4-aroyl-1,8-naphthalimide compound and preparation method and use thereof

A technology of naphthalimide and compound, which is applied in the field of 4-aroyl-1,8-naphthoimide compound and its preparation, can solve the problems of low yield, many side reactions, harsh reaction conditions, etc., and achieve The effect of high yield, low production cost, and easy control of reaction

Inactive Publication Date: 2014-08-27
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are not many reports on 4-acyl or aryl acetonitrile naphthalimides, and the related synthesis reports mainly focus on the 4-aryl CH obtained by Friedel-Crafts acylation reaction, which has harsh reaction conditions and side effects. More reactions, low yield and other disadvantages

Method used

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  • 4-aroyl-1,8-naphthalimide compound and preparation method and use thereof
  • 4-aroyl-1,8-naphthalimide compound and preparation method and use thereof
  • 4-aroyl-1,8-naphthalimide compound and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] A kind of 4-aryl acetonitrile-1,8-naphthalimide compound, its structural formula is as follows:

[0044]

[0045] where R 1 It is a C4 linear alkyl group;

[0046] R 2 For phenyl.

[0047] The preparation method of above-mentioned a kind of 4-aryl acetonitrile-1,8-naphthalimide compound, the reaction formula of its synthetic process is as follows:

[0048]

[0049] The preparation method of above-mentioned a kind of 4-aryl acetonitrile-1,8-naphthalimide compound, concrete steps are as follows:

[0050] In a 50ml three-neck flask, add 20ml of anhydrous toluene and phenylacetonitrile (0.40g, 3.42mmol), 0.20g of NaH solid, replace with nitrogen three times, stir magnetically for a period of time, and start adding N-butyl-4-bromo -1,8 Naphthalimide (1.0g, 3.02mmol) and 10ml of anhydrous toluene solution were added dropwise for about 30 minutes, after the drop was completed, stirred at room temperature for a period of time, followed by TLC spotting until the reaction...

Embodiment 2

[0058] A 4-arylacetonitrile-1,8-naphthalimide compound, its structural formula is as follows:

[0059]

[0060] where R 1 is n-butyl;

[0061] R 2 For 4-fluorophenyl.

[0062] The preparation method of above-mentioned a kind of 4-aryl acetonitrile-1,8-naphthalimide compound, the reaction formula of its synthetic process is as follows:

[0063]

[0064] The preparation method of above-mentioned a kind of 4-aryl acetonitrile-1,8-naphthalimide compound, concrete steps are as follows:

[0065] In a 100ml three-neck flask, add 25ml of anhydrous toluene and p-fluorophenylacetonitrile (0.50g, 3.70mmol), 0.25g of NaH solid, nitrogen replacement three times, after stirring at room temperature for a period of time, start to drop N-butyl- 4-Bromo-1,8 naphthalimide (1.10g, 3.32mmol) and 20ml of anhydrous toluene solution, after the dripping, began to heat for a period of time, TLC plate traced until the reaction was complete; Add 10% dilute hydrochloric acid solution, adjust th...

Embodiment 3

[0074] A kind of 4-aryl acetonitrile-1,8-naphthalimide compound, its structural formula is as follows:

[0075]

[0076] where R 1 is n-butyl;

[0077] R 2 Indolyl protected by BOC.

[0078] The preparation method of above-mentioned a kind of 4-aryl acetonitrile-1,8-naphthalimide compound, the reaction formula of its synthetic process is as follows:

[0079]

[0080] The preparation method of above-mentioned a kind of 4-aryl acetonitrile-1,8-naphthalimide compound, concrete steps are as follows:

[0081] Add 10ml of anhydrous toluene and sodium hydrogen (0.36g, 9.0mmol) to a 50ml three-necked flask at room temperature, and add indole-3-acetonitrile-N-methyl tert-butyl ester (0.29g, 1.13mmol) under nitrogen protection, 0.5 After 4h, 4-bromo-1,8-naphthoimide (0.25g, 0.76mmol) was added, and after 2h, the plate was followed to track the end of the reaction. After quenching with saturated brine, 50 ml of dilute hydrochloric acid was added to wash until acidic. The solut...

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Abstract

The invention discloses a 4-aroyl-1,8-naphthalimide compound and a preparation method and use thereof, wherein the 4-aroyl-1,8-naphthalimide compound has a structural formula as shown in the specification, R1 is C1-C10 straight chain or branched chain alkyl; and R2 is phenyl, naphthyl, biphenylyl, substituted phenyl, quinary or senary heteroaryl or benzo quinary or senary heteroaryl. The preparation method is as follows: a 4 bromo-1,8-naphthalimide compound is used as a raw material to react with substituted phenylacetonitrile or aromatic ring acetonitrile in an organic solvent in the presence of an alkali catalyst to obtain a 4-aryl acetonitrile-1,8-naphthalimide compound, and then the 4-aroyl-1,8-naphthalimide compound is obtained in the effects of fluoride ions or cyanide ions. The 4-aryl acetonitrile-1, 8-naphthalimide compound is used as a color or fluorescence sensor for detection of the fluoride ions or cyanide ions, and has high sensitivity and high selectivity during identifying of the cyanide ions in a mixed solvent.

Description

technical field [0001] The present invention is mainly used in the field of anion recognition, especially related to A kind of 4-aroyl-1,8-naphthalimide compound and its preparation method and application . Background technique [0002] Anion recognition, especially the recognition of fluoride and cyanide, has important applications in the fields of life, medicine, and the environment. Excessive intake of fluoride ions can lead to metabolic diseases of teeth and bone tissue; excessive fluoride ions in drinking water are also important detection indicators; at the same time, the detection of highly toxic CN ions has important applications in the environment and biological systems. [0003] Color and fluorescent chemical sensors can convert molecular recognition information into easily perceived color signals or fluorescent signals. They have the characteristics of sensitivity, rapidity and low detection limit, and can be widely used in biochemistry, cell biology and anal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C07D401/06G01N21/64G01N21/25G01N21/29
CPCC07D221/14C07D401/06C09K11/06C09K2211/1007C09K2211/1029G01N21/643G01N21/78
Inventor 刘传祥陈金聚张传秀周敏李白云
Owner SHANGHAI INST OF TECH
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