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5-aryl-5H-dibenzo[b,f] azepine-10(11H) ketone compounds and preparation method thereof

A technology of ketone compounds and azepines, which is applied in the field of preparation of 5-aryl-5H-dibenzo[b,f]azepine-10 ketones, and can solve the problems of low efficiency and low yield , to achieve the effect of simple operation, short reaction time and convenient post-processing

Inactive Publication Date: 2015-02-25
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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Problems solved by technology

[0004] At present, there are many reports on the preparation methods of 5H-dibenzo[b,f]azepine-10(11H) ketones with no substitution or non-aryl substitution on the nitrogen, such as: (1) using dibenzo 5H-dibenzo[b,f]azepine-10(11H)ketones were prepared from azepines as starting materials through multi-step reactions such as halogenation and dehalogenation (Fine Chemical Industry, 2008, 25(12) :1236–1239), but the method has many steps and low yield; (2) 5H-dibenzo[b,f]azepine- 10 (11H) ketones (Chinese Journal of Pharmaceutical Industry, 2006,37 (7): 443-445), but this method requires multi-step conversion, and the efficiency is low
Moreover, N-aryl substituted 5H-dibenzo[b,f]azepine-10(11H)ketones have not been reported

Method used

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  • 5-aryl-5H-dibenzo[b,f] azepine-10(11H) ketone compounds and preparation method thereof
  • 5-aryl-5H-dibenzo[b,f] azepine-10(11H) ketone compounds and preparation method thereof
  • 5-aryl-5H-dibenzo[b,f] azepine-10(11H) ketone compounds and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] The preparation of 5-(2-hydroxyl-5-methoxycarbonylphenyl)-8-fluoro-5H-dibenzo[b,f]azepin-10(11H)one comprises the following steps:

[0031] Step 1: Take 3-(4-fluoroanilino)-4-hydroxybenzoic acid methyl ester (0.26g, 1mmol), potassium carbonate (0.41g, 3mmol), cuprous oxide (0.14g, 1mmol), 2-bromo Phenylacetic acid (0.21g, 1mmol) and N,N-dimethylformamide (5ml) were reacted in a microwave reactor at 100°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 50ml of ice water and acidified with dilute hydrochloric acid. phenyl), (2-hydroxy-5-methoxycarbonylphenyl)amine (3).

[0032] Step 2: Add the above-mentioned intermediate, boron trifluoride diethyl ether (3ml) into a 25ml double-mouthed reaction bottle, react in an oil bath at 60°C for 3h, monitor the progress of the reaction by TLC, and wash the reaction solution with saturated saline ( 10ml), extracted with ethyl aceta...

Embodiment 2

[0035] The preparation of 5-(2-hydroxyl-5-methoxycarbonylphenyl)-8-fluoro-5H-dibenzo[b,f]azepin-10(11H)one comprises the following steps:

[0036]Step 1: Take 3-(4-fluoroanilino)-4-hydroxybenzoic acid methyl ester (0.26g, 1mmol), potassium carbonate (0.41g, 3mmol), cuprous oxide (71mg, 0.5mmol), 2-bromo Phenylacetic acid (0.21g, 1mmol) and N,N-dimethylformamide (5ml) were 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 50ml of ice water and acidified with dilute hydrochloric acid. phenyl), (2-hydroxy-5-methoxycarbonylphenyl)amine (3).

[0037] Step 2: Add the above intermediate, boron trifluoride diethyl ether (5ml) into a 25ml double-necked reaction bottle, react in an oil bath at 60°C for 3h, monitor the progress of the reaction by TLC, and wash the reaction solution with saturated saline ( 10ml), extracted with ethyl acetate (3x10ml...

Embodiment 3

[0040] The preparation of 5-(2-hydroxyl-5-methoxycarbonylphenyl)-8-fluoro-5H-dibenzo[b,f]azepin-10(11H)one comprises the following steps:

[0041] Step 1: Take 3-(4-fluoroanilino)-4-hydroxybenzoic acid methyl ester (0.26g, 1mmol), potassium carbonate (0.41g, 3mmol), cuprous oxide (29mg, 0.2mmol), 2-bromo Phenylacetic acid (0.21g, 1mmol) and N,N-dimethylformamide (5ml) were reacted in a microwave reactor at 100°C for 12min. The reaction was monitored by TLC. After the reaction was completed, it was cooled and filtered with suction. The filtrate was poured into 50ml of ice water and acidified with dilute hydrochloric acid. phenyl), (2-hydroxy-5-methoxycarbonylphenyl)amine (3).

[0042] Step 2: Add the above intermediate, boron trifluoride diethyl ether (5ml) into a 25ml double-necked reaction bottle, react in an oil bath at 40°C for 5h, monitor the progress of the reaction by TLC, and wash the reaction solution with saturated saline ( 10ml), extracted with ethyl acetate (3x10m...

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Abstract

The invention discloses 5-aryl-5H-dibenzo[b,f]azepine-10(11H) ketone compounds and a preparation method thereof. The preparation method comprises the following steps: reacting N-aryl-o-aminophenol compounds with o-bromophenylacetic acid compounds in the presence of an alkali, a catalyst and microwave to obtain a triarylamine intermediate substituted by carboxyl and hydroxyl; performing intramolecular acylation reaction and cyclization of the triarylamine intermediate in the presence of a catalyst to obtain the 5-aryl-5H-dibenzo[b,f] azepine-10(11H) ketone compounds. The method disclosed by the invention has the advantages of convenient and simple operation, short reaction time and convenient post treatment; and the ketone compounds are conveniently prepared by using simple raw materials, and therefore sustainable development and utilization can be achieved.

Description

technical field [0001] The present invention relates to the field of chemical industry, in particular to an N-aryl dibenzazepine compound and a preparation method thereof, in particular to a method for preparing 5-aryl- Method for 5H-dibenzo[b,f]azepine-10(11H)ones. Background technique [0002] 5H-Dibenzo[b,f]azepine-10(11H)one is a class of seven-membered nitrogen-containing heterocyclic compounds, and the related structure types are widely seen in biologically active molecules. For example: the chemical name of oxcarbazepine is 10,11-dihydro-10-oxo-5H-dibenzo[b,f]azepine-5-carboxamide, which is an N-formamido-substituted bis Benzo[b,f]azepinones, oxcarbazepine can activate peripheral benzodiazepine receptors, block sodium channels, and are used for localized and generalized seizures. [0003] [0004] At present, there are many reports on the preparation methods of 5H-dibenzo[b,f]azepine-10(11H) ketones with no substitution or non-aryl substitution on the nitrogen, s...

Claims

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Application Information

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IPC IPC(8): C07D223/22
CPCC07D223/22
Inventor 张恩生邹永徐田龙王德建魏文陈爱民
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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