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Palladium catalyst for catalyzing quinazolinone synthesis and olefination reaction

A palladium catalyst, oxidation reaction technology, applied in the direction of carbon compound catalyst, catalytic reaction, organic compound/hydride/coordination complex catalyst, etc. The effect of excellent catalytic activity

Active Publication Date: 2021-06-15
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2019, Xu's research group reported the synthesis of quinazolinones catalyzed by metal-free strong bases, but such bases are highly alkaline and corrosive
In the same year, Hu group reported Cu(OAc) 2 Catalyzes the synthesis of quinazolinones, a homogeneous metallic copper-catalyzed reaction that renders the catalyst unrecoverable

Method used

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  • Palladium catalyst for catalyzing quinazolinone synthesis and olefination reaction
  • Palladium catalyst for catalyzing quinazolinone synthesis and olefination reaction
  • Palladium catalyst for catalyzing quinazolinone synthesis and olefination reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Example 1: Preparation of Homogeneous Palladium Catalyst:

[0071] Under nitrogen atmosphere, the PdCl 2 (PPh 3 ) 3 (192 mg, 0.2 mmol), a mixture of L (64 mg, 0.2 mmol) and triethylamine (126 mg, 1.25 mmol) in isopropanol (5.0 mL) was refluxed for 8 hours. The mixture was cooled to room temperature to precipitate a reddish-brown microcrystalline solid. The solid was filtered off, washed with ether (3 x 15 mL), and dried under vacuum to give the homogeneous palladium catalyst NTP-Pd.

Embodiment 2

[0072] Example 2: Preparation of Heterogeneous Palladium Catalyst:

[0073] Cetyltrimethylammonium bromide (CTAB, 0.3 g) was dissolved in water (35.6 mL), potassium hydroxide (4.7 mL, 2 mol / L) was added, and the mixture was stirred at room temperature for 30 minutes. Then butyl orthosilicate (TBOS) was added dropwise, then stirred at room temperature for 13 hours, then aged for 12 hours, and filtered to obtain a white solid, which was then washed three times with water and then three times with ethanol. Finally, it was dried at a high temperature of 600 °C for 12 h to obtain mesoporous silica MSM.

[0074] Mesoporous silica MSM (1.0 g) and APTES (1.0 mL) were refluxed in toluene (100 mL) for 24 hours under nitrogen atmosphere. The mixture was cooled to room temperature by centrifugation to obtain a solid, which was then washed 3 times with ethanol. Finally, the modified MSM (450 mg), palladium complex (10 mg) and ethanol (4 mL), toluene (10 mL) solutions were combined under ...

Embodiment 3

[0077] A novel homogeneous palladium-catalyzed quinazolinone series reaction, comprising the following processing steps:

[0078] Under nitrogen atmosphere, in a 25 mL Schlenk flask, mix 2-aminobenzonitrile (0.5 mmol), benzyl alcohol (0.5 mmol) NTP-Pd catalyst (1.0 mol%), Cs 2 CO 3 (0.75 mmol) were sequentially introduced into a 25 mL Schlenk tube. Then the solvent DMSO:H is added 2 O (2.0 ml, 2:1), stirred at 120°C for 12 hours. After cooling to room temperature, water was added to quench the reaction and extracted with ethyl acetate, the organic phase was concentrated by removing the solvent in vacuo. Finally, the residue was purified by column chromatography using petroleum ether as eluent to give the desired product. The yield was 82%.

[0079] Product structure:

[0080] Structure Characterization:1 H NMR (400MHz, DMSO) δ 12.54 (s, 1H), 8.18 (dd, J=9.8, 8.2Hz, 3H), 7.91–7.80 (m, 1H), 7.75 (d, J=8.0Hz, 1H) ,7.64–7.47(m,4H). 13 C NMR (101MHz, DMSO) δ162.76, 152.84...

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Abstract

The invention discloses a palladium catalyst for catalyzing quinazolinone synthesis and olefination reaction, and belongs to the technical field of catalysts. A novel homogeneous palladium catalyst is prepared by combining a specific nitrogen-containing ligand with transition metal palladium, and a heterogeneous catalyst can be obtained by combining the homogeneous palladium catalyst with mesoporous silica. The obtained homogeneous or heterogeneous palladium catalyst is used for catalyzing quinazolinone cascade reaction and olefin synthesis reaction of alcohol and aryl sulfone, has excellent catalytic activity, and is more environment-friendly than a traditional catalyst.

Description

technical field [0001] The invention belongs to the technical field of catalysts, and in particular relates to a palladium catalyst for catalyzing quinazolinone synthesis and olefination reactions. Background technique [0002] Quinazolinones are one of the common nitrogen heterocycles widely found in many natural products and pharmaceuticals. These compounds have unique chemical properties, including medical properties such as anticancer, antibacterial, and anti-inflammatory. Based on its important value, some methods have been developed to synthesize quinazolinone derivatives. There are many methods for synthesizing such backbone compounds, mainly including (i) 2-aminobenzamide derivatives and aldehyde or carboxylic acid derivatives Condensation reaction of compounds; (ii) coupling reaction of 2-halobenzamide with benzylamine, α-amino acid, enaminone and nitrile; (iii) reaction of 2-arylindole with amine or ammonium. Processes for the preparation of quinazolinones from a...

Claims

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Application Information

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IPC IPC(8): B01J31/24B01J31/18B01J31/02C07D239/91C07C1/00C07C15/52C07C17/26C07C22/08
CPCB01J31/2404B01J31/1815B01J31/0274B01J31/0275C07D239/91C07C1/00C07C17/26C07C2531/24C07C2531/18C07C2531/02B01J2531/824B01J2531/0241B01J2231/4205C07C15/52C07C22/08Y02P20/584
Inventor 王大伟曹飞倪才华姚玮
Owner JIANGNAN UNIV
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