Stenhouse donor-receptor adduct of Meldrum's acid-activated furan and 3-pyridylethylamine, and synthesis method thereof

A synthetic method, technology of pyridineethylamine, applied in chemical instruments and methods, organic chemistry, color-changing fluorescent materials, etc., can solve problems such as harsh reaction conditions, poor selectivity, and rare raw materials, and achieve easy purification, easy acquisition, and low cost Effect

Active Publication Date: 2020-12-11
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to overcome the shortcomings of raw materials in the prior art, such as rare raw materials, harsh reaction conditions, low yield, and poor selectivity, the purpose of the present invention is to provide a Stenhouse donor-acceptor based on furan and 3-pyridine ethylamine activated by McFarland acid Adducts and their synthesis methods

Method used

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  • Stenhouse donor-receptor adduct of Meldrum's acid-activated furan and 3-pyridylethylamine, and synthesis method thereof
  • Stenhouse donor-receptor adduct of Meldrum's acid-activated furan and 3-pyridylethylamine, and synthesis method thereof
  • Stenhouse donor-receptor adduct of Meldrum's acid-activated furan and 3-pyridylethylamine, and synthesis method thereof

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Experimental program
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Embodiment 1

[0041] Aromatic compound I of the present invention, its molecular structure is as follows:

[0042]

[0043] The preparation method of the furan compound of present embodiment 1 comprises the following steps:

[0044] In the two-necked bottle, according to the molar ratio of 2-furyl aldehyde: cycloisopropylidene malonate=1:1.1, 2-furyl aldehyde and cycloisopropylidene malonate were mixed first, and then deionized water was added as Solvent, reacted at 75°C for 3h. After the reaction, add CH 2 Cl 2 Extract crude product, CH 2 Cl 2 Extract water (25ml*3) then concentrate CH 2 Cl 2 Phase, add saturated NH successively 4 Cl solution, saturated NaCl solution, saturated NaHSO 4 , saturated NaHCO 3 solution, for CH 2 Cl 2 phase was washed, and then a small amount of water in the aqueous phase was dried with anhydrous magnesium sulfate, rotary evaporated, and vacuumized by an oil pump to obtain a yellow blocky solid (to be stored in nitrogen). It was characterized by N...

Embodiment 2

[0046] The target compound, its molecular structure is shown in the following formula:

[0047]

[0048] The preparation method of the DASA compound of present embodiment 2 comprises the following steps:

[0049] Under nitrogen protection, in a one-necked flask according to the molar ratio 3-Pyridylethylamine mix. The mixture was added to a tetrahydrofuran solution, stirred at 23°C for 10 minutes, and then cooled at 0°C for 20 minutes. The reaction mixture was then filtered to collect the precipitated solid, which was washed with cold diethyl ether and dried in vacuo to give a red solid. NMR and IR characterization were performed on it, and the results were as follows: figure 2 , image 3 shown.

Embodiment 3

[0051]Compound II was recrystallized in methanol and allowed to stand for 1-2 days to obtain Compound III. It is characterized by XRD, such as Figure 4 shown.

[0052] The crystal data obtained after recrystallization of the red solid are shown in Table 1 below.

[0053]

[0054]

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Abstract

The invention discloses a Stenhouse donor-receptor adduct (DASA) based on Meldrum's acid activated furan and 3-pyridylethylamine, and a synthesis method of the Stenhouse donor-receptor adduct. The method specifically comprises the following steps: mixing 2-furan formaldehyde and cycloisopropyl malonate to react to synthesize an intermediate, and reacting the intermediate with 3-pyridylethylamine to generate a DASA compound. According to the method, the organic solvent with low toxicity is used for carrying out addition reaction under certain conditions to obtain the DASA compound with high yield and high content, and a catalyst is not needed, so that the production cost is effectively reduced; and the photophysical property test shows that the compound has different performances in different solvents, which indicates that the compound has a wide application range, can satisfy different demands in different fields, and fully exerts the excellent performances of the compound.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a Stenhouse donor-acceptor adduct based on McFarland acid-activated furan and 3-pyridylethylamine and a synthesis method thereof. Background technique [0002] DASA (Donor-Acceptor Stenhouse Adducts) is a class of molecules capable of light-driven photoisomerization (photochromism). In 1870, Stenhouse discovered that, in the presence of equivalent primary or secondary anilines, equivalent protic acid 2-furylcarbaldehyde undergoes ring opening to obtain a stable, intensely colored salt with an -OH group on the second carbon group of atoms. The initial imine / imine formation between 2-furfuraldehyde and aniline activates the furan nucleus into nucleophilic attack, which then leads to furan ring opening and the formation of the Stenhouse salt. Photovariable molecules have become a hot research topic in various fields, such as molecular electronics and information processing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12C09K9/02
CPCC07D405/12C09K9/02C09K2211/1029C09K2211/1088Y02P20/55
Inventor 蔡蔚暴欣陈天阳孙志伟杨拓
Owner NANJING UNIV OF SCI & TECH
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