CN107698469A - A kind of preparation method of α halos β amino ketones - Google Patents

A kind of preparation method of α halos β amino ketones Download PDF

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Publication number
CN107698469A
CN107698469A CN201710955215.2A CN201710955215A CN107698469A CN 107698469 A CN107698469 A CN 107698469A CN 201710955215 A CN201710955215 A CN 201710955215A CN 107698469 A CN107698469 A CN 107698469A
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phenyl
preparation
acid
halogen
amino ketones
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CN107698469B (en
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殷燕
段永斌
张华�
孙玉星
孙越
王媛
潘万勇
裴可可
陆成
潘金鹏
孟凡丽
赵连花
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Shanghai Institute of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups

Abstract

The invention discloses a kind of preparation method of α halos β amino ketones.The preparation method is with the cyclosubstituted propilolic alcohol of virtue, and amine and nitrogen N-halosuccinimides are raw material, the Meyer Schuster rearrangement reactions connected under catalytic amount acid effect, amine halogen addition reaction, so as to realize the one pot process of α halo β amino ketones.The preparation method yield of the α halo β amino ketones of the present invention is high, has the advantages that simple to operate and high atom utilization, the structure for α halo β amino ketone compounds provides a kind of brand-new synthetic method.

Description

A kind of preparation method of alpha-halogen-beta-amino ketones
Technical field
The invention belongs to technical field of organic synthesis, specifically, is related to a kind of preparation side of alpha-halogen-beta-amino ketones Method.
Background technology
Alpha-halogen-beta-amino ketones are a kind of important skeletons in organic synthesis, and under certain condition, α positions halogen atom can quilt Different nucleophilic group substitutions, so as to effectively build various heterocyclic compounds, therefore alpha-halogen-beta-amino ketones are modern organic There is important application value, its construction method has turned into one of focus of organic synthesis research in synthesis and pharmaceutical synthesis. Prepare alpha-halogen-Beta-aminoketones product, the ammonia halogen that mainly unsaturated double-bond is carried out in the presence of suitable catalysts at present Bifunctionalized reaction, and the phenyl ring contraposition that this method is only joined directly together with double bond is when having strong electron donating group (methoxyl group), The alpha-halogen target product of high yield can just be obtained.Enumerate following several synthetic methods.
Route one：With α, alpha, beta-unsaturated ketone, sulfonamide and NBS are respectively nitrogen source/halogen source, are acted in Louis acid catalysis Alpha-brominated-the beta-amino ketones of lower synthesis (J.Org.Chem.2009,74,1371-1373).Its synthetic route is as follows：
Route two：With high price iodine (iodobenzene diacetate) for catalyst, para toluene sulfonamide and N- bromo-succinimides are Nitrogen source/halogen source, to chalcone derivative unsaturated double-bond addition reaction (Org.Biomol.Chem., 2008,6,548- 553).Its synthetic route is as follows：
