[go: up one dir, main page]

CN110156681B - Synthesis method of 2-ester group quinoline - Google Patents

Synthesis method of 2-ester group quinoline Download PDF

Info

Publication number
CN110156681B
CN110156681B CN201910464156.8A CN201910464156A CN110156681B CN 110156681 B CN110156681 B CN 110156681B CN 201910464156 A CN201910464156 A CN 201910464156A CN 110156681 B CN110156681 B CN 110156681B
Authority
CN
China
Prior art keywords
reaction
aniline
substituted
phenylacetylene
acetoacetate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201910464156.8A
Other languages
Chinese (zh)
Other versions
CN110156681A (en
Inventor
张泽
徐自奥
余飞
徐绘
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xuancheng Institute Of Industrial Technology Anhui University Of Engineering Co ltd
Original Assignee
Xuancheng Institute Of Industrial Technology Anhui University Of Engineering Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Xuancheng Institute Of Industrial Technology Anhui University Of Engineering Co ltd filed Critical Xuancheng Institute Of Industrial Technology Anhui University Of Engineering Co ltd
Priority to CN201910464156.8A priority Critical patent/CN110156681B/en
Publication of CN110156681A publication Critical patent/CN110156681A/en
Application granted granted Critical
Publication of CN110156681B publication Critical patent/CN110156681B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides a method for synthesizing 2-ester group quinoline, which comprises mixing aniline or substituted aniline, phenylacetylene or substituted phenylacetylene and montmorillonite KSF, using chlorobenzene as solvent, heating for reaction; then adding acetoacetate and manganese acetate dihydrate catalyst, and heating for reaction; and after the reaction is finished, filtering, extracting, drying, filtering and concentrating the filtrate, and separating by silica gel column chromatography to obtain the 2-ester quinoline. Compared with the prior art, the raw materials of the invention are conventional, cheap and easily available; the two-step reaction is carried out in one pot, and the separation of intermediate products is not needed, so that the efficiency is high; the catalyst montmorillonite and manganese acetate dihydrate are cheap, safe and nontoxic reagents; the method has the advantages of mild reaction conditions, high selectivity, few side reactions, simple operations such as separation and purification and the like, and does not relate to special operations such as anhydrous, oxygen-free, high temperature and high pressure. The product is simple to separate and purify and has high yield. From the perspective of reaction mechanism, the method is a novel reaction path for synthesizing 2-ester group quinoline.

