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Method for preparing 3-alkynyl isocoumarins compounds

A technology of isocoumarin and compounds, which is applied in the field of preparation of 3-alkynyl isocoumarin compounds, can solve problems such as poor substrate adaptability, poor step economy, severe reaction conditions, etc., and achieve great use value and social Economic benefits, simple steps, and easy-to-obtain raw materials

Active Publication Date: 2018-08-07
ZUNYI MEDICAL UNIVERSITY
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  • Abstract
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AI Technical Summary

Problems solved by technology

This method has problems such as poor step economy, severe reaction conditions, unfriendly environment, the use of a toxic, harmful and dangerous reagent, phosphorus oxychloride, difficult access to raw materials, and poor adaptability of substrates.

Method used

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  • Method for preparing 3-alkynyl isocoumarins compounds
  • Method for preparing 3-alkynyl isocoumarins compounds
  • Method for preparing 3-alkynyl isocoumarins compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of 3-(3-(tert-butyldimethylsilyloxy)-1-propynyl)-1H-isochromen-1-one (1a)

[0032]

[0033] Under nitrogen protection, methyl 2-(2,2-dibromovinyl)benzoate (318mg, 1mmol), (2-propynyloxy)tert-butyldimethylsilane (170mg, 1mmol), Palladium acetate (11mg, 0.05mmol), cuprous iodide (9mg, 0.05mmol), triphenylphosphine (78mg, 0.3mmol) and cesium carbonate (977mg, 3mmol) were successively added to a 25mL Schlenk bottle, and then added Refined tetrahydrofuran (3mL) was placed in an oil bath for reaction, the reaction temperature was controlled at 70°C, and the reaction was carried out for 4 hours. After the reaction, the organic solvent was removed under reduced pressure; eluting with petroleum ether / ethyl acetate, and separating on a silica gel column, The yield of 3-(3-(tert-butyldimethylsilyloxy)-1-propynyl)-1H-isochromen-1-one was 75%. 1 H NMR (400MHz, Chloroform-d) δ8.26 (ddd, J = 8.0, 1.4, 0.7Hz, 1H), 7.76–7.64(m, 1H), 7.57–7.47(m, 1H), 7.43–7.34(m...

Embodiment 2

[0034] Example 2: Synthesis of 3-(4-(tert-butyldimethylsilyloxy)-1-butynyl)-1H-isochromen-1-one (1b)

[0035]

[0036] Under nitrogen protection, methyl 2-(2,2-dibromovinyl)benzoate (318mg, 1mmol), (3-butynyloxy)tert-butyldimethylsilane (184mg, 1mmol), Palladium acetate (11mg, 0.05mmol), cuprous iodide (9mg, 0.05mmol), triphenylphosphine (78mg, 0.3mmol) and cesium carbonate (977mg, 3mmol) were successively added to a 25mL Schlenk bottle, and then added Refined tetrahydrofuran (3mL) was placed in an oil bath for reaction, the reaction temperature was controlled at 70°C, and the reaction was carried out for 4 hours. After the reaction, the organic solvent was removed under reduced pressure; eluting with petroleum ether / ethyl acetate, and separating on a silica gel column, The yield of 3-(4-(tert-butyldimethylsilyloxy)-1-butynyl)-1H-isochromen-1-one was 72%. 1H NMR (400MHz, Chloroform-d) δ8.24(d, J=7.9Hz, 1H), 7.67(s, 1H), 7.48(t, J=7.7Hz, 1H), 7.36(d, J=7.9Hz ,1H),6.61(s,1H...

Embodiment 3

[0037] Example 3: Synthesis of 3-(4-phenyl-1-butynyl)-1H-isochromen-1-one (1c)

[0038]

[0039] Under nitrogen protection, methyl 2-(2,2-dibromovinyl)benzoate (318mg, 1mmol), 3-butynylbenzene (130mg, 1mmol), palladium acetate (11mg, 0.05mmol), Cuprous iodide (9mg, 0.05mmol), triphenylphosphine (78mg, 0.3mmol) and cesium carbonate (977mg, 3mmol) were successively added to a 25mL Schlenk bottle, and then purified tetrahydrofuran (3mL) was added and placed React in an oil bath, the reaction temperature is controlled at 70°C, and react for 4 hours. After the reaction, remove the organic solvent under reduced pressure; elute with petroleum ether / ethyl acetate, separate on a silica gel column, and 3-(4-phenyl-1 The yield of -butynyl)-1H-isochromen-1-one was 70%. 1 H NMR (400MHz, Chloroform-d) δ8.25 (d, J = 7.9Hz, 1H), 7.67 (td, J = 7.6, 1.4Hz, 1H), 7.48 (td, J = 7.6, 1.2Hz, 1H) ,7.38–7.28(m,3H),7.27–7.22(m,3H),6.59(s,1H),2.92(t,J=7.5Hz,2H),2.72(t,J=7.5Hz,2H). 13 C NMR (101MHz...

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Abstract

The invention discloses a method for synthesizing 3-alkynyl isocoumarins compounds. 2-(2, 2-ethylene dibromide) benzoic acid derivatives and terminal alkyne compounds are used as raw materials for the3-alkynyl isocoumarins compounds, bivalent palladium and univalent copper are used as catalysts, and tri-aryl phosphine compounds and alkali are used as additives. The method includes carrying out heating reaction in organic solvents to synthesize a series of 3-alkynyl isocoumarins compounds. A chemical reaction formula is shown. The method has the advantages of simple steps, mild conditions, short reaction time, high atom economy, easily available raw materials, environmental friendliness and the like. Besides, the 3-alkynyl isocoumarins compounds are a type of important bioactive moleculesand synthetic intermediates, and accordingly the method can be widely applied to the field of medicine synthesis and has high use value and a high social benefit.

Description

technical field [0001] The invention relates to a preparation method of 3-alkynyl isocoumarin compounds, belonging to the field of organic synthesis chemistry. Background technique [0002] 3-Substituted isocoumarins are important skeletons that are ubiquitous in various natural products, drug molecules, and synthetic compounds. 3-substituted isocoumarins not only have a wide range of biological activities such as anti-tumor, anti-bacterial, anti-fungal and anti-HIV, but also are widely used in organic synthesis as important synthetic building blocks. 3-Alkynylisocoumarin compounds are a class of important biologically active molecules and synthetic intermediates, and have a wide range of uses in the field of medicinal chemistry. About the synthesis of 3-alkynyl isocoumarin compounds, the following methods are usually adopted: [0003] [0004] This method requires a two-step reaction to synthesize 3-alkynyl isocoumarin compounds. First, it needs to prepare 3-chloro-1H-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C07D311/76
CPCC07D311/76C07F7/1892
Inventor 刘小卒刘培均钟强波周宇祥陈国均
Owner ZUNYI MEDICAL UNIVERSITY
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