CN104725305A - Pyridine-2-(1H) ketone compound and preparation method thereof - Google Patents

Pyridine-2-(1H) ketone compound and preparation method thereof Download PDF

Info

Publication number
CN104725305A
CN104725305A CN201510136768.6A CN201510136768A CN104725305A CN 104725305 A CN104725305 A CN 104725305A CN 201510136768 A CN201510136768 A CN 201510136768A CN 104725305 A CN104725305 A CN 104725305A
Authority
CN
China
Prior art keywords
pyridine
ketone compounds
preparation
organic solvent
enamino
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.)
Pending
Application number
CN201510136768.6A
Other languages
Chinese (zh)
Inventor
高宝昌
崔宝玉
田媛
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.)
Heilongjiang Academy of Sciences Daqing Branch
Original Assignee
Heilongjiang Academy of Sciences Daqing Branch
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 Heilongjiang Academy of Sciences Daqing Branch filed Critical Heilongjiang Academy of Sciences Daqing Branch
Priority to CN201510136768.6A priority Critical patent/CN104725305A/en
Publication of CN104725305A publication Critical patent/CN104725305A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention discloses a kind of pyridine -2- (1H) ketone compounds and preparation method thereof, belong to technical field of organic synthetic chemistry. The structure of pyridine -2- (1H) ketone compounds is in the present invention Wherein R is Ph, 4-ClC6H4,4-MeOC6H4,4-Cl-2, and 5- (MeO) 2C6H2,2,4-Me2C6H3,4-MeC6H4,5-Cl-2-MeOC6H3, Ph represent phenyl, and Me represents methyl. The present invention is using ketones with Enamino-esters as raw material, it is reacted under the action of the catalyst such as piperidines with malononitrile, reaction temperature is 25 DEG C, reaction time is 6~9 hours, obtain a kind of pyridine -2- (1H) ketone compound, not only reaction route is brief for this method, but also experiment condition is mild, separation and purification of products is easy, and product yield can achieve 90% or more.

