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Synthetic method for beta-aminocarbonyl compound, beta-mercapto ketone and beta-alkoxy ketone

A technology of carbonyl compounds and alkoxy ketones, which is applied in the field of synthesis of β-aminocarbonyl compounds, β-mercaptoketones, and β-alkoxy ketones, achieving the effects of strong controllability, wide application range and simple operation

Inactive Publication Date: 2013-05-01
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, it is necessary to use acid-functionalized ionic liquids to catalyze hetero-Michael addition reactions to synthesize β-aminocarbonyl compounds, β-mercaptoketones, and β-alkoxyketones, but patent CN200810167605.4 uses ionic liquids as catalysts to catalyze aza-Michael addition reaction, but only limited to catalyzing amines with strong nucleophilicity, and did not involve amino carboxylate compounds with weak nucleophilicity and sulfa-Michael, oxa-Michael

Method used

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  • Synthetic method for beta-aminocarbonyl compound, beta-mercapto ketone and beta-alkoxy ketone
  • Synthetic method for beta-aminocarbonyl compound, beta-mercapto ketone and beta-alkoxy ketone
  • Synthetic method for beta-aminocarbonyl compound, beta-mercapto ketone and beta-alkoxy ketone

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Experimental program
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Effect test

Embodiment 1

[0030]

[0031] At room temperature, cyclohexenone (0.5mmol, 49.0mg), ethyl carbamate (0.6mmol, 53.4mg) and [Hmim]OTs (1mL) were placed in a dry reaction bottle and reacted for 24h. After the reaction, qualitative analysis was carried out by Hewlett-Packard 6890 / 5973GC-MS and NMR. Agilent 6820 gas chromatograph was used for quantitative analysis. The yield of 3-carbamoylcyclohexanone was 75%. 1 H NMR (400MHz, CDCl 3 )δ=1.24(t, J=6.8Hz, 3H), 1.67-1.77(m, 2H), 1.99-2.03(m, 1H), 2.08-2.18(m, 1H), 2.27-2.40(m, 3H) , 2.27-2.40(m, 1H), 2.70(dd, J=4.8, 4.8Hz, 1H), 3.97(s, 1H), 4.10(t, J=2.0Hz, 2H), 5.09(d, J=7.2 Hz, 1H). 13 C NMR (100.8MHz, CDCl 3 )δ=14.6, 22.0, 31.2, 40.8, 48.0, 50.1, 60.8, 155.7, 209.0.

Embodiment 2

[0033] With example 1, catalyst used is [Hmim] HSO 4 , the yield of 3-carbamoylcyclohexanone was 70%.

Embodiment 3

[0035] With example 1, catalyst used is [Hmim] BF 4 , the yield of 3-carbamoylcyclohexanone was 71%.

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Abstract

The invention discloses a synthetic method for a beta-aminocarbonyl compound, beta-mercapto ketone and beta-alkoxy ketone. In the method, ionic liquid is used as a catalyst, and aza-Michael, sulfa-Michael and oxa-Michael reactions of electron-deficient ketene and a nucleophilic reagent are carried out at room temperature so as to synthesize corresponding compounds. According to the invention, usage amount of the catalyst is small, and the catalyst has the advantages of high catalytic activity, good stability, low corrosivity, cyclical usability, good selectivity of products, simple operation and strong controllability; a substrate has a wide application scope, and good yield is obtained in addition of alcohol compounds with low reaction activity; the reactions are mild; reaction products and the catalyst can be easily separated, and the catalyst can be cyclically used.

Description

technical field [0001] The invention belongs to the field of synthesis of β-aminocarbonyl compounds, β-mercaptoketones, and β-alkoxyketones, and specifically relates to a hetero-Michael reaction synthesis of α, β-unsaturated carbonyl compounds and nucleophilic reagents catalyzed by ionic liquids Methods for β-aminocarbonyl compounds, β-mercaptoketones, β-alkoxyketones. Background technique [0002] Compounds such as β-aminocarbonyl compounds, β-mercaptoketones, and β-alkoxyketones formed by chemical bonds such as C-N, C-S, and C-O constructed by hetero-Michael addition are important organic structural units. important role in chemistry. [0003] β-aminocarbonyl compounds can be used to synthesize 1,3-amino alcohols, β-amino acids, β-aminoketones, β-lactams and other nitrogen-containing organic compounds, and then can synthesize many drugs and natural products with life and physiological activities. It is an important organic synthesis intermediate. β-mercapto compounds ex...

Claims

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Application Information

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IPC IPC(8): C07C271/24C07C271/18C07C269/06C07C323/22C07C319/18C07C323/52C07C323/60C07C49/175C07C49/84C07C45/64C07D233/60C07D231/12C07D235/06C07D249/18C07D257/04C07D207/40C07D263/22C07D249/08
Inventor 夏春谷韩峰杨磊李臻
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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