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Preparation method for coumarin-3-carboxylic ester derivative

A technology for derivatives and coumarin, which is applied in the field of preparation of coumarin-3-carboxylate derivatives, can solve the problems of complicated steps, unenvironmental protection, and does not conform to the concept of green chemistry, and achieves simple steps and high catalytic efficiency. small amount of effect

Active Publication Date: 2014-03-12
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to provide a method with simple steps, high efficiency, Preparation method of coumarin-3-carboxylate derivatives that are environmentally friendly and meet the concept of green chemistry

Method used

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  • Preparation method for coumarin-3-carboxylic ester derivative
  • Preparation method for coumarin-3-carboxylic ester derivative
  • Preparation method for coumarin-3-carboxylic ester derivative

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preparation example Construction

[0032] The present invention provides a method for preparing coumarin-3-carboxylate derivatives as shown in formula (I) or formula (II), wherein the method comprises: 3 In the presence of , the salicylaldehyde derivative shown in formula (III) or 2-hydroxyl-1-naphthaldehyde shown in formula (IV) and the general formula are R 2 OH alcohol and Michaelis acid contact reaction,

[0033]

[0034] Among them, R 2 for C 1 -C 8 Alkyl or C 7 -C 13 The aryl; n is 1-4; R 1 selected from H, halogen, nitro, C 1 -C 6 Alkoxyl, C 1 -C 10 of alkyl and amine groups.

[0035] In the preparation method, when n in the salicylaldehyde derivative shown in formula (III) is 1-4, regardless of R 1 Whether it is a strong electron-withdrawing group substitution (such as nitro, fluorine, etc.) or a strong electron-donating group substitution (such as methoxy, diethylamino, etc.) is applicable to this method. In the case of n=2-4, R 1 Preferred is 3,5-di-tert-butyl.

[0036] R in formula (...

Embodiment 1-1

[0045] Synthesis of coumarin-3-methyl carboxylate: weigh 0.366g (3mmol) of salicylaldehyde, 0.518g (3.6mmol) of Michaelis acid, 5mL of methanol and 0.0082g (0.05mmol) of ferric chloride In the bottom flask, heated to 70°C and refluxed in an oil bath with stirring for 6h. After the reaction was completed, cooled to room temperature, concentrated the reaction solution, and then separated by column chromatography to obtain 0.538g of white solid product with a yield of 88%.

[0046]

[0047] The structure, color, state, yield and characterization data of coumarin-3-methyl carboxylate are as follows:

[0048]

[0049] Methyl coumarin-3-carboxylate: white solid; yield 88%; 1 HNMR (300MHz, CDCl 3 ) δ: 8.53 (s, 1H, CH), 7.56-7.64 (m, 2H, ArH), 7.28-7.34 (m, 2H, ArH), 3.92 (s, 3H, CH 3 ) ppm; 3 CNMR (75MHz, CDCl 3 ) δ: 163.7, 155.2, 149.1, 134.4, 129.5, 124.9, 117.9, 117.8, 116.7, 52.9ppm.

Embodiment 1-2

[0051] Synthesis of 6-chlorocoumarin-3-methyl carboxylate: according to the preparation method of Example 1-1, the difference is that 3 mmol of the salicylaldehyde derivative shown in formula (A) is used instead of Example 1-1 Salicylaldehyde in.

[0052]

[0053] The structure, color, state, yield and characterization data of 6-chlorocoumarin-3-methyl carboxylate are as follows:

[0054]

[0055] Methyl 6-chlorocoumarin-3-carboxylate: white solid; yield 83%; 1 HNMR (300MHz, CDCl 3 ) δ: 8.43 (s, 1H, CH), 7.70 (d, J=8.7Hz, 1H, ArH), 7.55 (d, J=8.7Hz, 1H, ArH), 7.21 (s, 1H, ArH), 3.92 (s, 3H, CH 3 ) ppm; 13 CNMR (75MHz, CDCl 3 ) δ: 163.4, 161.8, 150.1, 147.7, 135.6, 134.3, 133.2, 131.8, 130.2, 129.3, 119.3, 118.6, 53.0ppm.

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Abstract

The invention discloses a preparation method for a coumarin-3-carboxylic ester derivative shown as the formula (I) or the formula (II) in the specification. The method comprises the step that under the existence of FeCl3 being used as a catalyst, salicylaldehyde derivative shown as the formula (III) in the specification and 2-hydroxy-1-naphthaldehyde shown as the formula (IV) in the specification are in contact reaction with alcohol and meldrum's acid which have a general formula, namely R2OH. Through the fact that the salicylaldehyde derivative, the 2-hydroxy-1-naphthaldehyde, the alcohol or the meldrum's acid is catalyzed by FeCl3 in multi-component contact reaction under a relatively temperate condition, the coumarin-3-carboxylic ester derivative with relatively high productivity is synthesized in relatively short reaction time, and the method is simple in step, efficient and environment-friendly, and completely meets the concept of green chemistry.

Description

technical field [0001] The invention relates to a preparation method of coumarin derivatives, in particular to a preparation method of coumarin-3-carboxylate derivatives. Background technique [0002] Coumarin, also known as 1,2-benzopyrone, is scientifically named o-hydroxycinnamic acid lactone. Coumarin is a spice with a wide range of uses and is often used as a fixative. Coumarin derivatives are a class of oxygen-containing heterocyclic compounds with various biological activities, such as antibacterial, antiviral, antitumor, anticoagulant It can be used as a signal molecule to regulate the interaction between insects, symbiotic bacteria, pathogenic bacteria and organisms, so it is widely used in the pharmaceutical and pesticide industries. Using chemical principles and methods to introduce some special active structural units on the basic coumarin skeleton, it is possible to obtain biologically derived drugs and pesticides with better activity than natural compounds. T...

Claims

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Application Information

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IPC IPC(8): C07D311/12C07D311/14C07D311/16C07D311/92
CPCC07D311/12C07D311/14C07D311/16C07D311/92
Inventor 何心伟靳文静陈娇娇商永嘉
Owner ANHUI NORMAL UNIV
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