Description

A kind of pyridine-2-(1H) ketone compounds and preparation method thereof
Technical field
The invention belongs to technical field of organic synthetic chemistry, be specifically related to synthesize class polysubstituted pyridine-2-(1H) ketone compound and preparation method thereof by ketones with Enamino-esters.
Background technology
Pyridone and derivative thereof are the important nitrogen-containing heterocycle compounds of a class, be distributed in widely among natural product, there is important biology, pharmacologically active, simultaneously as the multi-functional organic synthesis intermediate of a class, pyridinone compounds tool in the synthesis of organic synthesis especially at heterogeneous ring compound has been widely used.
Pyridine compounds, according to ketone carbonyl quantity and N element position, can be divided into 2-pyridone, 4-pyridone, 2,4-bis-pyridine compounds.Their majorities all have the effects such as antibacterial and antitumor, and wherein 2-pyridine compounds is subject to the favor of researcher with its significant biological activity.Modern pharmacology research finds, the micromolecular compound with 2-pyridone structure has more biological activity, as the aspect effects such as antibacterial, antiviral, antitumor, antithrombotic are obvious, and the abundant 2-pyridine compounds of functional group shows more biological activity.
The synthetic method of current 2-pyridine compounds mainly contains two classes: a class adopts pyridinium salt chemical method or the synthesis of pyridine N-alkylated reaction; Another kind of is synthesized through cyclization by chain compound, comprises Dieckmann condensation reaction, aza-Diels-Alder reaction etc. in Guareschi-Thorpe reaction, molecule.But above-mentioned synthetic method exists certain shortcoming, the problems such as longer in needs metal catalyst, reaction times, powerful catalyst catalysis, purifying products difficulty, productive rate are lower, limit the application of 2-pyridine compounds.Due to the extensive use of 2-pyridine compounds, therefore development builds the novel method of 2-pyridone skeleton is Synthetic Organic Chemistry priority fields of study always.
Summary of the invention
The present invention seeks to pyridine-2-(1H) ketone compound that structure one class functional group is abundant, and prepared the synthetic method of pyridine-2-(1H) ketone compound by ketones with Enamino-esters simply, efficiently.
In the present invention, the structure of pyridine-2-(1H) ketone compounds is wherein R is Ph, 4-ClC 6h 4, 4-MeOC 6h 4, 4-Cl-2,5-(MeO) 2c 6h 2, 2,4-Me 2c 6h 3, 4-MeC 6h 4, 5-Cl-2-MeOC 6h 3, Ph represents phenyl, and Me represents methyl.
In the present invention, the preparation method of pyridine-2-(1H) ketone compounds carries out in the steps below:
By raw material ketones with Enamino-esters and propane dinitrile mixing, then organic solvent is added, be stirred to abundant dissolving, add catalyzer piperidines, react to ketones with Enamino-esters completely dissolve at 25 ~ 40 DEG C, be poured in saturated aqueous common salt, the solid of precipitation carries out suction filtration successively, washs, dries process, be separated with silica gel column chromatography, obtain pyridine-2-(1H) ketone compounds;
Wherein said organic solvent is DMF (DMF), dehydrated alcohol, tetrahydrofuran (THF), dimethylbenzene, methylene dichloride or dimethyl sulfoxide (DMSO) (DMSO);
Described catalyzer is salt of wormwood, sodium hydroxide, triethylamine, piperidines, sodium ethylate or sodium methylate.
The mol ratio of described ketones with Enamino-esters and propane dinitrile is 1:1.1 to 1:1.3.
