CN106518726B - Aryl Schiff base derivative and preparation method and application thereof - Google Patents

Aryl Schiff base derivative and preparation method and application thereof Download PDF

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CN106518726B
CN106518726B CN201610938622.8A CN201610938622A CN106518726B CN 106518726 B CN106518726 B CN 106518726B CN 201610938622 A CN201610938622 A CN 201610938622A CN 106518726 B CN106518726 B CN 106518726B
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schiff base
reaction
aryl
preparation
water
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CN106518726A (en
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黄杰
张兴隆
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Chongqing Xinren Technology Development Co ltd
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Chongqing University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0241—Imines or enamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses an aryl Schiff base derivative and a preparation method and application thereof, wherein the aryl Schiff base derivative has the following structural formula:

Description

A kind of aryl Schiff base derivatives and the preparation method and application thereof
Technical field
The present invention relates to a kind of schiff bases, and more particularly to a kind of aryl Schiff base derivatives, the invention further relates to one The preparation method of kind aryl Schiff base derivatives and application.
Background technology
Schiff bases is primarily referred to as a kind of organic compound containing imines or azomethine group (carbon-to-nitrogen double bon ,-RC=N-) Object is typically condensed by the compound containing active carbonyl and primary amine.Schiff bases and its complex have excellent resist The performances such as the bioactivity such as bacterium, anticancer, antiviral, weeding and special photoelectromagnetic.Therefore, in recent years medicine, biology, The fields such as catalysis and functional material cause the extensive research interest of researcher.
However, the traditional preparation methods of schiff bases be usually in organic solvent, by the compound containing active carbonyl with Amine carries out condensation reaction and obtains, and needs to use organic solvent and catalyst, the reaction time is longer, and side reaction is more, it is difficult to detach Purification has the deficiencies of energy consumption is high, pollution is larger.Therefore, novel Schiff base derivatives and environmentally protective, efficient are developed The preparation method easy, low energy consumption is of great significance.
Invention content
For deficiencies of the prior art, it is an object of the invention to propose a kind of aryl Schiff base derivatives, Aryl Schiff base derivatives of the present invention have good chemical stability and dissolubility.
The present invention goes back while providing the aryl Schiff base derivatives preparation method and application, this preparation method is simple, efficient, By-product is few, and yield is high.
The technical proposal of the invention is realized in this way：
A kind of aryl Schiff base derivatives, structural formula are as follows：
The preparation method of above-mentioned aryl Schiff base derivatives, first in hydrothermal reaction kettle, be added certain volume water and The molar ratio of suitable 2- amino -4- methylphenols and benzaldehyde, 2- amino -4- methylphenols and benzaldehyde is 1:1-1:2, so Reaction 20-150 minutes is carried out at 100 DEG C -150 DEG C afterwards；After reaction, after reaction kettle being cooled to room temperature, reaction is produced Object is filtered, dries, recrystallizes and dries, you can obtains aryl Schiff base derivatives.
The molar ratio preferably 1 of 2- amino -4- methylphenols and benzaldehyde:1-1:1.5, preferably 100 DEG C -130 of reaction temperature DEG C, the reaction time is 30-60 minutes preferred.
The compactedness of water is 20%-60%, the volume of volume/hydrothermal reaction kettle of compactedness=addition water.
Application of the above-mentioned aryl Schiff base derivatives in medicine, catalysis and field of functional materials.
Compared with the conventional method, the present invention at least has the advantages that：
1, the preparation method of aryl Schiff base derivatives of the invention using hydrothermal reaction kettle replace Conventional glass instrument as Reaction unit, high temperature high voltage resistant replace conventional organic solvent as reaction medium using water, nontoxic, and are urged without using any Reaction raw materials are mixed with suitable quantity of water in hydrothermal reaction kettle, are placed under high temperature and pressure by agent, main to be expanded using the high of high-temperature water Coefficient and strong solubility are dissipated, to make reaction efficiently, easily carry out.The preparation method is environmentally protective, mild condition, when reaction Between it is short, by-product is few and is easily isolated purification, and yield is high, is easy to operate and control, required equipment and raw material are easy to get, and price is low It is honest and clean.
