CN103193607A - Method for preparing chalcone and directive through multi-sulfonate ion liquid catalysis - Google Patents
Method for preparing chalcone and directive through multi-sulfonate ion liquid catalysis Download PDFInfo
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- CN103193607A CN103193607A CN2013100869224A CN201310086922A CN103193607A CN 103193607 A CN103193607 A CN 103193607A CN 2013100869224 A CN2013100869224 A CN 2013100869224A CN 201310086922 A CN201310086922 A CN 201310086922A CN 103193607 A CN103193607 A CN 103193607A
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- ketone
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- aldehyde
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- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 title claims abstract description 27
- 239000007788 liquid Substances 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 14
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 title abstract description 7
- 235000005513 chalcones Nutrition 0.000 title abstract description 7
- 238000006555 catalytic reaction Methods 0.000 title description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 10
- 150000002576 ketones Chemical class 0.000 claims abstract description 8
- 230000035484 reaction time Effects 0.000 claims abstract description 3
- 239000002994 raw material Substances 0.000 claims abstract 2
- -1 sulfonate ion Chemical class 0.000 claims description 22
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 14
- 238000005882 aldol condensation reaction Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 5
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 claims description 4
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 claims description 4
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 3
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 claims description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 claims description 2
- 239000002608 ionic liquid Substances 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 9
- 230000003197 catalytic effect Effects 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 6
- 239000011831 acidic ionic liquid Substances 0.000 abstract description 3
- 150000001789 chalcones Chemical class 0.000 abstract description 3
- 239000002841 Lewis acid Substances 0.000 abstract description 2
- 150000007517 lewis acids Chemical class 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明提供一种多磺酸根离子液体催化制备查耳酮及衍生物的方法，属于有机化学合成技术领域。本发明方法的缩合反应中原料醛与酮的摩尔比为1:1，多磺酸根离子液体催化剂的摩尔量是所用酮或醛的8-10%，反应温度为120-140℃，反应时间为8-20h，反应压力为1个大气压，反应后静置分层，分出的上层产物重结晶后得到产品查耳酮及衍生物。分出的下层含有多磺酸根离子液体催化剂在110℃真空干燥处理2h后可以循环使用。本发明与传统质子酸、路易斯酸及其它酸性离子液体作催化剂的制备方法相比，具有催化活性高、催化剂用量少、催化剂与产物分离简便、催化剂可以循环使用其催化活性未有明显降低。The invention provides a method for preparing chalcones and derivatives by catalyzing polysulfonate ionic liquids, belonging to the technical field of organic chemical synthesis. In the condensation reaction of the inventive method, the molar ratio of the raw material aldehyde to the ketone is 1:1, the molar weight of the polysulfonate ion liquid catalyst is 8-10% of the ketone or aldehyde used, the reaction temperature is 120-140°C, and the reaction time is 8-20h, the reaction pressure is 1 atmosphere, after the reaction, stand and separate layers, and the separated upper layer product is recrystallized to obtain the product chalcone and its derivatives. The separated lower layer containing the polysulfonate ionic liquid catalyst can be recycled after being vacuum-dried at 110° C. for 2 hours. Compared with the preparation method of traditional protonic acid, Lewis acid and other acidic ionic liquids as catalysts, the present invention has high catalytic activity, less catalyst consumption, easy separation of catalyst and product, and the catalyst can be recycled without significant reduction in catalytic activity.
Description
Technical field:
The invention belongs to the organic chemical synthesis technical field, be specifically related to the method for a kind of many sulfonate ions liquids catalytic preparation phenyl styryl ketone and derivative.
