Schiff base containing carbazolyl group and oxadiazole group and preparing method thereof

An oxadiazolyl and carbazole-based technology, which is applied in the field of chemical synthesis, can solve the problems of large solvent usage, long reaction time, and low yield, and achieve the effects of short reaction time, fast reaction speed, and shortened reaction time

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 carbazolyl group and oxadiazole group and preparing method thereof
  • Schiff base containing carbazolyl group and oxadiazole group and preparing method thereof
  • Schiff base containing carbazolyl group and oxadiazole group and preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1) Add 0.005mol 3,6-dimethylacyl-9-methylcarbazole, 0.011mol 2-amino-5-phenyl-1,3,4-oxadiazole and 0.011mol p-toluenesulfonic acid, that is, 3,6-dimethylacyl-9-methylcarbazole: 2-amino-5-phenyl-1,3,4-oxadiazole: p-toluenesulfonic acid is 1:2.2: 2.2; Grinding at room temperature for 15 minutes, TLC monitoring at this time showed that the raw material sites of 3,6-diformyl-9-methylcarbazole and 2-amino-5-phenyl-1,3,4-oxadiazole disappeared, Indicates that the raw materials are completely reacted, and then left to stand to remove water 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;

[0039] 2) After the mixture was washed with water and suction filtered, 3,6-diformyl-9-methylcarbazole 2-amino-5-phenyl-1,3,4-oxadiazole Schiff base was obtained. m.p.: 252.7-254.9°C, yield 88.0%.

[0040] IR (KBr tablet): 3067 (Ar-H); 2974 (saturated C-H); 1642 (C=N), 1592, 1479 (benzene ring skel...

Embodiment 2

[0045] 1) Add 0.005mol 3-formyl-9-methylcarbazole, 0.006mol 2-amino-5-p-chlorophenyl-1,3,4-oxadiazole and 0.006mol p-toluene to a dry mortar Sulphonic acid was ground at room temperature for 16 min. At this time, TLC monitoring showed that the raw material sites of 3-formyl-9-methylcarbazole and 2-amino-5-p-chlorophenyl-1,3,4-oxadiazole 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;

[0046] 2) After the mixture was washed with water and suction filtered, 3-formyl-9-methylcarbazole 2-amino-5-p-chlorophenyl-1,3,4-oxadiazole Schiff base was obtained. m.p.: 171.6-175.5°C, yield 83.2%.

[0047] IR (KBr tablet): 3092 (Ar-H); 2988 (saturated C-H); 1623 (C=N); 1598, 1488 (benzene ring skeleton vibration);

[0048] 1369(-CH 3 ); 1244(C-N); 1079(C-O-C), 688(C-Cl)

[0049] 1 H NMR (CDCl 3 -d 6 ,...

Embodiment 3

[0053] 1) Add 0.005mol 3,6-diacetyl-9-ethylcarbazole, 0.011mol 2-amino-5-p-chlorophenyl-1,3,4-oxadiazole and 0.011mol to a dry mortar mol of p-toluenesulfonic acid, ground for 15min at room temperature, at this time TLC monitoring showed that 3,6-diacetyl-9-ethylcarbazole and 2-amino-5-p-chlorophenyl-1,3,4-oxadi The raw material point of the azole disappears, indicating that the raw material is completely reacted, and then left to stand for 30 minutes to obtain a mixture; wherein the developing agent is a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3;

[0054] 2) After the mixture was washed with water and suction filtered, 3,6-diacetyl-9-ethylcarbazole 2-amino-5-p-chlorophenyl-1,3,4-oxadiazole Schiff base was obtained. m.p.: 252.3-257.5°C, yield 87.6%.

[0055] IR (KBr tablet): 3089 (Ar-H); 2990, 2872 (saturated C-H); 1598 (C=N); 1588 (benzene ring skeleton); 1476

[0056] (-CH 2 -);1369(-CH 3 ); 1236(C-N); 1089(C-O-C); 692(C-Cl)

[0057] ...

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Abstract

The invention relates to a schiff base containing a carbazolyl group and an oxadiazole group and a preparing method thereof. The method includes the steps that acylcarbazole, 2-amino-5-substituted-1,3,4-oxadiazole and p-toluenesulfonic acid are added into a dry reaction container and ground under the room temperature condition, TLC is used for monitoring the reaction until the raw materials react completely, and a crude product is obtained after standing, wherein the molar ratio of acylcarbazole: 2-amino-5-substituted-1,3,4-oxadiazole: p-toluenesulfonic acid is 1:A:B, wherein the range of A is 1-1.2 or 2-2.2, and the range of B is 1-1.2 or 2-2.2; the schiff base containing the carbazolyl group and the oxadiazole group is obtained after the crude product is washed and filtered in a suction mode. The preparing method is high in reactivity, high in reaction speed and short in reaction time, and the schiff base containing the carbazolyl group and the oxadiazole group contains multiple C=N fluorescent groups and the carbazole group with high hole-transport capacity and has a certain luminescence property.

Description

[0001] 【Technical field】 [0002] The invention belongs to the field of chemical synthesis, in particular to a Schiff base containing carbazolyl and oxadiazolyl 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] O...

Claims

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Application Information

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IPC IPC(8): C07D413/12C07D413/14C09K11/06
CPCC07D413/12C07D413/14C09K11/06C09K2211/1022C09K2211/1029C09K2211/1048
Inventor 刘玉婷吴倩倩李荻扬尹大伟黄涛王雨薇盛娇杨晓明
Owner SHAANXI UNIV OF SCI & TECH
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