CN109836384A - A kind of 3- aryl methylene -2,3- dihydro -4(1H)-quinolinone preparation method - Google Patents
A kind of 3- aryl methylene -2,3- dihydro -4(1H)-quinolinone preparation method Download PDFInfo
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Abstract
The present invention provides a kind of 3- aryl methylenes -2; 3- dihydro -4 (1H)-quinolinone preparation method; it is characterized in that; it include: o- propargyl alcohol-aniline, solvent and the acid that N protection is added in the reaction vessel; it is reacted under reflux conditions, aromatic aldehyde is added into reaction solution, the reaction was continued; obtain -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro.Preparation method maximum output of the invention is up to 90%, have many advantages, such as that easy to operate, mild condition and high conversion rate by-product are few, a kind of completely new synthetic method is provided for the building of -4 (1H)-quinolinones compound of 3- aryl methylene -2,3- dihydro.
Description
Technical field
The present invention relates to technical field of organic synthesis, specifically, are related to a kind of 3- aryl methylene -2,3- dihydro -4
The preparation method of (1H)-quinolinone.
Background technique
The drug of the structure containing quinolinone of mankind's discovery at present all has pharmacological action and 2,3- dihydro -4- quinoline mostly
Ketone is in medical chemistry as a kind of important medicine intermediate.Literature survey to 2,3- dihydro -4- quinolinones compound
Such compound is disclosed with certain anti-hypertension, antibacterial, anti-dopamine.3- aryl methylene -2,3- dihydro -4- quinolinone
Can by aniline be starting material, by 5 steps reaction (formula -1, Indian Journal of Chemistry.1980,19B:
279-300.).By this route synthesize the 2,3- dihydro -4- quinolinone that 3 aryl methylenes replace need 5 kinds it is different anti-
Environment is answered, 4 intermediates are separated；It is more unfavorable on the obvious economically and environmentally close friend of such reaction.Therefore simple, efficient
Ground building -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro is a problem to be solved.
Summary of the invention
The object of the present invention is to provide a kind of completely new, -4 (1H)-quinolines of 3- aryl methylene -2,3- dihydro easy to operate
The preparation method of quinoline ketone.
In order to achieve the above object, the present invention provides a kind of -4 (1H)-quinolinones of 3- aryl methylene -2,3- dihydro
Preparation method characterized by comprising o- propargyl alcohol-aniline, solvent and the acid of N protection are added in the reaction vessel, is returning
It is reacted under the conditions of stream, aromatic aldehyde is added into reaction solution, the reaction was continued, obtains 3- aryl methylene -2,3- dihydro -4
(1H)-quinolinone；Shown in the structural formula such as formula (I) of o- propargyl alcohol-aniline of the N protection, the 3- aryl methylene
Shown in the structural formula such as formula (III) of -4 (1H)-quinolinone of base -2,3- dihydro:
Wherein, the R1For hydrogen or alkyl or halogen；PG be selected from hydrogen, p-toluenesulfonyl, to fluorophenylsulphonyl, to bromine
Benzenesulfonyl, to Methoxybenzenesulfonyl, mesyl, benzoyl, to fluoro benzoyl or to chlorobenzene formacyl, Ar is virtue
Base.
Preferably, described aromatic aldehyde or derivatives thereof be benzaldehyde, p-tolualdehyde, 4-Fluorobenzaldehyde, to chlorobenzene first
Aldehyde, p-bromobenzaldehyde, parahydroxyben-zaldehyde, 4- nitrobenzaldehyde, 4- cyanobenzaldehyde, anisic aldehyde or 2 thiophene carboxaldehyde.
Preferably, the R1For hydrogen, C1-C20Alkyl, F, Cl, Br.
Preferably, the Ar is phenyl or derivatives thereof or thienyl.
The reaction equation of the preparation method are as follows:
Wherein: R1For hydrogen or alkyl or halogen；PG is selected from hydrogen, p-toluenesulfonyl, to fluorophenylsulphonyl, brosyl
Base, to Methoxybenzenesulfonyl, mesyl, benzoyl, to fluoro benzoyl or to any in chlorobenzene formacyl；Aromatic aldehyde
Or derivatives thereof (Ar-CHO) be selected from benzaldehyde, p-tolualdehyde, 4-Fluorobenzaldehyde, p-chlorobenzaldehyde, p-bromobenzaldehyde, to hydroxyl
Benzaldehyde, 4- nitrobenzaldehyde, 4- cyanobenzaldehyde, anisic aldehyde or 2 thiophene carboxaldehyde.