Description

Synthesis method of 2-ester group quinoline
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method of 2-ester quinoline.
Background
2-ester quinolines have attracted considerable attention for their potential anticancer, anti-aids, anti-inflammatory, antibacterial and anti-tubercular activities as well as for their use as biocompatible fluorescent markers. At present, the synthesis method of 2-ester group quinoline mainly comprises the following reactions: (1) coupling reaction of arylamine, glyoxylate and phenylacetylene; (2) The cross dehydrogenation coupling reaction of N-aryl glycine derivative or imine ethyl glyoxylate and olefin, tetrahydrofuran or alkyne; (3) The addition-cyclization-aromatization tandem reaction of beta-amino ester and styrene; (4) The o-aminoalkyne and the alkyne ester undergo a palladium-catalyzed photochemical reaction; (5) Cyclization reaction of N-arylamine butenoate and styrene under the catalysis of indium trichloride and tert-butyl nitrite.
However, these synthetic methods have the following limitations in different degrees: the raw material source is limited or the price is high, the catalyst is expensive or has high toxicity, the reaction condition is harsh, the product separation and purification are complicated, the yield is low, and the like.
Disclosure of Invention
The invention aims to provide a method for synthesizing 2-ester quinoline, which adopts a two-step one-pot method to synthesize the 2-ester quinoline and has the advantages of cheap and easily-obtained raw materials, cheap, safe and non-toxic catalyst, simple operation, high efficiency and the like.
The technical scheme adopted by the invention is as follows:
a synthetic method of 2-ester group quinoline comprises the following steps:
(a) Mixing aniline or substituted aniline, phenylacetylene or substituted phenylacetylene and montmorillonite KSF, taking chlorobenzene as a solvent, and heating for reaction;
(b) Cooling the reaction system in the step (a), adding a catalyst of acetoacetic ester and manganese (III) acetate dihydrate, and heating for reaction;
(c) And after the reaction is finished, filtering, extracting, drying, filtering and concentrating the filtrate, and separating by silica gel column chromatography to obtain the 2-ester quinoline.
The substituted aniline in the step (a) is p-methylaniline and p-bromoaniline; the substituted phenylacetylene is p-methyl phenylacetylene;
in the step (a), the heating reaction temperature is 120 ℃ and the reaction lasts for 3-5 h.
The ratio of the amount of the aniline or substituted aniline, phenylacetylene or substituted phenylacetylene, acetoacetate, manganese (III) acetate dihydrate is 1:1.1 to 1.3:1:2.
the mass ratio of the aniline or the substituted aniline to the montmorillonite KSF in the step (a) is 0.4-1: 0.54.
in the step (a), the concentration of the aniline or substituted aniline in chlorobenzene is 0.2-0.3 mol/L.
The acetoacetate in step (b) is: methyl acetoacetate, ethyl acetoacetate, or isopropyl acetoacetate.
In the step (b), the reaction system in the step (a) is cooled to 90 ℃, and the catalyst of the acetoacetic ester and the manganese acetate dihydrate is added to react for 5 hours at the temperature.
Extracting in the step (c) by using an extracting agent with a volume ratio of 1:1, a mixture of ethyl acetate and water;
the drying in step (c) means drying using anhydrous magnesium sulfate.
The synthesis mechanism of the 2-ester group quinoline provided by the invention is shown in figure 17 (taking example 3 as an example),the reaction process is described as follows: firstly, aniline or substituted aniline reacts with phenylacetylene or substituted phenylacetylene under the action of montmorillonite (KSF) to generate o-amino stilbene A; in the meantime, ethyl acetoacetate in Mn (OAc) 3 Oxidizing to form a radical intermediate B, free radical addition of A by B to form a radical intermediate C, intramolecular hydrogen transfer of C to a radical intermediate D, and subsequent addition of another equivalent of Mn (OAc) 3 Promoting to obtain Mn (III) -enolate E, cyclizing by free radicals to form an intermediate F (simultaneously, trivalent manganese is converted into divalent manganese), oxidizing, eliminating and dehydrating the intermediate F to obtain an intermediate G, and oxidizing and deacidifying to form a final target product 3.
Compared with the prior art, the invention has the advantages that: the adopted raw materials are all conventional, cheap and easily available raw materials; the two-step reaction is carried out in one pot, the intermediate product does not need to be separated, and the efficiency is high; the adopted catalysts montmorillonite and manganese acetate dihydrate are cheap, safe and nontoxic reagents; the method has the advantages of mild reaction conditions, high selectivity, few side reactions, simple operations such as separation and purification and the like, and does not relate to special operations such as anhydrous, oxygen-free, high temperature and high pressure. The product is simple to separate and purify and has high yield. From the perspective of reaction mechanism, the method is also a novel reaction path for synthesizing 2-ester group quinoline.
Drawings
FIG. 1 shows the NMR spectrum of the product of example 1 1 H-NMR chart;
FIG. 2 shows the NMR spectrum of the product of example 1 13 C-NMR chart;
FIG. 3 is the NMR hydrogen spectrum of the product of example 2 1 H-NMR chart;
FIG. 4 is the NMR hydrogen spectrum of the product of example 2 13 C-NMR chart;
FIG. 5 is the NMR spectrum of the product of example 3 1 H-NMR chart;
FIG. 6 is the NMR hydrogen spectra of the product of example 3 13 C-NMR chart;
FIG. 7 is the NMR carbon spectrum of the product of example 4 1 H-NMR chart;