The mol ratio of described ketones with Enamino-esters and catalyzer is 20:1 to 10:1.
Raw material of the present invention is easy to get, low price: acetoacetyl aromatic amine compounds is important chemical raw material, and synthesis is simple, low price, stores and transports all very convenient.
Ketones with Enamino-esters compound of the present invention be easy to preparation: prepared a series of ketones with Enamino-esters compound, reaction temperature and, reaction be easy to control, be separated and store all be easy to.
Good reaction selectivity of the present invention, and regioselectivity is good, product yield is up to more than 90%.
Atom economy of the present invention is high: from the synthesis precursor that a class is simple and easy to get, atom economy construct a class 2-pyridinone compounds.
Accompanying drawing explanation
Fig. 1 is production code member is 3a 1h NMR spectrogram; Fig. 2 is production code member is 3a 13c NMR spectrogram; Fig. 3 is production code member is 3b 1h NMR spectrogram; Fig. 4 is production code member is 3b 13c NMR spectrogram; Fig. 5 is production code member is 3c 1h NMR spectrogram; Fig. 6 is production code member is 3c 13c NMR spectrogram; Fig. 7 is production code member is 3d 1h NMR spectrogram; Fig. 8 is production code member is 3d 13c NMR spectrogram; Fig. 9 is production code member is 3e 1h NMR spectrogram; Figure 10 is production code member is 3e 13c NMR spectrogram; Figure 11 is production code member is 3f 1h NMR spectrogram; Figure 12 is production code member is 3f 13c NMR spectrogram; Figure 13 is production code member is 3g 1h NMR spectrogram; Figure 14 is production code member is 3g 13c NMR spectrogram.
Embodiment
Embodiment one: the structural formula of pyridine-2-(1H) ketone compounds in present embodiment:
In formula, R is Ph, 4-ClC 6h 4, 4-MeOC 6h 4, 4-Cl-2,5-(MeO) 2c 6h 2, 2,4-Me 2c 6h 3, 4-MeC 6h 4, 5-Cl-2-MeOC 6h 3,
Reaction equation:
In formula, R is Ph, 4-ClC 6h 4, 4-MeOC 6h 4, 4-Cl-2,5-(MeO) 2c 6h 2, 2,4-Me 2c 6h 3, 4-MeC 6h 4, 5-Cl-2-MeOC 6h 3.
Concrete preparation method is as follows: take ketones with Enamino-esters (1.0mmol), propane dinitrile (1.1mmol), be placed in 25ml round-bottomed flask, measure after dehydrated alcohol (15ml) joins in round-bottomed flask and stir and fully dissolve, add piperidines (0.05mmol), react at 25 DEG C, TLC monitors, be poured in saturated aqueous common salt Deng after ketones with Enamino-esters completely dissolve, separate out solid suction filtration, wash, dry, (developping agent: petrol ether/ethyl acetate: 5/1 is separated through silica gel column chromatography, v/v), obtain white solid 3, productive rate is 90%.Experimental result is in table 1
The preparation of table 1 pyridine-2-(1H) ketone compound
Structural characterization:
(3a)5-Acetyl-2-amino-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carbonitrile
White solid,mp 125-126℃；
Fig. 1: 1h NMR (300MHz, DMSO): δ=2.33 (s, 3H), 7.28 (t, 3H), 7.51 (m, 3H), 7.67 (s, 2H), 8.12 (s, 1H); Fig. 2: 13c NMR (100MHz, DMSO): δ=30.3,73.4,112.9,116.8,128.7,129.8,130.4,134.5,146.7,157.7,160.5,193.4;
IR(KBr,cm -1):ν＝3336,2210,1662,1283,1360,1310,688.
Anal.Calcd for C 14H 11N 3O 2:C,66.4；H,4.38；N,16.59；Found:C,66.3；H,4.36；N,16.61
(3b)5-Acetyl-2-amino-1-(4-chloro-phenyl)-6-oxo-1,6-dihydro-pyridine-3-carbonitrile
White solid,mp 120-122℃；
Fig. 3: 1h NMR (300MHz, DMSO): δ=2.56 (s, 3H), 5.39 (s, 2H), 7.24-7.26 (d, J=6Hz, 2H), 7.63-7.66 (d, J=9Hz, 2H), 8.39 (s, 1H);
Fig. 4 13c NMR (100MHz, DMSO): δ=30.3,73.6,112.7,116.8,130.5,130.8,133.6,134.6,147.0,157.8,160.5,193.4;
IR(KBr,cm -1):ν＝3414,3164,2216,1642,1405,834,812.
