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Preparation method of b-heterocyclic ketone compound

A technology of ketone compounds and compounds, which is applied in the field of preparation of β-heterocyclic substituted ketone compounds, can solve the problems of large industrial wastewater, complicated operation, high production cost, etc., and achieve high reaction yield, safe and convenient operation, and mild reaction conditions Effect

Inactive Publication Date: 2012-10-31
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method requires the use of equivalent copper reagents, high production costs, complicated operations, and a large amount of industrial wastewater

Method used

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  • Preparation method of b-heterocyclic ketone compound
  • Preparation method of b-heterocyclic ketone compound
  • Preparation method of b-heterocyclic ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation of 4-(2-5-methoxythiophene)-nonan-2-one: the molar ratio of feed material is 3-nonen-2-one: heterocyclic compound: catalyst is 1.0: 2.0: 0.1, wherein hetero The cyclic compound is 2-methoxythiophene, the catalyst is palladium dichloride, the organic solvent is tetrahydrofuran, and the dosage thereof is 10 times that of 3-nonen-2-one. Add 70.1 mg (0.5 mmol) of 3-nonen-2-one, 114.2 mg (1.0 mmol) of 2-methoxythiophene, and 8.8 mg (0.05 mmol) of palladium dichloride into a 25 mL Schlinker bottle equipped with a magnet. ), 1.0 mL of tetrahydrofuran, stirred at 0° C., and the reaction was complete after 0.25 h. After the reaction was complete, the solvent was removed under reduced pressure, and the product was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate=10:1) to obtain the 4-(2-5-methoxythiophene)-nonyl -2-Kone liquid, pure product 123.4mg, yield 97%.

Embodiment 2

[0030] The preparation of 4-(2-5-methylfuran)-non-2-one: the molar ratio of feed material is 3-nonen-2-one: heterocyclic compound: catalyst is 1.0: 3.0: 0.1, wherein heterocyclic The compound is 2-methylfuran, the catalyst is palladium acetate, the organic solvent is n-hexane, and the dosage thereof is 60 times that of 3-nonen-2-one. Into a 25 mL Schlink bottle equipped with a magnet, add 70.1 mg (0.5 mmol) of 3-nonen-2-one, 123.1 mg (1.5 mmol) of 2-methylfuran, 11.2 mg (0.05 mmol) of palladium acetate, n-hexyl Add 5.0 mL of alkanes, stir the reaction at 60°C, and the reaction is complete after 10 hours. After the reaction was complete, the solvent was removed under reduced pressure, and the product was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate=10:1)) to obtain the 4-(2-5-methylfuran)-nonyl- 2-ketone liquid, pure product 108.9 mg, yield 98%.

Embodiment 3

[0032] The preparation of 4-(3-N-methylindole)-non-2-one: the molar ratio of feed material is 3-nonen-2-one: heterocyclic compound: catalyst is 1.0: 1.0: 0.1, wherein hetero The cyclic compound is N-methylindole, the catalyst is bis(acetonitrile)palladium dichloride, the organic solvent is n-butanol, and its consumption is 100 times that of 3-nonen-2-one. In a 25mL Schlink bottle equipped with a magnet, add 3-nonen-2-one 70.1mg (0.5mmol), N-methylindole 65.6mg (0.5mmol), bis(acetonitrile)palladium dichloride 13.0 mg (0.05mmol), n-butanol 9.0mL, stirred and reacted at 130°C, and the reaction was complete after 48h. After the reaction was complete, the solvent was removed under reduced pressure, and the product was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate=10:1)) to obtain the 4-(3-N-methylindole)-nonyl -2-Kone liquid, pure product 115.3 mg, yield 85%.

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Abstract

The invention belongs to the field of fine chemical industry, and relates to a preparation method of a b-heterocyclic ketone compound. The method comprises the following steps of: activating a furan or thiofuran or indole or pyrrole type electron-rich heterocyclic compound by using a palladium catalyst; and performing an addition reaction with an alpha,beta-unsaturated ketone compound to obtain a b-heterocyclic ketone compound, wherein the obtained product has multiple biological activities and pharmacological activities; and a ketone compound of which the beta position is connected with furan can be transformed into beta-carbonyl carboxylic acid by oxidizing. A C-H activating method is applied to an 1,4-additon reaction, so that a simple and convenient method for synthesizing a heterocyclic ketone compound is determined. The method has the characteristics of cheap and readily available raw materials and catalyst, operating safety and convenience, mild reaction conditions, high reaction yield, high atom economy, and the like. The method has a high use value and high social and economic benefits.

Description

technical field [0001] The invention belongs to the field of fine chemical industry and related chemical technology, and relates to a preparation method of β-heterocyclic substituted ketone compounds. Background technique [0002] Ketones with electron-rich heterocycles (furan, thiophene, indole, and pyrrole) connected to the β position are very important organic compounds with various biological and pharmacological activities, and are widely used in spices, organic synthesis, pesticides, and pharmaceutical chemicals Intermediates and other fields. The 1,4-addition reaction of α,β-unsaturated ketones with heterocyclic organometallic reagents is an important method for preparing β-heterocyclic ketones, which has attracted widespread attention. Hayashi research group reported in 2003 that rhodium-catalyzed thiophene boronic acid carried out 1,4-addition reaction to α, β-unsaturated ketones, and prepared β-thiophene substituted ketones (Yoshida, K.; Hayashi, T .Heterocycles 2...

Claims

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Application Information

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IPC IPC(8): C07D209/12C07D207/333C07D333/32
Inventor 于晓强张新冯秀娟包明张譞
Owner DALIAN UNIV OF TECH
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