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Method for preparing beta-amino carbonyl compound through synergetic catalysis of titanocene dichloride and aminophenol ligand

A technology of titanocene dichloride and aminocarbonyl, which is applied in the field of synergistic catalytic preparation of titanocene dichloride and aminophenol ligands to prepare β-aminocarbonyl compounds, achieving the effects of short reaction time, mild reaction conditions and simple operation

Inactive Publication Date: 2014-09-17
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of the existing methods for preparing β-aminocarbonyl compounds, and to provide a method that does not need to add solvents, has mild reaction conditions, short reaction time, and is suitable for the Mannich reaction of aliphatic ketone substrates to prepare β-aminocarbonyl compounds. compound method

Method used

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  • Method for preparing beta-amino carbonyl compound through synergetic catalysis of titanocene dichloride and aminophenol ligand
  • Method for preparing beta-amino carbonyl compound through synergetic catalysis of titanocene dichloride and aminophenol ligand
  • Method for preparing beta-amino carbonyl compound through synergetic catalysis of titanocene dichloride and aminophenol ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Taking the preparation of 4-phenyl-4-phenylamino-2-butanone with the following structural formula as an example, the raw materials used and the preparation method thereof are as follows:

[0013]

[0014] Put 102 μL (1.0 mmol) of benzaldehyde, 100 μL (1.1 mmol) of aniline, 2 mL (27 mmol) of acetone, 12.5 mg (0.05 mmol) of titanocene dichloride, and 10.9 mg (0.1 mmol) of p-aminophenol in a reaction flask, 25 After reacting at ℃ for 2 hours, the reaction was stopped and separated by column chromatography to obtain the white solid product 4-phenyl-4-phenylamino-2-butanone with a yield of 88%. The resulting product was characterized by a Bruker Avance superconducting Fourier digital NMR spectrometer, and the characterization data were: 1 H NMR (400MHz, CDCl 3 )δppm: 7.21-7.37 (m, 5H), 7.09 (t, J = 7.7Hz, 2H), 6.68 (t, J = 7.3Hz, 1H), 6.56 (d, J = 8.2Hz, 2H), 4.84 ( t, J=6.4Hz, 1H), 2.94(d, J=6.4Hz, 2H), 2.09(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ: 207.34, 146.71, 142.45...

Embodiment 2

[0016] Taking the preparation of 4-(4-chlorophenyl)-4-phenylamino-2-butanone as an example with the following structural formula, the raw materials used and the preparation method thereof are as follows:

[0017]

[0018] In Example 1, the benzaldehyde used was replaced with equimolar p-chlorobenzaldehyde, and the other steps were the same as in Example 1 to prepare a yellow solid 4-(4-chlorophenyl)-4-phenylamino-2-butanol Ketone, its productive rate is 85%, and characteristic data is: 1 H NMR (400MHz, CDCl 3 )δppm: 7.22(m, 4H), 7.04(t, J=7.7Hz, 2H), 6.62(t, J=7.2Hz, 1H), 6.45(d, J=8.0Hz, 2H), 4.75(t, J=6.3Hz, 1H), 4.38(s, 1H), 2.85(d, J=6.3Hz, 2H), 2.05(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ: 206.69, 146.50, 141.11, 133.02, 129.19, 128.97, 127.73, 118.13, 113.79, 53.75, 51.02, 30.78.

Embodiment 3

[0020] Taking the preparation of 4-phenyl-4-(3-chloroanilino)-2-butanone as an example, the raw materials used and the preparation method thereof are as follows:

[0021]

[0022] In Example 1, the aniline used was replaced with equimolar m-chloroaniline, and other steps were the same as in Example 1 to prepare yellow solid 4-phenyl-4-(3-chloroanilino)-2-butanone, Its yield is 94%, and the characteristic data are: 1 H NMR (400MHz, CDCl 3 )δppm: 7.32(m, 4H), 7.24(d, J=1.7Hz, 1H), 6.98(t, J=8.0Hz, 1H), 6.61(d, J=7.9Hz, 1H), 6.52(s, 1H), 6.40(d, J=8.2Hz, 1H), 4.80(s, 1H), 4.59(s, 1H), 2.91(d, J=6.3Hz, 2H), 2.08(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ: 206.96, 147.98, 141.86, 134.82, 130.12, 128.90, 127.55, 126.17, 117.72, 113.49, 111.87, 54.17, 50.89, 30.82.

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Abstract

The invention discloses a method for preparing a beta-amino carbonyl compound through synergetic catalysis of titanocene dichloride and an aminophenol ligand. The method comprises the following step: directly reacting aliphatic ketone, aromatic aldehyde and aromatic amine under the synergetic catalysis condition of titanocene dichloride and the aminophenol ligand to obtain the beta-amino carbonyl compound. According to the method, a solvent does not need to be added, the used catalysts are cheap, nontoxic and stable to air and water, the operation is simple, the reaction conditions are mild, the reaction time is short, the atom economy is high, the product yield is high, and the prepared beta-amino carbonyl compound has very high application potential in preparation of drugs, natural products and organic synthetic intermediates.

Description

technical field [0001] The invention specifically relates to a method for synergistically catalyzing the preparation of beta-aminocarbonyl compounds by titanocene dichloride and aminophenol ligands. 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. The Mannich reaction is one of the traditional methods for preparing β-aminocarbonyl compounds. From the perspectives of environmental protection, energy saving, and atom economy, the direct, efficient and selective construction of β-aminocarbonyl compounds from unactivated aldehydes, amines, and ketones is attractive. At present, the Mannich reaction in which aromatic ketones are used as reactants has been well developed, and both organic catalysts and metal catalysts have obtained good reaction effects. However, when aliphatic ketones, especially acetone, are u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/16C07C225/18
Inventor 高子伟陈纯朱序阳张国防张伟强孙华明
Owner SHAANXI NORMAL UNIV
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