Preferably, aromatic aldehyde is being added, after the reaction was continued, water quenching is being added and goes out, successively extracts, organic phase washing, it is dry and
Concentration, obtained concentrate obtain -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro by column chromatographic purifying.
Preferably, the acid is trifluoromethanesulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid iron, trifluoromethanesulfonic acid ferrous iron, trifluoro
Copper methane sulfonate, Bismuth triflate, silver trifluoromethanesulfonate or trifluoromethanesulfonic acid scandium.
Preferably, the solvent is appointing in dioxane, dichloroethanes, benzotrifluoride, toluene, benzene and tetrahydrofuran
It is one or more of.
Preferably, the o- propargyl alcohol-aniline, aromatic aldehyde of N protection and the molar ratio of acid are 1:(1~1.2):
(0.1~0.2)；The feed ratio of o- propargyl alcohol-aniline and solvent is 1:5~1:20.
Compared to the prior art, the beneficial effects of the present invention are:
The preparation method of a kind of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro of the invention, i.e., with o- alkynes third
Alcohol-amino benzenes compounds, aromatic aldehyde and its derivative are raw material, pass through series connection Meyer-Schuster under the catalytic action of acid
Rearrangement reaction, cyclization reaction, electrophilic substitution reaction realize the one kettle way of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro
Synthesis.Reaction condition of the present invention is mild, omit intermediate process step, maximum output is up to 90%, has easy to operate, condition
The advantages that mild and high conversion rate by-product is few, preparation method of the invention are 3- aryl methylene -2,3- dihydro -4 (1H) -
The synthesis of quinolinones compound provides a completely new, synthetic method easy to operate.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Acid used in various embodiments of the present invention, aromatic aldehyde, dioxane, dichloroethanes, benzotrifluoride, toluene, benzene or
Tetrahydrofuran, ethyl acetate, petroleum ether and anhydrous sodium sulfate are traditional Chinese medicines reagent.
Equipment used in various embodiments of the present invention and the information of manufacturer are as follows:
Blender are as follows: the Shanghai Pu Mei Ying MYPII-2 constant temperature blender with magnetic force；
Water circulating pump are as follows: Shanghai Yu Kang recycles multiplex vavuum pump SHB-IIIA；
Rotary Evaporators are as follows: Shanghai Yu Kang Rotary Evaporators W.S 206B；
Oil pump are as follows: Shanghai Yu Kang 2XZ-2 type rotary-vane vaccum pump.
Embodiment 1
A kind of preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro, specific steps are as follows:
O- propargyl alcohol-aniline of N protection, solvent are sequentially added in a tube sealing, acid carries out anti-under reflux conditions
It answers, monitors that o- propargyl alcohol-aniline of N protection completely disappears by TLC (solvent is petroleum ether: ethyl acetate=4:1)
Afterwards, aromatic aldehyde is added into reaction solution；Continuation is reacted under reflux conditions, and by TLC, (solvent is petroleum ether: acetic acid
Ethyl ester=4:1) monitor that water quenching is added after benzaldehyde converts completely goes out, ethyl acetate (3 × 15mL) extraction is added, it is resulting to have
In being concentrated on Rotary Evaporators after machine is mutually washed with saturated sodium chloride solution, anhydrous sodium sulfate is dry, obtained concentrate passes through
