Quinazolinone compounds and preparation method thereof

A compound and quinazolone technology, applied in the field of quinazolone compounds and preparation thereof, can solve problems such as no relevant reports on the synthesis method of quinazolone compounds, and achieve the effects of easy large-scale production and mild reaction conditions

Inactive Publication Date: 2017-02-22
XINYANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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The synthetic method of quinazolones compound provided by t

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  • Quinazolinone compounds and preparation method thereof
  • Quinazolinone compounds and preparation method thereof
  • Quinazolinone compounds and preparation method thereof

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[0031] The preparation method of described a kind of quinazolones compound, comprises the following steps:

[0032] a) Alcohols with structure (I) and o-nitrobenzonitriles with structure (II) on Au / TiO 2 Under the catalysis, by stirring and heating in a solvent, the quinazolones compound of the present invention with structure (III) can be obtained:

[0033]

[0034] Among them, R 1 Is aryl, substituted aryl; R 2 is fluorine, chlorine, methyl or methoxy.

[0035] The R 1 is aryl, and said aryl is phenyl, naphthyl or thienyl;

[0036] The R 1 is a substituted aryl group, and the substituted aryl group is 4-chlorophenyl, 4-fluorophenyl, 3-fluorophenyl, 2-fluorophenyl, 4-methylphenyl, 3-methylphenyl, 3,4-dimethoxyphenyl, 4-methoxyphenyl, 3-methoxyphenyl, 2-methoxyphenyl;

[0037] The R 2 is fluorine, chlorine, methyl or methoxy;

[0038] The catalyst is Au / TiO 2 ;

[0039] The molar ratio of the o-nitrobenzonitrile compound and alcohol is 1:1-1:3;

[0040] The o-ni...

Embodiment 1

[0045] In a clean and dry 20 ml Schlenk reaction tube, sequentially add 1% Au / TiO 2 49 mg, 37 mg of o-nitrobenzonitrile, 81 mg of benzyl alcohol, and 2 ml of water were used as solvents, and a reflux tube was installed to react at 130° C. for 20 hours under nitrogen protection. After the reaction is finished, the recovered catalyst can be directly recycled next time by filtering, and the filtrate is directly spin-dried and dissolved with a small amount of petroleum ether and ethyl acetate (volume ratio of 3:1), separated by a short silica gel column, and obtained 49.9 mg of white solid, 90% yield.

[0046] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: figure 1 As shown, the carbon NMR spectrum is as figure 2 shown. It can be confirmed from the spectrum that the obtained product is 2-phenylquinazolone.

Embodiment 2

[0048] In a clean and dry 20 ml Schlenk reaction tube, sequentially add 1% Au / TiO 2 49 mg, 37 mg of o-nitrobenzonitrile, 70 mg of benzyl alcohol, and 2 ml of toluene were used as solvents, and a reflux tube was installed to react at 130° C. for 24 hours under nitrogen protection. After the reaction is finished, the recovered catalyst can be directly recycled next time by filtering, and the filtrate is directly spin-dried and dissolved with a small amount of petroleum ether and ethyl acetate (volume ratio of 3:1), separated by a short silica gel column, and obtained 44 mg of white solid, 80% yield.

[0049] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: figure 1 As shown, the carbon NMR spectrum is as figure 2 shown. It can be confirmed from the spectrum that the obtained product is 2-phenylquinazolone.

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Abstract

The invention discloses quinazolinone compounds with the specific structural formula shown in the specification, wherein R1 is an aryl group or a substitute aryl group; R2 is fluorine, chlorine, methyl or a methoxy group. Alcohol and o-nitrophenyl formonitrile compounds are taken as reaction raw materials and are heated and stirred in a solvent under the recyclable Au/TiO2 catalytic action, and the quinazolinone compounds can be prepared. With the adoption of the method, no oxidizing agent, reducing agent, ligand and alkaline additive are required, the reaction condition is mild, and mass production is easy to realize. Experimental results indicate that the yield of the obtained quinazolinone compounds can be as high as 90%.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a quinazolones compound and a preparation method thereof. Background technique [0002] Quinazolones exist widely in nature, especially in natural products and biologically active molecules, so they are the most important class of nitrogen-containing heterocyclic compounds (J.Med.Chem., 2006, 49, 4698 ). [0003] Due to the importance of quinazolones, they are widely concerned by the chemical, biological and medical circles. However, the traditional method is mainly to synthesize quinazolones through oxidative condensation of anthranilamide and benzaldehyde or benzoic acid in the presence of an oxidizing agent (Chem.Commun., 2014, 50, 6471; Org.Lett .2011, 13, 1274; Green Chem., 2009, 11, 1881). These methods require the use of excess oxidants, and the metal catalysts used are difficult to recover and recycle. [0004] Therefore, it is an urgent problem to improve the existi...

Claims

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Application Information

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IPC IPC(8): C07D239/91
CPCC07D239/91
Inventor 谭美容
Owner XINYANG NORMAL UNIVERSITY
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