2, on the one hand aryl Schiff base derivatives of the invention due to the connection of imines both ends are the structures containing phenyl ring, Chemical stability is good, on the other hand, is dissolved in common a variety of organic solvents, and dissolubility is good, and has photoluminescent property, in organic hair The fields such as optical function material have a good application prospect.
Description of the drawings
Fig. 1 is 1 obtained aryl Schiff base derivatives of the embodiment of the present invention1H-NMR spectrum.
Fig. 2 is 1 obtained aryl Schiff base derivatives (a concentration of 1 × 10 of the embodiment of the present invention-5Mol/L) in hexamethylene Normalization fluorescence emission spectrogram of compound (excitation wavelength in alkane, dichloromethane and absolute ethyl alcohol：300nm).
Fig. 3 is 2 obtained aryl Schiff base derivatives of the embodiment of the present invention1H-NMR spectrum.
Specific implementation mode
Aryl Schiff base derivatives of the present invention, structural formula are as follows：
Preparation method is：In the hydrothermal reaction kettle of certain volume, water (the compactedness 20%- of certain volume is added 60%, the volume of volume/hydrothermal reaction kettle of compactedness=addition water) and suitable 2- amino -4- methylphenols and benzene first Aldehyde (molar ratio 1:1-1:2) reaction 20-150 minutes, is carried out at 100 DEG C -150 DEG C.After reaction, reaction kettle is cooled down To after room temperature, reaction product is filtered, dry, recrystallize and is dried, you can obtains the aryl schiff bases that structural formula is (I) Derivative.
Its reaction equation is as follows：
The above-mentioned aryl Schiff base derivatives that the present invention obtains can be applied in fields such as medicine, catalysis and functional materials In.
In order to make technical problems, technical solutions and advantageous effects to be solved by the present invention be more clearly understood, with reference to The invention will be further described for attached drawing and specific preparation embodiment.
Embodiment 1
In the hydrothermal reaction kettle of 50ml, the water (i.e. compactedness is 50%) and 2mmol 2- amino -4- of 25ml is added Methylphenol and 3mmol benzaldehydes carry out reaction 40 minutes at 120 DEG C.After reaction, reaction kettle is cooled to room temperature Afterwards, reaction product is filtered, dried, recrystallized and dried, you can obtain target product.
Fig. 1 is 1 obtained aryl Schiff base derivatives of the embodiment of the present invention1H-NMR spectrum.
1H-NMR(400MHz,CDCl3)δ：8.68 (s, 1H) illustrate that schiff bases is successfully prepared, 7.92 (m, 2H), 7.48-7.49 (m, 3H), 7.25 (m, 1H), 7.09-7.12 (m, 1H), 7.09 (s, 1H), 6.92-7.02 (m, 1H), 2.32 (s, 3H)。
Fig. 2 is 1 obtained aryl Schiff base derivatives (a concentration of 1 × 10 of the embodiment of the present invention-5Mol/L) in hexamethylene Normalization fluorescence emission spectrogram of compound (excitation wavelength in alkane, dichloromethane and absolute ethyl alcohol：300nm).Curve a corresponds to ring in figure Hexane, curve b correspond to dichloromethane, and curve c corresponds to absolute ethyl alcohol.Figure it is seen that aryl Schiff base derivatives of the present invention With certain blue-fluorescence property, it is possible to apply in fields such as luminous organic materials.
Embodiment 2
In the hydrothermal reaction kettle of 25ml, the water (i.e. compactedness is 40%) and 1mmol 2- amino -4- of 10ml is added Methylphenol and 1mmol benzaldehydes carry out reaction 60 minutes at 100 DEG C.After reaction, reaction kettle is cooled to room temperature Afterwards, reaction product is filtered, dried, recrystallized and dried to get to target product.
Fig. 3 is 2 obtained aryl Schiff base derivatives of the embodiment of the present invention1H-NMR spectrum.
1H-NMR(400MHz,CDCl3)δ：8.67 (s, 1H) illustrate that schiff bases is successfully prepared, 7.90 (m, 2H), 7.46-7.49 (m, 3H), 7.25 (m, 1H), 7.01 (s, 1H), 6.92-7.02 (m, 1H), 6.89-6.90 (m, 1H), 2.31 (s, 3H)。
Embodiment 3
In the hydrothermal reaction kettle of 25ml, the water (i.e. compactedness is 40%) and 3mmol 2- amino -4- of 10ml is added Methylphenol and 3mmol benzaldehydes carry out reaction 100 minutes at 120 DEG C.After reaction, reaction kettle is cooled to room temperature Afterwards, reaction product is filtered, dried, recrystallized and dried to get to target product.
Embodiment 4
In the hydrothermal reaction kettle of 50ml, the water (i.e. compactedness is 60%) and 2mmol 2- amino -4- of 30ml is added Methylphenol and 4mmol benzaldehydes carry out reaction 20 minutes at 150 DEG C.After reaction, reaction kettle is cooled to room temperature Afterwards, reaction product is filtered, dried, recrystallized and dried to get to target product.
Finally, it should be noted that the above examples are only used to illustrate the technical scheme of the present invention and are not limiting, although Shen It asks someone to describe the invention in detail with reference to preferred embodiment, it will be understood by those of ordinary skill in the art that, to this hair Bright technical solution is modified or replaced equivalently, and without departing from the objective and range of the technical program, should all be covered at this In the right of invention.

