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Method for catalytically preparing 4,5-dihydropyran[c]chromene derivative

A technology of benzopyran derivatives and dihydropyran, which is applied in the field of catalytic preparation 4, can solve the problems of complex product purification process, large amount of catalyst usage, and difficult biodegradation, etc., and achieves the convenience of large-scale industrial production and high utilization High effect with less loss

Active Publication Date: 2016-07-27
日照新睿招商发展有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the use of alkaline ionic liquids in the prior art to prepare 4,5-dihydropyran [c] chromene derivatives in the process of ionic liquid catalyst usage is relatively large, difficult to biodegrade, raw materials With the disadvantages of low utilization rate, complex product purification process, and the need for purification treatment before the catalyst is used, a catalytic catalyst with high catalytic activity, easy biodegradation, high raw material utilization rate, simple product purification and direct recycling of the catalytic system is provided. Process for preparing 4,5-dihydropyran[c]chromene derivatives

Method used

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  • Method for catalytically preparing 4,5-dihydropyran[c]chromene derivative
  • Method for catalytically preparing 4,5-dihydropyran[c]chromene derivative
  • Method for catalytically preparing 4,5-dihydropyran[c]chromene derivative

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Experimental program
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Effect test

Embodiment 1

[0021] Add 1mmol benzaldehyde, 1mmol 4-hydroxycoumarin, 1.2mmol malononitrile and 0.10mmol alkaline ionic liquid into a 50ml single-necked flask with a stir bar and a condenser containing 8ml of 50% ethanol aqueous solution (volume ratio) . The reaction was heated and refluxed for 12 minutes, detected by TLC (Thin Plate Chromatography), the raw material point disappeared, cooled to room temperature, the precipitated solid was crushed, stood still, filtered with suction, the filter residue was washed with ethanol and dried in vacuum to obtain 2-amino-5-oxo -4-Phenyl-4,5-dihydropyran[c]benzopyran-3-carbonitrile, the yield was 92%, benzaldehyde, 4-hydroxycoumarin and malononitrile were directly added to the filtrate For repeated use.

[0022] 2-Amino-5-oxo-4-phenyl-4,5-dihydropyran[c]benzopyran-3-carbonitrile: mp257~259℃; IR(KBr): 3372, 3281, 3174 , 2192, 1704, 1670, 1609cm -1 ; 1 HNMR(500MHz, DMSO-d 6 ): δ = 4.32 (s, 1H), 7.18 (d, J = 7.8 Hz, 2H), 7.34 (brs, 1H), 7.36 (brs, 2H), ...

Embodiment 2

[0024] Add 1mmol of p-chlorobenzaldehyde, 1mmol of 4-hydroxycoumarin, 1.2mmol of malononitrile and 0.12mmol of alkaline ionic liquid to a 50ml single port containing 10ml of 50% ethanol aqueous solution (volume ratio) with stirring bar and condenser In the bottle. The reaction was heated and refluxed for 19 minutes, detected by TLC (Thin Plate Chromatography), the raw material point disappeared, cooled to room temperature, the precipitated solid was crushed, stood still, filtered with suction, the filter residue was washed with ethanol and dried in vacuum to obtain 2-amino-5-oxo -4-(4-chlorophenyl)-4,5-dihydropyran[c]benzopyran-3-carbonitrile, the yield is 90%, directly add p-chlorobenzaldehyde and 4-hydroxyl fragrance to the filtrate Beans and malononitrile are reused afterwards.

[0025] 2-Amino-5-oxo-4-(4-chlorophenyl)-4,5-dihydropyran[c]benzopyran-3-carbonitrile: mp256~258℃; IR(KBr): 3372, 3307, 3168, 2183, 1717, 1671, 1603cm -1 ; 1 HNMR(500MHz, DMSO-d 6 ): δ = 4.41 (s, 1H)...

Embodiment 3

[0027] 1mmol o-chlorobenzaldehyde, 1mmol 4-hydroxycoumarin, 1.2mmol malononitrile and 0.14mmol alkaline ionic liquid were added to a 50ml single port with a stir bar and a condenser containing 9ml of 50% ethanol aqueous solution (volume ratio) In the bottle. The reaction was heated and refluxed for 21min, detected by TLC (Thin Plate Chromatography), the raw material point disappeared, cooled to room temperature, crushed the precipitated solid, stood still, filtered with suction, the filter residue was washed with ethanol and vacuum dried to obtain 2-amino-5-oxo -4-(2-chlorophenyl)-4,5-dihydropyran[c]benzopyran-3-carbonitrile, the yield was 87%, and o-chlorobenzaldehyde and 4-hydroxyl Beans and malononitrile are reused afterwards.

[0028] 2-Amino-5-oxo-4-(2-chlorophenyl)-4,5-dihydropyran[c]benzopyran-3-carbonitrile: mp264~266℃; IR(KBr): 3381, 3290, 3172, 2188, 1703, 1679, 1601cm -1 ; 1 HNMR(500MHz, DMSO-d 6 ): δ = 4.47 (s, 1H), 7.19 (d, J = 7.8 Hz, 1H), 7.24 (t, J = 7.5 Hz, 2H)...

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Abstract

The invention discloses a method for catalytically preparing a 4,5-dihydropyran[c]chromene derivative, and belongs to the technical field of chemical material preparation.In the preparation reaction, the molar ratio of aromatic aldehyde to 4-hydroxycoumarin to malononitrile is 1:1:(1-1.2), the molar weight of an alkaline ionic liquid catalyst is 8%-15% of that of aromatic aldehyde, the volume dose of a 50% ethanol water solution serving as reaction solvent on a milliliter basis is 8-10 times of the molar weight of aromatic aldehyde on a millimole basis, the reflux reaction time ranges from 10 min to 28 min, after the reaction is finished, cooling is conducted to room temperature, extraction filtration is conducted, filter residues are washed with ethyl alcohol and vacuum-dried, and the 4,5-dihydropyran[c]chromene derivative is obtained.Compared with a preparation method adopting other alkaline ionic liquid catalysts, the method for catalytically preparing the 4,5-dihydropyran[c]chromene derivative has the advantages of being high in catalytic activity of the catalyst, free of treatment during the reuse process, high in raw material utilization rate, easy and convenient to operate in the whole preparation process and the like, and large-scale industrial application is convenient.

Description

Technical field [0001] The invention belongs to the technical field of chemical material preparation, and specifically relates to a method for catalytically preparing 4,5-dihydropyran[c]benzopyran derivatives. Background technique [0002] 4,5-Dihydropyran [c] benzopyran derivatives are a very important class of compounds with a wide range of physiological and pharmacological activities, such as anti-allergic, hypoglycemic, anti-bacterial, anti-cancer, and useful For the treatment of allergic bronchitis, diabetes, etc., it is one of the hot spots in the development and research of new drugs and new pesticides. Therefore, it is very important to study the preparation of 4,5-dihydropyran[c]benzopyran derivatives. At present, the preparation of this type of compound mainly uses K 2 CO 3 , (NH 4 ) 2 HPO 4 , H 6 P 2 W 18 O 62 ·18H 2 O, TBAB and DBU are used as catalysts, but this method has disadvantages such as long reaction time, low yield, serious environmental pollution, and the ...

Claims

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Application Information

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IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 岳彩波彭金中叶明富吴胜华储昭莲王楠楠
Owner 日照新睿招商发展有限公司
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