Column chromatography (eluant, eluent be (petroleum ether: ethyl acetate=8:1)) purify (E) -3- benzylidene -1- shown in above formula to toluene
Sulfonyl -2,3- dihydro -4 (1H)-quinolinone, yield 90%, o- propargyl alcohol-aniline, aromatic aldehyde, solvent and acid and its sample-adding
It measures and is respectively as follows: N- [2- (3- hydroxypropyl -1- alkynyl)-phenyl] -4- methyl benzenesulfonamide (2mmol), benzaldehyde (2mmol), two
Six ring of oxygen (10mL) and trifluoromethanesulfonic acid (0.2mmol)；Product nuclear-magnetism: 1H NMR (500MHz, CDCl3) δ 8.00-7.95 (m,
1H), 7.85 (d, J=8.0Hz, 1H), 7.69-7.64 (m, 1H), 7.55-7.47 (m, 4H), 7.42 (t, J=7.5Hz, 1H),
7.34 (d, J=7.5Hz, 2H), 7.03 (q, J=8.0Hz, 4H), 5.11-5.05 (d, J=1.0,2H), 2.37 (s, 3H)
Embodiment 2
A kind of preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro, specific steps are as follows:
O- propargyl alcohol-aniline of N protection, solvent are sequentially added in a tube sealing, acid carries out anti-under reflux conditions
It answers, monitors that o- propargyl alcohol-aniline of N protection completely disappears by TLC (solvent is petroleum ether: ethyl acetate=4:1)
Afterwards, aromatic aldehyde is added into reaction solution；Continuation is reacted under reflux conditions, and by TLC, (solvent is petroleum ether: acetic acid
Ethyl ester=4:1) monitor that water quenching is added after 2 thiophene carboxaldehyde converts completely goes out, and is added ethyl acetate (3 × 15mL) extraction, gained
Organic phase washed with saturated sodium chloride solution, after anhydrous sodium sulfate is dry in being concentrated on Rotary Evaporators, obtained concentrate
(E) -3- (thiophene -2- methylene) -1- first shown in above formula is purified to obtain by column chromatography (petroleum ether: ethyl acetate=8:1)
Benzenesulfonyl -2,3- dihydro -4 (1H)-quinolinone, yield 85%, o- propargyl alcohol-aniline, aromatic aldehyde, solvent and acid and its add
Sample amount is respectively as follows: N- [2- (3- the third hydroxyl -1- alkynyl) -4- tolyl] -4- methyl benzenesulfonamide (2mmol), 2 thiophene carboxaldehyde
(2.2mmol), dioxane (10mL) and Bismuth triflate (0.2mmol)；Product nuclear-magnetism:1H NMR(500MHz,CDCl3)δ
7.95 (d, J=7.5Hz, 1H), 7.86 (d, J=8.0Hz, 1H), 7.72-7.62 (m, 2H), 7.58 (s, 1H), 7.39 (m
2H), 7.25-7.21 (m, 1H), 7.14 (d, J=7.0Hz, 2H), 6.97 (d, J=7.0Hz, 2H), 5.14 (s, 2H), 2.32
(s,3H).
Embodiment 3
A kind of preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro, specific steps are as follows:
O- propargyl alcohol-aniline of N protection, solvent are sequentially added in a tube sealing, acid carries out anti-under reflux conditions
It answers, monitors that o- propargyl alcohol-aniline of N protection completely disappears by TLC (solvent is petroleum ether: ethyl acetate=4:1)
Afterwards, aromatic aldehyde is added into reaction solution；Continuation is reacted under reflux conditions, and by TLC, (solvent is petroleum ether: acetic acid
Ethyl ester=4:1) monitor that water quenching is added after 4-Fluorobenzaldehyde converts completely goes out, and is added ethyl acetate (3 × 15mL) extraction, gained
Organic phase washed with saturated sodium chloride solution, after anhydrous sodium sulfate is dry in being concentrated on Rotary Evaporators, obtained concentrate
(E) -3- (4- fluorobenzylidene) -1- toluene sulphur shown in above formula is purified to obtain by column chromatography (petroleum ether: ethyl acetate=8:1)
Acyl group -2,3- dihydroquinoline -4 (1H) -one, yield 85%, o- propargyl alcohol-aniline, aromatic aldehyde, solvent and acid and its sample-adding amount
It is respectively as follows: N- [2- (3- the third hydroxyl -1- alkynyl) -4,5- xylyl] -4- methyl benzenesulfonamide (2mmol), 4-Fluorobenzaldehyde