Route three：Using zinc powder as catalyst, para toluene sulfonamide and DBDMH are nitrogen Source/halogen source, to the ammonia bromine addition reaction system of ethylene linkage, (SCI, 2013,34 (5), 1151-1159).Its Synthetic route is as follows：
The content of the invention
It is an object of the invention to provide a kind of preparation method of alpha-halogen-beta-amino ketones of one kettle way.Its preparation method letter It is single, product yield high.
Technical scheme is specifically described as follows.
The present invention provides a kind of preparation method of alpha-halogen-beta-amino ketones, by the cyclosubstituted propilolic alcohol 1 of virtue, amine 2 and nitrogen halogen For succimide 3 in a solvent, under counterflow condition, alpha-halogen-beta-amino ketones 4 are obtained through acid effect；Its reaction equation is such as Shown in lower：
Wherein：
R1For phenyl, substituted-phenyl, naphthyl, thienyl, pyridine radicals, furyl or pyrrole radicals, preferably：4- fluoro-phenyls, 4- The bromo- phenyl of chloro- phenyl, 4-, phenyl, 4- methylphenyls, 4- phenyl-phenyls, 4- methoxyl groups-phenyl, 3- methoxyl groups-phenyl, 2- Methoxyl group-phenyl, 2- naphthyls, 3- thienyls；
R2For sulfonyl and acyl group, preferably：To MethOxybenzenesulfonyl, to Methyl benzenesulfonyl base, benzenesulfonyl, to bromobenzene Sulfonyl, to chlorobenzenesulfonyl, to fluorophenylsulphonyl, mesyl or ethylsulfonyl；
R3For hydrogen, methyl, ethyl or propyl group.
In the present invention, solvent is dioxane, dichloroethanes, benzotrifluoride, toluene, benzene, tetrahydrofuran or ethylene glycol two It is any one or more in methyl ether.
In the present invention, acid is trifluoromethanesulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid iron, Bismuth triflate, trifluoromethanesulfonic acid It is any in copper, silver trifluoromethanesulfonate, trifluoromethanesulfonic acid scandium or ferric trichloride.
In the present invention, the cyclosubstituted propilolic alcohol 1 of virtue, amine 2, halogen source 3 and sour mol ratio are 1:(1.95~2.05): (1.50~1.80):(0.01~0.25).
In the present invention, the ratio of the cyclosubstituted propilolic alcohol 1 of virtue and solvent is 1:5~1:10mol/L.
Compared to the prior art, the beneficial effects of the present invention are：
A kind of preparation method of alpha-halogen-beta-amino ketones of the present invention, urged first by the cyclosubstituted propilolic alcohol of virtue through acid Change and Meyer-Schuster rearrangement reactions occur, the amine halogen addition reaction then carried out with amine and N- N-halosuccinimides, obtain It is one pot reaction to target product alpha-halogen-beta-amino ketones；The preparation method yield of alpha-halogen-beta-amino ketones of the present invention Height, raw material are easy to get, simple to operate, have higher atom utilization；A kind of preparation side of alpha-halogen-beta-amino ketones of the present invention Method provides a brand-new synthetic method for the synthesis of alpha-halogen-Beta-aminoketones compound.
Brief description of the drawings
Fig. 1 is the nuclear magnetic spectrum for alpha-halogen-beta-amino ketones product that embodiment 1 obtains.
Fig. 2 is the nuclear magnetic spectrum for alpha-halogen-beta-amino ketones product that embodiment 2 obtains.
