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Dihydroquinazolone compounds and preparation methods thereof

A technology for dihydroquinazolinones and compounds is applied in the field of dihydroquinazolinones and their preparation, and can solve the problems of harsh reaction conditions, single reaction raw materials, complicated post-processing processes and the like

Active Publication Date: 2021-06-18
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods not only have a single reaction raw material, but also have some obvious shortcomings. Most of the reaction conditions are relatively harsh, such as the need for dangerous organic solvents, higher temperatures, strong acids, expensive catalysts, and complicated post-treatment processes.

Method used

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  • Dihydroquinazolone compounds and preparation methods thereof
  • Dihydroquinazolone compounds and preparation methods thereof
  • Dihydroquinazolone compounds and preparation methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] 2-Nitrobenzonitrile (0.2mmol, 29.6mg), tetrahydroxydiboron (1mmol, 89.6mg), glacial acetic acid (0.24mmol, 14.5mg), cuprous chloride (0.04mmol, 4.0mg), benzene Formaldehyde (0.24mmol, 25.4mg), methanol (1ml), and water (1ml) were sequentially added to the test tube, and reacted at 60°C for 3h. Analysis (petroleum ether: ethyl acetate = 4:1) separation, yield: (40.8mg, 91%). m.p.225-226℃. 1 HNMR (400MHz, CDCl 3 )δ=7.99(dd,J 1 =8.0Hz,J 2 =1.6Hz,1H),7.65(m,2H),7.50(m,2H),7.39(dt,J 1 =7.6Hz,J 2 =1.6Hz,1H),6.95(dd,J 1 =7.6Hz,J 2 =0.8Hz,1H),6.72(d,J=8.0Hz,1H),5.95(s,1H),5.80(s,1H),4.44(s,1H). 13 C NMR (100MHz, CDCl 3 )δ=164.7, 147.2, 138.6, 134.0, 130.2, 129.2, 128.8, 127.4, 119.7, 115.7, 114.6, 69.2.

Embodiment 2

[0026]

[0027] Add 2-nitrobenzonitrile (0.2mmol, 29.6mg), tetrahydroxydiboron (1mmol, 89.6mg), benzaldehyde (0.24mmol, 25.4mg), methanol (1ml), water (1ml) into the test tube in turn , reacted at 60°C for 12h, after the end, the reaction solution was extracted 3 times with ethyl acetate, the combined organic phase was concentrated to dryness, and separated by column chromatography (petroleum ether: ethyl acetate = 4:1), the yield: (6.7mg, 15%).

Embodiment 3

[0029]

[0030] 2-Nitrobenzonitrile (0.2mmol, 29.6mg), tetrahydroxydiboron (1mmol, 89.6mg), glacial acetic acid (0.24mmol, 14.5mg), cuprous chloride (0.04mmol, 4.0mg), benzene Add formaldehyde (0.24mmol, 25.4mg) and water (2ml) into the test tube in turn, and react at 60°C for 3h. Ethyl acetate=4:1) isolated, yield: (13.2 mg, 30%).

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Abstract

The present invention relates to dihydroquinazolone compounds and a preparation method thereof, the specific structure of which is shown in III. The method uses cheap and easy-to-obtain o-nitrobenzonitrile (I) and aldehydes or ketones (II) as raw materials, alcohol and water as solvents, under the action of tetrahydroxydiboron, glacial acetic acid and a catalytic amount of cuprous chloride , the target product (III) was obtained through nitro reduction, cyano hydrolysis and condensation in a one-pot reaction system. The method uses 2-nitrobenzonitrile (I) as a raw material for the first time, and has the advantages of simple operation, easy-to-obtain raw material and high yield, and has the advantages of green synthesis such as step economy, atom economy, and mild reaction conditions.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a dihydroquinazolone compound and a preparation method thereof. Background technique [0002] The skeleton structure of dihydroquinazolones widely exists in natural products and drug molecules, and has important biological activity and medicinal value. In the reported synthetic methods, 2-aminobenzamide, isatoic anhydride derivatives, 2-aminobenzonitrile, 2-nitroaniline, etc. are used as starting materials to condense with carbonyl compounds under certain conditions. reaction to obtain dihydroquinazolone compounds. These methods not only have a single reaction raw material, but also have some obvious shortcomings. Most of the reaction conditions are relatively harsh, such as the need for dangerous organic solvents, higher temperatures, strong acids, expensive catalysts, and complicated post-treatment processes. The innovation of the present invention is th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/91C07D239/88C07D239/90C07D401/04C07D405/04
CPCC07D239/88C07D239/90C07D239/91C07D401/04C07D405/04
Inventor 周海峰隋月波江小兰杨兵余涛
Owner CHINA THREE GORGES UNIV
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