Claims (1)

1. a kind of preparation method of aryl Schiff base derivatives, it is characterised in that：The structural formula of the aryl Schiff base derivatives It is as follows：
The specific preparation method of the aryl Schiff base derivatives is：First in hydrothermal reaction kettle, be added the water of certain volume with And suitable 2- amino -4- methylphenols and benzaldehyde, the molar ratio of 2- amino -4- methylphenols and benzaldehyde is 1:1-1: 1.5, then reaction 30-60 minutes is carried out using the high diffusibility of high-temperature water and strong solubility at 100 DEG C -130 DEG C；Reaction knot Shu Hou after reaction kettle is cooled to room temperature, is filtered reaction product, dries, recrystallizes and dries, you can obtains aryl seat Husband's alkali derivant；
The compactedness of the water is 20%-60%, the volume of volume/hydrothermal reaction kettle of compactedness=addition water.
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CN107619380A (en) * 2017-11-10 2018-01-23 重庆理工大学 A kind of single Schiff base derivatives and preparation method thereof
CN107673991A (en) * 2017-11-10 2018-02-09 重庆理工大学 A kind of Schiff base derivatives and preparation method thereof
CN107673992A (en) * 2017-11-10 2018-02-09 重庆理工大学 A kind of ortho-aminophenol Schiff base derivatives and preparation method thereof
CN111233699B (en) * 2018-11-28 2023-10-27 中国科学院宁波材料技术与工程研究所 Cardanol Schiff base antioxidant and preparation method and application thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1220988A (en) * 1997-12-24 1999-06-30 南京大学 Method for synthesising schiff base in the absence of solvent

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1220988A (en) * 1997-12-24 1999-06-30 南京大学 Method for synthesising schiff base in the absence of solvent

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Antioxidant and antiproliferative activities of hydroxyl-substituted Schiff bases";Li-Xia Cheng, et al.;《Bioorganic & Medicinal Chemistry Letters》;20100311;第20卷;2417-2420 *
"Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation";Yeon-Ho Cho, et al.;《Tetrahedron》;20130607;第69卷;6565-6573 *
Yeon-Ho Cho, et al.."Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation".《Tetrahedron》.2013,第69卷6565-6573. *

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