Schiff base containing carbazyl and thiadiazolyl and preparation method thereof

A thiadiazolyl and carbazole-based technology, which is applied in the field of chemical synthesis, can solve problems such as low yield, large amount of solvent used, and long reaction time, and achieve shortened reaction time, short reaction time, and fast reaction speed Effect

Inactive Publication Date: 2017-02-22
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The synthesis of Schiff base compounds reported in the existing literature mostly uses ethanol, DMF, etc. as the reaction medium, with acid as the catalyst, and is prepared by conventional heating methods, so there are disadvantages such as long reaction time, low yield, and large solvent usage

Method used

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  • Schiff base containing carbazyl and thiadiazolyl and preparation method thereof
  • Schiff base containing carbazyl and thiadiazolyl and preparation method thereof
  • Schiff base containing carbazyl and thiadiazolyl and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1) Add 0.005mol 3,6-diethylacyl-9-ethylcarbazole, 0.011mol 2-amino-1,3,4-thiadiazole and 0.011mol p-toluenesulfonic acid to a dry mortar, That is, 3,6-diethylacyl-9-ethylcarbazole: 2-amino-1,3,4-thiadiazole: p-toluenesulfonic acid is 1:2.2:2.2; Grinding at room temperature for 15min, at this time TLC Monitoring showed that the raw material points of 3,6-diacetyl-9-ethylcarbazole and 2-amino-1,3,4-thiadiazole disappeared, indicating that the raw materials were completely reacted, and then stood to remove water for 30 minutes to obtain a mixture; Wherein the developer is a mixed solvent of ethyl acetate and sherwood oil with a volume ratio of 1:3;

[0037] 2) After the mixture was washed with water and suction filtered, 3,6-diacetyl-9-ethylcarbazole 2-amino-1,3,4-thiadiazole Schiff base was obtained. m.p.: 169.3-171.5°C, yield 84.8%.

[0038] IR (KBr tablet): 3045 (Ar-H); 2975 (saturated C-H); 1657 (C=N); 1611, 1580, 1487 (benzene ring skeleton vibration); 1386 (-CH 3 ...

Embodiment 2

[0042] 1) Add 0.005mol 3-acetyl-9-methylcarbazole, 0.006mol 2-amino-5-p-chlorophenyl-1,3,4-thiadiazole and 0.006mol p-toluene to a dry mortar Sulphonic acid was ground at room temperature for 16min. At this time, TLC monitoring showed that the raw material sites of 3-acetyl-9-methylcarbazole and 2-amino-5-p-chlorophenyl-1,3,4-thiadiazole disappeared, Indicates that the raw materials are completely reacted, and then left to stand for 30 minutes to obtain a mixture; wherein the developer is a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3;

[0043] 2) After the mixture was washed with water and suction filtered, 3-acetyl-9-methylcarbazole 2-amino-5-p-chlorophenyl-1,3,4-thiadiazole Schiff base was obtained. m.p.: 184.6-188.5°C, yield 82.3%.

[0044] IR (KBr tablet): 3053 (Ar-H); 2929, 2820 (saturated C-H), 1595 (C=N), 1479 (benzene ring skeleton vibration); 1355 (-CH 3 ); 1246(C-N); 627(C-S)

[0045] 1 H NMR (CDCl 3 -d 6 ,400Hz,TMS internal st...

Embodiment 3

[0048] 1) Add 0.005mol 3-acetyl-9-ethylcarbazole, 0.006mol 2-amino-5-methyl-1,3,4-thiadiazole and 0.006mol p-toluenesulfonic acid to a dry mortar , Grinding at room temperature for 15 minutes, TLC monitoring at this time showed that the raw material sites of 3-acetyl-9-ethylcarbazole and 2-amino-5-methyl-1,3,4-thiadiazole disappeared, indicating that the raw materials were completely reacted , and then left to stand for 30min to obtain a mixture; wherein the developing agent is a mixed solvent of ethyl acetate and sherwood oil with a volume ratio of 1:3;

[0049] 2) After the mixture was washed with water and suction filtered, 3-acetyl-9-ethylcarbazole 2-amino-5-methyl-1,3,4-thiadiazole Schiff base was obtained. m.p.>300°C, yield 86.7%.

[0050] IR (KBr tablet): 3053 (Ar-H); 2983 (saturated C-H); 1642 (C=N); 1564 (benzene ring skeleton vibration); 1487 (-CH2-); 1378 (-CH 3 ); 1223(C-N); 627(C-S)

[0051] 1 H NMR (CDCl 3 -d 6 ,400Hz, TMS internal standard, δ:ppm):7.82(m,4...

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Abstract

The invention relates to Schiff base containing carbazyl and thiadiazolyl and a preparation method thereof; the preparation method comprises: adding acyl carbazole, 2-amino-5-substituted-1,3,4-thiadiazole and p-toluenesulfonic acid, grinding at room temperature, performing TLC (thin layer chromatography) monitoring on reaction until the materials react completely, and standing to obtain a crude product, wherein a molar ratio of the acyl carbazole, 2-amino-5-substituted-1,3,4-thiadiazole and p-toluenesulfonic acid is 1:A:B, and wherein A is 1-1.2 or 2-2.2, and B is 1-1.2 or 2-2.2; subjecting the crude product to washing and suction filtering to obtain the Schiff base containing carbazyl and thiadiazolyl. The reaction time is short, reaction conditions are mild, reacting may be performed at room temperature, equipment requirements are low, post-processing is simple, no solvents are required, and the yield is high; the Schiff base containing carbazyl and thiadiazolyl prepared herein contains multiple C=N fluorescent groups and carbazole groups with good hole transport capacity, and have certain luminescent properties.

Description

[0001] 【Technical field】 [0002] The invention belongs to the field of chemical synthesis, in particular to a Schiff base containing carbazolyl and thiadiazolyl and a preparation method thereof. [0003] 【Background technique】 [0004] Schiff base compounds refer to a class of compounds containing methyleneamine groups obtained by the affinity addition-dehydration reaction of primary amines and active carbonyl compounds. There are N atoms with strong coordination ability in its structure, and the possibility of exocyclic Heteroatoms such as N and S containing lone pairs of electrons, so the Schiff base compound is an organic ligand with excellent performance. Since the metal ion contains an empty d orbital, it can accept the lone electron pair provided by the heteroatom of the ligand, making the metal Coordinate with heteroatoms to form metal complexes. Functionalized Schiff alkali metal complexes have been widely used in many fields due to their stable structures. [0005] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D417/14C09K11/06
CPCC07D417/12C07D417/14C09K11/06C09K2211/1022C09K2211/1029C09K2211/1051
Inventor 尹大伟吴倩倩刘玉婷李荻扬王雨薇黄涛辛宏杨晓明
Owner SHAANXI UNIV OF SCI & TECH
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