Synthesis method of pyranocoumarin derivatives

A technology of coumarin derivatives and synthetic methods, which is applied in chemical recovery, organic chemistry, etc., can solve the problems of difficult recovery of catalysts, large amount of catalysts, and unfriendly environment, so that the product yield is not affected and the reaction time is not affected. Short, the effect of improving the catalytic effect

Inactive Publication Date: 2012-10-31
李佰林 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to solve a series of problems such as large amount of catalyst used in the existing technology of preparing pyranocoumarin derivatives, the catalyst is not easy to recycle, the reaction time is long, some reactions require high temperature, and it is not

Method used

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  • Synthesis method of pyranocoumarin derivatives
  • Synthesis method of pyranocoumarin derivatives
  • Synthesis method of pyranocoumarin derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]

[0022] Add [DBU][Ac] ionic liquid (0.125mmol), benzaldehyde (25mmol), malononitrile (25mmol), 4-hydroxycoumarin (27.5mmol), and deionized water 15mL into the reaction vessel in sequence, Place it in an ultrasonic container, and react ultrasonically at room temperature for 10 minutes (ultrasonic input power 400W), filter the mixture, recrystallize with ethanol, and dry to obtain the pure product with a yield of 94%.

[0023] Characterization data: 1 H NMR (200MHz, DMSO-d 6 ):δ4.45(s,1H),7.23-7.31(m,4H),7.42-7.17(m,4H),7.31(br s,2H),7.40-7.54(m,2H),7.69(t, J=6.4Hz),7.90(d,J=7.8Hz); 13 C NMR (62.5MHz, DMSO-d 6 ) 160.0, 158.7, 154.0, 152.8, 144.0, 133.6, 129.2 (2C), 127.8 (2C), 125.3, 123.1, 119.9, 117.2, 113.6, 104.7, 58.6, 37.6.

Embodiment 2

[0025]

[0026] Add [DBU][Ac] ionic liquid (0.125mmol), 4-chlorobenzaldehyde (25mmol), malononitrile (25mmol), 4-hydroxycoumarin (27.5mmol), and deionized water 15mL to the reaction in sequence Put it in the container, put it in an ultrasonic container, react with ultrasonic wave at room temperature for 10 minutes (ultrasonic input power 400W), filter the mixed solution, recrystallize with ethanol, and dry to obtain the pure product with a yield of 96%.

[0027] Characterization data: 1 H NMR (200MHz, DMSO-d 6 ):δ4.49(s,1H),7.29-7.40(m,4H),7.49(br s,2H),7.54-7.74(m,2H),7.88-8.55(m,2H); 13 C NMR (62.5MHz, DMSO-d 6 ): 160.1, 158.6, 154.2, 152.9, 142.9, 133.6, 129.1 (2C), 127.8 (2C), 125.3, 123.2, 119.9, 117.2, 113.6, 104.1, 58.2, 37.1.

Embodiment 3

[0029]

[0030] Add [DBU][Ac] ionic liquid (0.125mmol), 3-chlorobenzaldehyde (25mmol), malononitrile (25mmol), 4-hydroxycoumarin (27.5mmol), and deionized water 15mL to the reaction in sequence Put it in the container, put it in an ultrasonic container, react with ultrasonic wave at room temperature for 10 minutes (ultrasonic input power 400W), filter the mixed solution, recrystallize with ethanol, and dry to obtain the pure product with a yield of 90%.

[0031] characterizing data 1 H NMR (200MHz, DMSO-d 6 ):δ4.51(s,1H),7.26-7.35(m,4H),7.45(br s,2H),7.47-7.54(m,2H),7.68-7.76(m,2H),7.78-7.82( m,2H); 13 CNMR (62.5MHz, DMSO-d 6 ): 160.2, 158.7, 154.4, 152.9, 146.5, 134.3, 132.0, 129.3, 128.3, 127.9, 127.3, 125.3, 123.1, 119.7, 117.2, 113.7, 103.9, 58.1, 37.4.

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Abstract

The invention discloses a green synthesis method of pyranocoumarin derivatives disclosed as Formula (4a) in the following reaction equation. According to the synthesis method, by using DBU-type ionic liquid disclosed as Formula (b) in the following reaction equation as a catalyst, aromatic aldehyde disclosed as Formula (1a), malononitrile disclosed as Formula (2a) and 4-hydroxycoumarin disclosed as Formula (3a) which are used as raw materials react in water under the promoting action of microwaves to obtain the target products. The operational method disclosed by the invention is simple and environment-friendly, and has the advantages of mild reaction conditions and the like; and the products can be easily separated, and the catalyst can be recycled. The reaction equation is as follows.

Description

technical field [0001] The invention relates to a synthesis method of pyranocoumarin derivatives. Background technique [0002] In recent years, the synthesis of pyranocoumarins and their derivatives has attracted considerable attention because some of them are potential inhibitors of measles virus replication, uterine contraction-inhibiting pharmacophores, and potential multidrug resistance reversal Reagents; there are also some derivatives that prevent [3H]thymidine from binding to human leukemia cells (HL-60); in addition, some have been reported to have brain stimulating activity, antifungal and antibacterial activity. With the continuous expansion of the application fields of pyranocoumarins and their derivatives, there are more and more studies on their synthetic methods. Among them, M.K.Jitender uses DBU as a catalyst to reflux synthesis in water, which is considered to be one of the convenient and economical methods (Tetrahedron, 2011, 66:5637-5641), but the catalys...

Claims

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Application Information

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IPC IPC(8): C07D493/04C07D519/00
CPCY02P20/584
Inventor 李佰林
Owner 李佰林
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