A kind of preparation method of benzofuranocoumarin compound

A technology of benzofuran and compounds, applied in the field of organic chemical drug synthesis, to achieve the effect of large industrialization potential, low price, and easy operation

Active Publication Date: 2021-11-19
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the preparation process of the compound also has an important impact on the promotion of its application. Therefore, it is necessary to provide a simpler and higher yield preparation method for this type of compound. This problem has also become one of the difficulties in current research and needs to be overcome.

Method used

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  • A kind of preparation method of benzofuranocoumarin compound
  • A kind of preparation method of benzofuranocoumarin compound
  • A kind of preparation method of benzofuranocoumarin compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The preparation of compound 001 to compound 022 was carried out with reference to the above-mentioned synthetic route 1.

[0053] 1. The specific route of compound 001 is shown in the following formula:

[0054]

[0055] Concrete preparation process is as follows:

[0056] Step S1:

[0057] (1) In a round bottom flask, benzofuran (1.0 eq) of formula (1) was added and dissolved in dichloromethane (50.0 mL). After the round bottom flask was stirred at room temperature for 5 min, aluminum oxide (36.0 eq) and benzaldehyde (1.05 eq) were added in sequence, and the reaction was stirred at room temperature for 3 hours. After the reaction, the alumina was removed by suction filtration, the filtrate was collected, concentrated and dried to obtain a crude product, which was recrystallized or separated by a silica gel column to obtain the compound of formula (3).

[0058] (2) In a round bottom flask, dissolve the compound of formula (3) (1.0eq) and p-toluenesulfonamide (1.5e...

Embodiment 2

[0154] The preparation of compound 023 to compound 029 was carried out with reference to the above-mentioned synthetic route 2.

[0155]1. The specific preparation process of compound 023 is as follows:

[0156] Step S1:

[0157] (1) In a round bottom flask, benzofuran (1.0 eq) of formula (1) was added and dissolved in dichloromethane (50.0 mL). After the round bottom flask was stirred at room temperature for 5 min, aluminum oxide (36.0 eq) and benzaldehyde (1.05 eq) were added in sequence, and the reaction was stirred at room temperature for 3 hours. After the reaction, the alumina was removed by suction filtration, the filtrate was collected, concentrated and dried to obtain a crude product, which was recrystallized or separated by a silica gel column to obtain the compound of formula (3).

[0158] (2) In a round bottom flask, dissolve the compound of formula (3) (1.0eq) and p-toluenesulfonamide (1.5eq) in toluene (40mL), and add triethylamine in sequence at 0°C under nitr...

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Abstract

The invention discloses a preparation method of a photoactive benzofuranocoumarin compound. The photoactive benzofuranocoumarin compound is the compound shown in formula I; the enantioselectivity of the compound shown in formula I is as high as 95-99%. The photoactive benzofuranocoumarin skeleton of the present invention contains two chiral centers, adopts a 1,4-addition reaction strategy, uses a common and easily available chiral base as a catalyst, and uses 3-acylcoumarins of different structures, Benzofuranimine is used as a substrate to synthesize a photoactive benzofuranocoumarin compound containing two chiral centers; this method has low raw material prices, simple operation, low equipment requirements, environmental friendliness, and operator Safety, mild reaction conditions, high yield, high enantioselectivity, wide range of substrates, and great industrialization potential.

Description

technical field [0001] The invention relates to the technical field of organic chemical drug synthesis, and more specifically, to a preparation method of a benzofuranocoumarin compound. Background technique [0002] Coumarin is an important class of heterocyclic compounds and one of the most advantageous scaffold materials in the field of medicinal chemistry and material science. It is widely distributed in a large number of bioactive molecules, especially furanocoumarin derivatives, which are composed of many An important coumarin compound produced by this plant. [0003] In view of the multiple biological activities of coumarin compounds, it has become a research hotspot to use it as the parent structure to carry out chemical modification of substituents in order to obtain compounds with wider activities and better effects. For example, the patent CN1062179083 records a furanocoumarin derivative and its preparation method; the patent CN102617585 records the related furano...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/06C07D409/14C07B53/00
CPCC07B53/00C07B2200/07C07D407/06C07D409/14
Inventor 黄慧才晏聚章詹若挺
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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