Fig. 3 is the nuclear magnetic spectrum for alpha-halogen-beta-amino ketones product that embodiment 3 obtains.
Fig. 4 is the nuclear magnetic spectrum for alpha-halogen-beta-amino ketones product that embodiment 4 obtains.
Fig. 5 is the nuclear magnetic spectrum for alpha-halogen-beta-amino ketones product that embodiment 5 obtains.
Fig. 6 is the nuclear magnetic spectrum for alpha-halogen-beta-amino ketones product that embodiment 6 obtains.
Fig. 7 is the nuclear magnetic spectrum for alpha-halogen-beta-amino ketones product that embodiment 7 obtains.
Embodiment
The present invention is expanded on further below by specific embodiment, but is not intended to limit the present invention.
Acid used in various embodiments of the present invention, sulfonamide, acid amides, dioxane, dichloroethanes, benzotrifluoride, toluene, Benzene, tetrahydrofuran, glycol dimethyl ether, ethyl acetate, petroleum ether and anhydrous sodium sulfate are traditional Chinese medicines reagent.
Equipment used and the information of manufacturer are as follows in various embodiments of the present invention：
Agitator is：Shanghai Mei Ying Pus MYPII-2 constant temperature blender with magnetic force；
Water circulating pump is：Shanghai Yu Kang circulation multiplex vavuum pumps SHB-IIIA；
Rotary Evaporators are：Shanghai Yu Kang Rotary Evaporators W.S 206B；
Oil pump is：Shanghai Yu Kang 2XZ-2 type rotary-vane vaccum pumps；
Preparation HPLC is：Shimadzu LC-20A.
In embodiment, the preparation method of general alpha-halogen-beta-amino ketones, specifically comprise the following steps：
Sequentially add alkynol analog (2mmol) in a 15mL tube sealing, solvent (10~20mL), acid (0.02~ 0.5mmol), amine (3.9~4.1mmol) and halides (3.0~4.0mmol), are reacted, pass through TLC under reflux conditions Monitoring reaction, when the reaction of alkynol analog completely after, into reaction solution adding 20mL water quenchings goes out, and adds 50mL ethyl acetate extraction Take, the organic phase of gained is washed with saturated sodium-chloride, and anhydrous sodium sulfate drying on Rotary Evaporators after concentrating, obtained concentration Liquid purifies to obtain alpha-halogen-beta-amino ketones by column chromatography.
Embodiment 1
4- methyl-N- (2- bromo -3- oxos -3- phenyl-propyl group)-benzsulfamide.Alkynol analog, solvent, acid, amine and NBS sample-adding situations are phenylpropyl alcohol alkynol (2mmol), dioxane (15mL), Bismuth triflate (0.1mmol), TsNH2 (4mmol) and NBS (3mmol)；Yield：92%.
The nuclear magnetic spectrum of product is as shown in Figure 1.1H NMR(500MHz,CDCl3)δ2.41(s,3H),3.54-3.60(m, 1H), 3.68-3.72 (m, 1H), 5.22-5.26 (m, 2H), 7.28 (d, J=7.5Hz, 2H), 7.48 (t, J=8.0Hz, 2H), 7.60-7.63 (m, 1H), 7.74 (d, J=8.0Hz, 2H), 7.93 (d, J=7.0Hz, 2H)
Embodiment 2
N- [the bromo- 3- of 2- (4- methoxyl groups-phenyl) -3- oxo-propylls] -4- methyl-benzene sulphonamides.Alkynol analog, it is molten Agent, acid, amine and NBS sample-adding situations are to methoxybenzene propilolic alcohol (2mmol), dichloroethanes (10mL), Bismuth triflate (0.02mmol), TsNH2(3.90mmol) and NBS (3.0mmol)；Yield：91%.
The nuclear magnetic spectrum of product is as shown in Figure 2.1H NMR(500MHz,CDCl3)δ2.42(s,3H),3.52-3.58(m, 1H), 3.63-3.70 (m, 1H), 3.90 (s, 3H), 5.10 (t, J=6.5Hz, 1H), 5.18 (dd, J1=8.5,5.5Hz, 1H), 6.95 (d, J=9.0Hz, 2H), 7.29 (d, J=8.0,2H), 7.74 (d, J=8.0,2H), 7.92 (d, J=9.0,2H)
