Polysubstituted benzo[b][1,4] oxazepine derivative and preparation method thereof

A multi-substitution, oxazepine technology, applied in the direction of organic chemistry, can solve the problems that are rarely reported, and achieve the effects of short reaction time, wide substrate range and high yield

Active Publication Date: 2016-01-06
HUAQIAO UNIVERSITY
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The research on the synthesis of traditional [1,4]oxazepine compounds mainly focuses on dibenzoxazepine compounds, while the synthe

Method used

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  • Polysubstituted benzo[b][1,4] oxazepine derivative and preparation method thereof
  • Polysubstituted benzo[b][1,4] oxazepine derivative and preparation method thereof
  • Polysubstituted benzo[b][1,4] oxazepine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 2,4-diphenylbenzo[b][1,4]oxazepine

[0030]

[0031] (Z)-3-((2-bromophenyl)amino)-1,3-diphenylprop-2-en-1-one 0.5mmol, cesium carbonate 1mmol, N-methyl-2-pyrrolidone 5mL Add it into a 10mL reaction tube, place it in an oil bath at 120°C, and react for 12h. Add appropriate amount of water or sodium chloride solution to stop the reaction, and cool to room temperature. The reaction solution was diluted with 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 121.8 mg of the target product with a yield of 82%. The NMR characterization of this compound is as follows: 1 HNMR (400MHz, CDCl 3 )δ8.01(dd, J=6.6,3.1Hz,2H),7.91(dd,J=6.5,3.2Hz,2H),7.50–7.42(m,7H),7.25–7.19(m,2H),7.13 –7.06(m,1H),6.63(s,1H); 13 CNMR (100MHz, CDCl 3 )δ164.1, 163.2, 151.0, 142.1, 139.7, 133.7, 130.5, 130.3, 128.8, 128.6, 128.4, 128.1, 127.5, 126.2, 125.7,...

Embodiment 2

[0033] Preparation of 9-methyl-2,4-diphenylbenzo[b][1,4]oxazepine

[0034]

[0035] (Z)-3-((2-bromo-3-methylphenyl)amino)-1,3-diphenylprop-2-en-1-one 0.5mmol, potassium hydroxide 1mmol, N,N - Add 3mL of dimethylformamide into a 10mL reaction tube, place in an oil bath at 130°C, and react for 20h. Add appropriate amount of water or sodium chloride solution to stop the reaction, and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dried, filtered, concentrated, and purified by column chromatography to obtain 80.9 mg of the target product with a yield of 52%. The NMR characterization of this compound is as follows: 1 HNMR (400MHz, CDCl 3 )δ8.02–7.93(m,2H),7.92–7.79(m,2H),7.52–7.36(m,6H),7.28(d,J=1.4Hz,1H),7.09(t,J=7.6Hz ,1H),7.06–6.98(m,1H),6.55(s,1H),2.25(s,3H); 13 CNMR (100MHz, CDCl 3 )δ164.1, 163.4, 150.3, 142.1, 139.8, 134.4, 130.4, 130.3, 130.1, ...

Embodiment 3

[0037] Preparation of 8-methyl-2,4-diphenylbenzo[b][1,4]oxazepine

[0038]

[0039] (Z)-3-((2-iodo-4-methylphenyl)amino)-1,3-diphenylprop-2-en-1-one 0.5mmol, sodium tert-butoxide 1mmol, N- Add 3mL of methyl-2-pyrrolidone into a 10mL reaction tube, place in an oil bath at 120°C, and react for 12h. Add appropriate amount of water or sodium chloride solution to stop the reaction, and cool to room temperature. The reaction solution was diluted with 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 112.0 mg of the target product with a yield of 72%. The NMR characterization of this compound is as follows: 1 HNMR (400MHz, CDCl 3 )δ8.02–7.97(m,2H),7.93–7.87(m,2H),7.45(dt,J=7.0,2.6Hz,6H),7.34(d,J=8.0Hz,1H),7.02(dd ,J=8.0,1.1Hz,1H),6.90(d,J=1.0Hz,1H),6.60(s,1H),2.32(s,3H); 13 CNMR (100MHz, CDCl 3 )δ163.2, 162.7, 150.5, 139.8, 139.6, 138.7, 133.5, 130....

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Abstract

The invention discloses a polysubstituted benzo[b][1,4] oxazepine derivative and a preparation method thereof. The polysubstituted benzo[b][1,4] oxazepine derivative has the structural formula as shown in the description. The benzo[b][1,4] oxazepine derivative with multiple substituents, which cannot be synthesized by other methods, is synthesized, and profound and lasting significance is achieved from the angle of medical chemistry; the method has the advantages of easily available raw materials, high yield, mild reaction conditions, short reaction time, wide substrate range, strong reaction specificity, simple post-treatment and greenness.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a multi-substituted benzo[b][1,4]oxazepine derivative and a preparation method thereof. Background technique [0002] [1,4] Oxazepine compounds are a class of pharmaceutical molecules with various biological activities, and have important application value in anti-tumor, anti-depression, anti-inflammatory and anti-HIV drugs. Therefore, the research on new synthesis methods of [1,4]oxazepine compounds and their analogues has important application value and has attracted the attention of researchers in related fields. [0003] The research on the synthesis of traditional [1,4]oxazepine compounds mainly focuses on dibenzoxazepine compounds, while the synthesis of monobenzoxazepine compounds, especially multi-substituted benzo[b][1 ,4] The synthesis of oxazepine derivatives is rarely reported. Based on the wide range of biological activities of [1,4]oxazepine c...

Claims

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Application Information

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IPC IPC(8): C07D267/14
CPCC07D267/14
Inventor 崔秀灵沈金海
Owner HUAQIAO UNIVERSITY
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