Anal.Calcd for C 14H 10ClN 3O 2:C,58.45；H,3.50；N,14.6；Found:C,58.47；H,3.48；N,14.59.
3C)5-Acetyl-2-amino-1-(4-methoxy-phenyl)-6-oxo-1,6-dihydro-pyridine-3-carbonitrile
White solid,mp 114-115℃；
Fig. 5: 1h NMR (300MHz, DMSO): δ=2.37 (s, 3H), 3.82 (s, 3H), 7.08-7.11 (d, J=9Hz, 2H), 7.20-7.23 (d, J=9Hz, 2H), 7.67 (s, 2H), 8.14 (s, 1H);
Fig. 6: 13c NMR (100MHz, DMSO): δ=30.3,55.5,73.5,112.7,115.6,116.9,127.0,129.9,146.6,158.1,160.0,160.8,193.5;
IR(KBr,cm -1):ν＝3414,3176,2210,1659,1408,840,815.
Anal.Calcd for C 15H 13N 3O 3:C,63.60；H,4.63；N,14.83；Found:C,63.62；H,4.61；N,14.85.
(3d)5-Acetyl-2-amino-1-(4-chloro-2,5-dimethoxy-phenyl)-6-oxo-1,6-dihydro-pyridine-3-carbonitrile
White solid,mp 130-131℃；
Fig. 7: 1h NMR (300MHz, DMSO): δ=2.37 (s, 3H), 3.72 (s, 3H), 3.78 (s, 3H), 7.21 (s, 1H), 7.36 (s, 1H), 7.92 (s, 2H), 8.16 (s, 1H);
Fig. 8: 13c NMR (100MHz, DMSO): δ=30.2,56.8,56.9,73.2,112.5,114.7,115.3,116.7,121.7,123.2,147.1,149.1,149.6,157.7,159.9,193.3;
Anal.Calcd for C 15H 14ClN 3O 4:C,55.26；H,4.06；N,12.08；Found:C,55.27；H,4.04；N,12.09.
(3e)5-Acetyl-2-amino-1-(2,4-dimethyl-phenyl)-6-oxo-1,6-dihydro-pyridine-3-carbonitrile
White solid,mp 130-131℃；
Fig. 9: 1h NMR (300MHz, DMSO): δ=2.09 (s, 3H), 2.41 (s, 3H), 2.57 (s, 3H), 5.40 (s, 2H), 7.04-7.07 (d, J=9Hz), 7.27 (t, 2H), 8.39 (s, 1H);
Figure 10: 13c NMR (100MHz, DMSO): δ=16.7,20.9,30.3,73.4,112.7,116.8,128.3,128.6,130.9,132.3,135.3,139.4,146.8,157.4,160.0,193.4;
Anal.Calcd for C 16H 15N 3O 2:C,68.3；H,5.37；N,14.94；Found:C,68.1；H,5.38；N,14.95.
(3f)5-Acetyl-2-amino-6-oxo-1-p-tolyl-1,6-dihydro-pyridine-3-carbonitrile
White solid,mp 119-121℃；
Figure 11: 1h NMR (300MHz,
DMSO):δ＝2.46(s,3H),2.56(s,3H),5.40(s,2H),7.15-7.17(d,J＝6Hz,2H),
7.44-7.47(d,J＝9Hz,2H),8.38(s,1H)；
Figure 12: 13c NMR (100MHz, DMSO):
δ＝20.8,30.2,73.3,112.7,116.7,128.3,130.7,131.8,139.0,146.5
157.8,160.4,193.0；
IR(KBr,cm -1):ν＝3313,3186,2212,1641,1413,806.
Anal.Calcd for C 15H 13N 3O 2:C,67.40；H,4.90；N,15.72；Found:C,67.38；H,4.88；N,15.73.
(3g)5-Acetyl-2-amino-1-(5-chloro-2-methoxy-phenyl)-6-oxo-1,6-dihydro-pyridine-3-carbonitrile
White solid,mp 115-117℃；
Figure 13: 1h NMR (300MHz,
DMSO):δ＝2.32(s,3H),3.70(s,3H),7.19-7.22(d,J＝9Hz,2H),7.41(s,1H),
7.51(dd,J 1＝3Hz,J 2＝3Hz,1H),8.12(s,1H)；
Figure 14: 13c NMR (100MHz, DMSO):
δ＝30.2,56.4,73.2,112.5,114.8,116.7,123.6,124.7,130.0,131.3,
147.1,154.0,159.8,193.2；
Anal.Calcd for C 15H 12ClN 3O 3:C,56.70；H,3.81；N,13.23；Found:C,56.71；H,3.82；N,13.21.
Embodiment two: present embodiment is with structural formula the ketones with Enamino-esters of (wherein R is phenyl) is that pyridine-2-(1H) ketone compounds prepared by raw material, and its structural formula is:
in formula, R is Ph.
Reaction equation in present embodiment:
Concrete preparation method is as follows: take 1.0mmol ketones with Enamino-esters, 1.1mmol propane dinitrile, be placed in 25ml round-bottomed flask, measure 15ml organic solvent, join in round-bottomed flask after stirring fully dissolving, add 0.05mmol catalyzer, react at 25 DEG C, TLC monitors, be poured into after ketones with Enamino-esters completely dissolve in saturated aqueous common salt, separate out solid suction filtration, wash, dry, be separated (developping agent: petrol ether/ethyl acetate: 5/1, v/v) through silica gel column chromatography, obtain pyridine-2-(1H) ketone compounds, white solid.
Table 2 present embodiment catalyzer and organic solvent table
Adopt following verification experimental verification invention effect
Table 3, different catalysts and organic solvent prepare the productive rate of pyridine-2-(1H) ketone compound
As shown in Table 3, using piperidines as catalyzer and the product yield that obtains using dehydrated alcohol as organic solvent the highest.

