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Synthesis method of benzoxazin ketone compound

The technology of a benzoxazinone and a synthesis method is applied in the field of synthesis of 2-substituted benzoxazinone compounds, which can solve problems such as harsh reaction conditions, equipment corrosion, and high toxicity of reagents, and achieve mild reaction conditions, The effect of low production cost and high synthesis yield

Inactive Publication Date: 2013-10-16
NORTHWEST UNIV(CN)
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Problems solved by technology

However, the traditional synthesis of 2-substituted benzoxazinones has disadvantages such as harsh reaction conditions, high cost of catalysts or oxidants, limited range of substrates, low yields, and unsuitability for large-scale production. In the past ten years, the synthetic method of 2-substituted benzoxazinone compounds has always been a hot spot and difficult point in the field of organic synthesis. The methods can be summarized into three categories: 1. anthranilic acid and its derivatives or isatoic anhydride and Cyclization reactions of its analogues; 2. Palladium-catalyzed carbonylation reactions; 3. Transition metal-catalyzed cyclization reactions
However, these methods are not in line with the development direction of green chemistry, and the reagents used are highly toxic, expensive, serious environmental pollution, strong corrosion to equipment, and difficult to prepare raw materials.

Method used

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  • Synthesis method of benzoxazin ketone compound
  • Synthesis method of benzoxazin ketone compound
  • Synthesis method of benzoxazin ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: Prepare 2-phenylbenzoxazinone by 2-phenylindole

[0016]

[0017] Into a 50mL round bottom flask, add 2-phenylindole (0.97 g, 0.005 mol), potassium monopersulfate complex salt (9.23g, 0.015 mol) and 20mL of nitromethane, and heat to 90°C in air, The reaction was detected by thin-layer chromatography. After the reaction was completed, it was cooled to room temperature. The reaction mixture was extracted with ethyl acetate and water. The organic phases were combined and spin-dried in vacuum. The crude product was separated by recrystallization or column chromatography to obtain 0.95 g of pure product , the product is a white solid, and the yield is 85%.

[0018] Structural analysis: 1 H NMR (CDCl 3 , 400 MHz): δ 8.31 (d, J = 8.0 Hz, 2 H), 8.24 (d, J = 8.0 Hz, 1 H), 7.85-7.81 (t, J = 7.6 Hz, 1 H), 7.69 (d, J = 8.0 Hz, 1 H), 7.60-7.50 (m, 4 H); 13 C NMR (CDCl 3 , 100 MHz):δ 159.5, 157.0, 146.9, 136.5, 132.6, 130.2, 128.7, 128.5, 128.3, 128.2, 12...

Embodiment 2

[0019] Example 2: Preparation of 5,7-dimethyl-2-phenylbenzoxazinone from 5,7-dimethyl-2-phenylindole

[0020]

[0021] Into a 10 mL round bottom flask, add 5,7-dimethyl-2-phenylindole (44.2 mg, 0.2 mmol), potassium monopersulfate (369.3 mg, 0.6 mol) and 2.0 mL of nitromethane , heated to 100°C in air, and the reaction was detected by thin-layer chromatography until the end of the reaction. The reaction mixture was extracted with water and ethyl acetate, and the organic phase was combined and dried in vacuum. The crude product of the reaction was separated by column chromatography to obtain the pure product 46.5 mg, the product is a light yellow solid, and the yield can reach 92%.

[0022] Structural analysis: 1 H NMR (CDCl3, 400 MHz): δ 8.17 (d, J = 7.2 Hz, 2 H), 7.72 (s, 1 H), 7.44-7.23 (m, 3 H), 2.48 (s, 3 H), 2.30 (s, 3 H). 13 C NMR (CDCl3, 100 MHz): δ 160.1, 154.9, 142.9, 138.5, 137.8, 135.8, 132.1, 130.5, 128.5, 128.0, 125.6, 116.5, 77.3, 77.0, 66.7, 21.9c. / z for...

Embodiment 3

[0023] Example 3: Preparation of 5-chloro-2-phenylbenzoxazinone from 5-chloro-2-phenylindole

[0024]

[0025] To a 10mL round-bottomed flask, add 5-chloro-2-phenylindole (45.4 mg, 0.2 mmol), potassium monopersulfate (369.3 mg, 0.6 mmol) and 2.0 mL of nitromethane in air Heat to 100°C. After the reaction is over, cool to room temperature. Extract the reaction mixture with water and ethyl acetate. Combine the organic phases and spin them dry in vacuum. The crude reaction product is separated by column chromatography to obtain 43.2 mg of pure product. The product is a white solid , yield 84%.

[0026] Structural analysis: 1 H NMR (CDCl 3 , 400 MHz): δ 8.27 (d, J = 7.2 Hz, 2 H), 8.17 (s, 1 H), 7.74 (d, J = 8.0 Hz, 1 H), 7.63-7.50 (m, 4 H). 13 C NMR (CDCl 3 , 100 MHz):δ 158.4, 157.2, 145.4, 136.8, 133.8, 132.8, 129.7, 128.7, 128.7, 128.3, 127.9, 118.0, 77.3, 77.0, 76.7. HRMS Calcd (ESI) m / z 10 h 8 N 2 Na: [M+Na] + 280.0136, found: 280.0126.

[0027] Use different...

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Abstract

A synthesis method of a 2-substituted benzoxazin ketone compound shown in the chemical formula (I) comprises the following steps: using 2-aryl indole as a raw material, using potassium hydrogen sulfate compound salt 2KHSO5. KHSO4. K2SO4 oxidation as an oxidizing agent, and performing oxidation reaction to obtain the 2-substituted benzoxazin ketone compound, wherein R represents a hydrogen atom, an alkyl of C1-C6, a naphthenic base, an alkoxy of C1-C6, halogen and an aryl group, and R' represents an aryl group or a substituted aryl group, an alkoxy of C1-C6, an aryloxy group, an alkoxy group of C1-C6 and an aryl amine group. The synthesis method has the advantages of green, high efficiency, mild reaction condition, simple operation, wide application range, low manufacturing cost, high synthesis yield and the like.

Description

technical field [0001] The invention relates to a synthesis method of 2-substituted benzoxazinone compounds, belonging to the technical field of organic synthesis. Background technique [0002] In the modern pharmaceutical and pesticide industries, 2-substituted benzoxazinones are widely used in the preparation of organic heterocyclic intermediates and the synthesis of drugs. In medicine, 2-substituted benzoxazinone itself has important biological and pharmaceutical activities, such as antibacterial, antiviral, anticancer, etc., and it is also an important pharmacophore, which can be used as chymotrypsin, HSV- 1 Inhibitors of protease, serine proteases, human leukocyte elastase, cathepsin G and human chymase, etc. It is worth mentioning that 2-substituted benzoxazinone compounds can also be used as useful intermediates in organic synthesis to prepare quinazolones with a wider range of drug activities, which greatly expands their application in drug synthesis. application. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/22C07D265/26C07D265/24
Inventor 关正辉连晓利
Owner NORTHWEST UNIV(CN)
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