FIG. 8 is the NMR carbon spectrum of the product of example 4 13 C-NMR chart；
FIG. 9 is the NMR carbon spectrum of the product of example 5 1 H-NMR chart;
FIG. 10 is the NMR carbon spectrum of the product of example 5 13 C-NMR chart;
FIG. 11 is the NMR carbon spectrum of the product of example 6 1 H-NMR chart;
FIG. 12 is the NMR carbon spectrum of the product of example 6 13 C-NMR chart;
FIG. 13 is a NMR carbon spectrum of the product of example 7 1 H-NMR chart;
FIG. 14 is the NMR carbon spectrum of the product of example 7 13 C-NMR chart;
FIG. 15 is the NMR carbon spectrum of the product of example 8 1 H-NMR chart;
FIG. 16 is the NMR carbon spectrum of the product of example 8 13 C-NMR chart;
FIG. 17 is a diagram of the mechanism of synthesis of the product of example 3.
Detailed Description
Example 1
A synthetic method of 2-ester group quinoline comprises the following steps:
(a) Taking 0.535 g of p-toluidine, 0.696 g of p-toluylene acetylene and 0.54 g of KSF (montmorillonite), putting the materials into a reaction bottle, adding 20ml of chlorobenzene, heating and stirring the materials at 120 ℃ to react for 3 hours;
(b) The temperature of the system of step (a) was lowered to 90 ℃ and 0.580 g of methyl acetoacetate and 2.68 g of Mn dihydrate (OAc) were added to the reaction flask 3 Continuing the reaction for 5 hours at 90 ℃, and cooling to room temperature;
(c) The reaction mixture obtained in step (b) was filtered, the filtrate was extracted with a mixture of ethyl acetate and water in a volume ratio of 1, the ethyl acetate phases were combined and collected and dried over anhydrous magnesium sulfate and filtered, and the filtrate was evaporated to dryness and separated by silica gel column chromatography (eluent: V petroleum ether/V ethyl acetate = 3.
Examples 2 to 8
Aniline or different substituted anilines, phenylacetylene or different substituted phenylacetylenes, methyl/ethyl/isopropyl acetoacetate are used to prepare 2-ester group quinoline, which is specifically shown in the following table 1, and the amounts of the solvent and the catalyst and the experimental operation are the same as those in example 1.
Table 1 examples 1-8 starting materials and products
Figure BDA0002078944170000031
Figure BDA0002078944170000041
The product properties, melting points and NMR spectra of examples 1-8 were as follows:
example 1 product: 6-methyl-4-p-tolyl-2-quinolinecarboxylic acid methyl ester:
white solid, mp 77-79 ℃;
1 H NMR(500MHz,DMSO-d 6 )δ(ppm)8.15(d,J＝8.5Hz,1H,ArH),7.93(s,1H,ArH),7.75(d,J＝8.5Hz,1H,ArH),7.72(s,1H,ArH),7.49(d,J＝8.0Hz,2H,ArH),7.43(d,J＝8.0Hz,2H,ArH),3.96(s,3H,OCH 3 ),2.49(s,3H,CH 3 ),2.45(s,3H,CH 3 )；
13 C NMR(125MHz,DMSO-d 6 )δ(ppm)165.9,148.7,146.8,146.7,139.6,138.9,134.5,133.2,130.7,129.9(2C),129.8(2C),127.5,124.5,121.2,53.1,22.1,21.4。
example 2 product: 6-methyl-4-phenyl-2-quinolinecarboxylic acid methyl ester:
white solid, mp 83-85 ℃;
1 H NMR(500MHz,DMSO-d 6 )δ(ppm)8.16(d,J＝9.0Hz,1H,ArH),7.95(s,1H,ArH),7.76(d,J＝8.5Hz,1H,ArH),7.70(s,1H,ArH),7.65–7.57(m,5H,ArH),3.97(s,3H,OCH 3 ),2.49(s,3H,CH 3 )；
13 C NMR(125MHz,DMSO-d 6 )δ(ppm)165.8,148.7,146.8,146.6,139.7,137.4,133.3,130.7,129.8(2C),129.4(2C),129.3,127.4,124.4,121.3,53.1,22.1。
example 3 product: 6-methyl-4-phenyl-2-quinolinecarboxylic acid ethyl ester:
white solid, mp 106-108 deg.C;
1 H NMR(400MHz,CDCl 3 )δ(ppm)8.30(d,J＝8.4Hz,1H,ArH),8.12(s,1H,ArH),7.73(s,1H,ArH),7.65(dd,J＝8.6,1.8Hz,1H,ArH),7.62–7.52(m,5H,ArH),4.59(q,J＝7.2Hz,2H,CH 2 ),2.52(s,3H,CH 3 ),1.51(t,J＝7.2Hz,3H,CH 3 )；
13 C NMR(100MHz,CDCl 3 )δ(ppm)165.6,149.0,146.9,146.8,139.0,137.8,132.3,130.9,129.6(2C),128.7(2C),128.6,127.8,124.4,121.4,62.2,22.1,14.4。
example 4 product: 4-phenyl-2-quinolinecarboxylic acid ethyl ester:
white solid, mp 117-119 ℃;
1 H NMR(400MHz,DMSO-d 6 )δ(ppm)8.27(d,J＝8.4Hz,1H,ArH),7.98(s,1H,ArH),7.96–7.88(m,2H,ArH),7.74(t,J＝8.2Hz,1H,ArH),7.64–7.58(m,5H,ArH),4.45(q,J＝7.2Hz,2H,CH 2 ),1.39(t,J＝7.1Hz,3H,CH 3 )；
13 C NMR(100MHz,DMSO-d 6 )δ(ppm)167.7,164.7,149.0,147.5,136.8,130.5,130.4,129.4(2C),129.1,128.9,128.8(2C),126.8,125.4,120.6,61.6,14.1。
example 5 product: 6-methyl-4-p-tolyl-2-quinolinecarboxylic acid ethyl ester:
white solid, mp 96-98 ℃;
1 H NMR(400MHz,DMSO-d 6 )δ(ppm)8.14(d,J＝8.4Hz,1H,ArH),7.91(s,1H,ArH),7.73(d,J＝8.8Hz,1H,ArH),7.70(s,1H,ArH),7.47(d,J＝8.0Hz,2H,ArH),7.41(d,J＝8.0Hz,2H,ArH),4.43(q,J＝7.2Hz,2H,CH 2 ),2.48(s,3H,CH 3 ),2.43(s,3H,CH 3 ),1.38(t,J＝7.0Hz,3H,CH 3 )；
13 C NMR(100MHz,DMSO-d 6 )δ(ppm)164.8,148.2,146.6,146.1,139.0,138.3,134.1,132.6,130.2,129.4(2C),129.2(2C),126.9,124.0,120.7,61.4,21.5,20.8,14.2。
example 6 product: 6-bromo-4-phenyl-2-quinolinecarboxylic acid ethyl ester:
pale yellow solid, mp 134-136 ℃;
1 H NMR(500MHz,DMSO-d 6 )δ(ppm)8.22(d,J＝9.0Hz,1H,ArH),8.05(dd,J＝9.0,2.0Hz,1H,ArH),8.02(s,1H,ArH),8.01(d,J＝2.0Hz,1H,ArH),7.67–7.59(m,5H,ArH),4.45(q,J＝7.0Hz,2H,CH 2 ),1.39(t,J＝7.0Hz,3H,CH 3 )；
13 C NMR(125MHz,DMSO-d 6 )δ(ppm)165.0,148.8,148.5,146.6,136.6,134.2,133.2,129.9(2C),129.7,129.5(2C),128.6,127.8,123.2,122.0,62.2,14.6。
example 7 product: 4-phenyl-2-quinolinecarboxylic acid isopropyl ester:
white solid, mp 103-105 ℃;
1 H NMR(500MHz,DMSO-d 6 )δ(ppm)8.28(d,J＝8.0Hz,1H,ArH),7.98(s,1H,ArH),7.95–7.89(m,2H,ArH),7.75(t,J＝7.8Hz,1H,ArH),7.65–7.59(m,5H,ArH),5.31–5.23(m,1H,CH),1.40(d,J＝6.0Hz,6H,CH 3 )；
13 C NMR(125MHz,DMSO-d 6 )δ(ppm)164.7,149.5,148.3,148.0,137.3,131.01,130.95,129.9(2C),129.6,129.4,129.3(2C),127.3,125.9,121.1,69.8,22.1(2C)。
example 8 product: 6-bromo-4-phenyl-2-quinolinecarboxylic acid isopropyl ester:
pale yellow solid, mp 122-124 ℃;
1 H NMR(500MHz,DMSO-d 6 )δ(ppm)8.23(d,J＝9.0Hz,1H,ArH),8.04(dd,J＝9.0,2.0Hz,1H,ArH),8.01(s,1H,ArH),8.00(d,J＝2.5Hz,1H,ArH),7.66–7.60(m,5H,ArH),5.31–5.23(m,1H,CH),1.40(d,J＝6.0Hz,6H,CH 3 )；
13 C NMR(125MHz,DMSO-d 6 )δ(ppm)164.4,148.8,148.8,146.6,136.7,134.2,133.2,129.8(2C),129.7,129.5(2C),128.6,127.8,123.1,122.0,70.0,22.1(2C)。

