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Benzopyranone compound, as well as preparation method and application thereof

A technology of benzopyrone and compound, applied in the field of pharmaceutical synthesis, can solve problems such as low yield, and achieve the effect of low cost

Active Publication Date: 2013-12-18
SHANDONG LUKANG SHELILE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Both of the above routes use the expensive catalytic reagent AgNO 3 , and the yield is low

Method used

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  • Benzopyranone compound, as well as preparation method and application thereof
  • Benzopyranone compound, as well as preparation method and application thereof
  • Benzopyranone compound, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment one Preparation of 3-[(4-tert-butylcyclohexyl) dimethylene]-1,4-benzopyrandione

[0043] Under argon protection, add 1.62g (0.01mol) of 1,4-benzopyrandione to a 50ml three-necked flask, slowly add 20ml of acetic acid solution of 1.82g (0.01mol) of p-tert-butylcyclohexylaldehyde, and add 0.87ml (0.01mol) of isobutylamine was heated to 60°C for 4h. 20ml of water was added dropwise, solids were precipitated, filtered by suction, and recrystallized with 50ml of methyl tert-butyl ether to finally obtain 2.14g of a yellow solid with a yield of 65.6%.

Embodiment 2

[0044] Embodiment two Preparation of 3-[(4-tert-butylcyclohexyl) dimethylene]-1,4-benzopyrandione

[0045] Under the protection of nitrogen, add 3.24g (0.02mol) of 1,4-benzopyrandione into a 100ml three-necked flask, slowly add 20ml of acetic acid solution of 7.48g (0.04mol) of p-tert-butylcyclohexylaldehyde, and add iso Butylamine 1.74ml (0.02mol), heated to 30°C for 10h. 40ml of water was added dropwise, solids were gradually precipitated, and the crude product was obtained by suction filtration.

[0046] It was recrystallized with 100ml of diethyl ether and dried under vacuum at 50°C to obtain 4.22g of a yellow solid with a yield of 64.8%.

Embodiment 3

[0047] Embodiment Three Preparation of 3-[(4-tert-butylcyclohexyl) dimethylene]-1,4-benzopyrandione

[0048] Under argon protection, add 1.62g (0.01mol) of 1,4-benzopyrandione to a 50ml three-necked flask, slowly add 20ml of acetic acid solution of 1.82g (0.01mol) of p-tert-butylcyclohexylaldehyde, and add Morpholine 2.61ml (0.03mol), warmed up to 40°C for 4h. 20ml of water was added dropwise, solids were gradually precipitated, and the crude product was obtained by suction filtration.

[0049] Recrystallized with 50ml of isopropyl ether, dried in vacuo at 70°C to obtain 2.07g of yellow solid, yield 63.5%.

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PUM

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Abstract

The invention discloses a benzopyranone compound, as well as a preparation method and an application thereof, belonging to the field of synthesis of medicaments. The method comprises the following steps of: based on 1, 4-benzopyrandione and p-tert-butyl cyclohexyl acetaldehyde as raw materials, performing condensation reaction to get 3-((4-tert-butyl-cyclohexyl) dimethylene)-1, 4-benzopyrandione. The invention further discloses the method for preparing buparvaquone by utilizing the compound. The method has the characteristics of simple synthesis method, effect of avoiding the use of AgNO3, high total yield and the like.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a benzopyrone compound, its preparation method and its application. Background technique [0002] Benzopyrone compounds widely exist in natural compounds and have good biological activity. Although some preparation methods of benzopyrone compounds are disclosed in the prior art, there are many by-products in the preparation process, which easily lead to environmental pollution and other shortcomings. [0003] Buparvaquinone (2-[(4-tert-butylcyclohexyl)methyl]-3-hydroxy-1,4-naphthalenedione, CAS number: 88426-33-9, English name: Buparvaquone) is from Pitman-Moore Company A drug for the treatment of bovine theilex worm was developed, which was first launched in some countries in Africa, the Middle East and the Far East in 1991 under the trade name Butalex. It is the most effective drug for the treatment of theilerisis, and its effect exceeds that of the same drug - pavaquinone. Int...

Claims

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Application Information

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IPC IPC(8): C07D311/76C07C50/32C07C46/00
Inventor 马浩杰郭强颜丙春董坤彭欣桑艳丽
Owner SHANDONG LUKANG SHELILE PHARMA
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