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Dihydroquinoxalinone compound and preparation method thereof
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A technology for dihydroquinazolinones and compounds is applied in the field of dihydroquinazolinones and their preparation, and can solve the problems of complex post-treatment process, harsh reaction conditions, single reaction raw materials and the like
Active Publication Date: 2018-09-21
CHINA THREE GORGES UNIV
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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.
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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), benzeneFormaldehyde (0.24mmol, 25.4mg), methanol (1ml), and water (1ml) were sequentially added to the test tube, and reacted at 60°C for 3h. Analysis (petroleumether: 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 (petroleumether: 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 invention relates to a dihydroquinoxalinone compound and a preparation method, and the specific structure is shown in III. The method uses cheap and readily available o-nitrobenzonitrile (I) and aldehyde or ketone (II) as raw materials, and alcohol and water as solvent. The target product (III) is obtained by a nitro reduction, a cyano hydrolysis, and a condensation reaction in a one-pot reaction system under the action of tetrahydroxydiboron, glacial acetic acid and catalytic amount of cuprous chloride. The preparation method uses 2-nitrobenzonitrile (I) as a raw material for the first time, which is easy to operate, easy to obtain raw materials, high in yield, and has the advantages of green synthesis such as step economy, atomic economy, mild reaction conditions and the like. The specific formula is shown in the description.
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...
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