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A kind of oxazine phenyl ether derivative and preparation method thereof

A technology for oxazine phenyl ether and derivatives, applied in the field of oxazine phenyl ether derivatives and their preparation, can solve problems such as complex and diverse structures, and achieve the effects of complex and diverse structures, simple preparation methods, and excellent heat resistance

Active Publication Date: 2022-04-19
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Oxazine phenyl ether derivatives have multiple rings, and their structures are more complex and diverse

Method used

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  • A kind of oxazine phenyl ether derivative and preparation method thereof
  • A kind of oxazine phenyl ether derivative and preparation method thereof
  • A kind of oxazine phenyl ether derivative and preparation method thereof

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preparation example Construction

[0042] A kind of preparation method of oxazine phenyl ether derivative, described preparation method comprises the following steps:

[0043] (1) With 830mmol sodium hydride as a catalyst, 200mmol dimethyl malonate and 440mmol propargyl bromide were added to 210mL anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry to obtain a brownish-yellow solid product, namely compound 1;

[0044]

[0045] (2) Mix 80mmol of compound 1 with 200mmol of p-methylphenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system (2.56mmol / 0.85mmol), the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as base, 150mL anhydrous acetonitrile as solvent, stirring and reacting at room temperature for 12 hours, the product was washed with water, extracted with ethyl acetate, spin-dried under reduced pressure, using a volume ratio of 1 ...

Embodiment 2

[0054] An oxazine phenyl ether derivative, the structural formula of the oxazine phenyl ether derivative is:

[0055]

[0056] A kind of preparation method of oxazine phenyl ether derivative, described preparation method comprises the following steps:

[0057] (1) Using 830mmol of sodium hydrogen as a catalyst, 200mmol of diethyl malonate and 440mmol of propargyl bromide were added to 210mL of anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, Spin-dried under reduced pressure to obtain a brownish-yellow solid product, namely compound 1;

[0058]

[0059] (2) Mix 80mmol compound 1 with 200mmol p-ethylphenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system (2.56mmol / 0.85mmol), the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as base, 150ml anhydrous acetonitrile as solvent, stirred and reacted at room temperature fo...

Embodiment 3

[0068] An oxazine phenyl ether derivative, the structural formula of the oxazine phenyl ether derivative is:

[0069]

[0070] A kind of preparation method of oxazine phenyl ether derivative, described preparation method comprises the following steps:

[0071] (1) Using 830mmol of sodium hydrogen as a catalyst, 200mmol of diisopropyl malonate and 440mmol of propargyl bromide were added to 210mL of anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, and extracted with ethyl acetate , spin-dried under reduced pressure to obtain a brown-yellow solid product, namely compound 1;

[0072]

[0073] (2) Mix 80mmol compound 1 with 200mmol phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system (2.56mmol / 0.85mmol), the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as base, 150ml anhydrous acetonitrile as solvent, stirred and reacted at room temperature for...

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Abstract

The invention provides an oxazine phenyl ether derivative and a preparation method thereof. In the state of no catalyst, no additive, and no protection, the invention uses toluene as a solvent, tetrakyne and 2-phenyl-3,4-di Hydrogen-2H-benzo[1,3]oxazin-4-one is reacted at 110-115°C for more than 15 hours. The reaction process is firstly cyclized by the tetrayne substrate itself, because the benzyne generated by the tetrayne is An electron-deficient intermediate, extremely unstable and highly active. Tetrayne reacts with HDDA to form a benzyne intermediate, which then undergoes nucleophilic nucleophilic reaction with 2‑phenyl‑3,4‑dihydro‑2H‑benzo[1,3]oxazin‑4‑one Addition to obtain oxazine phenyl ether derivatives. Compared with the prior art, the oxazine phenyl ether derivatives prepared by the present invention have multiple rings, and their structures are more complex and diverse, and the preparation method provided by the present invention is simple, short in reaction time and high in efficiency.

Description

technical field [0001] The invention belongs to the field of organic compounds, and in particular relates to an oxazine phenyl ether derivative and a preparation method thereof. Background technique [0002] Oxazine phenyl ether derivatives have multiple rings, and their structures are more complex and diverse. Oxazine phenyl ether derivatives have excellent heat resistance and are widely used in high heat-resistant copper clad laminates, and are also widely used in many fields such as aerospace, automobiles and trains; they are also used in the perfume industry, synthetic resins and other organic synthesis production; there are many kinds of oxazine phenyl ether derivatives, some of which have medical value, and are valued by many domestic and foreign pharmaceutical companies and research institutions. The pyrazinidine derivatives will also show a broader application prospect in chemical production. Contents of the invention [0003] The purpose of the present invention...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/22
CPCC07D265/22
Inventor 徐小亮胡益民
Owner ANHUI NORMAL UNIV
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