Claims (9)

1. the method for synthesizing the 2-ester group quinoline is characterized by comprising the following steps of:
(a) Mixing aniline or substituted aniline, phenylacetylene or substituted phenylacetylene and montmorillonite KSF, taking chlorobenzene as a solvent, and heating for reaction;
(b) Cooling the reaction system in the step (a), adding an acetoacetate and a manganese (III) acetate dihydrate catalyst, and reacting;
(c) And after the reaction is finished, filtering, extracting, drying, filtering and concentrating the filtrate, and separating by silica gel column chromatography to obtain the 2-ester quinoline.
2. The method of claim 1, wherein the substituted aniline of step (a) is para-methylaniline or para-bromoaniline.
3. The method of synthesis according to claim 1 or 2, wherein the substituted phenylacetylene in step (a) is: p-methylphenylacetylene.
4. The synthesis method according to claim 1, wherein in the step (a), the heating reaction temperature is 120 ℃ for reaction for 3 to 5 hours.
5. The synthesis method according to claim 1, characterized in that the substances of aniline or substituted aniline, phenylacetylene or substituted phenylacetylene, acetoacetate, manganese (III) acetate dihydrate are present in a ratio of 1:1.1 to 1.3:1:2.
6. the synthesis method according to claim 1, wherein the mass ratio of the aniline or substituted aniline to the montmorillonite KSF in the step (a) is 0.4 to 1:0.54.
7. the synthesis method according to claim 1, wherein the concentration of the aniline or substituted aniline in chlorobenzene in step (a) is 0.2 to 0.3mol/L.
8. The method of claim 1, wherein the acetoacetate in step (b) is: methyl acetoacetate, ethyl acetoacetate, or isopropyl acetoacetate.
9. The synthesis method of claim 1, wherein in the step (b), the temperature of the reaction system in the step (a) is reduced to 90 ℃, and the catalyst of the acetoacetic ester and the manganese (III) acetate dihydrate is added to react for 5 hours at the temperature.
CN201910464156.8A 2019-05-30 2019-05-30 Synthesis method of 2-ester group quinoline Active CN110156681B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910464156.8A CN110156681B (en) 2019-05-30 2019-05-30 Synthesis method of 2-ester group quinoline