(2.4mmol), dioxane (20mL) and copper trifluoromethanesulfcomposite (0.4mmol)；Product nuclear-magnetism:1H NMR(500MHz,CDCl3)δ
7.97 (dd, J=1.5,1.5Hz, 1H), 7.85 (d, J=8.0Hz, 1H), 7.70-7.66 (m, 1H), 7.51 (td, J=8.0,
6.0Hz, 1H), 7.45-7.40 (m, 2H), 7.20 (td, J=8.0,2.2Hz, 1H), 7.12 (d, J=8.0Hz, 1H), 7.05
(t, J=8.0Hz, 4H), 7.01 (d, J=9.5Hz, 1H), 5.05 (d, J=1.5Hz, 2H), 2.38 (s, 3H)
Embodiment 4
A kind of preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro, specific steps are as follows:
O- propargyl alcohol-aniline of N protection, solvent are sequentially added in a tube sealing, acid carries out anti-under reflux conditions
It answers, monitors that o- propargyl alcohol-aniline of N protection completely disappears by TLC (solvent is petroleum ether: ethyl acetate=4:1)
Afterwards, aromatic aldehyde is added into reaction solution；Continuation is reacted under reflux conditions, and by TLC, (solvent is petroleum ether: acetic acid
Ethyl ester=4:1) monitor that water quenching is added after 4- tolyl aldehyde converts completely goes out, and is added ethyl acetate (3 × 15mL) extraction, institute
Organic phase wash with saturated sodium chloride solution, after anhydrous sodium sulfate is dried in being concentrated on Rotary Evaporators, obtained concentration
Liquid purifies to obtain (E) -3- (4- methyl benzylidene) -1- first shown in above formula by column chromatography (petroleum ether: ethyl acetate=8:1)
Benzenesulfonyl -2,3- dihydroquinoline -4 (1H) -one, yield 85%, o- propargyl alcohol-aniline, aromatic aldehyde, solvent and acid and its add
Sample amount is respectively as follows: N- [2- (3- hydroxypropyl -1- alkynyl)-phenyl] -4- methyl benzenesulfonamide (2mmol), p-tolyl aldehyde
(2.4mmol), dichloroethanes (15mL) and trifluoromethanesulfonic acid (0.2mmol)；Product nuclear-magnetism:1H NMR(500MHz,CDCl3)δ
7.97 (d, J=7.5Hz, 1H), 7.84 (d, J=8.5Hz, 1H), 7.66 (t, J=7.5Hz, 1H), 7.45 (s, 1H), 7.42
(t, J=7.5,3H), 7.33 (d, J=7.5Hz, 2H), 7.25 (d, J=7.5Hz, 2H), 7.02 (m, 4H), 5.09 (s, 2H),
2.47(s,3H),2.36(s,3H).
Embodiment 5
A kind of preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro, specific steps are as follows:
O- propargyl alcohol-aniline of N protection, solvent are sequentially added in a tube sealing, acid carries out anti-under reflux conditions
Answer, by TLC (petroleum ether: ethyl acetate=4:1) monitor N protection o- propargyl alcohol-aniline completely disappear after, Xiang Fanying
Aromatic aldehyde is added in liquid；Continuation is reacted under reflux conditions, is passed through TLC (solvent is petroleum ether: ethyl acetate=4:1)
It monitors that water quenching is added after anisic aldehyde converts completely goes out, is added ethyl acetate (3 × 15mL) extraction, resulting organic phase is with full
In being concentrated on Rotary Evaporators after drying with sodium chloride solution washing, anhydrous sodium sulfate, obtained concentrate chromatographs (stone by column
Oily ether: ethyl acetate=8:1) purify to obtain (E) -3- (4- benzylidene) -1- tosyl -2,3- two shown in above formula
Hydrogen quinoline -4 (1H) -one, yield 85%, o- propargyl alcohol-aniline, aromatic aldehyde, solvent and acid and its sample-adding amount are respectively as follows: N- [2-
(3- hydroxypropyl -1- alkynyl)-phenyl] -4- methyl benzenesulfonamide (2mmol), P-methoxybenzal-dehyde (2.4mmol), fluoroform
Benzene (20mL) and trifluoromethanesulfonic acid (0.2mmol)；Product nuclear-magnetism: 1H NMR (500MHz, CDCl3) δ 7.97 (d, J=7.5Hz,
1H), 7.84 (d, J=8.0Hz, 1H), 7.65 (t, J=8.0Hz, 1H), 7.42 (s, 2H), 7.33 (d, J=8.5Hz, 2H),
7.05 (d, J=7.5Hz, 4H), 6.99 (d, J=8.0Hz, 2H), 5.09 (s, 2H), 3.93 (s, 3H), 2.36 (s, 3H)
