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N-aryl oxazepine ketone compound and preparation method thereof

A technology for aryl oxazepine and ketone compounds, which is applied in the chemical industry, can solve the problems of compound synthesis that have not been reported, and achieve the effects of sustainable development and utilization, simple operation, and convenient post-processing

Inactive Publication Date: 2014-09-03
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dibenzo[b,e][1,4]oxazepine-11(5H)-ketone of the present invention is dibenzo[b,f][1,4]oxazepine-11(10H) The positional isomer of the nitrogen-oxygen atom of )-ketone belongs to the structural type of benzo seven-membered nitrogen-containing heterocyclic ring, but the synthesis of this type of compound has not been reported yet

Method used

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  • N-aryl oxazepine ketone compound and preparation method thereof
  • N-aryl oxazepine ketone compound and preparation method thereof
  • N-aryl oxazepine ketone compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] The preparation of 5-phenyl-7-methoxycarbonyldibenzo[b,e][1,4]oxazepin-11(5H)-one comprises the following steps:

[0034] Step 1: Methyl 3-dehydroshikimate (0.41g, 2.2mmol), aniline (0.19g, 2.0mmol), p-toluenesulfonic acid (19.0mg, 0.1mmol), 5ml N,N-dimethylformamide Add to the microwave reaction vial at one time. The reaction system was reacted at 130° C. for 8 min in a microwave reactor.

[0035] Step 2: Potassium carbonate (0.83g, 6mmol), cuprous oxide (0.29g, 2mmol), o-iodobenzoic acid (0.50g, 2mmol) were added to the above system and reacted in a microwave reactor at 130°C for 5min. The reaction was monitored by TLC. After the reaction was completed, suction filtered after cooling. The filtrate was poured into 100ml of ice water and acidified with dilute hydrochloric acid. A large amount of off-white solids were precipitated. After suction filtration, drying, and recrystallization with ethyl acetate-petroleum ether, white crystals of N -Phenyl-N-(2-carboxyphenyl)...

Embodiment 2

[0039] The preparation of 5-(4-methylphenyl)-7-methoxycarbonyldibenzo[b,e][1,4]oxazepin-11(5H)-one comprises the following steps:

[0040] Step 1: Methyl 3-dehydroshikimate (0.37g, 2.0mmol), p-methylaniline (0.22g, 2.0mmol), formic acid (4.6mg, 0.1mmol), 5ml N,N-dimethylformamide Add to the microwave reaction vial at one time. The reaction system was reacted at 80°C for 20 min in a microwave reactor.

[0041] Step 2: Potassium carbonate (1.10g, 8mmol), cuprous oxide (29mg, 0.2mmol), o-iodobenzoic acid (0.50g, 2mmol) were added to the above system and reacted in a microwave reactor at 100°C for 15min. The reaction was monitored by TLC. After the reaction was completed, it was cooled and filtered with suction. The filtrate was poured into 100ml of ice water and acidified with dilute hydrochloric acid. A large amount of off-white solid precipitated, filtered with suction, dried, and recrystallized with ethyl acetate-ethanol to obtain light yellow crystals N -(4-methylphenyl)-N-...

Embodiment 3

[0045] The preparation of 5-(4-bromophenyl)-7-methoxycarbonyldibenzo[b,e][1,4]oxazepin-11(5H)-one comprises the following steps:

[0046] Step 1: Methyl 3-dehydroshikimate (0.45g, 2.4mmol), p-bromoaniline (0.35g, 2.0mmol), acetic acid (6.0mg, 0.1mmol), and 5ml dimethyl sulfoxide were added to the microwave reaction at one time in the bottle. The reaction system was reacted at 180° C. for 3 min in a microwave reactor.

[0047] Step 2: Sodium carbonate (0.64g, 6mmol), cuprous oxide (0.29g, 2mmol) and o-iodobenzoic acid (0.50g, 2mmol) were added to the above system and reacted in a microwave reactor at 160°C for 5min. The reaction was monitored by TLC. After the reaction was completed, it was cooled and filtered with suction. The filtrate was poured into 100ml of ice water and acidified with dilute hydrochloric acid. A large amount of off-white solids were precipitated, filtered with suction, dried, and recrystallized with dichloromethane-petroleum ether to obtain white crystals...

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Abstract

The invention discloses a 5-aryl-7-methoxycarbonyl dibenzo [b, e][1, 4] oxazepine-11(5H)-ketone compound and a preparation method thereof. The preparation method comprises the steps of carrying out condensation, isomerization and dehydration reaction on 3-dehydrogenated methyl shikimate and an aryl amine compound in the presence of an organic solvent and a catalyst in the microwave condition to obtain an aryl-substituted o-aminophenol intermediate; further adding o-halogen benzoic acid and an alkali neutralization catalyst in the microwave condition, cooling, pumping filtering, and carrying out recrystallization to obtain an N, N-diaryl-substituted o-aminophenol intermediate; and in the organic solvent, carrying out molecular lactonization cyclization reaction on the N, N-diaryl-substituted o-aminophenol intermediate in the presence of the catalyst and alkali to obtain the 5-aryl-7-methoxycarbonyl dibenzo [b, e][1, 4] oxazepine-11(5H)-ketone compound. The preparation method is simple, is short in the reaction time, is convenient for postprocessing and is high in the yield.

Description

technical field [0001] The present invention relates to the field of chemical engineering, in particular to a kind of N-aryl oxazepine compound and its preparation method, in particular to a kind of 5-aryl-7-methoxycarbonyl dibenzo[b,e][1 ,4] Oxazepine-11(5H)-ketone compounds and their preparation methods. Background technique [0002] Benzazepines are an important class of benzo seven-membered nitrogen-containing heterocyclic compounds, and the related structure types are widely seen in drugs and biologically active molecules. For example: carbamazepine (chemical name 5H-dibenzo[b,f]azepine-5-carboxamide), is a broad-spectrum antiepileptic drug with antiepileptic and antimanic effects; carbamazepine Produces antiepileptic effect by activating peripheral benzodiazepine receptors and blocking sodium channels, and is used for grand mal seizures and complex partial seizures that are difficult to control with other drugs such as phenytoin (Chinese Journal of Hospital Pharmacy, ...

Claims

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Application Information

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IPC IPC(8): C07D267/18
CPCC07D267/18
Inventor 邹永张恩生王德建魏文陈爱民徐田龙
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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