolved in 1,2-dichloroethane ( 0.5 mL) was stirred at room temperature for one hour, and then 2 mg of pentamethylcyclopentadienyl rhodium(III) chloride dimer, 5 mg of bistrifluoromethanesulfonimide silver salt, 20 mg of sodium acetate and 30 mg of acetic acid Copper, use a syringe to inject a solution of terminal olefin 4a (20 μL, 0.30 mmol) in 1,2-dichloroethane (0.5 mL) into the reactor, place the reactor on the reaction device and adjust the temperature to 100 ° C, carry out After 12 hours of reaction, the end of the reaction was confirmed by thin-layer chromatography ...

Embodiment 3

[0067] This example carries out the preparation of 1-((1E,3Z)-6-nitro-2-phenyl-3-(phenylamino)isoindoline-1-enyl-2-propanone (1c), which The reaction formula is as follows:

[0068]

[0069] Under the air atmosphere, the aromatic aldehyde compound 2c (30 mg, 0.2 mmol) shown in the formula II was sequentially added to the reactor, and the amine compound 3a (46 mg, 0.5 mmol) shown in the formula III was dissolved in 1,2-dichloroethane ( 0.5mL) solution was stirred at room temperature for one hour, then 2mg pentamethylcyclopentadienyl rhodium(III) chloride dimer, 5mg bistrifluoromethanesulfonimide silver salt, 10mg sodium acetate and 40mg acetic acid were added successively Copper, use a syringe to inject a solution of terminal olefin 4a (30 μL, 0.30 mmol) in 1,2-dichloroethane (0.5 mL) into the reactor, place the reactor on the reaction device and adjust the temperature to 100 ° C at the same time, carry out After 12 hours of reaction, the end of the reaction was confirmed by ...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to an isoindoline derivative and a preparation method thereof. The invention provides the isoindoline derivative, and the structural formula of the isoindoline derivative is shown in a formula I. The invention further provides the preparation method of the isoindoline derivative. The preparation method comprises the following steps: placing a compound represented by a formula II, a compound represented by a formula III and a compound represented by a formula IV in an inert solvent, and under the actionof an oxidizing agent and a metal catalyst, adding an alkali to carry out a reaction under an alkaline condition to obtain the isoindoline derivative. The invention provides the isoindoline derivativeand the preparation method thereof, and can effectively solve the technical problems that an existing preparation method of isoindoline derivatives is poor in compatibility and the amount of byproducts is large.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to an isoindoline derivative and a preparation method thereof. Background technique [0002] Isoindoline derivatives are widely used in human production and life. Isoindole is a very important type of nitrogen-containing heterocyclic skeleton, which is ubiquitous in nature and is a relatively common heterocyclic skeleton in natural source alkaloids. , is also the key core structure of many bioactive and pharmaceutically active molecules. For example: AKS186 can be used to inhibit the vasoconstriction induced by thromboxane analogs, (+)-Lenoxamine is an alkaloid isolated from natural plants, EM-12 has a special anti-cancer effect, and Indoprofen can be used as an effective anti-inflammatory drug Element. Isoindoline compounds not only play an important role in biological activity, but also can be used as excellent luminescent materials. Because these compounds have broad...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/44C07D209/70
CPCC07D209/44C07D209/70
Inventor 饶建行李先纬霍延平
Owner GUANGDONG UNIV OF TECH
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