Method for synthesizing beta-amidocarbonyl compounds

A technology of carbonyl compounds and compounds, which is applied in the field of synthesizing β-amide carbonyl compounds, can solve the problems of expensive catalysts, narrow substrate range, and high temperature, and achieve the effects of cheap and easy-to-obtain catalysts, mild reaction conditions, and a wide range of applications

Inactive Publication Date: 2012-12-12
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] (2) In 2011, the Bahulayan group in India used metal organic compounds Metalopthalocyanines as catalysts to synthesize such compounds in the presence of acid chlorides, but the catalysts used in this method are more toxic
[0011] (3) Momeni et al. used Zn(HSO 4 ) 2 and Co(HSO 4 ) 2 Such compounds were collectively weighed as catalysts at room temperature, but this method only involves CH 3 CN is used as a reactant and a solvent, and no other nitrile compounds are involved as a solvent, and the structure of the reaction substrate is relatively limited
[0013] (4) In 2007, Khan et al reported the use of FeC

Method used

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  • Method for synthesizing beta-amidocarbonyl compounds
  • Method for synthesizing beta-amidocarbonyl compounds
  • Method for synthesizing beta-amidocarbonyl compounds

Examples

Experimental program
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example example 1

[0032] Add 5ml of dried acetonitrile to a 25ml round bottom flask, add 2mmol of benzaldehyde, 2mmol of acetophenone, and then add 1.5ml of acetyl chloride and 2mmol of TiCl under stirring 4 , the mixed solution was stirred and reacted for 3h. After the reaction was completed, the reaction solution was poured into 25ml of ice-water mixture, a mixture of oil and solid was separated out, and the product was separated by column chromatography, ethyl acetate:petroleum ether (1:1, v :v), N-(3-oxo-1,3-diphenylpropyl)acetamide (1) was obtained with a yield of 90%, Mp103-104°C. Benzaldehyde and acetophenone, the reaction formula of acetonitrile is:

[0033]

[0034] The spectral data of product (1) is: 1 H NMR (400MHz, CDCl 3 )δ:2.00(3H,s,COCH 3 ),3.42(1H,dd,J 6.0,16.8Hz,CH 2 ),3.71(1H,dd,J 4.8,17.2Hz,CH 2),5.49-5.54(1H,m,CH),6.60(1H,d,J 8.4Hz,NH),7.27-7.30(5H,m,Ph),7.44(2H,t,J 8.0Hz,Ph), 7.56(1H,t,J 7.2Hz,Ph),7.88(2H,d,J8.4Hz,Ph);IR(film)ν max 3275,3082,2926,1693,1646,1552,...

Embodiment 2

[0036] Replace benzaldehyde with p-chlorobenzaldehyde, and others are with embodiment 1. The target compound (2) was obtained with a yield of 96%, Mp143-145°C. p-Chlorobenzaldehyde and acetophenone, the reaction formula of acetonitrile is:

[0037]

[0038] The spectral data of product (2) is: 1 H NMR (400MHz, CDCl 3 )δ:2.04(3H,s,COCH 3 ),3.42(1H,dd,J 6.4,17.2Hz,CH 2 ),3.74(1H,dd,J 4.8,17.2Hz,CH 2 ),5.52–5.59(1H,m,CH),6.77(1H,d,J 8.0Hz,NH),7.26–7.27(4H,m,Ph),7.46(2H,t,J 7.6Hz,Ph), 7.59(1H,t,J 7.2Hz,Ph),7.85(2H,d,J7.6Hz,Ph);IR(film)ν max 3289,3084,2926,1686,1651,1551,1372,1199,987,757cm -1 ;MS(ESI):m / z(relative intensity)224.1([M+Na] + ,100).

Embodiment 3

[0040] P-fluorobenzaldehyde was used instead of benzaldehyde, and the others were the same as in Example 1 to obtain the target compound (3), with a yield of 93%, Mp 108-111°C. p-Fluorobenzaldehyde and acetophenone, the reaction formula of acetonitrile is:

[0041]

[0042] The spectral data of product (3) is: 1 H NMR (400MHz, CDCl 3 )δ:2.04(3H,s,COCH 3 ),3.43(1H,dd,J 6.0,16.8Hz,CH 2 ),3.75(1H,dd,J 5.2,17.2Hz,CH 2 ),5.52–5.58(1H,m,CH),6.77(1H,d,J 5.6Hz,NH),6.97-7.01(2H,m,Ph),7.30-7.33(2H,m,Ph),7.47( 2H,t,J 7.6Hz,Ph),7.59(1H,t,J 7.2Hz,Ph),7.91(2H,d,J 8.0Hz,Ph);IR(film)ν max 3286,3082,2956,2844,1687,1648,1550,1508,1371,1226,990,751cm -1 ;MS(ESI):m / z(relative intensity)308.0([M+Na] + ,100).

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Abstract

The invention provides a method for synthesizing beta-amidocarbonyl compounds. The reaction general formula is disclosed in the specification, wherein R1, R2, R3 and R4 are respectively a substituent group; R1 can be H, F, Cl, Br, NO2, CH3, OCH3 or any other single group, and can also be 2,4-2Cl, 2-Cl-5-F or any other double-substituent group, and the quantity and position of the substituent groups are not defined; R2 can be H, and can also be NO2, CH3, OCH2CH3, aromatic group or any other substituent group; and R3 can be H, and can also be CH3, COOC2H5 or any other substituent group, or hexahydric cycloalkyl group formed by R2, R3 and carbon atom connected with R2 and R3. The reaction is carried out at room temperature in the presence of acetyl chloride by using titanium tetrachloride as a catalyst; and the purification adopts recrystallization, column chromatography or any other separation method. The invention has the advantages of accessible raw materials, simple technique, mild reaction conditions and cheap and nontoxic catalyst; and the applicable substrate range for reaction is wide, and thus, different substrates can be utilized to synthesize a series of beta-amidocarbonyl compounds.

Description

(1) Technical field [0001] The invention relates to a synthesis method for preparing β-acetamide carbonyl compounds (β-acetamide carbonyl compounds) through the reaction of aromatic aldehydes, carbonyl compounds and nitrile compounds. (2) Background technology [0002] In recent years, β-amide ketones have attracted the attention of chemists and medical scientists because their structures widely exist in many natural drug structures with physiological and pharmacological activities. β-amide carbonyl compounds can be easily converted into 1,3-diaminoalcohols, or β-amino acids and other compounds. Compounds such as 1,3-diaminoalcohol and β-amino acid are the core structures for the synthesis of some nucleoside peptide antibiotics, such as nikkomycin and neosporin. The precursor of β-aryl isotreonine can be combined with a molecule of amino acid to form the corresponding dipeptide isomer, and it can also be synthesized using β-amide carbonyl compound as a precursor. Mechanism...

Claims

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Application Information

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IPC IPC(8): C07B43/06C07C231/14C07C233/31C07C233/47C07C233/36
Inventor 李加荣杨德利史大昕张奇
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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