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Polysubstituted 2-hydroxy-1,4-benzoxazine derivative

A benzoxazine and multi-substitution technology, applied in the field of multi-substituted 2-hydroxyl-1, can solve the problems of many steps and low yield, and achieve the effects of mild reaction conditions, short reaction time and high yield

Active Publication Date: 2017-11-24
HUAQIAO UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The traditional synthetic method of 2-hydroxyl-1,4-benzoxazine derivatives is mainly based on substituted o-aminophenol or halogenated arene derivatives as raw materials, and different 1,2-dihaloalkanes, α-substituted halogenated Acid or ester reaction, but the method has many steps and the yield is not high

Method used

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  • Polysubstituted 2-hydroxy-1,4-benzoxazine derivative
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  • Polysubstituted 2-hydroxy-1,4-benzoxazine derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of product 1

[0027]

[0028] (Z)-3-((2-hydroxyphenyl)amino)-1,3-diphenylprop-2-en-1-one 0.2mmol, iodobenzene acetate 0.24mmol, triethylamine 0.4mmol, ethanol Add 2 mL into a 10 mL reaction tube and react at room temperature for 3 h. After distilling off ethanol, the reactant was dissolved in ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 55.3 mg of the target product with a yield of 84%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ7.79(d, J=7.5Hz, 2H), 7.74-7.64(m, 3H), 7.44(t, J=7.4Hz, 1H), 7.35-7.24(m, 5H), 7.23-7.17(m , 2H), 7.04(dd, J=8.0, 0.9Hz, 1H), 5.95(s, 1H); 13 C NMR (100MHz, CDCl 3 )δ192.20, 156.11, 141.92, 135.38, 134.41, 131.72, 131.54, 130.60, 130.25, 129.78, 128.62, 128.55, 128.53, 127.68, 123.26, 116.94, 90.38; 21 h 16 NO 3 (M+H) + 330.1125, found 330.1125.

Embodiment 2

[0030] Preparation of product 2

[0031]

[0032] (Z)-3-((2-hydroxy-5-fluorophenyl)amino)-1,3-diphenylprop-2-en-1-one 0.2mmol, iodobenzene acetate 0.24mmol, triethylamine Add 0.4mmol and 2mL of methanol into a 10mL reaction tube, and react at room temperature for 3.5h. After methanol was evaporated, the reactant was dissolved in ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 40.3 mg of the target product with a yield of 58%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ7.77(d, J=7.7Hz, 2H), 7.67(d, J=7.1Hz, 2H), 7.47-7.39(m, 2H), 7.25(m, 5H), 7.08-6.94(m, 2H ), 5.95(s, 1H); 13 C NMR (101MHz, CDCl 3 )δ191.98, 158.33 (d, J=240.5Hz), 157.32, 138.05 (d, J=2.4Hz), 135.03, 134.46, 132.07 (d, J=11.3Hz), 131.62, 130.89, 130.20, 128.55, 128.55 , 127.72, 117.56 (d, J=8.8Hz), 116.26 (d, J=23.9Hz), 114.65 (d, J=23...

Embodiment 3

[0034] Preparation of Product 3

[0035]

[0036] (Z)-3-((2-hydroxy-4-methylphenyl)amino)-1,3-diphenylprop-2-en-1-one 0.2mmol, iodobenzene acetate 0.24mmol, K 3 PO 4 ·3H 2 O 0.4mmol, ethanol 2mL were added to a 10mL reaction tube, and reacted at room temperature for 3h. After distilling off ethanol, the reactant was dissolved in ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 41.2 mg of the target product with a yield of 60%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ7.78(d, J=7.9Hz, 2H), 7.66(d, J=6.3Hz, 2H), 7.58(d, J=7.9Hz, 1H), 7.42(t, J=7.1Hz, 1H) , 7.35-7.15(m, 5H), 7.00(d, J=7.8Hz, 1H), 6.85(s, 1H), 5.94(s, 1H), 2.38(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ192.30, 155.00, 141.55, 140.51, 135.46, 134.32, 131.74, 130.36, 130.18, 129.34, 128.49, 128.45, 128.25, 127.56, 124.08, 117.22, 90.44, HRMS) ca...

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Abstract

The invention discloses a polysubstituted 2-hydroxy-1,4-benzoxazine derivative, which has a structural formula shown as in the description. The polysubstituted 2-hydroxy-1,4-benzoxazine derivative which cannot be synthesized by other methods is synthesized; the profound significance is realized in the aspects of organic synthesis and medicinal chemistry; the raw materials used by the method are easily obtained; the yield is high; the reaction conditions are mild; the reaction time is short; the substrate range is wide; the reaction specificity is high; the post treatment is simple and convenient and achieves an environment-friendly effect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a multi-substituted 2-hydroxyl-1,4-benzoxazine derivative. Background technique [0002] 2-Hydroxy-1,4-benzoxazine derivatives are a class of molecules with various biological activities. They have good insecticidal, bactericidal and anti-inflammatory activities, and have important application values ​​in medicine and pesticides. Therefore, the research on new synthetic methods of 2-hydroxy-1,4-benzoxazine compounds and their analogues has important application value and has attracted the attention of researchers in related fields. [0003] The traditional synthetic method of 2-hydroxyl-1,4-benzoxazine derivatives is mainly based on substituted o-aminophenol or halogenated arene derivatives as raw materials, and different 1,2-dihaloalkanes, α-substituted halogenated Acid or ester reaction, but the method has many steps and the yield is not high. Based on the extensive...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/36C07D413/04C07D413/06
CPCC07D265/36C07D413/04C07D413/06
Inventor 崔秀灵张红
Owner HUAQIAO UNIVERSITY
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