Synthesis method of perfluoroalkyl-substituted polycyclic quinazolinone derivative

A kind of polycyclic quinazolinone, perfluoroalkyl technology, applied in the field of synthesis of polycyclic quinazolinone derivatives, can solve the problems of harsh conditions, difficult preparation and the like

Active Publication Date: 2021-05-07
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the inventive technology disclosed in this patent still has defects such as harsh conditions, the need for metal participation and difficult preparation of substrates.

Method used

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  • Synthesis method of perfluoroalkyl-substituted polycyclic quinazolinone derivative
  • Synthesis method of perfluoroalkyl-substituted polycyclic quinazolinone derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Add 3-(pent-4-en-1-yl)quinazolinone (0.2mmol, 43mg), sodium trifluoromethanesulfinate (0.6mmol, 94mg) into a 10mL solvent storage bottle, add DMSO (2.0mL ) as a solvent, the reaction was carried out under open conditions, irradiated with 10w of visible light with a wavelength of 410-415nm and reacted at a temperature of 25°C for 8h. After the reaction, the reaction system was washed with water and extracted with dichloromethane, then separated into an organic layer and an aqueous layer. After the organic layer was dried with anhydrous sodium sulfate, it was evaporated and concentrated under reduced pressure to remove the solvent to obtain a yellow oil. The yellow oil was separated by column chromatography, using a mixture of petroleum ether and ethyl acetate with a volume ratio of 15:1 as the eluent, collecting the eluate containing the target compound, distilling off the solvent and drying to obtain 41 mg of white solid 6-( 2,2,2-trifluoroethyl)-8,9-dihydro-6hydro-pyri...

Embodiment 2

[0024] The experimental method of Example 2 was repeated in Example 1, except that "the solvent in the system was replaced with water (2ml)", and other operations were the same as in Example 1 to obtain 28 mg of white solid 6-(2,2,2- Trifluoroethyl)-8,9-dihydro-6hydro-pyrido[2,1-b]quinazolin-11(7hydrogen)-one, yield 50%.

Embodiment 3

[0026] The experimental method of embodiment 3 repeats embodiment 1, and difference is only " change sodium trifluoromethanesulfinate dosage into 0.4mmol ", other operations are the same as embodiment 1, obtain 38mg white solid 6-(2,2 ,2-trifluoroethyl)-8,9-dihydro-6hydro-pyrido[2,1-b]quinazolin-11(7hydrogen)-one, the yield was 67%.

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Abstract

The present invention discloses a synthesis method of a perfluoroalkyl-substituted polycyclic quinazolinone derivative. The synthesis method comprises the following steps: dissolving a quinazolinone derivative containing an inactive double bond as shown in a formula (I) and perfluoroalkyl sodium sulfinate as shown in a formula (II) in a solvent, carrying out a reaction under an open condition at room temperature under visible light irradiation for 3-24 hours, and after the reaction is finished, performing post-treatment on the reaction system to obtain the perfluoroalkyl-substituted polycyclic quinazolinone derivative as shown in a formula (III). According to the present invention, light is adopted as the reaction energy source, the inactive double bond-containing quinazolinone perfluoroalkylation / cyclization reaction is achieved without any additive, the process is safe, the cost is low, the operation is simple and convenient, and the green synthesis method of the perfluoroalkyl-substituted polycyclic quinazolinone derivative is provided.

Description

technical field [0001] The invention relates to a method for synthesizing perfluoroalkyl-substituted polycyclic quinazolinone derivatives. Background technique [0002] The quinazolinone structure is a commonly used pharmacophore in the field of drug design. Studies have confirmed that derivatives containing the core of this structure have various pharmacological activities, including the treatment of diseases such as inflammation, infection, bronchitis and asthma. As potential lead compounds, quinazolinone structures have broad research prospects in the field of new drug development. In recent years, some progress has been made in the synthesis of polycyclic quinazolinone derivatives, mainly including: (1) by the cyclization reaction (A.Kamal, K.V.Ramana and M.V.Rao, J. Org. Chem. 2001, 66, 997; C. Gil and S. Chem. Eur. J., 2005, 11, 2680; A. Kamal, N. Markandeya, N. Shankaraiah, C. R. Reddy, S. Prabhakar, C. S. Reddy, M. N. Eberlin and L. S. Santos, Chem. Eur. J., 2009,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D487/04
CPCC07D471/04C07D487/04
Inventor 金灿孙彬黄盼怡
Owner ZHEJIANG UNIV OF TECH
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