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Method for preparing dinitrogen heterocyclooctatetraene

A technology of cyclooctatetraene and diazepine, which is applied in the field of organic synthesis, can solve problems such as harsh preparation conditions, easy polymerization, and expensive products, and achieve the effects of simplifying the difficulty of synthesis conditions, reducing one-step reactions, and reducing production costs

Inactive Publication Date: 2012-07-18
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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Problems solved by technology

However, the preparation conditions are relatively harsh, requiring strong Lewis acid catalysis such as boron trifluoride, and the system requires strict water removal; and the preparation route of aminobenzophenone is long, and the total yield is not high, resulting in relatively expensive products
O-aminobenzaldehyde compounds are unstable and easy to polymerize, which is not conducive to the large-scale preparation of diazooctene

Method used

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  • Method for preparing dinitrogen heterocyclooctatetraene
  • Method for preparing dinitrogen heterocyclooctatetraene
  • Method for preparing dinitrogen heterocyclooctatetraene

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preparation example Construction

[0018] The method that the present invention proposes to prepare diazacyclooctene is as follows:

[0019] 1) Preparation of substituted benzoylbenzoic acid: using anhydrous aluminum chloride as Friedel-Crafts reagent, anhydride reacts with aromatic compound to replace benzoylbenzoic acid;

[0020] 2) Preparation of benzoyl azide: first, benzoyl chloride is prepared by using substituted benzoyl benzoic acid under the condition of chlorinating reagent; then the corresponding acyl azide is prepared from benzoyl chloride and azide salt.

[0021] 3) Preparation of diazaoctene: the acyl azide compound is subjected to a ring closure reaction at a certain temperature under the condition of an acidic reagent to prepare diazaoctatetraene.

Embodiment 1

[0023] In a 500mL three-necked round-bottomed flask equipped with a thermometer, a stirrer, and a nitrogen inlet tube, add 200 ml of benzene (5) (R 1 =H) and 50 grams of phthalic anhydride (4a) (R 2 =H), 118 grams of aluminum trichloride, stirred at room temperature for 2 hours, then raised the temperature to 50 degrees Celsius, and reacted with stirring for 5 hours. The reaction was terminated, cooled to room temperature, and poured into a large amount of ice water. Extract with dichloromethane, concentrate the solvent under reduced pressure, and the resulting product is recrystallized with ethanol to obtain o-benzoylbenzoic acid (6a) (R 1 , R 2 =H), yield 85%.

[0024] Phthaloylbenzoic acid (6a) (R 1 , R 2 = H) 3.0 g, 20 ml of thionyl chloride, reflux for 4 hours, concentrate under reduced pressure to prepare o-benzoylbenzoyl chloride; add 30 ml of anhydrous tetrahydrofuran to the system, stir to dissolve and put it in an ice bath; configure Add 5 ml of an aqueous solu...

Embodiment 2

[0035] With embodiment 1, used benzene compound is bromobenzene, 6,12-bis (4'-bromophenyl) dibenzo (b, f) diazacyclooctatetraene (1a) (R 1 =Br,R 2 =H), the overall yield was 78%.

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Abstract

A method for preparing dinitrogen heterocyclooctatetraene comprises the following steps of (1) conducting friedel-craft reaction with anhydride and aromatic compounds serving as reaction raw materials, and preparing substituted benzene formoxyl benzoic acid compounds; (2) preparing benzoyl chloride by using substituted benzene formoxyl benzoic acid under the condition of chlorination reagent, and using reaction of sodium azide and the benzoyl chloride at -10-50 DEG C to prepare benzoyl azide compounds; and (3) enabling the benzoyl azide compounds to conduct ring gathering reaction under an acidity system at 20-120 DEG C, and preparing the dinitrogen heterocyclooctatetraene. The method for preparing the dinitrogen heterocyclooctatetraene is low in price of used raw materials and soft in reaction condition, greatly reduces cost for prepare the dinitrogen heterocyclooctatetraene, can be used in the fields of photoelectrical materials, medicines and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis research, and specifically relates to a preparation method of diazacyclooctene, and more particularly relates to a method for preparing diazacyclooctene with high purity and high efficiency. Background technique [0002] Diazacyclooctene is an important nitrogen-containing heterocyclic compound. It not only has certain biochemical activity (its derivatives have hormone-like functions), but also can be used as a chromophoric group in dyes, optoelectronics, etc. Materials and other fields have broad application prospects in the field of modern science and technology. [0003] In neutral state, diazacyclooctatetraene has an antiaromatic molecular configuration, which is a boat conformation, and can be applied to the field of ferroelectric liquid crystal materials; after obtaining two electrons, diazacyclooctatetraene is It has an aromatic structure and a planar conformation. Through the change of t...

Claims

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Application Information

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IPC IPC(8): C07D245/04C07D245/02
Inventor 万晓波李建忠王啸赵娜
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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