Claims (9)

1. pyridine-2-(1H) ketone compounds, is characterized in that the structure of pyridine-2-(1H) ketone compounds is wherein R is Ph, 4-ClC 6h 4, 4-MeOC 6h 4, 4-Cl-2,5-(MeO) 2c 6h 2, 2,4-Me 2c 6h 3, 4-MeC 6h 4, 5-Cl-2-MeOC 6h 3.
2. the preparation method of pyridine-2-(1H) ketone compounds as claimed in claim 1, is characterized in that the preparation method of pyridine-2-(1H) ketone compounds carries out in the steps below:
By raw material ketones with Enamino-esters and propane dinitrile mixing, then organic solvent is added, be stirred to abundant dissolving, add catalyzer, react at 25 ~ 40 DEG C is poured in saturated aqueous common salt to ketones with Enamino-esters completely dissolve, the solid of separating out carries out suction filtration successively, washs, dries process, is separated, obtains pyridine-2-(1H) ketone compounds with silica gel column chromatography;
Wherein said organic solvent is DMF (DMF), dehydrated alcohol, tetrahydrofuran (THF), dimethylbenzene, methylene dichloride or dimethyl sulfoxide (DMSO) (DMSO);
Described catalyzer is salt of wormwood, sodium hydroxide, triethylamine, piperidines, sodium ethylate or sodium methylate.
3. the preparation method of a kind of pyridine-2-(1H) ketone compounds according to claim 2, is characterized in that the mol ratio of ketones with Enamino-esters and propane dinitrile is 1:1.1 to 1:1.3.
4. the preparation method of a kind of pyridine-2-(1H) ketone compounds according to claim 3, is characterized in that the mol ratio of ketones with Enamino-esters and catalyzer is 20:1 to 10:1.
5. a kind of preparation method of pyridine-2-(1H) ketone compounds according to claim 2,3 or 4, is characterized in that the structure of described ketones with Enamino-esters is for described organic solvent is dehydrated alcohol; Described catalyzer is piperidines.
6. a kind of preparation method of pyridine-2-(1H) ketone compounds according to claim 2,3 or 4, is characterized in that described organic solvent is dehydrated alcohol; Described catalyzer is sodium ethylate.
7. a kind of preparation method of pyridine-2-(1H) ketone compounds according to claim 2,3 or 4, is characterized in that described organic solvent is dehydrated alcohol; Described catalyzer is sodium methylate.
8. a kind of preparation method of pyridine-2-(1H) ketone compounds according to claim 2,3 or 4, is characterized in that described organic solvent is DMF; Described catalyzer is salt of wormwood.
9. a kind of preparation method of pyridine-2-(1H) ketone compounds according to claim 2,3 or 4, is characterized in that described organic solvent is DMF; Described catalyzer is sodium ethylate.
CN201510136768.6A 2015-03-26 2015-03-26 Pyridine-2-(1H) ketone compound and preparation method thereof Pending CN104725305A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510136768.6A CN104725305A (en) 2015-03-26 2015-03-26 Pyridine-2-(1H) ketone compound and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510136768.6A CN104725305A (en) 2015-03-26 2015-03-26 Pyridine-2-(1H) ketone compound and preparation method thereof

Publications (1)

Publication Number Publication Date
CN104725305A true CN104725305A (en) 2015-06-24

Family

ID=53449786

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201510136768.6A Pending CN104725305A (en) 2015-03-26 2015-03-26 Pyridine-2-(1H) ketone compound and preparation method thereof

Country Status (1)

Country Link
CN (1) CN104725305A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113897631A (en) * 2021-10-24 2022-01-07 昆明学院 Method for electrochemically synthesizing pyridine-2-one derivatives

