Method for synthesizing amidine compounds through oxidative amidation of aryl methyl ketone under catalysis of copper (II)

A technology for oxidizing amides and aryl methyl ketones with aryl methyl ketones, which is applied in the field of synthesis of amidine compounds, can solve the problems of unfavorable large-scale production, poor stability, and unseen problems, and achieve low cost and good stability , the effect of simple steps

Active Publication Date: 2018-01-19
YUANJIANG HUALONG CATALYST TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These reports mainly use aryl aldehydes as raw materials, which are high in cost and poor in stability, which is not conducive to large-scale production.
The aryl methyl ketone has good stability and low cost, but so far, no three SPs of aryl methyl ketone have been seen. 3 A report on the one-step direct amidinization of -H with amines

Method used

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  • Method for synthesizing amidine compounds through oxidative amidation of aryl methyl ketone under catalysis of copper (II)
  • Method for synthesizing amidine compounds through oxidative amidation of aryl methyl ketone under catalysis of copper (II)
  • Method for synthesizing amidine compounds through oxidative amidation of aryl methyl ketone under catalysis of copper (II)

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Experimental program
Comparison scheme
Effect test

Embodiment 1～19

[0046] Embodiment 1~19 carries out according to the following method:

[0047] Add ketones (0.5 mmol), aniline (1.1 mmol), CuCl to the sealed tube 2 (13.4mg, 0.1mmol), PhCOONa (36mg, 0.25mmol) and DMSO (1.0mL), and the reaction mixture was stirred at 80°C under 1atm oxygen atmosphere for 30 hours, the organic layers were mixed, washed with Na 2 SO 4 Drying, filtration and concentration in vacuo and purification by silica gel column color classification (eluent: petroleum ether / ethyl acetate) gave amidines.

[0048] Concrete reaction process is as follows:

[0049]

Embodiment 1

[0051] Ketone compound raw material:

[0052] Target product:

[0053] Obtained 128.4 mg of the target product with a yield of 86%; a yellow solid; 1 H NMR (400MHz, DMSO) δ9.79(s, 1H), 7.85(d, J=7.9Hz, 2H), 7.80(d, J=7.7Hz, 2H), 7.62(t, J=7.3Hz, 1H ),7.48(t,J=7.4Hz,2H),7.34(t,J=7.5Hz,2H),7.04(t,J=7.4Hz,3H),6.78(t,J=7.2Hz,1H), 6.71(d,J=7.6Hz,2H). 13 C NMR (101 MHz, DMSO) δ 192.00, 152.01, 148.35, 140.11, 134.56, 133.71, 129.28, 129.03, 128.66, 128.44, 122.64, 122.38, 121.81, 119.48.

Embodiment 2

[0055] Ketone compound raw material:

[0056] Target product:

[0057] 105 mg of the target product was obtained; the yield was 67%; a yellow solid; 1 H NMR (400MHz, DMSO) δ9.80(s, 1H), 7.88(d, J=7.7Hz, 2H), 7.69(d, J=7.7Hz, 1H), 7.40(t, J=7.4Hz, 1H ),7.34(t,J=7.5Hz,2H),7.29(t,J=7.6Hz,1H),7.16(d,J=7.5Hz,1H),7.05(d,J=7.9Hz,2H), 7.00(s,1H),6.77(t,J=7.1Hz,1H),6.64(d,J=7.5Hz,2H),2.34(s,3H). 13 C NMR (101MHz, DMSO) δ194.22, 153.04, 148.38, 140.22, 139.36, 133.20, 133.17, 131.84, 131.81, 128.64, 128.29, 126.10, 122.56, 122.27, 121.62, 119.49.2

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Abstract

The invention discloses a method for synthesizing amidine compounds through oxidative amidation of aryl methyl ketone under the catalysis of copper (II). The method comprises the following steps: in an oxygen-containing atmosphere and in an organic carboxylate / DMSO mixed system, performing a reaction on the aryl methyl ketone and aryl primary amine under the catalysis of divalent copper salt, or performing a reaction on the aryl methyl ketone and the aryl primary amine and secondary amine under the catalysis of the divalent copper salt to obtain the amidine compounds. By the method, the aryl methyl ketone and amine compounds are used as raw materials for producing the amidine compounds through the one-step reaction; the method has the characteristics of a simple step, low cost and the like, and is conducive to industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing amidine compounds, in particular to a method for producing amidine compounds by using aryl methyl ketones and amine compounds as raw materials in the next step reaction of copper (II) catalysis, and belongs to the field of organic intermediate synthesis . Background technique [0002] An amidine is a structure in which an amino group and an imino group are connected to the same carbon atom, mainly including cyclic amidines or acyclic amidines. Amidines are important structural groups in many natural products and bioactive molecules, and compounds containing amidine structures are widely used in different fields, such as medicinal chemistry, synthetic intermediates, catalyst design, materials science, supramolecular chemistry, and coordination chemistry wait. [0003] The original method for synthesizing compounds containing amidine structure in the prior art is obtained by condensation of imine chlor...

Claims

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Application Information

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IPC IPC(8): C07C257/18
Inventor 刘强谢典科郭欣郭灿城
Owner YUANJIANG HUALONG CATALYST TECH
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