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Method for photocatalytic synthesis of quinazolinone

A quinazolinone, photocatalytic technology, applied in chemical instruments and methods, catalytic reactions, physical/chemical process catalysts, etc., can solve the problems of high price and low reserves, and achieve short reaction time, high academic value, and reaction mild conditions

Active Publication Date: 2021-07-30
上海橡实化学有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the synthesis of quinazolinones by transition metal catalysis can avoid the formation of by-products and improve the atom economy of the reaction, it is inevitable to use transition metals.
Ir, Ru, Rh and other transition metals are not only low in reserves on the earth but also expensive, and they will also have a certain impact on the separation and purification of products

Method used

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  • Method for photocatalytic synthesis of quinazolinone
  • Method for photocatalytic synthesis of quinazolinone
  • Method for photocatalytic synthesis of quinazolinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: 2-phenyl-4-quinazolinone

[0031] 2-Phenyl-4-quinazolinone

[0032]

[0033] Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%), and acetonitrile (2 mL) were sequentially added to a 15 mL reaction tube. The reaction mixture was reacted under the irradiation of 10 w blue light for 2 h. After the reaction, the solvent was removed by rotary evaporation, and then the pure The target compound was a white solid (39.1 mg) with a melting point of 237-238°C.

[0034] The NMR spectrum of the product is as figure 1 and 2 As shown, the details are as follows:

[0035] 1 H NMR (400 MHz, [D 6 ]DMSO) δ 12.56 (br s, 1H), 8.19-8.15 (m, 3H), 7.84(t, J = 7.5 Hz, 1H), 7.76 (d, J = 8.1 Hz, 1H), 7.59-7.51 (m, 4H); 13 C NMR (100MHz, [D 6 ]DMSO) δ 162.3, 152.3, 148.8, 134.6, 131.4, 128.6, 127.8, 127.5, 126.6, 125.9, 121.0, 39.5.

Embodiment 2

[0036] Example 2: 2-phenyl-4-quinazolinone

[0037] 2-Phenyl-4-quinazolinone

[0038]

[0039] Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (10.2 mg, 30 mol%), and acetonitrile (2 mL) were sequentially added to a 15 mL reaction tube. The reaction mixture was reacted under the irradiation of 10 w blue light for 2 h. After the reaction, the solvent was removed by rotary evaporation, and then the pure The target compound was a white solid (39.1 mg) with a melting point of 237-238°C.

Embodiment 3

[0040] Example 3: 2-phenyl-4-quinazolinone

[0041] 2-Phenyl-4-quinazolinone

[0042]

[0043] Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (0.7 mg, 1 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%), and acetonitrile (2 mL) were sequentially added to a 15 mL reaction tube. The reaction mixture was reacted under the irradiation of 10 w blue light for 2 h. After the reaction, the solvent was removed by rotary evaporation, and then the pure The target compound was a white solid (35.3 mg) with a melting point of 237-238°C.

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Abstract

The invention discloses a method for photocatalytic synthesis of quinazolinone. Anthranilamide and aldehyde are used as raw materials, fluorescein is used as a photocatalyst, p-toluene sulfonic acid is used as an auxiliary catalyst, and the quinazolinone is obtained through photocatalytic reaction under the irradiation of visible light. The non-metal catalyst is used, so that the reaction cost is reduced; the reaction conditions are mild, and the reaction can be completed at room temperature; and the method is simple to operate, short in reaction time, simple in post-treatment, high in product yield and more environment-friendly. The method not only has high academic value, but also has a certain industrialization prospect.

Description

technical field [0001] The invention relates to a method for photocatalytically synthesizing quinazolinone, in particular to a method for photocatalytically synthesizing quinazolinone with simple operation and mild reaction conditions, and belongs to the technical field of organic synthesis chemistry. Background technique [0002] Quinazolinones are an important class of nitrogen-containing heterocyclic aromatic compounds with a wide range of biological and pharmacological activities, including antibacterial, antiviral, anti-inflammatory, anticonvulsant, and anticancer properties. In recent decades, a variety of methods for the synthesis of quinazolinones have been developed, but the most classic method is still to generate intermediates through the condensation reaction of anthranilamide and aldehydes, which are then oxidized to generate quinazolinones. However, these methods for synthesizing quinazolinones require the use of excessive amounts of harmful oxidants (KMnO 4 ,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/91C07D401/04C07D239/88C07D239/90B01J31/02
CPCC07D239/91C07D401/04C07D239/88C07D239/90B01J31/0208B01J2231/4283B01J35/39Y02P20/584
Inventor 王荣周马松邢令宝马德龙潘琳琳王才朋
Owner 上海橡实化学有限公司
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