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHIKHALIKAR, SANDIP ET AL: "Synthesis of Pyridin-2(1H)-one Derivatives: Temperature-Dependent Selectivity", 《EUROPEAN JOURNAL OF ORGANIC CHEMISTRY》 *
ELMAATI, T. A. ET AL: "1-(N,N-dimethylamino)-2-(N-phenylcarbamoyl)-block for the synthesis of heterocyclic compounds", 《POLISH JOURNAL OF CHEMISTRY》 *
HUSSEIN, A. M. ET AL: "β-Oxoanilides in heterocyclic synthesis: an expeditious synthesis of new polyfunctionally substituted pyridine and pyrazole derivatives", 《JOURNAL OF HETEROCYCLIC CHEMISTRY》 *
VALERIYA P. TKACHOVA ET AL，: "Competing transformations of 2-cyanoacetanilides in reactions with derivatives of ethoxymethylenemalonic acid", 《ARKIVOC》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113897631A (en) * 2021-10-24 2022-01-07 昆明学院 Method for electrochemically synthesizing pyridine-2-one derivatives
CN113897631B (en) * 2021-10-24 2023-05-09 昆明学院 Method for electrochemical synthesis of pyridin-2-one derivatives

Similar Documents

Publication Publication Date Title
Pradhan et al. Synthesis of 3, 4-dihydropyridin-2-one derivatives in convergent mode applying bio catalyst vitamin B1 and polymer supported catalyst PEG–SO3H from two different sets of building blocks
CN102424645B (en) Method for synthesizing aromatic amide and aromatic methanol
Battula et al. A mild and efficient copper-catalyzed N-arylation of unprotected sulfonimidamides using boronic acids
Willy et al. A novel consecutive three-component coupling-addition-SNAr (CASNAR) synthesis of 4H-thiochromen-4-ones
CN104725305A (en) Pyridine-2-(1H) ketone compound and preparation method thereof
CN112480015A (en) Method for synthesizing 2-trifluoromethyl substituted quinazolinone by multi-component one-pot method
CN105820174A (en) Polysubstituted thienoindole derivative and preparation method thereof
CN111592509B (en) Method for synthesizing aryl (3-sulfuryl benzofuran-2-yl) ketone compound by copper catalysis
CN104829553A (en) New method of synthesizing 2,4-di-substituted benzothiazole
CN101628904B (en) Synthesis method of 2-nitro-3-aryl-2,3,5,7-tetrahydrobenzofuran-4-one derivative
CN108484509A (en) One kind carries Boc amino barbiturates-cyclohexadiene spiro-compound and its synthetic method
CN104592222B (en) The preparation method of antiplatelet drug AZD6482
CN103288707B (en) A kind of preparation method of 3-benzene sulfydryl indole derivative
CN102718694B (en) 3-cyan substituted indole compound and synthetic method thereof
CN107382867B (en) 4-isothiocyanato pyrazolones
CN102127014A (en) Azaphenanthrone compound and preparation method thereof
CN102336763B (en) Synthesis method for pyranocoumarin derivatives
CN106938984B (en) 5-substituted arylation/heterocycle 8-acylamino quinoline compound and one-pot preparation method thereof
CN105481865A (en) Preparation method of pyrimidine [1,6-a] indole heterocyclic derivative
Singh et al. Synthesis of o, m-cymene-cored biaryls through a carbanion-induced ring transformation strategy
CN105622493B (en) Method for synthesizing fully-substituted pyridine compound through cascade reaction of enaminone and aldehyde
CN111362973A (en) Synthetic method of 1, 2-benzothiazine derivative
CN104163798A (en) Synthesis method of 3-amino-8-trifluoromethyl quinoline
CN104045599B (en) The preparation method of 2- amino-3-aryl quinoline
CN112480016B (en) (E) -1-acyl-1- (3-quinoxalinone) methyl ketoxime and synthesis method thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20150624

WD01 Invention patent application deemed withdrawn after publication