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Beta-enaminone ester compounds, and synthesis method and application of beta-enaminone ester compounds

A synthesis method and compound technology, applied in the field of β-enaminone ester compounds and their synthesis, can solve the problems of post-treatment of polluted environment, high reaction temperature, low yield, etc., and achieve simple operation, easy-to-obtain raw materials, and high yield high rate effect

Inactive Publication Date: 2014-07-09
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional synthesis method of β-enaminone (ester) is to use aromatic hydrocarbons as water-carrying agents, and synthesize them from 1,3-dicarbonyl compounds and amines under the catalysis of protonic acids such as hydrochloric acid, but this method has high reaction temperature and high production Low efficiency, polluting the environment and troublesome post-processing, etc.
At present, no relevant reports have been found to obtain β-enaminone esters by using β-carbonyl ester and azide as raw materials in the catalyzed next step reaction of a strong basic catalyst

Method used

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  • Beta-enaminone ester compounds, and synthesis method and application of beta-enaminone ester compounds
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  • Beta-enaminone ester compounds, and synthesis method and application of beta-enaminone ester compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the synthesis of compound 1a

[0030] Add 0.5mmol (0.0652g) ethyl acetoacetate, 1.5mmol (0.1995g) benzyl azide, 1mmol (0.224g) potassium tert-butoxide and 2ml N,N-dimethylformamide to the sealed tube, Seal the seal, stir and react at 50°C for 8 hours, and after the reactant is cooled to room temperature, filter the reactant, pour the filtrate into 20mL water, extract with 20mL ethyl acetate, wash with saturated saline (3×15mL), and finally use Water Na 2 SO 4 Dry, filter, remove the solvent under reduced pressure, and purify by silica gel thin-layer chromatography (ethyl acetate / petroleum ether=1:10) to obtain 142 mg of light yellow oily liquid 1a, with a yield of 81%.

[0031] Gained pale yellow oily liquid 1a is analyzed, and its spectral characteristics are as follows:

[0032] 1 H NMR (500MHz, CDCl 3 )δ12.56(s,1H),7.43–7.36(m,3H),7.31–7.28(m,2H),7.26–7.21(m,3H),7.12-7.10(m,2H),4.23(d, J=6.2Hz,3H),3.67(q,J=7.0Hz,3H),2.35(s,3H),0.70(t,J=7.1Hz,3H). ...

Embodiment 2

[0035] Embodiment 2: the synthesis of compound 2a

[0036] Add 0.6mmol (0.0696g) methyl acetoacetate, 0.8mmol (0.1064g) benzyl azide, 2.4mmol (0.2693g) potassium tert-butoxide and 2ml N,N-dimethylformamide to the sealed tube, Seal the seal, stir and react at 50°C for 4 hours, then add 0.8mmol (0.1064g) benzyl azide, continue to keep warm and stir for 4 hours, after the reactants are cooled to room temperature, filter the reactants, pour the filtrate into 20mL water, and use Extract with 20mL ether, wash with saturated brine (3×15mL), and finally wash with anhydrous Na 2 SO 4 Dry, filter, remove the solvent under reduced pressure, and purify by silica gel thin-layer chromatography (ethyl acetate / petroleum ether=1:10) to obtain 139 mg of light yellow oily liquid 2a with a yield of 78%.

[0037] Gained pale yellow oily liquid 2a is analyzed, and its spectral characteristics are as follows:

[0038] 1 H NMR (500MHz, CDCl 3 )δ12.54(s,1H),7.40–7.37(m,,3H),7.31–7.28(m,2H),7.26–7...

Embodiment 3

[0041] Embodiment 3: the synthesis of compound 3a

[0042] Add 1.4mmol (0.2215g) tert-butyl acetoacetate, 2.1mmol (0.2793g) benzyl azide, 2.8mmol (0.3136g) potassium tert-butoxide and 5ml N,N-dimethylformamide to the sealed tube , seal, and stir and react at 60°C for 4 hours, add 2.1mmol (0.2793g) benzyl azide, continue to keep warm and stir for 5 hours, after the reactant is cooled to room temperature, filter the reactant, pour the filtrate into 20mL water, and extracted with 20 mL ethyl acetate, washed with saturated brine (3×15 mL), and finally washed with anhydrous Na 2 SO 4 Dry, filter, remove the solvent under reduced pressure, and purify by silica gel thin-layer chromatography (ethyl acetate / petroleum ether=1:5) to obtain 224 mg of yellow oily liquid 3a, with a yield of 85%.

[0043] The obtained yellow oily liquid 3a is analyzed, and its spectral characteristics are as follows:

[0044] 1 H NMR (500MHz, CDCl 3 )δ12.36(s,1H),7.42–7.37(m,3H),7.30–7.27(m,2H),7.26–7.2...

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Abstract

The invention discloses a series of beta-enaminone ester compounds, and a synthesis method and application of the beta-enaminone ester compounds. The beta-enaminone ester compounds are prepared by taking beta-carbonyl acid ester and nitrine as raw materials and reacting under the catalysis of a strong-alkaline catalyst for one step. The whole synthesis method disclosed by the invention is easy to obtain raw materials, simple, easy to operate and high in yield; the prepared beta-enaminone ester compounds have better activity to both a human cervical carcinoma cell line Hela and a human hepatoma cell line 7404. The beta-enaminone ester compounds have a structural formula as shown in the specification.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a series of β-enaminone ester compounds and their synthesis methods and applications. Background technique [0002] β-enaminone (ester) compound molecule contains N—C=C—Z (Z=COR, CO 2 R) Structural units, which are important intermediates for the synthesis of a series of biologically and pharmacologically active substances α- and β-amino acids, peptides, alkaloids and pyrazoles. The traditional synthesis method of β-enaminone (ester) is to use aromatic hydrocarbons as water-carrying agents, and synthesize them from 1,3-dicarbonyl compounds and amines under the catalysis of protonic acids such as hydrochloric acid, but this method has high reaction temperature and high production The disadvantages are low efficiency, polluting the environment and troublesome post-processing. At present, there is no relevant report on obtaining β-enaminone esters by using β-carbonyl e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/10C07C229/34A61K31/216A61P35/00
Inventor 颜志明潘英明吴娜王恒山
Owner GUANGXI NORMAL UNIV