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3-(2-benzoxazole)coumarin formamide compound, and preparation method and application thereof

A technology of coumarin amide and benzoxazole, which is applied in organic chemistry, optics, instruments, etc., can solve the problem of less research on coumarin base, and achieve the effect of great implementation value, simple process and mild reaction conditions

Active Publication Date: 2018-11-06
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the coumarin base has been less studied in nonlinear applications, while many of its derivatives have been extensively studied for various photophysical applications

Method used

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  • 3-(2-benzoxazole)coumarin formamide compound, and preparation method and application thereof
  • 3-(2-benzoxazole)coumarin formamide compound, and preparation method and application thereof
  • 3-(2-benzoxazole)coumarin formamide compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Preparation of 2-(2-oxo-2H-coumarin-3-yl)benzo[d]oxazole-5-carboxylic acid (abbreviated as compound IIIa): according to the amount of substance, formula (II): cyanoacetic acid Ethyl: 4-carboxy-2-aminophenol: organic acid is 1.0: 1.0: 1.1: 0.3 feed, where formula (II) is salicylaldehyde (ie R 1 Is hydrogen), the feed mass is 61.1g, ethyl cyanoacetate is 56.6g, 4-carboxy-2-aminophenol is 84.2g, the organic acid is p-toluenesulfonic acid, and the feed mass is 25.8g; alcohol solvent A is ethanol 240mL, The volume dosage is about 4 times the mass of formula (II) (mL / g).

[0062] Add salicylaldehyde, ethyl cyanoacetate, 4-carboxy-2-aminophenol, ethanol and p-toluenesulfonic acid into the reaction flask, and heat to reflux for reaction. TLC (Thin Layer Chromatography) tracking, after the reaction was completed, cooling in an ice bath, a large amount of light yellow solid precipitated, filtered, the filter cake was rinsed with water, and dried to obtain 102.3 g of the product, nam...

Embodiment 2

[0064] According to the quantity ratio of the substance, the formula (II): ethyl cyanoacetate: 4-carboxy-2-aminophenol: organic acid is 1.0: 1.2: 1.2: 0.1 feeding, where the formula (II) is salicylaldehyde, and the feeding quality is 61.1 g, ethyl cyanoacetate 67.9g, 4-carboxy-2-aminophenol 91.9g, organic acid is benzoic acid, feed mass is 6.1g; alcohol solvent A is n-propanol 360mL, and its volume dosage is formula (II ) About 6 times the mass (mL / g).

[0065] Other operations were the same as in Example 1, to obtain 99.6 g of the product, namely compound IIIa, with a yield of 64.8%. Combined with the characterization data, compound IIIa is a compound of formula (III), where R 1 Is hydrogen.

Embodiment 3

[0067] Preparation of 2-(7-(diethylamino)-2-oxo-2H-coumarin-3-yl)benzo[d]oxazole-5-carboxylic acid (abbreviated as compound IIIb): according to the amount of substance Formula (II): ethyl cyanoacetate: 4-carboxy-2-aminophenol: organic acid is 1.0: 0.9: 0.9: 0.6 feeding, wherein formula (II) is 4-diethylamino salicylaldehyde (ie R 1 Is diethane substituted amino), the feed mass is 96.6g, ethyl cyanoacetate is 50.9g, 4-carboxy-2-aminophenol is 68.9g, the organic acid is acetic acid, and the feed mass is 18.0g; the alcohol solvent A is iso For 300 mL of propanol, its volumetric dosage is about 3 times the mass of formula (II) (mL / g).

[0068] Other operations were the same as in Example 1, to obtain 116.5 g of the product, namely compound IIIb, with a yield of 68.4%. Combined with the characterization data, compound IIIb is a compound of formula (III), where R 1 Amino substituted with diethane.

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Abstract

The invention discloses a 3-(2-benzoxazole)coumarin formamide compound, a preparation method thereof, and an application thereof as a third-order nonlinear optical material. The preparation method comprises the following steps: reacting substituted salicylaldehyde, ethyl cyanoacetate and 4-carboxy-2-aminophenol in an alcohol solvent A under the catalysis of an organic acid to obtain a 3-(2-benzoxazole)coumarin carboxylic acid compound; reacting the 3-(2-benzoxazole)coumarin carboxylic acid compound with oxalyl chloride in chlorination solvent B under the catalysis of DMF to obtain a 3-(2-benzoxazole)coumarin chloride compound; and reacting the 3-(2-benzoxazole)coumarin chloride compound with amine in an organic solvent C under the action of an inorganic alkali to obtain the target compoundhaving a structure represented by formula (I). The preparation method has the advantages of short route, easily available raw materials, simple process, reaction conditions, realization of the development of the application of the 3-(2-benzoxazole)coumarin formamide compound in third-order nonlinear optics, great enforcement values and good social and economic benefits.

Description

Technical field [0001] The invention relates to the technical field of preparation of coumarin derivatives, in particular to a 3-(2-benzoxazole) coumarin amide compound, a preparation method thereof, and application as a third-order nonlinear optical material. Background technique [0002] In the development of optoelectronic technology, nonlinear optics (Nonlinera Optics, NLO) materials have played a key role in optical technology applications such as optical computing, optical communications, and optical limiting. Organic nonlinear optical materials have significant advantages such as large nonlinear optical coefficients, fast response speed, high optical damage threshold, and low DC dielectric constant. They are used in all-optical switches, laser instruments, laser ranging, optical communications and optical information storage It has potential applications in fields such as optical materials. Therefore, it is subject to long-term and persistent research by scientific researc...

Claims

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Application Information

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IPC IPC(8): C07D413/04G02F1/361
CPCC07D413/04G02F1/3612
Inventor 贾建洪叶孙斌冯东胡成坤张久明
Owner ZHEJIANG UNIV OF TECH
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