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Synthesis method for Z-difuryl imine compounds

A technology for furyl imines and compounds, which is applied in the field of synthesizing Z-bisfuryl imines to achieve the effects of easy separation and purification, easy availability of raw materials, and high regioselectivity

Inactive Publication Date: 2011-04-27
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is currently no method for synthesizing these compounds

Method used

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  • Synthesis method for Z-difuryl imine compounds
  • Synthesis method for Z-difuryl imine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Potassium carbonate (27.6mg, 0.20mmol), palladium chloride (1.9mg, 0.011mmol), sodium iodide (15.0mg, 0.10mmol), N-benzyl-4-methyl-2,3 -divinyl valeric acid amide (40.0mg, 0.20mmol), and 2mL dimethylformamide, then place the reaction tube in an oil bath at 80°C and stir for 8 hours, add 10mL water to quench the reaction, and extract three times with 25mL diethyl ether , combined the organic phases, washed once with salt water, dried over anhydrous sodium sulfate, concentrated the solution, and performed flash column chromatography to obtain the product Z-5,5,5',5'-tetramethyl-2,5,2',5' -Tetrahydro-[4,4']difuryl-2,2'-dibenzylimine 27.2 mg, yield 68%, the product is a white solid. The melting point is 164.2-165.3°C (ether).

[0020] 1 H NMR (300MHz, CDCl 3 )δ7.41-7.29 (m, 8H), 7.28-7.20 (m, 2H), 6.23 (s, 2H), 4.56 (s, 4H), 1.61 (s, 12H);

[0021] 13 C NMR (75MHz, CDCl 3 ): δ161.4, 151.2, 140.6, 128.4, 127.9, 126.6, 123.0, 90.4, 51.6, 26.7; MS (m / z): 400 (M + , 74.3...

Embodiment 2

[0025] According to the method described in Example 1, the difference is that the amount of catalyst used is different: N-benzyl-4-methyl-2,3-dienyl valeric acid amide (40.3mg, 0.20mmol), palladium chloride ( 0.4mg, 0.002mmol), sodium iodide (15.7mg, 0.10mmol), potassium carbonate (28.1mg, 0.20mmol), reacted at 80°C for 30 hours to obtain the product Z-5,5,5',5'- Tetramethyl-2,5,2',5'-tetrahydro-[4,4']difuryl-2,2'-dibenzylimine 22.5 mg, yield 60%.

Embodiment 3

[0027] According to the method described in Example 1, the difference is that the substrates and reagents used are: N-n-butyl-4, methyl-2,3-dienyl valeric acid amide (34.0mg, 0.20mmol), palladium chloride (1.9mg, 0.011mmol), sodium iodide (15.7mg, 0.10mmol), potassium carbonate (27.6mg, 0.20mmol), dimethylformamide (2mL), reacted for 11 hours to obtain product Z-5,5, 5',5'-tetramethyl-2,5,2',5'-tetrahydro-[4,4']difuryl-2,2'-di-n-butylimine 22.4mg, the yield was 66%. The product is a white solid. The melting point is 109.0-110.0°C (n-hexane / ethyl acetate).

[0028] 1 H NMR (300MHz, CDCl 3 )δ6.12(s, 2H), 3.31(t, J=6.9Hz, 4H), 1.62-1.50(m, 4H), 1.54(s, 12H), 1.44-1.30(m, 4H), 0.91(t , J=7.2Hz, 6H);

[0029] 13 C NMR (75MHz, CDCl 3 ): δ160.9, 150.8, 122.8, 90.0, 47.1, 33.1, 26.6, 20.6, 13.9;

[0030] MS (m / z): 332 (M + , 31.44), 289(100);

[0031] IR (KBr, cm -1 ): 2958, 2932, 2871, 1670, 1460, 1369, 1276, 1194, 1130;

[0032] Anal.calcd.for C 20 h 32 N 2 o 2 : C ...

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Abstract

The invention relates to a method for synthesizing Z-bisfuran imine compounds. The method comprises the following steps: 2,3-allenamide is subject to self ring closing coupling reaction in the presence of additives (potassium carbonate and sodium iodide) under the catalysis of palladium chloride to generate the Z-bisfuran imine compounds. The method has the advantages of simple operation, ready availability of raw materials and reagents, high reaction regioselectivity and easy separation and purification of a product, and is applicable to synthesizing various substituted Z-bisfuran imine compounds.

Description

technical field [0001] The invention relates to a method for synthesizing Z-bisfuryl imine compounds. Background technique [0002] Z-bisfuryl imine compounds are one of the most important intermediates in organic synthesis and one of the most common structural units in natural products. They have a variety of important physiological activities and are widely used in biotechnology, medicine and pesticides There is a huge value of development and utilization. There is currently no method for synthesizing such compounds. Contents of the invention [0003] The purpose of the present invention is to provide a method for effectively synthesizing Z-bisfuryl imine compounds, that is, 2,3-allenamide undergoes a self-ring-closing coupling reaction, and synthesizes Z-bisfuryl imine with high regioselectivity. Amine compounds, the reaction can introduce different substituents. [0004] The invention provides a method for effectively synthesizing Z-bisfuryl imine compounds. Under t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/66B01J27/13
Inventor 陈国飞傅春玲麻生明
Owner ZHEJIANG UNIV