A kind of saddle-shaped cyclic compound containing thiadiazo aromatic aldehyde schiff base and preparation method thereof

A technology for cyclic compounds and aromatic aldehydes, which is applied in the field of thiadiazonium-containing aromatic aldehyde Schiff base saddle-type cyclic compounds and their preparation, can solve the problems of inability to satisfy scientific research and actual production, and achieves convenient industrial scale production, The effect of mild reaction temperature and cheap and readily available raw materials

Active Publication Date: 2020-11-17
TAISHAN UNIV
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  • Abstract
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Problems solved by technology

But the contriver finds, up to now, the Schiff base compound containing thiadiazo aromatic aldehyde that people synthesize is still less, can't meet the needs of scientific research and actual production

Method used

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  • A kind of saddle-shaped cyclic compound containing thiadiazo aromatic aldehyde schiff base and preparation method thereof
  • A kind of saddle-shaped cyclic compound containing thiadiazo aromatic aldehyde schiff base and preparation method thereof
  • A kind of saddle-shaped cyclic compound containing thiadiazo aromatic aldehyde schiff base and preparation method thereof

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preparation example Construction

[0039] The second aspect of the present invention provides the preparation method of the Schiff base saddle-type cyclic compound containing thiadiazo aromatic aldehyde, comprising:

[0040] Under nitrogen atmosphere, mix 2-amino-5-mercapto-1,3,4-thiadiazole and p-fluorobenzaldehyde into ethanol, add trifluoroacetic acid, heat to reflux, and purify to obtain the product.

[0041] In the present invention, using ethanol solvent as the reaction medium, trifluoroacetic acid can protonate the N ion on the thiadiazide ring, and promote the "head-to-tail" addition between Schiff base molecules to obtain a cyclic compound.

[0042] In another specific embodiment of the present invention, the molar ratio of 2-amino-5-mercapto-1,3,4-thiadiazole, p-fluorobenzaldehyde and trifluoroacetic acid is 1:1~2:0.05~ 0.15; By controlling the ratio of the amount of each reactant, it is beneficial to improve the reaction yield and save the reaction time;

[0043] In yet another specific embodiment o...

Embodiment 1

[0050] Under nitrogen range, add 15 milliliters of ethanol to 25 milliliters of two-necked flasks, 396mg (3mmol) 2-amino-5-mercapto-1,3,4-thiadiazole and 409.2mg p-fluorobenzaldehyde are mixed in ethanol, drop into 0.02ml of trifluoroacetic acid was refluxed at 80°C for 2 hours, the solution changed from light yellow to orange yellow to light yellow precipitate, filtered, washed with 20 ml of water three times, and then washed with ether. The washing solvent was evaporated, and recrystallized overnight using dichloromethane / petroleum ether (v / v=1:1.5), to finally obtain 451 mg of light yellow crystalline powder with a yield of 81%.

[0051] Mass Spectrum: (calculated value) for C 44 h 44 f 4 N 12 o 4 S 8 : 1136.30 (M+); (measured value): 1136.13. Elemental analysis: (calculated value) (%) for C 44 h 44 f 4 N 12 o 4 S 8 : C, 46.46; H, 3.90; N, 14.78. Found: C, 46.24; H, 3.81; N, 14.22.

Embodiment 2

[0053] Under nitrogen range, 10 ml of ethanol was added to a 25 ml two-necked flask, 396 mg (3 mmol) of 2-amino-5-mercapto-1,3,4-thiadiazole and 500 mg of p-fluorobenzaldehyde were mixed into ethanol, and 0.01 ml of trifluoroacetic acid, refluxed at 80°C for 2 hours, the solution changed from light yellow to orange yellow to light yellow precipitate, filtered, washed three times with 20 ml of water, and then washed with ether. The washing solvent was evaporated, and dichloromethane / petroleum ether (v / v=1:1.5) was used for recrystallization overnight to finally obtain 462 mg of light yellow crystalline powder with a yield of 83%.

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Abstract

The invention provides a Schiff-base saddle-shaped ring compound containing a thiadiazole aromatic aldehyde and a preparation method of the Schiff-base saddle-shaped ring compound. The molecular formula of the compound is C44H44F4N12O4S8. The preparation method comprises the steps that 2-amino-5-mercapto-1,3,4-thiiodiazole and p-fluorobenzaldehyde are mixed to be added into ethyl alcohol, trifluoroacetic acid is added, and through heating reflux and purification, the Schiff-base saddle-shaped ring compound is obtained. The Schiff-base saddle-shaped ring compound containing the thiadiazole aromatic aldehyde has a novel structure, the Schiff-base saddle-shaped ring compound family containing thiadiazole aromatic aldehydes is enriched, and a foundation is laid for further research of application of the Schiff-base saddle-shaped ring compound. Besides, the ring compound is directly prepared by using the one-pot method, the reaction temperature is mild, the reaction steps are simple, the raw materials are low in cost and easy to obtain, the yield is high and reaches 80% or above, and industrial scaled production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a Schiff base saddle-shaped cyclic compound containing thiadiazo aromatic aldehyde and a preparation method thereof. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Thiodiazo compounds are aromatic heterocyclic compounds containing nitrogen and sulfur. The compound has strong electron migration ability, is easy to form relatively stable positive ions, has excellent hole transport ability, and good thermal oxidation stability. properties, photochemical stability, etc. Schiff bases are a class of compounds with C=N bond structures that can emit fluorescen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/22A61P35/00
CPCA61P35/00C07B2200/13C07D513/22
Inventor 孙君善赵娜
Owner TAISHAN UNIV
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