Preparation method of isocoumarin derivative

A technology for isocoumarin and derivatives, which is applied in the field of preparation of isocoumarin derivatives, can solve the problems of difficulty in introducing five-membered rings or six-membered rings, poor thermal stability of peroxides, and reaction uncertainty.

Active Publication Date: 2017-09-01
东营市广利临港产业园有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional method of synthesizing isocoumarin is mainly divided into two classes: (1) the two-component reaction that contains unsaturated bond (as: alkyne, alkene, isonitrile) class compound to participate in: this kind of method is often to the reaction of substrate The site requirements are relatively high, and it is only suitable for the reaction of specific sites and specific substituents, and it is difficult to introduce other five-membered rings or six-membered rings in the reaction, and the vinyl compounds used are easy to self-polymerize, and it is difficult to achieve atomic Maximization of utilization; (2) Reaction involving CO gas: This type of reaction needs to be in a CO atmosphere, requires closed reaction conditions and a specific catalyst, and has great limitations for industrial production, and CO gas is a

Method used

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  • Preparation method of isocoumarin derivative
  • Preparation method of isocoumarin derivative
  • Preparation method of isocoumarin derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] To the 25mL reaction flask, add [RhCp*Cl 2 ] 2 (0.01mmol), Cu(OAc) 2 (0.1mmol), salicylamide (1mmol), 5,5-dimethyl-2-diazo-1,3-cyclohexanedione (1mmol), 1,2-dichloroethane (1,2- DCE) (5mL), reacted at 80°C for 8h, and tracked the reaction by thin layer chromatography (TLC). After the reaction, extracted with 15mL×2 dichloromethane and 10mL saturated brine, combined the organic phases, and added anhydrous sulfuric acid Sodium drying for 6h column chromatography (developing agent petroleum ether / ethyl acetate v / v=6:1) can give white product, the product is carried out 1 H NMR and 13 C NMR detects, and obtained result is as follows:

[0043] 1 H NMR (300MHz CDCl 3 )δ: 10.87(s, 1H), 8.47(d, J=8.1Hz, 1H), 7.68(t, J=8.1Hz, 1H), 7.01(d, J=8.4Hz, 1H), 2.78(s, 2H), 2.51(s, 2H), 1.17(s, 6H). 13 C NMR (75MHz CDCl 3 )δ: 196.4, 166.9, 164.7, 161.7, 138.4, 133.7, 116.5, 115.9, 111.3, 105.3, 52.8, 42.2, 31.8, 28.1. Depend on 1 The hydroxyl peak at 10.87 in H NMR and 13 The...

Embodiment 2

[0046] In addition to salicylamide, 5,5-dimethyl-2-diazo-1,3-cyclohexanedione, [RhCp * Cl 2 ] 2 Except that the amount of copper acetate added is 1mmol, 0.9mmol, 0.01mmol, 0.08mmol respectively, other conditions and steps are the same as in Example 1, the white product can be obtained, and the product is carried out 1 H NMR and 13 C NMR detection, the obtained result is the same as the detection result of compound 1 in Example 1, which is confirmed to be compound 1, and the yield of compound 1 is calculated to be 81%.

Embodiment 3

[0048] In addition to salicylamide, 5,5-dimethyl-2-diazo-1,3-cyclohexanedione, [RhCp * Cl 2 ] 2 Except that the amount of copper acetate added is 1mmol, 1.1mmol, 0.03mmol, 0.12mmol respectively, other conditions and steps are the same as in Example 1, the white product can be obtained, and the product is carried out 1 H NMR and 13 C NMR detection, the obtained result is the same as the detection result of compound 1 in Example 1, which is confirmed to be compound 1, and the yield of compound 1 is calculated to be 84%.

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Abstract

The invention discloses a preparation method of an isocoumarin derivative shown as a formula III. The formula III is shown in the description, wherein R1 and R2 are independently selected from one of hydrogen group, phenyl, C1 to C3 linear alkyl and C3 branched alkyl respectively; R3, R4 and R6 are independently selected from one of hydrogen group, hydroxyl, C1 to C3 linear alkyl, C3 branched alkyl, methoxyl and phenyl respectively; R5 is selected from halogeno, nitryl, halogenated methyl, phenyl and halogenated phenyl; R7, R8, R9, R10, R11 and R12 are independently selected from one of halogeno, nitryl, C1 to C3 linear alkyl, C3 branched alkyl, methoxyl, phenyl and halogenated phenyl respectively. Compared with the prior art, the method has the advantages that reaction raw materials are cheap and easy to obtain and the stability is relatively high; the yield of reaction products is high, side reactions are few and post-treatment of reaction is simple; various starting raw materials can be selected and the same target molecule is obtained.

Description

technical field [0001] The present invention relates to isocoumarin derivatives, in particular to a preparation method of isocoumarin derivatives. Background technique [0002] Isocoumarin compounds are a class of common and useful oxygen-containing heterocyclic compounds, which are widely used in the fields of medicine, materials and organic synthesis. It is a common vitamin K anti-caking agent in medicine, which can also prevent the formation and development of thrombus, and has a long drug effect; it also has pharmacological activities of laxative, antibacterial, anti-inflammatory, anti-cancer and protease inhibition, especially for the elderly Dementia has a better curative effect. In the field of materials, because isocoumarin compounds have a large conjugated system and a planar structure, they have important applications in organic light-emitting materials. The hydroxyl-containing isocoumarin compounds also have the above-mentioned properties, and the presence of th...

Claims

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Application Information

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IPC IPC(8): C07D311/80
CPCC07D311/80
Inventor 左有鹏何心伟商永嘉
Owner 东营市广利临港产业园有限公司
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