Background technology:
Phenyl styryl ketone is a kind of flavonoid compound, be that the natural compounds of parent is present in the plants such as Radix Glycyrrhizae, safflower with it, be the precursor of synthetic flavones in the plant materials, have very strong pharmacological action, show as anti-oxidant, antitumor, anti-inflammatory activity, anti-liver virus, effect such as antibiotic.At present, this compounds has been widely used in the treatment of common diseases such as cardiovascular disorder, cancer, disease of immune system, and simultaneously, it also is a kind of important organic synthesis intermediate, can be used for the synthetic of fine chemicals such as spices and medicine.Phenyl styryl ketone and derivative thereof adopt the Claisen-Schmidt condensation reaction under highly basic or the strong acid to be prepared usually, and these acid or alkali comprise AlCl
3, dense H
2SO
4, solid super-strong acid, solid alkali etc.But the use of above-mentioned strong acid, alkali catalyst causes selectivity of product relatively poor through regular meeting, and yield is lower, and has disadvantages such as etching apparatus, contaminate environment.Therefore, the environment-friendly preparation method thereof of exploitation phenyl styryl ketone and derivative thereof becomes the important topic of current common concern.
Acidic ion liquid, particularly bronsted acid ionic liquid owing to have green non-pollution, to organicly having good solubility, the acidic site that is evenly distributed with mineral compound, being easy to that product separates and advantage such as can be recycled is used in the preparation of phenyl styryl ketone and derivative.Such as Shen Jianghan etc. with the imidazoles that contains sulfonate radical or pyridinium salt acidic ion liquid as the solvent catalyzer of holding concurrently, catalysis efficiently phenyl aldehyde and methyl phenyl ketone by the Claisen-Schmidt condensation reaction prepare phenyl styryl ketone (
Acidic ionic liquids as dual catalyst and solvent for environmentally friendly synthesis of chalcone, Journal of Molecular Catalysis A:Chemical, 2008,280:24-28; A kind of method of using ionic liquid synthesizing chalcone and derivative thereof, CN101289378A).Above-mentioned owing to the expense of using glyoxaline ion liquid to produce in order to reduce, Qian Hua etc. use sulfation N, N, N-triethyl-N-fourth sulfonic acid ammonium salt ionic liquids etc. are as catalyzer, obtain various phenyl styryl ketone and derivative by Claisen-Schmidt condensation reaction high yield, and ionic liquid can be recycled 5 times at least, its catalytic activity has reduction (Synthesis of chalcones via Claisen-Schmidt reaction catalyzed by sulfonic acid-functional ionic liquids, Industrial﹠amp slightly; Engineering Chemistry Research, 2011,50:1146-1149).In order further to reduce the preparation expense of ionic liquid, Fang Dong etc. use sulfation N, N, N-trimethylammonium-N-propanesulfonic acid ammonium salt ionic liquid is as catalyzer, under the condition of no solvent effectively catalytic preparation various phenyl styryl ketone and derivative (Synthesis of chalcones via Claisen-Schmidt condensation reaction catalyzed by acyclic acidic ionic liquids thereof, Catalysis Communications, 2008,9:1924-1927).
Summary of the invention:
The objective of the invention is to overcome that the environmental pollution that exists in the prior art is serious, severe reaction conditions, product separation difficulty, catalyzer usage quantity and recycle in the equal shortcoming such as very big of number of dropouts, provide a kind of many sulfonate ions liquid catalyst to prepare the method for phenyl styryl ketone and derivative.
The structural formula of many sulfonate ions liquid used in the present invention is:
N is 3 or 4 in the formula.When n=3, acidic ion liquid is designated as IL-SO
3H-a; When n=4, acidic ion liquid is designated as IL-SO
3H-b.
The method of a kind of many sulfonate ions liquid catalyst catalytic preparation phenyl styryl ketone provided by the present invention and derivative, its Claisen-Schmidt condensation reaction formula is:
Wherein the mol ratio of raw ketone (I) and aldehyde (II) is 1:1 in the reaction, the molar weight of many sulfonate ions liquid catalyst is the 8-10% of used ketone or aldehyde, temperature of reaction is 120-140 ℃, reaction times is 8-20h, reaction pressure is 1 normal atmosphere, reaction back standing demix obtains product phenyl styryl ketone and derivative behind the upper strata product recrystallization of telling.The lower floor that tells contains many sulfonate ions liquid catalyst and can recycle behind 110 ℃ of vacuum drying treatment 2h.
The used ketone (I) of the present invention is any in methyl phenyl ketone, 4-methoxyacetophenone, the acetone.
The used aldehyde (II) of the present invention is any in phenyl aldehyde, 4-methoxybenzaldehyde, 3-methoxybenzaldehyde, 2-methoxybenzaldehyde, 3-chlorobenzaldehyde, the 4-chlorobenzaldehyde.
