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Novel synthesis method of diimide macrocyclic compound

A technology based on macrocyclic compounds and imide groups, applied in the field of supramolecular chemistry, can solve the problems of difficult removal of templates, high dilution of solutions, cumbersome reaction operations, etc., and achieve good chemical properties of host and guest. The method is simple and time-consuming short effect

Inactive Publication Date: 2019-03-08
BEIJING INSTITUTE OF TECHNOLOGYGY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional method of synthesizing macrocyclic compounds has the following disadvantages: the solution needs to be highly diluted, the template agent is not easy to remove, the reaction operation is cumbersome and the synthesis yield is low

Method used

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  • Novel synthesis method of diimide macrocyclic compound
  • Novel synthesis method of diimide macrocyclic compound
  • Novel synthesis method of diimide macrocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of imide macrocyclic compound, the chemical formula of the macrocyclic compound is C 52 h 36 N 4 o 4 2+ , whose structure is:

[0037]

[0038] The synthetic method step of described macrocyclic compound is as follows:

[0039] (1) 2-bromo-4-methylaniline (7.00g, 37.63mmol), 4-hydroxymethylphenylboronic acid (6.86g, 45.16mmol), bis(triphenylphosphine)palladium dichloride (1.81g , 2.57mmol), sodium carbonate solution (75mL, 2M), DMF (115mL) were added into the round bottom flask, nitrogen protection ensured the reaction under anaerobic conditions, heated and stirred at 100°C for 4h, after the reaction was completed, water (230mL) was added Dilute, and then extract three times with ethyl acetate, the amount of ethyl acetate each time is 115mL, the organic phase is dried with anhydrous magnesium sulfate, after drying, the magnesium sulfate is removed by filtration, the filtrate is concentrated, and the solid powder A1 is separated by column chromatography 6....

Embodiment 2

[0044] A kind of imide macrocyclic compound, the chemical formula of the macrocyclic compound is C 53 h 38 N 4 o 5 2+ , whose structure is:

[0045]

[0046] The first three steps of the synthetic method of the macrocyclic compound are the same as in Example 1, and the fourth step is as follows: the intermediate product syn-A1 (204mg, 0.26mmol), (5-pyridin-3-ylpyridin-3-yl) Methanol (48mg, 0.26mmol) and acetonitrile (5mL) were added to a round-bottomed flask, under nitrogen protection to ensure the reaction under anaerobic conditions, stirred at 55°C for 6h, after the reaction, the obtained solid was dissolved in water (20mL), and saturated Ammonium hexafluorophosphate solution (20mL), precipitated, filtered, washed with water, dried to obtain solid powder, i.e. 154 mg of the target macrocyclic compound, the reaction yield was 55%, the macrocyclic compound NMR analysis, the data are as follows: 1 H NMR (600MHz, DMSO-d 6 ,298K): δ(ppm)=9.598(s,1H),9.483(s,1H),9.412(d,J...

Embodiment 3

[0048] A kind of imide macrocyclic compound, the chemical formula of the macrocyclic compound is C 57 h 39 N 5 o 4 2+ , whose structure is:

[0049]

[0050] The first three steps of the synthetic method of described macrocyclic compound are identical with embodiment 1, and the 4th step is as follows:

[0051] Intermediate product syn-A1 (204mg, 0.26mmol), raw material 3,5-bis(pyridin-3-yl)pyridine (61mg, 0.26mmol), acetonitrile (5mL) were added in a round bottom flask, nitrogen protection ensured that there was no React under oxygen conditions, stir at 55°C for 8h, after the reaction, dissolve the obtained solid in water (20mL), add saturated ammonium hexafluorophosphate solution (20mL), a precipitate precipitates, filter, wash the precipitate with water, and dry to obtain a solid Powder, that is, 149 mg of the target macrocyclic compound, the reaction yield is 50%, and the nuclear magnetic analysis of the macrocyclic compound shows the following data: 1 H NMR (600MH...

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Abstract

The invention belongs to the technical field of supramolecular chemistry, and particularly relates to a novel diimide macrocyclic compound. The compound has the following general structural forma shown in the description, wherein R1 is pyridyl or phenyl; R2 is straight chain or branch-chain-comprising alkane; R3 is 1,4,5,8-naphthalenetetracarboxylic acid dianhydride or 1,6,7,12-tetrachloro-3,4,9,10-tetracarboxylic acid dianhydride; R4 is one of 3,3-bipyridine, 3,5-bis(pyridin-3-yl)pyridine, (5-pyridin-3-ylpyridin-3-yl) methanol, 1,4-bis(bromomethyl) benzene, 2,6-bis(bromomethyl) naphthalene or1,4-bis(bromomethyl) benzene.

Description

technical field [0001] The application belongs to the technical field of supramolecular chemistry, and specifically relates to a method for synthesizing a novel imide-based macrocyclic compound. [0002] In particular, it relates to a method for synthesizing imide-based macrocyclic compounds without any template and high synthesis yield, and belongs to the technical field of supramolecular chemistry. Background technique [0003] Macrocycles play a decisive and irreplaceable role in the development of supramolecular chemistry, and some macrocycles have been developed as excellent candidates for studying non-covalent interactions such as anion-π interactions. Macrocyclic synthetic receptors with preorganized cavities and multivalent binding sites have played a crucial role in the birth and rapid development of modern supramolecular chemistry. The design and development of novel macrocyclic hosts with unique structures and favorable host-guest properties is a permanent and ch...

Claims

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Application Information

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IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 许颜清杨飞尹迪魏玮
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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