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2-aryl quinazoline or 2-heterocyclic aryl quinazoline derivative and preparation method thereof

A technology of heterocyclic aryl quinazoline and aryl quinazoline is applied in the field of preparation of 2-aryl quinazoline or 2-heterocyclic aryl quinazoline derivatives, and can solve the problem of high corrosiveness of equipment, It is difficult to separate and purify, and the reaction conditions are demanding, so as to achieve the effects of easy purification, high yield and simple synthesis method.

Inactive Publication Date: 2013-05-22
NANJING UNIV OF POSTS & TELECOMM
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Problems solved by technology

Although there are many methods for direct ring-closing synthesis of 2-arylquinazolines, and the selection and use of raw materials are also more flexible, these methods are harsh on the reaction conditions and usually need to be carried out under high temperature and high pressure conditions. Some synthesis methods use strong acids and strong bases, Therefore, it is highly corrosive to the equipment, and some reactions also produce a large number of by-products, which are not easy to separate and purify

Method used

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  • 2-aryl quinazoline or 2-heterocyclic aryl quinazoline derivative and preparation method thereof
  • 2-aryl quinazoline or 2-heterocyclic aryl quinazoline derivative and preparation method thereof
  • 2-aryl quinazoline or 2-heterocyclic aryl quinazoline derivative and preparation method thereof

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preparation example Construction

[0029] The preparation method of above-mentioned 2-aryl quinazoline or 2-heterocyclic aryl quinazoline derivative is characterized in that comprising the following steps:

[0030]

[0031] a. In the presence of a catalyst, aromatic formaldehyde or heterocyclic aromatic formaldehyde reacts with anthranilamide to obtain a class of 2-arylquinazolin-4(3H)-one derivatives or 2 as shown in formula (2) -Heterocyclic arylquinazolin-4(3H)-one derivatives;

[0032] b. 2-arylquinazolin-4(3H)-one derivatives or 2-heterocyclic arylquinazolin-4(3H)-one derivatives are reduced by a reducing agent to obtain a class such as formula (3) Represented 2-aryl-3, 4-dihydroquinazoline derivatives or 2-heterocyclic aryl-3, 4-dihydroquinazoline derivatives;

[0033] c. Under oxidizing conditions, 2-aryl-3, 4-dihydroquinazoline derivatives or 2-heterocyclic aryl-3, 4-dihydroquinazoline derivatives are dehydrogenated to obtain a class such as (i) represented 2-arylquinazoline or 2-heterocyclic arylq...

Embodiment 1

[0038] Example 1: Preparation of 2-(4-(diphenylamino)phenyl)quinazolin-4(3H)-one

[0039] Weigh 4.08 g (30 mmol) anthranilamide and 6.24 g (60 mmol) NaHSO 3 Add two-neck bottle, N 2 Add 30 mL of N,N-dimethylacetamide and 8.18 g (30 mmol) of 4-(diphenylamino)benzaldehyde under protection, raise the temperature to 150°C and stir for 8 h. After the reaction is complete, cool to room temperature. The reaction solution was poured into a large amount of water, a white precipitate appeared, suction filtered, washed with water and ethanol respectively, and dried to obtain 2-(4-(diphenylamino)phenyl)quinazolin-4(3H)-one in the form of white crystals . Yiled: 95.7%. 1 H NMR (400 MHz, DMSO- d 6 )δ(ppm): 8.07-8.11 (m, 3H), 7.76-7.80 (m, 1H), 7.65-7.67 (d, 1H), 7.43-7.47 (m, 1H), 7.35-7.39 (m, 4H) , 7.11-7.17 (m, 6H), 6.94-6.96 (d, 2H).

Embodiment 2

[0040] Embodiment 2: the preparation of compound N,N-diphenyl-4-(quinazolin-2-yl)aniline (TPAQx)

[0041]Weigh 0.39 g (10.24 mmol) LiAlH 4 Add it to a two-neck flask, add 5 mL tetrahydrofuran (THF) under nitrogen protection, and dissolve 1 g (2.56 mmol) 2-(4-(diphenylamino)phenyl)quinazolin-4(3H)-one in THF Slowly add it dropwise into the reaction flask, raise the temperature to 70°C and stir for 12 hours, after the reaction is completed, cool to room temperature, pour the reaction solution into a large amount of water, extract with ethyl acetate, and purify by silica gel column chromatography to obtain 2-(4- (diphenylamino)phenyl)-3,4-dihydroquinazoline. Yield: 72.5%. 1 H NMR (400 MHz, DMSO- d 6 )δ(ppm): 8.07-8.11 (m, 3H), 7.76-7.80 (m, 1H), 7.65-7.67 (d, 1H), 7.43-7.47 (m, 1H), 7.35-7.39 (m, 4H) , 7.11-7.17 (m, 6H), 6.94-6.96 (d, 2H).

[0042] Weigh 0.3 g (0.8 mmol) of 2-(4-(diphenylamino)phenyl)-3,4-dihydroquinazoline and 0.14 g (1.6 mmol) of manganese dioxide into a ...

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Abstract

The invention discloses a 2-aryl quinazoline or 2-heterocyclic aryl quinazoline derivative and a preparation method thereof. The structural formula of the product is shown in a formula (i), wherein Ar represents aryl, substituted aryl, heterocyclic aryl or substituted heterocyclic aryl. The preparation method of the 2-aryl quinazoline or 2-heterocyclic aryl quinazoline derivative comprises the following steps of: reacting aromatic formaldehyde or heterocyclic aromatic formaldehyde with ortho-amino toluamide at high temperature to obtain a 2-aryl quinazoline-4(3H)-ketone derivative or a 2-heterocyclic aryl quinazoline-4(3H)-ketone derivative; subsequently reducing the 2-aryl quinazoline-4(3H)-ketone derivative or the 2-heterocyclic aryl quinazoline-4(3H)-ketone derivative into a 2-aryl-3,4-dihydro quinazoline derivative or a 2-heterocyclic aryl-3,4-dihydro quinazoline derivative by using an appropriate reducing agent; and finally synthesizing the 2-aryl quinazoline or 2-heterocyclic aryl quinazoline derivative by using an oxidizing agent in an oxidation mode. Compared with the conventional synthesis method, the preparation method has the advantages of easy and available raw material, simple synthesis method, temperate reaction condition, high yield and the like, is easy to purify, and is a synthesis method applicable to industrial production.

Description

technical field [0001] The present invention relates to a kind of preparation method of 2-aryl quinazoline or 2-heterocyclic aryl quinazoline derivatives, specifically adopts reduction oxidation method to synthesize 2-aryl quinazoline or 2-heterocyclic aromatic The method of base quinazoline derivatives. Background technique [0002] Quinazoline derivatives also exist in some biologically active natural products, which provide the basic framework for drug design and functional materials. 2-Aryl-substituted quinazoline derivatives are dihydrofolate reductase inhibitors, and thus exhibit excellent biological activities in antitumor, antibacterial, antimalarial, antihypertensive, and anti-HIV. Due to the unique biological activity of quinazoline compounds in medicine, they have been widely studied in the fields of heterocyclic chemistry and combinatorial chemistry. In terms of materials science, quinazoline derivatives are often used to prepare metal complexes due to their st...

Claims

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Application Information

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IPC IPC(8): C07D239/74
Inventor 梅群波张彬黄维翁洁娜王玲霞蒋渊知周筱忠
Owner NANJING UNIV OF POSTS & TELECOMM
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