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Method for synthesizing 2-benzoyl-2H-furo[3, 2-c]coumarin derivatives

A technology of coumarin derivatives, 2-c, applied in the direction of organic chemistry and the like, can solve problems such as unfavorable industrial production, and achieve the effects of good regioselectivity, few operation steps, and convenient separation and purification

Inactive Publication Date: 2014-02-19
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] This reaction has good results under microwave conditions, but it is not conducive to industrial production
[0014] Visible, prior art synthesis 2-benzoyl-2 H -The method of furo [3,2-c] coumarin derivatives all has certain weak points

Method used

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  • Method for synthesizing 2-benzoyl-2H-furo[3, 2-c]coumarin derivatives
  • Method for synthesizing 2-benzoyl-2H-furo[3, 2-c]coumarin derivatives
  • Method for synthesizing 2-benzoyl-2H-furo[3, 2-c]coumarin derivatives

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Experimental program
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Embodiment 1

[0055] In this embodiment, 4-hydroxycoumarin, benzaldehyde and ω-bromoacetophenone pyridinium salt are used as reaction raw materials. Specifically, 0.162 grams (1 mmol) of 4-hydroxycoumarin, 0.106 grams (1 mmol) of benzaldehyde, 0.277 grams (1 mmol) of ω-bromoacetophenone pyridinium salt and 0.025 grams (0.25 mmol) of triethylamine ) was placed in a reaction flask, 5 mL of water was added, heated to reflux, tracked by TLC until the reaction was completed, cooled to room temperature, and filtered to obtain a solid. The solid was recrystallized with 95% ethanol to obtain the target product (yield 65%). Product data: IR (KBr) ν : 1720, 1650, 1411, 1041, 932, 761, 694 cm -1 . 1 H NMR (400 MHz, CDCl 3 ) δ 7.91 (d, J = 7.6 Hz, 2H), 7.85 (d, J = 7.3 Hz, 1H), 7.66 (t, J = 7.6 Hz, 1H), 7.60 (d, J = 7.4 Hz, 1H), 7.50 (t, J = 7.7 Hz, 2H), 7.42 – 7.28 (m, 7H), 6.18 (d, J = 4.9 Hz, 1H), 4.81 (d, J = 4.9 Hz, 1H). 13 C NMR (101 MHz, CDCl 3 ) Δ 192.10, 166.33, 159.23, 155.44...

Embodiment 2

[0058] In this embodiment, 4-hydroxycoumarin, 4-chlorobenzaldehyde and ω-bromoacetophenone pyridinium salt are the reaction

[0059] raw material.

[0060] Specifically, 0.162 grams (1 mmol) of 4-hydroxycoumarin, 0.141 grams (1 mmol) of 4-chlorobenzaldehyde, 0.277 grams (1 mmol) of ω-bromoacetophenone pyridinium salt and 0.025 grams of triethylamine (0.25 mmol) was placed in a reaction flask, 5 mL of ethanol was added, heated to reflux, tracked by TLC until the reaction was completed, cooled to room temperature, and filtered to obtain a solid. The solid was recrystallized from 95% ethanol to obtain the target product (70% yield). Product data: IR (KBr) ν : 1712, 1649, 1414, 1090, 1042, 937, 770 cm -1 . 1 H NMR (400 MHz, DMSO-d 6 ) δ 7.92 (d, J = 7.6 Hz, 2H), 7.85 (d, J = 7.6 Hz, 1H), 7.75 (m, J = 17.8, 8.1 Hz, 2H), 7.58 (t, J = 7.6 Hz, 2H), 7.52 (d, J = 8.4 Hz, 1H), 7.46 (m, J = 14.9, 7.9 Hz, 3H), 7.32 (d, J = 8.3 Hz, 2H), 6.68 (d, J = 5.0 Hz, 1H), 4.75 ...

Embodiment 3

[0064] In this embodiment, 4-hydroxycoumarin, 4-methylbenzaldehyde and ω-bromoacetophenone pyridinium salt are used as reactants

[0065] material.

[0066] Specifically, 0.162 grams (1 mmol) of 4-hydroxycoumarin, 0.120 grams (1 mmol) of 4-methylbenzaldehyde, 0.277 grams (1 mmol) of ω-bromoacetophenone pyridinium salt and triethylamine 0.025 g (0.25 mmol) was placed in a reaction flask, 5 mL of methanol was added, heated to reflux, tracked by TLC until the reaction was completed, cooled to room temperature, and filtered to obtain a solid. The solid was recrystallized from 95% ethanol to obtain the target product (85% yield). Product data: IR (KBr) ν : IR (KBr) ν : 1713, 1649, 1410, 1040, 936, 759, 692 cm -1 . 1 H NMR (400 MHz, DMSO-d 6 ) δ 7.88 (d, J = 7.6 Hz, 2H), 7.84 (d, J = 7.7 Hz, 1H), 7.73 (m, J = 18.0, 7.8 Hz, 2H), 7.55 (t, J = 7.7 Hz, 2H), 7.50 (d, J = 8.4 Hz, 1H), 7.46 (t, J = 7.6 Hz, 1H), 7.17 (d, J = 8.0 Hz, 2H), 7.13 (d, J = 8.0 Hz, 2H), 6.62 ...

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Abstract

The invention discloses a method for synthesizing 2-benzoyl-2H-furo[3, 2-c]coumarin derivatives. The method comprises: taking 4-hydroxycoumarin, an aldehyde and omega-bromoacetophenone pyridinium salt as reactants, dissolving the reactants in a solvent, taking an alkali as a catalyst, and preparing 2-benzoyl-2H-furo[3, 2-c]coumarins at 25 DEG C-150 DEG C. According to the method, the employed raw materials and catalyst are cheap and easily available, the reaction condition is mild; by multiple selection on different materials, multiple combined reactions can be carried out, so that the structure of reaction products is developed, and the large-scale preparation and the industrialized application of the products can be realized; the technological process of the method is short, the operation steps are less, intermediate products need not separating and the products are convenient to separate and purify, so "three wastes (waste gas, waste water and industrial residue)" are less and energy consumption is low; and additionally, the method possesses good regioselectivity and a wide application scope. The synthetic method belongs to an efficient economic environment-friendly green synthetic method.

Description

[0001] technical field [0002] The invention belongs to the field of organic chemical synthesis, and relates to a preparation method of compound coumarin, in particular to a method for synthesizing 2-benzoyl-2 H - A method of furo[3,2-c]coumarin derivatives. Background technique [0003] Furanocoumarins are natural products with strong physiological, pharmacological and biological activities. It has anti-coagulation, anti-tumor, anti-virus, enhanced autoimmunity, anti-cell proliferation, anti-bacterial, anti-AIDS, anti-fatigue and calcium antagonistic effects. Therefore, the coumarin-derived compounds have wide application value in the field of medicine. [0004] And in the prior art, synthetic 2-benzoyl-2 H -Technology of furo[3,2-c]coumarin derivatives, there are only three similar reports: [0005] First, Wang et al. used benzyl bromide, coumarin, and aromatic aldehydes to generate 2,3-diaryl-2 through a series reaction of pyridinium salts generated in situ. H - Fu...

Claims

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Application Information

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IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 安礼涛周建峰朱凤霞张路路
Owner HUAIYIN TEACHERS COLLEGE
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