Embodiment 3
N- (the bromo- 3- oxos -3- phenyl-propyl group of 2-)-Methanesulfomide.Alkynol analog, solvent, acid, amine and NBS sample-adding feelings Condition is phenylpropyl alcohol alkynol (2mmol), benzotrifluoride (15mL), copper trifluoromethanesulfcomposite (0.5mmol), MsNH2(4.1mmol) and NBS (3.0mmol)；Yield：80%.
The nuclear magnetic spectrum of product is as shown in Figure 3.1H NMR(500MHz,CDCl3)δ3.01(s,3H),3.69-3.75(m, 1H),3.85-3.91(m,1H),5.23(s,1H),5.31-5.35(dd,J1=8.5,5.5Hz, 1H), 7.50 (t, J= 7.5Hz, 2H), 7.63 (t, J=7.5Hz, 1H), 8.01 (d, J=7.0Hz, 2H)
Embodiment 4
N- (2- chloro -3- oxos -3- phenyl-propyl group)-benzamide.Alkynol analog, solvent, acid, amine and NBS sample-addings Situation is phenylpropyl alcohol alkynol (3mmol), toluene (15mL), silver trifluoromethanesulfonate (0.45mmol), benzamide (6mmol) and NCS (4.5mmol)；Yield：93%.
The nuclear magnetic spectrum of product is as shown in Figure 4.1H NMR(500MHz,CDCl3)δ2.42(s,3H),3.46-3.52(m, 1H), 3.59-3.66 (m, 1H), 5.13 (t, J=6.0Hz, 1H), 5.20 (dd, J1=7.5,5.5Hz, 1H), 7.30 (d, J= 8.0Hz, 2H), 7.50 (t, J=7.5Hz, 2H), 7.63 (d, J=7.5Hz, 1H), 7.75 (d, J=8.5Hz, 2H), 7.95 (t, J=8.0Hz, 2H)
Embodiment 5
4- methyl-N- (2- iodo -3- oxos -3- phenyl-propyl group)-benzsulfamide.Alkynol analog, solvent, acid, amine and NIS sample-adding situations are phenylpropyl alcohol alkynol (2mmol), benzene (13mL), trifluoromethanesulfonic acid scandium (0.35mmol), TsNH2(4.05mmol) With NIS (3.0mmol)；Yield：90%.
The nuclear magnetic spectrum of product is as shown in Figure 5.1H NMR(500MHz,CDCl3)δ2.39(s,3H),3.55-3.61(m, 1H), 3.68-3.75 (m, 1H), 5.46 (q, J=5.0Hz, 1H), 5.50 (t, J=7.0Hz, 1H), 7.25 (d, J=8.5Hz, 2H), 7.45 (t, J=7.5Hz, 2H), 7.57-7.61 (m, 1H), 7.72 (d, J=8.5Hz, 2H), 7.84 (d, J=8.0Hz, 2H).
Embodiment 6
N, 4- dimethyl-N-(2- bromo -3- oxo -3- phenyl propyls)-benzsulfamide.Alkynol analog, solvent, acid, Amine and NBS sample-adding situations are phenylpropyl alcohol alkynol (2mmol), tetrahydrofuran (15mL), trifluoromethanesulfonic acid iron (0.4mmol), TsNH2 (4mmol) and NBS (3.0mmol)；Yield：91%.
The nuclear magnetic spectrum of product is as shown in Figure 6.1H NMR(500MHz,CDCl3)δ2.44(s,3H),2.87(s,3H), 3.61-3.64 (m, 2H), 5.57-5.61 (m, 1H), 7.34 (d, J=8.0Hz, 2H), 7.51 (t, J=8.5Hz, 2H), 7.63 (t, J=7.5Hz, 1H), 7.70 (d, J=7.5Hz, 2H), 8.04 (d, J=7.5Hz, 2H)
Embodiment 7
4- methyl-N- (the bromo- 3- of 2- (2- naphthyls) -3- oxopropyls)-benzsulfamide.Alkynol analog, solvent, acid, amine It is naphthalene propilolic alcohol (2.0mmol) with NBS sample-adding situations, glycol dimethyl ether (15mL), trifluoromethanesulfonic acid (0.4mmol), TsNH2 (4.0mmol) and NBS (3.0mmol)；Yield：81%.
The nuclear magnetic spectrum of product is as shown in Figure 7.1H NMR(500MHz,CDCl3)δ2.33(s,3H),3.61-3.68(m, 1H), 3.72-3.79 (m, 1H), 5.18 (t, J=6.5Hz, 1H), 5.38 (dd, J1=8.5,5.5Hz, 1H), 7.25 (d, J= 5.5Hz, 2H), 7.58-7.67 (m, 2H), 7.75 (d, J=8.0Hz, 2H), 7.90 (t, J=7.5Hz, 2H), 7.97 (t, J= 7.5Hz,2H),8.44(s,1H).
Described 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, some improvement and modification can also be made, these improve and become Type also should be regarded as protection scope of the present invention.

