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Environment-friendly method for preparing pyrano[2,3-d]pyrimidone derivate through catalysis

A catalytic preparation and environmentally friendly technology, applied in organic chemistry and other fields, can solve the problems of complex product purification process, difficult biodegradation, low utilization rate of raw materials, etc., and achieve convenient large-scale production, good biodegradability and high utilization rate Effect

Active Publication Date: 2016-07-27
HOPE (NANJING) LIFE SCI INNOVATION INST CO LTD
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the use of acidic ionic liquids to catalyze and prepare pyrano[2,3-d]pyrimidinone derivatives in the prior art. The product purification process is complicated and the catalyst needs to be purified before use. However, a catalyst with good catalytic activity, easy biodegradation, high raw material utilization rate, simple product purification, mild reaction conditions and a catalytic system that can be directly recycled is provided. Process for preparing pyrano[2,3-d]pyrimidinone derivatives

Method used

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  • Environment-friendly method for preparing pyrano[2,3-d]pyrimidone derivate through catalysis
  • Environment-friendly method for preparing pyrano[2,3-d]pyrimidone derivate through catalysis
  • Environment-friendly method for preparing pyrano[2,3-d]pyrimidone derivate through catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 1mmol of p-bromobenzaldehyde, 1mmol of barbituric acid, 1.4mmol of malononitrile and 0.05mmol of acidic ionic liquid were added to 50ml single-necked bottles containing 8ml of 60% ethanol aqueous solution with a stirring bar and a condenser. Heated to reflux for 23 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, crushed the precipitated solid, allowed to stand, suction filtered, and the filter residue was washed with ethanol and dried in vacuo to obtain 7-amino-5-(4 -Bromophenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile, the yield was 91%, in the filtrate Repeated use after direct addition of p-bromobenzaldehyde, barbituric acid and malononitrile.

[0027] 7-Amino-5-(4-bromophenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile: m.p.292~294℃; IR(KBr): 3368, 3343, 3181, 3074, 2214, 1681, 1563cm -1 ; 1 HNMR (400MHz, DMSO-d 6 ): δ=3.79(s, 1H), 6.85(...

Embodiment 2

[0029] 1mmol p-nitrobenzaldehyde, 1mmol barbituric acid, 1.2mmol malononitrile and 0.04mmol acidic ionic liquid were respectively added to 50ml single-necked flasks containing 8ml60% ethanol aqueous solution with a stirring bar and a condenser tube. Heated to reflux for 17 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, crushed the precipitated solid, left standstill, suction filtered, and the filter residue was washed with ethanol and dried in vacuo to obtain 7-amino-5-(4 -Nitrophenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile, the yield was 93%, the filtrate Add p-nitrobenzaldehyde, barbituric acid and malononitrile directly to the mixture for repeated use.

[0030] 7-Amino-5-(4-nitrophenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile : m.p.236~238℃; IR(KBr): 3407, 3201, 3171, 2992, 2203, 1728, 1464cm -1 ; 1 HNMR (400MHz, DMSO-d 6): δ=4.98(s, 1H), 6...

Embodiment 3

[0032] 1mmol o-methoxybenzaldehyde, 1mmol barbituric acid, 1.4mmol malononitrile and 0.05mmol acidic ionic liquid were respectively added to 50ml single-necked flasks containing 7ml60% ethanol aqueous solution with a stirring bar and a condenser. Heated to reflux for 25 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, crushed the precipitated solid, left to stand, suction filtered, and the filter residue was washed with ethanol and dried in vacuo to obtain 7-amino-5-(2 -methoxyphenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile, the yield was 87%, The filtrate was directly added m-methoxybenzaldehyde, barbituric acid and malononitrile and reused.

[0033] 7-Amino-5-(2-methoxyphenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6- Nitrile: m.p.>300℃; IR(KBr): 3421, 3205, 3142, 3013, 2278, 1761, 1612cm -1 ; 1 HNMR (400MHz, DMSO-d 6 ): δ=3.77(s, 1H), 4.18(s, 1H), 7.12~7.42...

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Abstract

The invention discloses an environment-friendly method for preparing pyrano[2,3-d]pyrimidone derivate through catalysis, and belongs to the technical field of ion liquid catalysis.In the preparation reaction, the mole ratio of aromatic aldehyde to barbituric acid to malononitrile is 1:1:1-1.4.The molar weight of an acidic ionic liquid catalyst is 3-5% that of adopted aromatic aldehyde, the volume dose of a 60% ethanol aqueous solution measured by milliliter is 7-9 times molar weight of aromatic aldehyde measured by millimole, backflow reaction time is 10-25 min, the product is cooled to reach room temperature after the reaction is finished, suction filtration is performed, and filter residue is washed with ethyl alcohol and subjected to vacuum drying to obtain the pyrano[2,3-d]pyrimidone derivate.Compared with a preparation method adopting other acidic ionic liquid catalysts, the method has the advantages that the catalyst is biodegradable, the raw material utilization rate is high, the catalysis ability is strong, and the whole preparation process is easy and convenient to operate, and industrial large-scale application is convenient.

Description

technical field [0001] The invention belongs to the technical field of ionic liquid catalysis, and in particular relates to an environment-friendly catalytic method for preparing pyrano[2,3-d]pyrimidinone derivatives. Background technique [0002] Pyrimidinone derivatives are a class of compounds containing nitrogen heterocyclic structures with important application value. Because of their structural variability, they have a wide range of biological activities and are widely used in the fields of medicine and pesticides. In the field of medicine, they It can be used as antineoplastic drugs, analgesic drugs, fungicides, herbicides, insecticides, etc., and is one of the hot spots in the development and research of new drugs and new pesticides. In addition, with the in-depth research on this type of compounds, it is found that some heterocyclic fused pyrimidinone derivatives also have excellent biological activities, such as pyrano[2,3-d]pyrimidinone derivatives can be used as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052
CPCC07D491/052
Inventor 周安娜邵文杰吴胜华岳彩波储昭莲
Owner HOPE (NANJING) LIFE SCI INNOVATION INST CO LTD
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