Method of the present invention, wherein said Claisen-Schmidt condensation reaction is reflected under nitrogen or the argon shield to be carried out.
The preparation method of many sulfonate ions liquid that the present invention is used sees pertinent literature (Synthesis of a novel multi – SO
3H functionalized ionic liquid and its catalytic activities for biodiesel synthesis, Green Chemistry, 12 (2010), 201-204; A kind of preparation method of multi-sulfonic functional ion liquid, CN101348487A).
The synthetic method that the present invention and traditional protonic acid, Lewis acid and other acidic ion liquid are made catalyzer is compared has following characteristics:
1, the sour density height that contains many sulfonate radicals acidic ion liquid, the catalytic activity height;
2, the catalyzer usage quantity few and recycle in loss amount also less;
3, catalyzer is more convenient with separating of reaction product, can separate by modes such as decants.
Embodiment
Embodiment 1: under nitrogen protection with 10mmol phenyl aldehyde, 10mmol methyl phenyl ketone and 0.8mmol IL-SO
3H-a joins 50mL and has in the there-necked flask of stirrer and reflux condensing tube.Vigorous stirring is warming up to 120 ℃, and reaction 8h is cooled to room temperature, is divided into two-layerly after reaction soln leaves standstill, and tells upper solution by decant, and it is 94% that recrystallization purifying can get 1,3-phenylbenzene-2-propylene-1-ketone (phenyl styryl ketone) productive rate.Contain IL-SO
3Lower floor's solution of H-a can be recycled after through 110 ℃ of vacuum-drying 2h.
Embodiment 2: under nitrogen protection with 10mmol4-methoxybenzaldehyde, 10mmol methyl phenyl ketone and 1mmol IL-SO
3H-a joins 50mL and has in the there-necked flask of stirrer and reflux condensing tube.Vigorous stirring is warming up to 140 ℃, and reaction 9h is cooled to room temperature, is divided into two-layerly after reaction soln leaves standstill, and tells upper solution by decant, and it is 90% that recrystallization purifying can get 4-methoxyl group phenyl styryl ketone productive rate.Contain IL-SO
3Lower floor's solution of H-a can be recycled after through 110 ℃ of vacuum-drying 2h.
Embodiment 3: under argon shield with 10mmol3-chlorobenzaldehyde, 10mmol methyl phenyl ketone and 1mmol IL-SO
3H-b joins 50mL and has in the there-necked flask of stirrer and reflux condensing tube.Vigorous stirring is warming up to 140 ℃, and reaction 8h is cooled to room temperature, is divided into two-layerly after reaction soln leaves standstill, and tells upper solution by decant, and it is 87% that recrystallization purifying can get 3-chlorine phenyl styryl ketone productive rate.Contain IL-SO
3Lower floor's solution of H-b can be recycled after through 110 ℃ of vacuum-drying 2h.
Embodiment 4: be probe reaction with embodiment 1, make the active replica test of catalysts, catalyzer is reused 4 times.The productive rate data of reaction see Table 1.
Table 1IL-SO
3The reaction of the synthetic phenyl styryl ketone of H-a catalysis phenyl aldehyde and methyl phenyl ketone
| IL-SO 3The H-a access times | Phenyl styryl ketone productive rate (%) |
| 1 | 94 |
| 2 | 92 |
| 3 | 93 |
| 4 | 90 |
Claims (4)
1. sulfonate ion liquid catalyst more than a kind prepares the method for phenyl styryl ketone and derivative, it is characterized in that this method is specific as follows:
Prepare that the mol ratio of raw material aldehyde and ketone is 1:1 in the Claisen-Schmidt condensation reaction of described phenyl styryl ketone and derivative, the molar weight of many sulfonate ions liquid catalyst is the 8-10% of used ketone or aldehyde, temperature of reaction is 120-140 ℃, reaction times is 8-20h, reaction pressure is 1 normal atmosphere, reaction back standing demix obtains product phenyl styryl ketone and derivative behind the upper strata product recrystallization of telling; The described structural formula that contains many sulfonate ions liquid is:
N is 3 or 4 in the formula.
