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

A technology of formaldehyde condensed diphenylenediamine and double Schiff bases, which can be used in chemical instruments and methods, luminescent materials, organic chemistry and other directions, and can solve problems such as synthesis that no relevant reports have been reported.

Inactive Publication Date: 2013-08-07
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 Schiff bases with conjugated structures.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Weigh 1.84g (0.01mol) of benzidinediamine and 2.89g (0.02mol) of indole-3-carboxaldehyde, dissolve in 50ml of acetone, and add to a 100ml four-necked bottle equipped with a thermometer and a stirring device . Stirring was started, the reaction temperature was controlled at 25°C, and the constant temperature was reacted for 3 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: indole-3-formaldehyde condensate Biphenyldiamine bis-Schiff base.

[0033] Elemental Analysis: C 30 h 22 N 4 : %C: 82.17 (82.15); %H: 5.06 (5.00); %N: 12.78 (12.85) (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 in total, and the peak that appea...

Embodiment 2

[0040] Weigh 1.84g (0.01mol) of benzidinediamine, weigh 2.89g (0.02mol) of indole-3-carboxaldehyde, dissolve in 50ml of anhydrous methanol, and add it to a 100ml four-port tube equipped with a thermometer and a stirring device. in the bottle. Stirring was started, the reaction temperature was controlled at 35°C, and the constant temperature reaction was carried out for 12 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 acetal Biphenyldiamine bis-Schiff base.

[0041] Elemental Analysis: C 30 h 22 N 4 : %C: 82.17 (83.15); %H: 5.06 (5.10); %N: 12.78 (11.75) (measured values ​​in brackets).

[0042] NMR analysis (NMR spectrum see figure 2 ): see compound 1 for the analysis results.

Embodiment 3

[0044] Weigh 1.84g (0.01mol) of benzidinediamine, weigh 6.75g (0.05mol) of 7-fluoroindole-3-carboxaldehyde, dissolve in 50ml of methanol, and add to 100ml of tetrachloride equipped with a thermometer and a stirring device. in the bottle. Stirring was started, the reaction temperature was controlled at 35°C, and the constant temperature reaction was carried out for 8 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 biphenylenediamine bis-Schiff base.

[0045] Elemental Analysis: C 30 h 20 N 4 f 2 : %C: 75.94 (75.84); %H: 4.25 (4.29); %N: 11.81 (11.71); %F: 8.01 (8.16) (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 ha...

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Abstract

The invention relates to bis-Schiff bases synthesized by condensing indole-3-carboxaldehyde and benzidine and a preparation method thereof. A series of indole Schiff bases with a conjugate structure are obtained by taking benzidine 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 appliedto the field of materials as fluorescent materials.

Description

Technical field: [0001] The invention relates to an indole-3-formaldehyde biphenylenediamine bis-Schiff base and a preparation method thereof. The Schiff base has excellent antibacterial and anti-tumor activities, and the Schiff base has conjugation and rigid plane The structure 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-po...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14C09K11/06A61P31/04
Inventor 孟霞卜娟段洪东王兴建张玉森秦大伟
Owner QILU UNIV OF TECH
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