Claims (7)

  1. A kind of 1. preparation method of alpha-halogen-beta-amino ketones, it is characterised in that by the cyclosubstituted propilolic alcohol 1 of virtue, amine 2 and nitrogen halogen For succimide 3 in a solvent, under counterflow condition, alpha-halogen-beta-amino ketones 4 are obtained through acid effect, its reaction equation is such as Shown in lower：
    Wherein：
    R1For phenyl, substituted-phenyl, naphthyl, thienyl, pyridine radicals, furyl or pyrrole radicals；
    R2For sulfonyl and acyl group；
    R3For hydrogen, methyl, ethyl or propyl group.
  2. 2. preparation method according to claim 1, it is characterised in that R1For 4- fluoro-phenyls, the chloro- phenyl of 4-, the bromo- benzene of 4- Base, phenyl, 4- methylphenyls, 4- phenyl-phenyls, 4- methoxyl groups-phenyl, 3- methoxyl groups-phenyl, 2- methoxyl groups-phenyl, 2- Naphthyl or 3- thienyls.
  3. 3. preparation method according to claim 1, it is characterised in that R2For 4- fluoro-phenyls, the chloro- phenyl of 4-, the bromo- benzene of 4- Base, phenyl, 4- methylphenyls, 4- phenyl-phenyls, 4- methoxies are to MethOxybenzenesulfonyl, to Methyl benzenesulfonyl base, benzene sulfonyl Base, brosyl, to chlorobenzenesulfonyl, to fluorophenylsulphonyl, mesyl or ethylsulfonyl.
  4. 4. preparation method according to claim 1, it is characterised in that solvent is dioxane, dichloroethanes, fluoroform It is any in benzene, toluene, benzene, tetrahydrofuran or glycol dimethyl ether.
  5. 5. preparation method according to claim 1, it is characterised in that acid is trifluoromethanesulfonic acid, trifluoroacetic acid, fluoroform sulphur It is any in sour iron, Bismuth triflate, copper trifluoromethanesulfcomposite, silver trifluoromethanesulfonate, trifluoromethanesulfonic acid scandium or ferric trichloride.
  6. 6. preparation method according to claim 1, it is characterised in that the cyclosubstituted propilolic alcohol 1 of virtue, amine 2, nitrogen halogenated succinimide The mol ratio of acid imide 3 and acid is 1:(1.95~2.05):(1.50~1.80):(0.01~0.25).
  7. 7. preparation method according to claim 1, it is characterised in that the rate of charge of the cyclosubstituted propilolic alcohol 1 of virtue and solvent For 1:5~1:10mol/L.
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CN110407739A (en) * 2019-08-26 2019-11-05 上海应用技术大学 A kind of preparation method of (4,6- diaryl-tetrahydropyridine -3- base) (aryl) ketone
CN110483474A (en) * 2019-08-26 2019-11-22 上海应用技术大学 A kind of preparation method of 2- methylene -1,3,5- triaryl -1,5- pentanedione
CN113200915A (en) * 2021-04-21 2021-08-03 上海应用技术大学 3-aryl-4, 5-dihydro-1H-pyrazole-5 amine and preparation method thereof
CN113200901A (en) * 2021-04-21 2021-08-03 上海应用技术大学 Aziridine-2-yl- (aryl) ketone derivative and preparation method thereof
CN113214183A (en) * 2021-04-21 2021-08-06 上海应用技术大学 5- (aminomethyl) -4-arylthiophene-2-amine derivative and preparation method thereof
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CN109912473A (en) * 2019-04-02 2019-06-21 上海应用技术大学 A kind of preparation method of 2- ((sulfenyl) methyl) -1,3,5- triaryl -1,5- diketone
CN109836410B (en) * 2019-04-02 2021-07-23 上海应用技术大学 (4, 6-diaryl-3, 4-dihydro-2H-thiopyran-3-yl) -aryl ketone and preparation
CN110407739A (en) * 2019-08-26 2019-11-05 上海应用技术大学 A kind of preparation method of (4,6- diaryl-tetrahydropyridine -3- base) (aryl) ketone
CN110483474A (en) * 2019-08-26 2019-11-22 上海应用技术大学 A kind of preparation method of 2- methylene -1,3,5- triaryl -1,5- pentanedione
CN110407739B (en) * 2019-08-26 2021-09-28 上海应用技术大学 Preparation method of (4, 6-diaryl-tetrahydropyridine-3-yl) (aryl) ketone
CN110483474B (en) * 2019-08-26 2021-09-28 上海应用技术大学 Preparation method of 2-methylene-1, 3, 5-triaryl-1, 5-pentanedione
CN113200915A (en) * 2021-04-21 2021-08-03 上海应用技术大学 3-aryl-4, 5-dihydro-1H-pyrazole-5 amine and preparation method thereof
CN113200901A (en) * 2021-04-21 2021-08-03 上海应用技术大学 Aziridine-2-yl- (aryl) ketone derivative and preparation method thereof
CN113214183A (en) * 2021-04-21 2021-08-06 上海应用技术大学 5- (aminomethyl) -4-arylthiophene-2-amine derivative and preparation method thereof
CN113264865A (en) * 2021-04-21 2021-08-17 上海应用技术大学 2-amino-4-benzoyl-4, 5-dihydro-1H-pyrrole-3-carbon nitrile and preparation method thereof

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