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Catalytic oxidation synthesis method of 4H-3,1-benzoxazine compound

A benzoxazine and catalytic oxidation technology, applied in the direction of organic chemistry, can solve the problem of unavoidable metal pollution, achieve the effect of avoiding metal pollution, easy and safe operation, and reducing environmental costs

Active Publication Date: 2017-06-13
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the use of copper salts in this method, metal contamination is unavoidable

Method used

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  • Catalytic oxidation synthesis method of 4H-3,1-benzoxazine compound
  • Catalytic oxidation synthesis method of 4H-3,1-benzoxazine compound
  • Catalytic oxidation synthesis method of 4H-3,1-benzoxazine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: 2-Phenyl-4 H Preparation of -3,1-benzoxazine (formula (3-1))

[0035] In a 50 mL round bottom flask, add 2 mmol of 2-aminobenzyl alcohol (formula (1-1)), 2 mmol of benzaldehyde (formula (2-1)), 0.2 mmol of ABNO, 0.6 mmol of KOH and 4 mL of Toluene, replace the air in the bottle with oxygen, seal the mouth of the bottle with a rubber stopper, insert an oxygen bulb, put the reaction bottle into a preheated oil bath and heat to 80°C, and react for 4 hours. The solvent was evaporated under reduced pressure, and then separated by column chromatography, using a mixture of ethyl acetate / petroleum ether with a volume ratio of 1:50 as the eluent, the eluate containing the target compound was collected, and the solvent was evaporated to obtain the product 2- Phenyl-4 H -3,1-Benzoxazine, the isolated yield is 95%.

Embodiment 2

[0036] Example 2: 2-Phenyl-4 H Preparation of -3,1-benzoxazine (formula (3-1))

[0037] The reaction steps are the same as in Example 1, and the difference is that toluene is changed into mixed xylenes, and 2-phenyl-4 H The isolated yield of -3,1-benzoxazine was 63%.

Embodiment 3

[0038] Example 3: 2-Phenyl-4 H Preparation of -3,1-benzoxazine (formula (3-1))

[0039] Reaction step is the same as embodiment 1, and difference is that toluene changes ethyl acetate into, 2-phenyl-4 H The isolated yield of -3,1-benzoxazine was 81%.

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Abstract

The invention discloses a catalytic oxidation synthesis method of a 4H-3,1-benzoxazine compound. The method comprises the following steps: using a 2-aminobenzyl alcohol compound and aldehyde as reaction substrates in a molar ratio of 100: (100 to 120), using 9-azabicyalo[3.3.1] nonane-N-oxygen radical as a catalyst, using potassium hydroxide as an assistant, enabling the molar ratio of the reaction substance of the 2-aminobenzyl alcohol compound, the 9-azabicyalo[3.3.1] nonane-N-oxygen radical to the potassium hydroxide to be 100: (6 to 20): (10 to 50), using oxygen as an oxidant, reacting the reaction substances in an organic solvent, enabling the using amount of the organic solvent to be 8 to 20 times of that of the reaction substance of the 2-aminobenzyl alcohol compound, carrying out a reaction under the conditions of ordinary pressure and the temperature of 60 to 110 DEG C, enabling the reaction to last for 2 to 12 h, carrying out separation treatment after the reaction is finished so as to obtain a target product of the 4H-3,1-benzoxazine compound. The method is simple, convenient and safe in operation, the environmental cost is greatly reduced, and transition metal catalysts are prevented from being used, so that the problem of metal pollution is solved.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a 4 H - Catalytic oxidation synthesis method of 3,1-benzoxazine compounds. Background technique [0002] 4 H -3,1-Benzoxazine compounds exist in many biologically active natural products and synthetic drugs with important biological properties. This kind of nitrogen-containing compound has been deeply studied as the core skeleton structure in many drugs, for example, etifoxine, a GABA receptor inhibitor used as an anxiolytic and anticonvulsant, and cetilistat, a pancreatic lipase inhibitor used to treat obesity. [0003] [0004] Therefore, the research and development of synthetic methods for such compounds has attracted the attention of many people. The most classic synthetic method uses 2-aminobenzyl alcohol compounds and aldehydes as raw materials. First, these two types of compounds undergo condensation reactions to generate intermediates, and then oxidative dehydrogen...

Claims

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Application Information

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IPC IPC(8): C07D265/16C07D413/04
CPCC07D265/16C07D413/04
Inventor 沈振陆李美超马佳颀胡信全胡宝祥
Owner ZHEJIANG UNIV OF TECH