2. a kind of many sulfonate ions liquid catalyst according to claim 1 prepares the method for phenyl styryl ketone and derivative, it is characterized in that described ketone is any in methyl phenyl ketone, 4-methoxyacetophenone, the acetone.
3. a kind of many sulfonate ions liquid catalyst according to claim 1 prepares the method for phenyl styryl ketone and derivative, it is characterized in that described aldehyde is any in phenyl aldehyde, 4-methoxybenzaldehyde, 3-methoxybenzaldehyde, 2-methoxybenzaldehyde, 3-chlorobenzaldehyde, the 4-chlorobenzaldehyde.
4. a kind of many sulfonate ions liquid catalyst according to claim 1 prepares the method for phenyl styryl ketone and derivative, it is characterized in that described Claisen-Schmidt condensation reaction carries out under nitrogen or argon shield.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310086922.4A CN103193607B (en) | 2013-03-18 | 2013-03-18 | Method for preparing chalcone and directive through multi-sulfonate ion liquid catalysis |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310086922.4A CN103193607B (en) | 2013-03-18 | 2013-03-18 | Method for preparing chalcone and directive through multi-sulfonate ion liquid catalysis |
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| CN103193607B CN103193607B (en) | 2015-03-04 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566234A (en) * | 2015-12-24 | 2016-05-11 | 南阳市天华制药有限公司 | Quinocetone preparation method |
| CN107162970A (en) * | 2017-06-30 | 2017-09-15 | 马鞍山市泰博化工科技有限公司 | A kind of ionic liquid-catalyzed synthesis dihydro 4 of 2 aryl 2,3 of highly acidity（1H）The method of qualone derivative |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101289378A (en) * | 2007-04-18 | 2008-10-22 | 中国科学院大连化学物理研究所 | A method for synthesizing chalcones and derivatives thereof using ionic liquids |
| CN101348487A (en) * | 2008-09-04 | 2009-01-21 | 华东师范大学 | A kind of preparation method of polysulfonic acid functionalized ionic liquid |
| CN101927182A (en) * | 2010-07-05 | 2010-12-29 | 北京林业大学 | A kind of biodiesel catalyst and the method for using the catalyst to prepare biodiesel |
| CN102584569A (en) * | 2011-12-15 | 2012-07-18 | 北京林业大学 | Method for preparing diphenolic acid in ionic liquid |
-
2013
- 2013-03-18 CN CN201310086922.4A patent/CN103193607B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101289378A (en) * | 2007-04-18 | 2008-10-22 | 中国科学院大连化学物理研究所 | A method for synthesizing chalcones and derivatives thereof using ionic liquids |
| CN101348487A (en) * | 2008-09-04 | 2009-01-21 | 华东师范大学 | A kind of preparation method of polysulfonic acid functionalized ionic liquid |
| CN101927182A (en) * | 2010-07-05 | 2010-12-29 | 北京林业大学 | A kind of biodiesel catalyst and the method for using the catalyst to prepare biodiesel |
| CN102584569A (en) * | 2011-12-15 | 2012-07-18 | 北京林业大学 | Method for preparing diphenolic acid in ionic liquid |
Non-Patent Citations (1)
| Title |
|---|
| XUEZHENG LIANG等: "Synthesis of a novel multi –SO3H functionalized ionic liquid and its catalytic activities for biodiesel synthesis", 《GREEN CHEM.》, vol. 12, 27 November 2009 (2009-11-27) * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566234A (en) * | 2015-12-24 | 2016-05-11 | 南阳市天华制药有限公司 | Quinocetone preparation method |
| CN107162970A (en) * | 2017-06-30 | 2017-09-15 | 马鞍山市泰博化工科技有限公司 | A kind of ionic liquid-catalyzed synthesis dihydro 4 of 2 aryl 2,3 of highly acidity（1H）The method of qualone derivative |
| CN107162970B (en) * | 2017-06-30 | 2019-12-20 | 马鞍山市泰博化工科技有限公司 | Method for synthesizing 2-aryl-2, 3-dihydro-4 (1H) -quinolinone derivative under catalysis of high-acidity ionic liquid |
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