A method for the synthesis of benzo[1,4]-oxazepine compounds by iron-catalyzed multi-component reaction

A multi-component reaction, oxazapine technology, applied in the direction of organic chemistry, etc., to achieve the effect of reducing pollution, wide application, and wide adaptability

Active Publication Date: 2019-12-10
南通华胜数码纺织科技有限公司
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Problems solved by technology

There is no report about the method of using carbon dioxide to synthesize benzo-1,4-oxazepine derivatives

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  • A method for the synthesis of benzo[1,4]-oxazepine compounds by iron-catalyzed multi-component reaction
  • A method for the synthesis of benzo[1,4]-oxazepine compounds by iron-catalyzed multi-component reaction
  • A method for the synthesis of benzo[1,4]-oxazepine compounds by iron-catalyzed multi-component reaction

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[0038] The present invention will be further described in detail below in conjunction with specific examples.

[0039] See Table 1 for the impact of different reaction conditions on the present invention.

[0040] Table 1

[0041]

[0042] The present invention is achieved like this, in a 25 mL round bottom flask, add 3 mmol aniline compounds and 3.6 mmol halogenated hydrocarbons respectively, then add 10 mL DMSO, 0.6 mmol FeCl successively 3 and 0.6 mmol of enaminone ligand, reacted at 100 o C for 8 hours. After cooling, 10 mL of saturated NaCl aqueous solution was added to the system, extracted three times with ethyl acetate, 10 mL each time, the organic phases were combined, and washed with anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated, and the pure product was obtained by 200-300 mesh silica gel column chromatography with a yield of 79-90%.

[0043] .

[0044] See Table 2 for the impact of different substituted embodiments on the yield of the pr...

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Abstract

The invention relates to a method using iron to catalyze multi-component reaction to synthesize a benzo[1,4]-oxygen azepine compound. The method is characterized in that substituted anilines, substituted halohydrocarbons and carbon dioxide are used as the raw materials, an iron catalyst is used as the catalyst, enaminone is used as the ligand, alkali carbonate is used as the alkali, reaction is performed in an organic solvent to obtain a reaction product, and the reaction product is subjected to post-processing to obtain the benzo[1,4]-oxygen azepine compound, various different substituted anilines and different substituted halohydrocarbons serving as the initiators can have reverse generation to obtain corresponding products, and a reaction formula is as shown in the specification. The method has the advantages that the method is simple in raw material, easy in raw material obtaining, mild in synthesizing condition, high and controllable in chemical selectivity, capable of saving cost, low in equipment requirement, convenient in post-processing and applicable to large-scale industrial production, the solvent and water are mutually soluble, and a catalyzing system is wide in adaptability.

Description

technical field [0001] The invention belongs to the technical field of biosynthesis, and in particular relates to a method for synthesizing benzo[1,4]-oxazepine compounds by iron-catalyzed multi-component reaction. Background technique [0002] [1,4] Oxazepine compounds are an important class of pharmaceutical intermediates, which have pharmacological activities such as anticonvulsant, antitumor, and improvement of cerebral ischemia, and have good medicinal value. The synthesis method and pharmacological activity of dibenzo[1,4]oxazepines have been extensively studied, and there are many kinds of medicines on the market, such as dibenzo-1,4- Oxazepine derivatives, antipsychotic loxapine I, antidepressant Piclozotan II, Sintamil analogue benzozapine III. However, due to its good medicinal value, it is necessary to develop a method for synthesizing this compound efficiently and conveniently from cheap and easy-to-obtain raw materials. [0003] [0004] In the chemical ind...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D267/14
CPCC07D267/14
Inventor 徐润生徐锦
Owner 南通华胜数码纺织科技有限公司
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