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Method for efficiently preparing quinazolinone derivants under promotion of ethyl alcohol and catalysis of titanocene dichloride

A dichloro-titanocene catalysis and dichloro-titanocene technology, which is applied in organic chemistry and other fields, achieves the effects of short time, mild reaction conditions and high atom economy

Inactive Publication Date: 2015-11-18
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of the existing preparation methods of quinazolinone derivatives, and provide a method for preparing quinazolinone derivatives with simple operation, mild reaction conditions and high efficiency

Method used

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  • Method for efficiently preparing quinazolinone derivants under promotion of ethyl alcohol and catalysis of titanocene dichloride
  • Method for efficiently preparing quinazolinone derivants under promotion of ethyl alcohol and catalysis of titanocene dichloride
  • Method for efficiently preparing quinazolinone derivants under promotion of ethyl alcohol and catalysis of titanocene dichloride

Examples

Experimental program
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Effect test

Embodiment 1

[0012] Taking the preparation of 2-phenyl-2,3-dihydroquinazolin-4(1H)-one as an example, the raw materials used and the preparation method are as follows:

[0013]

[0014] Add 0.0025g (0.01mmol) titanocene dichloride, 0.1362g (1mmol) anthranilamide, 102μL (1mmol) benzaldehyde, 0.2mL ethanol to a 10mL Shrek tube, and stir the reaction at 40°C for 10 minutes to stop the reaction. Add 10-15 mL of ethyl acetate, remove ethyl acetate by rotary evaporation, separate and remove the catalyst with a silica gel column (ethyl acetate: petroleum ether = 1:1), and recrystallize with 95% ethanol aqueous solution to obtain 2- The yield of phenyl-2,3-dihydroquinazolin-4(1H)-one is 96%. The spectral data of the product is: 1 HNMR(400MHz, DMSO-d 6 )δ: 8.30 (s, 1H), 7.64 (d, J = 7.6 Hz, 1H), 7.51 (d, J = 7.2 Hz, 2H), 7.40 (s, 3H), 7.30-7.20 (m, 1H), 7.12(s, 1H), 6.77(d, J=8.1Hz, 1H), 6.69(s, 1H), 5.77(s, 1H); 13 CNMR(101MHz, DMSO-d 6 ) δ: 165.50, 149.76, 143.52, 135.20, 130.34, 130.21, 129.25, 128...

Embodiment 2

[0020] Taking the preparation of the compound 2-(4'-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one as an example, the raw materials used and the preparation method are as follows:

[0021]

[0022] In Example 1, the benzaldehyde used was replaced with an equimolar 4-methoxybenzaldehyde, and the other steps were the same as in Example 1, to obtain 2-(4-methoxyphenyl)-2,3-dihydro The yield of quinazolin-4(1H)-one is 97%. The spectral data of the product is: 1 HNMR(400MHz, DMSO-d 6 )δ: 8.19(s, 1H), 7.62(d, J=7.6Hz, 1H), 7.43(d, J=8.6Hz, 2H), 7.25(s, 1H), 7.02(s, 1H), 6.96( s, 2H), 6.75(d, J=8.1Hz, 1H), 6.68(s, 1H), 5.72(s, 1H), 3.75(s, 3H); 13 CNMR(101MHz, DMSO-d 6 ) δ: 165.59, 161.32, 149.90, 135.36, 135.12, 130.10, 129.23, 118.97, 116.89, 116.30, 115.52, 68.20, 57.06.

Embodiment 3

[0024] Taking the preparation of the compound 2-cyclohexane-2,3-dihydroquinazolin-4(1H)-one of the following formula as an example, the raw materials used and the preparation method are as follows:

[0025]

[0026] In Example 1, the benzaldehyde used was replaced with an equimolar cyclohexylformaldehyde, and the other steps were the same as in Example 1, to obtain 2-cyclohexane-2,3-dihydroquinazolin-4(1H)-one , The yield is 95%, and the spectrum data of the product is: 1 HNMR(400MHz, DMSO-d 6 )δ: 7.87(s, 1H), 7.55(d, J=7.6Hz, 1H), 7.19(s, 1H), 6.74(d, J=8.1Hz, 1H), 6.60(s, 1H), 6.54( s, 1H), 4.44 (s, 1H), 1.70 (d, J=10.6 Hz, 6H), 1.11 (s, 5H); 13 CNMR(101MHz, DMSO-d 6 ) δ: 165.58, 150.24, 134.90, 129.11, 118.30, 116.68, 115.96, 70.45, 44.74, 41.63, 41.42, 41.21, 28.88, 28.56, 27.82, 27.50, 27.44.

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Abstract

The invention discloses a method for efficiently preparing quinazolinone derivants under promotion of ethyl alcohol and catalysis of titanocene dichloride. According to the method, aminobenzamide and aldehyde or ketone are used as raw materials, ethyl alcohol is used as a solvent and a promoter, titanocene dichloride is used as a catalyst, and the quinazolinone derivants are efficiently prepared in high yield under the synergetic promotion action of titanocene dichloride and ethyl alcohol. The catalyst is less in dosage, cheap, nontoxic, and stable to air; the reaction conditions are mild, and the reaction time is short; the operation is simple; the atom economy is high; after the reaction is finished, the product only needs to be subjected to simple separation and recrystallization to obtain the quinazolinone derivants; a new, low-cost, environment-friendly and efficient path is opened up for preparation of the quinazolinone derivants, and wide application prospects are achieved.

Description

Technical field [0001] The invention relates to a method for efficiently preparing quinazolinone derivatives through the catalyst of titanocene dichloride and ethanol promoted. Background technique [0002] Quinazolinone derivatives have a wide range of pharmacological activities, showing good activities in anti-allergic, anti-cancer, anti-tumor, anti-inflammatory, anti-hypertensive, anti-microbial and anti-fungal, anti-malarial and insecticidal and sterilization. For example, methaqualone, a drug with sedative and hypnotic effects, piriqualone, a drug with anticonvulsant and anticonvulsant effects, and chloroqualone, a drug with antitussive effects, are all quinazolinones derivative. [0003] Currently, the catalysts used to prepare quinazolinone derivatives include gallium trifluoromethanesulfonate, potassium aluminum sulfate dodecahydrate, nano-ferric oxide, molecular iodine, cobalt dichloride, copper chloride dihydrate, and nano-sulfonic acid Zirconium, zirconium dodecyl sulf...

Claims

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Application Information

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IPC IPC(8): C07D239/91C07D239/88C07D239/90C07D239/70
CPCC07D239/70C07D239/88C07D239/90C07D239/91
Inventor 高子伟罗艳龙杨丹丹孙华明张伟强张国防吴亚王璟王秀
Owner SHAANXI NORMAL UNIV
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