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910464156.8A CN110156681B (en) 2019-05-30 2019-05-30 Synthesis method of 2-ester group quinoline

Publications (2)

Publication Number Publication Date
CN110156681A CN110156681A (en) 2019-08-23
CN110156681B true CN110156681B (en) 2022-11-11

Family

ID=67630511

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910464156.8A Active CN110156681B (en) 2019-05-30 2019-05-30 Synthesis method of 2-ester group quinoline

Country Status (1)

Country Link
CN (1) CN110156681B (en)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3533567B2 (en) * 2000-12-07 2004-05-31 独立行政法人 科学技術振興機構 A new synthetic method to produce substituted quinolines from substituted anilines
CN106336378B (en) * 2016-08-08 2021-06-11 江西师范大学 Preparation method of quinoline-2-formic ether series
CN106366035B (en) * 2016-08-30 2021-05-07 南阳师范学院 Synthesis method of quinoline derivative
CN107739333B (en) * 2017-11-14 2019-09-27 大连理工大学 A kind of preparation method of green quinoline compound
CN109053566A (en) * 2018-09-13 2018-12-21 江苏师范大学 A kind of synthetic method of 2- methylquinoline

Also Published As

Publication number Publication date
CN110156681A (en) 2019-08-23

Similar Documents

Publication Publication Date Title
Guo et al. One-pot three-component synthesis of functionalized spirooxindoles in gluconic acid aqueous solution
US10442816B2 (en) Synthesis of substituted salicylaldehyde derivatives
CN107805232B (en) Synthetic method of derivative containing methylthio furan
KR20170016754A (en) New method for preparation of chromanone derivatives
CN107629028A (en) A kind of method based on intermolecular ring-closure reaction synthesis furan derivatives
WO2016146048A1 (en) Industrial manufacturing method for midazolam derivative
CN110156681B (en) Synthesis method of 2-ester group quinoline
CN113264843A (en) Synthetic method of 3-aminobicyclo [1.1.1] pentane-1-carboxylic ester derivative
CN110092751B (en) Synthesis method of 2-alkyl quinoline
JP7545696B2 (en) Pyrrolinone compounds and synthesis methods thereof
CN107954960B (en) A kind of synthetic method of 1,3-dihydroisobenzofuran compounds
CN111004141B (en) New method for synthesizing nintedanib intermediate 2-chloro-N-methyl-N- (4-nitrophenyl) acetamide
CN104072495B (en) The preparation method of natural product alkaloid A aptamine
CN110028394B (en) Synthetic method of indanone and derivatives thereof
KR101894091B1 (en) New method for preparation of chromanone derivatives
Rouhi et al. Nano-cellulose-SBCL5 as a new heterogeneous nano catalyst for the one-pot synthesis of spirooxindoles under mild conditions
CN113651788A (en) A kind of 3-aminoalkyl chromone compound and preparation method thereof
CN117229206B (en) A method for preparing polysubstituted 2-quinolinone compounds by base catalysis
CN105111175B (en) Synthetic method of 3-hydroxy-6-nitroflavone prepared through adopting one-step method
CN108586331B (en) A kind of intermediate for synthesizing nitrogen-containing heterocyclic compound and preparation method thereof
CN100389110C (en) A kind of method for preparing aromatic ring substituted isoxazoline compounds
CN109970703A (en) Preparation method and application of 1,3-heterocyclic substituted aromatic ketones
CN116332839B (en) Preparation method of montelukast sodium drug intermediate
KR102292794B1 (en) Preparation method of 2-substituted 1,2,3,4-tetrahydroquinoline compound
CN112778198A (en) Synthesis method of dihydroquinolinone compound

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant