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Bis-Schiff bases synthesized by condensing indole-3-carboxaldehyde and pyridine diamine and preparation method thereof

A technology of formaldehyde pyridine diamine bis-Schiff base and pyridine diamine, which is applied in the field of indole-3-formaldehyde pyridine diamine bis-Schiff base and its preparation, and can solve the problem of indole bis-Schiff base synthesis. Related reports and other issues

Inactive Publication Date: 2012-07-18
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Many researchers have synthesized a large number of Schiff bases by using the condensation reaction of indole-3-carbaldehyde with primary amines, but there is no relevant report on the synthesis of indole bis-Schiff bases

Method used

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  • Bis-Schiff bases synthesized by condensing indole-3-carboxaldehyde and pyridine diamine and preparation method thereof
  • Bis-Schiff bases synthesized by condensing indole-3-carboxaldehyde and pyridine diamine and preparation method thereof
  • Bis-Schiff bases synthesized by condensing indole-3-carboxaldehyde and pyridine diamine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Weigh 1.09g (0.01mol) of pyridine-3,5-diamine, weigh 2.89g (0.02mol) of indole-3-carbaldehyde, dissolve in 50ml of tetrahydrofuran, and add it to a 100ml container equipped with a thermometer and a stirring device. In a four-neck bottle. Stirring was started, the reaction temperature was controlled at 65°C, and the constant temperature was reacted for 3 hours. The solvent was distilled off under reduced pressure to obtain a white solid powder, which was recrystallized with ethanol and dried in vacuum at 50°C for 6 hours to obtain the target product: indole-3-formaldehyde condensate Pyridine-3,5-diamine bis-Schiff base.

[0033] Elemental Analysis: C 23 h 17 N 5 : %C: 76.01 (75.99); %N 19.27 (19.17); %H 4.71 (4.84) ​​(measured values ​​in brackets).

[0034] NMR analysis (NMR spectrum see figure 2 ):

[0035] Table 1 was obtained by analyzing the structural formula and proton nuclear magnetic resonance spectrum of compound 1. Compound 1 has nine kinds of hydrogen ...

Embodiment 2

[0040] Weigh 1.09g (0.01mol) of pyridine-3,5-diamine, weigh 2.89g (0.02mol) of indole-3-carboxaldehyde, dissolve in 50ml of acetone, and add to 100ml of acetone equipped with a thermometer and a stirring device. In a four-neck bottle. Stirring was started, the reaction temperature was controlled at 65°C, and the reaction was carried out at constant temperature for 3 hours. The solvent was distilled off under reduced pressure to obtain a light yellow solid powder, which was recrystallized with ethanol and dried in vacuum at 50°C for 6 hours to obtain the target product: indole-3-carbaldehyde Pyridine-3,5-diamine bis-Schiff base.

[0041] Elemental Analysis: C 23 h 17 N 5 : %C: 76.01 (75.89); %N19.27 (19.19); %H4.71 (4.92) (measured values ​​in brackets).

[0042] NMR analysis (NMR spectrum see figure 2 ): The analysis result is the same as that of compound 1.

Embodiment 3

[0044] Weigh 1.09g (0.01mol) of pyridine-3,5-diamine, weigh 6.75g (0.05mol) of 7-fluoroindole-3-carbaldehyde, dissolve in 50ml of 1,4-dioxane, add To a 100ml four-necked bottle equipped with a thermometer and a stirring device. Stirring was started, the reaction temperature was controlled at 65°C, and the constant temperature reaction was carried out for 12 hours. The solvent was distilled off under reduced pressure to obtain a yellow solid powder, which was recrystallized with ethanol and dried in vacuum at 50°C for 6 hours to obtain the target product: 7-fluoroindole-3 -Formaldehyde p-phenylenediamine bis-Schiff base.

[0045] Elemental Analysis: C 23 h 15 N 5 f 2 : %C: 69.17 (70.00); %H: 3.79 (3.89); %N: 17.53 (17.43); %F: 9.51 (8.68) (measured values ​​in brackets).

[0046] NMR analysis (NMR spectrum see image 3 ):

[0047]Table 2 was obtained by analyzing the structural formula and proton nuclear magnetic resonance spectrum of compound 2. Compound 2 has eight ki...

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Abstract

The invention relates to bis-Schiff bases synthesized by condensing indole-3-carboxaldehyde and pyridine diamine and a preparation method thereof. A series of indole Schiff bases with conjugate structure are obtained by taking 3,5-pyridine diamine and indole-3-carboxaldehyde and derivatives thereof as the raw materials and adopting condensation reaction between aldehyde group and primary amine. The bis-Schiff bases and the preparation method have the following beneficial effects: the synthesis cost is low; the yield is high; the reaction conditions are mild; the products are easy to purify; the compounds have good bioactivity and can be applied to the field of medicines as antibacterial agents; and with conjugate and rigid plane structures, the compounds also show stronger fluorescence and can be applied to the field of materials as fluorescent materials.

Description

Technical field: [0001] The invention relates to an indole-3-carbaldehyde pyridinediamine bis-Schiff base and a preparation method thereof. The Schiff base has excellent antibacterial and antibacterial activities, and the Schiff base has a conjugated and rigid planar structure It also exhibits strong fluorescence properties. Background technique: [0002] Indole (Indole) [Chemical Intermediates, 2011(1): 9~13] is an important heterocyclic fine chemical raw material and intermediate. Because of its unique structure, most of its derivatives have unique and efficient physiological activities. It is widely used in medicine, pesticide and other fields. [0003] Due to the special structure of the indole ring, the indole ring is relatively active [Chemistry and Adhesion, 2010, 32(3): 42~45], so different groups can be introduced on the indole ring to obtain a large number of indole derivatives. things. Indole-3-carboxaldehyde obtained by introducing an aldehyde group at the 3-p...

Claims

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Application Information

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IPC IPC(8): C07D401/14A61P31/04C09K11/06
Inventor 段洪东卜娟孟霞王兴建张玉森秦大伟
Owner QILU UNIV OF TECH
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