Method for synthesizing 4(3H)-quinazolinone derivative by using cyclization elimination one-pot method

A technology for quinazolinone and derivatives, which is applied in the field of one-pot synthesis of 4(3H)-quinazolone derivatives through cyclization and elimination, which can solve the problems of low product yield, harsh reaction conditions and long reaction time and other problems, to achieve the effect of high yield, simple operation and short reaction time

Active Publication Date: 2014-06-25
BIRDO (SHANGHAI) PHARMATECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the above methods have their characteristics and certain potential application value, because many of them have the disadvantages of difficult acquisition of raw materials, harsh reaction conditions, lo...

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  • Method for synthesizing 4(3H)-quinazolinone derivative by using cyclization elimination one-pot method
  • Method for synthesizing 4(3H)-quinazolinone derivative by using cyclization elimination one-pot method
  • Method for synthesizing 4(3H)-quinazolinone derivative by using cyclization elimination one-pot method

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Embodiment 1

[0041] A method for synthesizing 4(3H)-quinazolinone derivatives (2-phenylquinazolin-4(3H)-one (I-a)) by one-pot method of cyclization elimination, comprising the following steps:

[0042] 2-Amino-N-methoxybenzamide (II-a) (166 mg) was dissolved in acetic acid (4 ml), and benzaldehyde (III-a) (117 mg) was added thereto, at 100°C The reaction was complete for 1.5 hours, cooled to room temperature, diluted with ethyl acetate (20 ml), then neutralized by adding saturated sodium bicarbonate solution (20 ml), and the aqueous phase was extracted with ethyl acetate (3 × 20 ml ), the combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography to obtain 206 mg of 2-phenylquinazolin-4(3H)-one (I-a) as a white solid with a yield of 93%.

[0043] 1 H NMR (600MHz, DMSO-d 6):δ12.56(br s,1H),8.21(d...

Embodiment 2

[0045] A method for synthesizing 4(3H)-quinazolinone derivatives (2-phenylquinazolin-4(3H)-one (I-a)) by one-pot method of cyclization elimination, comprising the following steps:

[0046] 2-Amino-N-methoxybenzamide (II-a) (166 mg) was dissolved in formic acid (4 ml), and benzaldehyde (III-a) (117 mg) was added thereto, at 100°C The reaction was complete under 5.0 hours, cooled to room temperature, diluted with ethyl acetate (20 ml), then neutralized by adding saturated sodium bicarbonate solution (20 ml), the aqueous phase was extracted with ethyl acetate (3 × 20 ml ), the combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography to obtain 89 mg of 2-phenylquinazolin-4(3H)-one (I-a) as a white solid with a yield of 40%.

[0047] 1 H NMR (600MHz, DMSO-d 6 ):δ12.56(br s,1H),8.21(d,J...

Embodiment 3

[0049] A method for the one-pot synthesis of 4(3H)-quinazolinone derivatives (2-(4-bromophenyl)quinazolin-4(3H)-one (I-b)) by cyclization elimination, comprising the following steps step:

[0050] 2-Amino-N-methoxybenzamide (II-a) (166 mg) was dissolved in trifluoroacetic acid (4 ml), to which was added p-bromobenzaldehyde (III-b) (204 mg) , reacted at 70°C for 1.0 hour to complete the reaction, cooled to room temperature, added ethyl acetate (20 ml) to it for dilution, then added saturated sodium bicarbonate solution (20 ml) for neutralization, and extracted the aqueous phase with ethyl acetate ( 3×20 ml), the combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography to obtain 245 mg of 2-(4-bromophenyl)quinazolin-4(3H)-one (I-b) as a white solid with a yield of 82%.

[0051] 1 H ...

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Abstract

The invention discloses a method for synthesizing a 4(3H)-quinazolinone derivative by using a cyclization elimination one-pot method. The method comprises the following step: (1) by using acetic acid, formic acid, trifluoroacetic acid or dichloroacetic acid as a solvent, reacting substituted N-methoxy-o-aminobenzene formamide (II) with substituted aldehyde (III) at 70-100 DEG C for 0.3-5.0 hours, so as to generate the 4(3H)-quinazolinone derivative (I) through cyclization elimination, wherein the reaction formula is as shown in the specification. The method disclosed by the invention has the advantages that the method is environment-friendly as no oxidant or heavy metal is adopted for oxidation or catalysis, the operation is simple, reaction raw materials and reaction reagents are easy to obtain, the reaction time is relatively short, the yield is relatively high, and the like.

Description

technical field [0001] A One-Pot Synthesis of 4(3H)-Quinazolinone Derivatives via Cyclization Elimination. Background technique [0002] 4(3H)-Quinazolinone and its derivatives are a very important class of alkaloids, which can be extracted from a wide range of animals, plants and microorganisms, and have many pharmacological and biological activities [1] , such as the camelamine base extracted and isolated from camel [2] (A), with cytotoxic features. 4(3H)-Quinazolinone core structure is also used in medicine, such as Quinazolinone [3] (B), is a sedative-hypnotics used to treat insomnia, banned after 1985 due to its addictive properties. And Huoshanone [4] , for the treatment of malaria, cancer, especially in the treatment of coccidiosis in chickens, it is a broad-spectrum antiparasitic drug. [0003] [0004] The relevant literature is as follows: [0005] [1] (a) Reisch, J.; Gunaherath, G.J. Nat. Prod.1989, 52, 404-407. (b) Liu, J.; Wilson, C.J.; Ye, P.; Sprague,...

Claims

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Application Information

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IPC IPC(8): C07D239/91C07D239/90
CPCC07D239/90C07D239/91
Inventor 杜云飞程然赵康
Owner BIRDO (SHANGHAI) PHARMATECH CO LTD
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