Embodiment 6
A kind of preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro, specific steps are as follows:
O- propargyl alcohol-aniline of N protection, solvent are sequentially added in a tube sealing, acid carries out anti-under reflux conditions
It answers, monitors that o- propargyl alcohol-aniline of N protection completely disappears by TLC (solvent is petroleum ether: ethyl acetate=4:1)
Afterwards, aromatic aldehyde is added into reaction solution；Continuation is reacted under reflux conditions, and by TLC, (solvent is petroleum ether: acetic acid
Ethyl ester=4:1) monitor that water quenching is added after 4- bromobenzaldehyde converts completely goes out, and is added ethyl acetate (3 × 15mL) extraction, gained
Organic phase washed with saturated sodium chloride solution, after anhydrous sodium sulfate is dry in being concentrated on Rotary Evaporators, obtained concentrate
(E) -3- (4- bromine benzal) -1- tosyl shown in above formula is purified to obtain by column chromatography (petroleum ether: ethyl acetate=8:1)
Base -2,3- dihydroquinoline -4 (1H) -one, yield: 70%, o- propargyl alcohol-aniline, aromatic aldehyde, solvent and acid and its sample-adding amount are divided
Not are as follows: N- [2- (3- hydroxypropyl -1- alkynyl)-phenyl] -4- benzamide (2mmol), p-bromobenzaldehyde (2.2mmol), toluene
(15mL) and trifluoromethanesulfonic acid iron (0.4mmol)；Product nuclear-magnetism:1H NMR(500MHz,CDCl3) δ 7.97 (d, J=8.0Hz,
1H), 7.85 (d, J=8.5Hz, 1H), 7.67 (d, J=8.0Hz, 3H), 7.42 (t, J=7.5Hz, 1H), 7.39 (s, 1H),
7.21 (d, J=8.0Hz, 2H), 7.03 (q, J=8.0Hz, 4H), 5.03 (s, 2H), 2.37 (s, 3H)
Embodiment 7
A kind of preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro, specific steps are as follows:
O- propargyl alcohol-aniline of N protection, solvent are sequentially added in a tube sealing, acid carries out anti-under reflux conditions
It answers, monitors that o- propargyl alcohol-aniline of N protection completely disappears by TLC (solvent is petroleum ether: ethyl acetate=4:1)
Afterwards, aromatic aldehyde is added into reaction solution；Continuation is reacted under reflux conditions, and by TLC, (solvent is petroleum ether: acetic acid
Ethyl ester=4:1) monitor that water quenching is added after benzaldehyde converts completely goes out, ethyl acetate (3 × 15mL) extraction is added, it is resulting to have
In being concentrated on Rotary Evaporators after machine is mutually washed with saturated sodium chloride solution, anhydrous sodium sulfate is dry, obtained concentrate passes through
Column chromatography (petroleum ether: ethyl acetate=8:1) purifies to obtain (E) -3- benzylidene -1- ((4- fluorophenyl) sulphonyl shown in above formula
Base) -2,3- dihydroquinoline -4 (1H) -one, yield 75%, o- propargyl alcohol-aniline, aromatic aldehyde, solvent and acid and its sample-adding amount point
Not are as follows: the fluoro- N- of 4- (2- (3- hydroxyl propyl- 1- alkynes -1- base) phenyl) benzsulfamide (2mmol), benzaldehyde (2.2mmol), dioxy
Six rings (15mL) and trifluoromethanesulfonic acid (0.2mmol)；Product nuclear-magnetism: 1H NMR (500MHz, CDCl3) δ 8.03-7.95 (m,
1H), 7.84 (d, J=8.0Hz, 1H), 7.69 (t, J=8.0Hz, 1H), 7.59-7.41 (m, 5H), 7.35 (d, J=7.0Hz,
2H), 7.19-7.12 (m, 2H), 6.90 (t, J=8.0Hz, 2H), 5.10 (s, 2H)
The above is only the citing of embodiments of the present invention, it is noted that for the ordinary skill of the art
For personnel, without departing from the technical principles of the invention, several improvements and modifications can also be made, these improve and become
Type also should be regarded as protection scope of the present invention.
