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Pure aqueous phase synthesis method of β-aminocarbonyl compound

An aminocarbonyl and compound technology, which is applied in the field of catalytic organic synthesis and achieves the effects of high yield, good selectivity and less dosage

Inactive Publication Date: 2014-10-15
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of the existing preparation methods of β-aminocarbonyl compounds, and provide a pure aqueous phase synthesis method of β-aminocarbonyl compounds with less catalyst consumption, high catalytic activity and reusability

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Synthesis of 2-[(4-chlorophenyl)(4-chloroanilino)methyl]-cyclohexanone

[0013] Add 0.0218g (0.1mmol) 5-sulfosalicylic acid, 0.2810g (2mmol) p-chlorobenzaldehyde, 0.2805g (2.2mmol) p-chloroaniline, 309μL (3mmol) cyclohexanone to a 10mL round bottom flask, and then Add 2mL of distilled water, stir, react at room temperature for 3 hours, filter and separate, and the solid is separated and purified by column chromatography to obtain 2-[(4-chlorophenyl)(4-chloroanilino)methyl]-cyclohexanone, and the yield is 94%, the cis-trans ratio is 33:67, and the spectral data of the product are: 1 H NMR (400MHz, CDCl 3 )δppm: 7.31-7.24(m, 4H), 7.04-6.98(m, 2H), 6.42(d, J=8.8Hz, 2H), 4.79(s, 1H), 4.52(d, J=6.2Hz, 1H ), 2.72(dd, J=8.7, 4.9Hz, 1H), 2.45-2.27(m, 2H), 2.05-1.83(m, 3H), 1.83-1.62(m, 3H); 13 C NMR (101MHz, CDCl 3 ) δppm: 211.29, 144.64, 138.88, 131.92, 127.93, 127.67, 127.60, 121.37, 113.75, 56.81, 56.18, 41.17, 30.68, 26.84, 23.12.

[0014] Add 0.2810g (2mmol) p-chlorob...

Embodiment 2

[0019] Synthesis of 2-[(phenyl)(anilino)methyl]-cyclohexanone

[0020] In Example 1, the p-chlorobenzaldehyde used is replaced with equimolar benzaldehyde, and p-chloroaniline is replaced with equimolar aniline, and other steps are the same as in Example 1 to obtain 2-[(phenyl)(anilino) Methyl]-cyclohexanone, its productive rate is 90%, and the cis-trans ratio is 18:82, and the catalyst is reused 5 times, and the productive rate of 2-[(phenyl)(anilino)methyl]-cyclohexanone remains the same. It can reach 88%, and its spectral data is: 1 H NMR (400MHz, CDCl 3 )δppm: 7.42-7.36(m, 2H), 7.31(d, J=7.1Hz, 2H), 7.24-7.18(m, 1H), 7.06(t, J=6.9Hz, 2H), 6.63(t, J =7.2Hz, 1H), 6.54(d, J=7.6Hz, 2H), 4.72(dd, J=71.2, 5.2Hz, 2H), 2.88-2.29(m, 2H), 1.90(dd, J=17.1, 9.1Hz, 6H), 1.80-1.68(m, 1H); 13 C NMR (101MHz, CDCl 3 ) δppm: 212.33, 146.01, 140.21, 127.96, 127.58, 126.26, 125.84, 116.64, 112.63, 58.22, 51.25, 49.84, 34.50, 10.55, 6.48, 6.38.

Embodiment 3

[0022] Synthesis of 2-[(phenyl)(anilino)methyl]-cyclohexanone

[0023] In Example 1, the 5-sulfosalicylic acid used is replaced with equimolar salicylic acid, p-chlorobenzaldehyde is replaced with equimolar benzaldehyde, and p-chloroaniline is replaced with equimolar aniline. Other steps and implementation Example 1 is identical, obtains 2-[(phenyl) (anilino) methyl]-cyclohexanone, and its productive rate is 80%, and the cis-trans ratio is 30:70, and catalyst is reused 5 times, and 2-[(phenyl )(anilino)methyl]-cyclohexanone yield is essentially unchanged.

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Abstract

The invention provides a method for synthesizing a beta-amino-carbonyl compound by a pure water phase. Water is used as a reacting solvent, aldehydes, amines and ketones are used as raw materials, and salicylic acid or salicylic acid derivatives is or are adopted as a catalyst to react. The method opens a new low-cost, green and effective way to the preparation of beta-amino-carbonyl compounds, and has the advantages that a target product is good in selectivity and high in yield; the catalyst is small in dose and does not need to be separated from the solvent after the reaction is completed, and can be recycled directly in an aqueous solution manner; experiment results prove that the catalyst still has high catalytic activity after being recycled for 5 times, and the yield of the product is basically the same.

Description

technical field [0001] The invention belongs to the technical field of catalytic organic synthesis, and specifically relates to a method for synthesizing beta-aminocarbonyl compounds by using salicylic acid or salicylic acid derivatives as catalysts. Background technique [0002] β-Aminocarbonyl compounds are key intermediates in the synthesis of drugs and natural products (β-amino alcohols, β-amino acids, β-lactams, etc.), and are widely used in organic synthesis. Various types of compounds can be obtained from β-aminocarbonyl compounds. β-Aminocarbonyl compounds are also an important class of biologically active substances, which have various biological activities such as antitussive, antibacterial, anti-inflammatory, anticancer, antiviral, sedative, analgesic, antihypertensive, edema inhibitory, and anticoagulant. From the perspectives of environmental protection, energy saving, and atom economy, the direct, efficient and selective construction of β-aminocarbonyl compoun...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C221/00C07C225/18C07C225/16
Inventor 高子伟陈纯吴亚朱序阳张伟强孙华明
Owner SHAANXI NORMAL UNIV
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