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Synthesis method for quinazoline derivative

A synthetic method and derivative technology, applied in chemical recycling, organic chemistry, etc., can solve problems such as difficult industrial implementation, unsuitable for industrial production, and high cost, and achieve the effects of low cost, cost saving, and high yield

Inactive Publication Date: 2015-06-17
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] This method uses microwave conditions, although it is relatively simple, it is more difficult to implement in industry
[0022] In summary, there are many methods for preparing quinazolines at present, but some of these methods use precious metal palladium etc. as catalysts, some use strong bases such as cesium carbonate or organic oxidants such as THBP, the cost is relatively expensive, and it is not suitable for industrial production

Method used

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  • Synthesis method for quinazoline derivative
  • Synthesis method for quinazoline derivative
  • Synthesis method for quinazoline derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] 2, the synthesis of 4-diphenylquinazoline comprises the following steps:

[0065] Take 40.8mmol N-phenylbenzamidine and 40.8mmol benzaldehyde in a 250mL round bottom flask, then add 3mmol nano-CuO, 8mmol o-phenanthroline and 160mL toluene to it, and stir and react at 110°C for 24 hours. The product was extracted with ethyl acetate, dried to obtain a crude product, and the crude product was purified by silica gel column chromatography (solvent volume ratio: petroleum ether: ethyl acetate = 20:1) to obtain a yellow solid that is 2,4-diphenyl Quinazoline, the yield is 86%, and the melting point is 116°C.

[0066] 1 H NMR (300MHz, CDCl 3 )δ8.75-8.73 (m, 2H), 8.32-8.31 (m, 1H), 8.16 (d, J = 8.1Hz, 1H), 7.96-7.90 (m, 3H), 7.63-7.54 (m, 7H) ;

[0067] 13 C NMR (75MHz, CDCl 3 )δ168.3, 160.2, 152.0, 138.2, 137.7, 133.5, 130.5, 130.2, 129.9, 129.2, 128.7, 128.5, 127.0, 121.7.

Embodiment 2

[0069] The synthesis of 6-methyl-2,4-diphenylquinazoline comprises the following steps:

[0070] Take 28.5mmol N-(p-tolyl)benzamidine and 42.8mmol benzaldehyde in a 250mL round bottom flask, then add 3mmol nano-copper oxide, 5mmol o-phenanthroline and 160mL xylene to it, and stir at 120°C After reacting for 18 hours, the product was extracted with ethyl acetate and dried to obtain a crude product; the crude product was purified by silica gel column chromatography (volume ratio of petroleum ether:ethyl acetate=20:1) to obtain a white solid, namely 6-methyl -2,4-diphenylquinazoline, yield 98%, melting point: 178-180°C.

[0071] 1 H NMR (300MHz, CDCl 3 )δ8.68(d, J=6.2Hz, 2H), 8.11(d, J=7.6Hz, 1H), 7.88-7.87(m, 3H), 7.74(d, J=7.9Hz, 1H), 7.62- 7.51(m, 6H), 2.52(s, 3H);

[0072] 13 C NMR (75MHz, CDCl 3 )δ167.6, 159.5, 150.4, 138.2, 137.8, 137.2, 135.9, 130.4, 130.1, 129.8, 128.8, 128.6, 128.5, 125.6, 121.6, 21.9.

Embodiment 3

[0074] The synthesis of 4-phenyl-2-(4-chlorophenyl) quinazoline comprises the following steps:

[0075] Take 26mmol N-phenyl p-chlorobenzamidine and 39mmol benzyl alcohol in a 250mL round bottom flask, then add 5mmol nano-copper oxide, 5mmol o-phenanthroline and 160mL toluene to it, and stir and react at 100°C for 36 hours , the product was extracted with ethyl acetate, and dried to obtain a crude product; the crude product was purified by silica gel column chromatography (volume ratio of petroleum ether:ethyl acetate=20:1) to obtain a yellow solid that is 4-phenyl-2-( 4-chlorophenyl) quinazoline. Yield 91%, melting point: 187°C.

[0076] 1 H NMR (300MHz, CDCl 3 )δ8.58 (d, J=8.5, 2H), 8.08 (t, J=9.2, 2H), 7.85-7.79 (m, 3H), 7.54-7.40 (m, 6H);

[0077] 13 C NMR (75MHz, CDCl 3 )δ 167.4, 158.1, 150.8, 136.5, 135.7, 135.6, 132.7, 129.1, 129.0, 128.9, 128.0, 127.7, 127.5, 126.2, 126.0, 120.7.

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Abstract

The invention discloses a synthesis method for a quinazoline derivative. The synthesis method comprises the following steps: mixing an N-aryl amidined compound, aromatic aldehyde or aromatic alcohol, nano copper oxide and phenanthroline and then adding an organic solvent to react under the condition of 90-120 DEG C in the air for 6-36 hours; extracting an obtained product by using ethyl acetate and drying with anhydrous sodium sulfate; decompressing and concentrating to obtain a rough product; and carrying out column chromatography isolation to obtain a quinazolines compound. Compared with the prior art, the synthesis method does not use noble metal, a strong alkali or an organic oxidant and directly utilizes the air as the oxidant; raw materials are easy to obtain and the reaction conditions are moderate; the selectivity is strong and few side reactions occur; the nano copper oxide catalyst can be recycled so that the cost is saved and the synthesis method is applicable to large-scale industrial production.

Description

technical field Background technique [0001] [0002] The method of the synthetic quinazoline compound of report in the literature mainly contains following several kinds: [0003] (1) o-halogen benzaldehyde or benzophenone and amidine are substrates, and the reaction equation is as follows: [0004] [0005] However, this method uses a strong base and generates hydrogen halide, which has high cost and serious environmental pollution. [0006] (2) o-amino aryl ketone and benzylamine are substrates, and the reaction equation is as follows: [0007] [0008] However, this method uses organic oxidants, which are sensitive and dangerous. [0009] (3) N-arylamidine and isonitrile are substrates, and the reaction equation is as follows: [0010] [0011] However, this method not only uses a strong base, but also uses a noble metal catalyst, which is expensive and causes serious environmental pollution. [0012] (4) After amidine and halogenated benzene synthesize N-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/74
CPCY02P20/584
Inventor 张武郭飞俞丹汪飞
Owner ANHUI NORMAL UNIV