Claims (8)
1. a kind of preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro characterized by comprising reacting
O- propargyl alcohol-aniline, solvent and the acid of N protection are added in container, is reacted, is added into reaction solution under reflux conditions
Aromatic aldehyde, the reaction was continued, obtains -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro；The o- alkynes third of the N protection
Shown in alcohol-aniline structural formula such as formula (I), the structural formula of -4 (the 1H)-quinolinone of 3- aryl methylene -2,3- dihydro is such as
Shown in formula (III):
Wherein, the R1For hydrogen or alkyl or halogen；PG be selected from hydrogen, p-toluenesulfonyl, to fluorophenylsulphonyl, to bromobenzene sulphur
Acyl group, to Methoxybenzenesulfonyl, mesyl, benzoyl, to fluoro benzoyl or to chlorobenzene formacyl, Ar is aryl.
2. the preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro as described in claim 1, feature exist
In, described aromatic aldehyde or derivatives thereof be benzaldehyde, p-tolualdehyde, 4-Fluorobenzaldehyde, p-chlorobenzaldehyde, to bromobenzene first
Aldehyde, parahydroxyben-zaldehyde, 4- nitrobenzaldehyde, 4- cyanobenzaldehyde, anisic aldehyde or 2 thiophene carboxaldehyde.
3. the preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro as described in claim 1, feature exist
In the R1For hydrogen, C1-C20Alkyl, F, Cl, Br.
4. the preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro as described in claim 1, feature exist
In the Ar is phenyl or derivatives thereof or thienyl.
5. the preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro as described in claim 1, feature exist
In in addition aromatic aldehyde, after the reaction was continued, addition water quenching is gone out, and is successively extracted, and organic phase washing dries and concentrates, and what is obtained is dense
Contracting liquid obtains -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro by column chromatographic purifying.
6. the preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro as described in claim 1, feature exist
In the acid is trifluoromethanesulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid iron, trifluoromethanesulfonic acid ferrous iron, copper trifluoromethanesulfcomposite, three
Fluorine methanesulfonic acid bismuth, silver trifluoromethanesulfonate or trifluoromethanesulfonic acid scandium.
7. the preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro as described in claim 1, feature exist
In the solvent is any one or more of dioxane, dichloroethanes, benzotrifluoride, toluene, benzene and tetrahydrofuran.
8. the preparation method of -4 (1H)-quinolinone of 3- aryl methylene -2,3- dihydro as described in claim 1, feature exist
In the molar ratio of o- propargyl alcohol-aniline, aromatic aldehyde and acid that the N is protected is 1:1~1.2:0.1~0.2；O- alkynes third
The feed ratio of alcohol-aniline and solvent is 1:5~1:20.
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| GUOFENG SUN等: ""Superacid-Catalyzed Tandem Meyer-Schuster Rearrangement/Intramolecular Hydroamination of o-Anilinopropargyl Alcohols for the Synthesis of 2,3-dihydro-4(1h)-quinolones"", 《SYNTHETIC COMMUNICATIONS》 * |
| HIDEKI MINAMI等: "Reaction of 2-propargylphenylcarbamates with diphenyl-iodonium salts via Meyer-Schuster rearrangement", 《TETRAHEDRON LETTERS》 * |
| KELKAR, PRABHAKAR M.等: ""Studies in antifertility agents. Part XXVII. Synthesis of 2-acetyl-3-aryl-5-tosyl-7/8-H (or methoxy)-3,3a,4,5-tetrahydropyrazolo[4,3-c]quinolines"", 《INDIAN JOURNAL OF CHEMISTRY SECTION B》 * |
| NORIKO OKAMOTO等: "Bi(OTf)3-Catalyzed Tandem Meyer-Schuster Rearrangement and 1,4-Addition to the Resulting Vinyl Ketone", 《J. ORG. CHEM.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110172076A (en) * | 2019-06-14 | 2019-08-27 | 安徽师范大学 | One kind quinoline containing exocyclic double bond and preparation method thereof |
| CN110172076B (en) * | 2019-06-14 | 2021-08-27 | 安徽师范大学 | Quinoline derivative containing exocyclic double bond and preparation method thereof |
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