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Method for synthesizing alpha-pyranone derivatives

A synthesis method and derivative technology, applied in the direction of organic chemistry, etc., can solve the problems of harsh reaction conditions, large environmental pollution, and large reaction waste liquid, and achieve the effects of mild reaction conditions, less environmental pollution, and easy operation

Inactive Publication Date: 2007-12-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two methods all have the shortcomings of many reaction steps, harsh reaction conditions, complicated operation, more reaction waste liquid, and greater environmental pollution.

Method used

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  • Method for synthesizing alpha-pyranone derivatives
  • Method for synthesizing alpha-pyranone derivatives
  • Method for synthesizing alpha-pyranone derivatives

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0018] Example 1 Preparation of 3-(3-nitrobenzyl)-7,8-dihydro-6H-chromene-2,5-dione (1a)

[0019] In a 250mL three-necked flask equipped with a thermometer, a reflux condenser, and mechanical stirring, 11.16 g (40 mmol) of 2-(acetoxy-(3-nitrophenyl))methyl methacrylate, 1,3-cyclo 4.48g (40mmol) of hexanedione, 2.76g (20mmol) of potassium carbonate, and 33.48g of acetone were stirred and reacted at 60°C for 4 hours. TLC was followed until the reaction of the raw materials was complete, then saturated saline was added, and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and the solvent was recovered under reduced pressure. The crude product was recrystallized from petroleum ether to obtain 9.39 g of 3-(3-nitrobenzyl)-7,8-dihydro-6H-chromene-2,5 - Diketone, pale yellow crystal, the yield is 78.5%, the melting point is 144.3-144.7°C, and the HPLC purity is 98.7%. 1 H NMR (CDCl 3 , 400MHz) δ8.11(m, 2H), 7.63(m, 2H), 7.49(t, 2H, J=7.6Hz),...

Embodiment 2

[0020] Example 2 Preparation of 3-(3-nitrobenzyl)-7,8-dihydro-6H-chromene-2,5-dione (1a)

[0021] The molar ratio of the feed material is Baylis-Hillman adduct: 1,3-cyclohexanedione: base is 1.0: 1.0: 1.0, wherein the Baylis-Hillman adduct is 2-(acetoxy-(3-nitro Phenyl)) methyl methacrylate, the base is potassium carbonate, and the organic solvent is acetone, and its consumption is 5 times that of 2-(acetoxy-(3-nitrophenyl)) methyl methacrylate.

[0022] Others are with embodiment 1. The product is 3-(3-nitrobenzyl)-7,8-dihydro-6H-chromene-2,5-dione, the yield is 82.2%, the melting point is 143.9-144.5°C, and the HPLC purity is 98.5%.

Embodiment 3

[0023] Example 3 Preparation of 3-(3-nitrobenzyl)-7,8-dihydro-6H-chromene-2,5-dione (1a)

[0024]The molar ratio of the feed material is Baylis-Hillman adduct: 1,3-cyclohexanedione: base is 1.0: 1.0: 2.0, wherein the Baylis-Hillman adduct is 2-(acetoxy-(3-nitro Phenyl)) methyl methacrylate, the base is N, N-dimethylaniline, the organic solvent is 1,2-dichloroethane, and its consumption is 2-(acetoxy-(3-nitrophenyl )) 8 times that of methyl methacrylate, stirred and reacted at 60°C for 2 hours.

[0025] Others are with embodiment 1. The product is 3-(3-nitrobenzyl)-7,8-dihydro-6H-chromene-2,5-dione, the yield is 82.6%, the melting point is 144.5-144.8°C, and the HPLC purity is 98.6%.

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Abstract

The invention discloses a method for synthesizing alpha- pyranone derivant demonstrated in formula (I). It comprises following steps: carrying out cyclic reaction with affixture of Baylis-Hillman and 1, 3- cyclohexanone and its derivant demonstrated in formula (III) under catalytic action of alkali and with existence of organic disslovant or without disslovant at subzero 20 to 10 Deg. C, reacting for 1- 12 hours, post-treating after reaction and getting said alpha- pyranone derivant. The invention is characterized by easy got raw material, simple and safe operation, temperate reaction condition, high productivity, simple post-treatment, little environmental pollution, and great performing value and social and economic benefit.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing alpha-pyrone derivatives. (2) Background technology [0002] α-Pyrone derivatives are an important class of organic heterocyclic compounds, which widely exist in natural products, and many of them have shown good physiological activities, such as anti-HIV, antibacterial, antifungal, anti-leukemia, etc., in medicine, Pesticides are widely used. [0003] Before the present invention is made, the method for synthesizing α-pyrone derivatives in the prior art has: 1) α, β-unsaturated ketone compound obtains [(a) Bickel, C.L.J.Am.Chem through lactonization reaction .Soc.1950,72,1022.(b) Migliorese, K.G.et al., J.Org.Chem.1974,39,843.(c)Dieter, R.K.et al., J.Org.Chem.1983,48 , 4439.]; 2) 3,5-dioxocarboxylic acid compounds are obtained by cyclization reaction (Harris, T.M.etal., J.Org.Chem.1966, 31, 1032.); 3) palladium-catalyzed Coupling-lactonization reaction of β-iodoacrylic acid and allenyl tin comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/74C07D417/06
Inventor 钟为慧苏为科赵永志
Owner ZHEJIANG UNIV OF TECH
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