CN106883152A - A kind of preparation method of β amino ketones - Google Patents

A kind of preparation method of β amino ketones Download PDF

Info

Publication number
CN106883152A
CN106883152A CN201710224079.XA CN201710224079A CN106883152A CN 106883152 A CN106883152 A CN 106883152A CN 201710224079 A CN201710224079 A CN 201710224079A CN 106883152 A CN106883152 A CN 106883152A
Authority
CN
China
Prior art keywords
phenyl
preparation
acid
amino ketones
propilolic alcohol
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
CN201710224079.XA
Other languages
Chinese (zh)
Inventor
殷燕
陶瑞衡
张华�
段永斌
孙玉星
孙越
魏华征
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.)
Shanghai Institute of Technology
Original Assignee
Shanghai Institute of Technology
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 Shanghai Institute of Technology filed Critical Shanghai Institute of Technology
Priority to CN201710224079.XA priority Critical patent/CN106883152A/en
Publication of CN106883152A publication Critical patent/CN106883152A/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Abstract

The invention discloses a kind of preparation method of β amino ketones.With fragrant cyclosubstituted propilolic alcohol and acid amides as raw material, the Meyer Schuster rearrangement reactions and intermolecular amine connected under acid effect hydrogenate addition reaction to the preparation method, so as to realize the one pot process of β amino ketones.The preparation method maximum output of β amino ketones of the invention has the advantages that simple to operate and 100% atom economy up to 94%, for the structure of β amino ketone compounds provides a kind of brand-new synthetic method.

Description

A kind of preparation method of beta-amino ketones
Technical field
The invention belongs to technical field of organic synthesis, specifically, it is related to a kind of preparation method of beta-amino ketones.
Background technology
Beta-amino ketones are a kind of important skeletons in organic synthesis, and it is easy to be changed into α, alpha, beta-unsaturated ketone, 1,3- ammonia The ketone of base alcohol and other functions.Beta-aminoketones compound shows many bioactivity simultaneously, for example：It is anti-inflammatory, anticancer, anti- Tuberculosis, antibacterial, analgesic and cough-relieving.The current chemical synthesis process on it has following three kinds.
Route one：Mannich reactions (Eur.J.Org.Chem.2007,5797- with ketone, aldehyde and amine as initiation material 5815).Its synthetic route is as follows：
Route two：With copper acetate as catalyst, ring propyl alcohol and sulfonyl azide compound are the opening of raw material (Rsc Adv.2015,5,98757-98761).Its synthetic route is as follows：
Route three：I.e. with α, alpha, beta-unsaturated ketone, sulfonamide and NBS are raw material, and synthesis has chiral beta-amino ketones (Angew.Chem.Int.Ed.2011,50,7734-7736 and Org.Chem.2009,74,1371-1373).Its synthetic route It is as follows：
The content of the invention
It is an object of the invention to provide a kind of preparation method of the brand-new, beta-amino ketones that atom usability is high.
Technical scheme is specifically described as follows.
The present invention provides a kind of preparation method of beta-amino ketones, returns by fragrant cyclosubstituted propilolic alcohol 1 and amine 2 in a solvent Under the conditions of stream, beta-amino ketones 3 are obtained through acid effect；Its reaction equation is as follows：
Wherein：
R1It is 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 or 3- thienyls；
R2It is hydrogen, methyl, ethyl, propyl group or phenyl；
R3It is sulfonyl or acyl group, preferably：To MethOxybenzenesulfonyl, to Methyl benzenesulfonyl base, benzenesulfonyl, to bromobenzene Sulfonyl, to chlorobenzenesulfonyl, to fluorophenylsulphonyl, mesyl or ethylsulfonyl；
R4It is hydrogen, methyl, ethyl or propyl group.
In the present invention, solvent is dioxane, dichloroethanes, benzotrifluoride, toluene, benzene, tetrahydrofuran or ethylene glycol two In methyl ether any one or more.
In the present invention, acid is TFMS, trifluoroacetic acid, TFMS iron, Bismuth triflate, TFMS In copper, silver trifluoromethanesulfonate, TFMS scandium or ferric trichloride any one.
In the present invention, the mol ratio of fragrant cyclosubstituted propilolic alcohol 1, amine 2 and acid is 1:(1.95~2.05):(0.15~ 0.25)。
In the present invention, the ratio of fragrant cyclosubstituted propilolic alcohol 1 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 beta-amino ketones of the invention, occurs by fragrant cyclosubstituted propilolic alcohol through acid catalysis first , then there is Isosorbide-5-Nitrae-addition reaction with aminated compounds and obtain target product beta-amino ketones in Meyer-Schuster rearrangement reactions. The method raw material is easy to get, simple to operate, 100% atom utilization.A kind of preparation method of beta-amino ketones i.e. of the invention be β- The synthesis of amino ketone compound provides a brand-new synthetic method.
Specific 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.
The information of equipment used and manufacturer is 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 beta-amino ketones specifically includes following steps：
Propilolic alcohol (2mmol), solvent (10~20mL), sour (0.3~0.5mmol) are sequentially added in a 15mL tube sealing With amine (3.9~4.1mmol), reacted under reflux conditions, monitored by TLC and reacted, after propilolic alcohol reaction is complete, to 20mL water is added in reaction solution, the extraction of 50mL ethyl acetate is added, the organic phase of gained is washed with saturated sodium-chloride, anhydrous slufuric acid After being concentrated on Rotary Evaporators, the concentrate for obtaining purifies to obtain beta-amino ketones by column chromatography for sodium drying.
Embodiment 1
4- methyl-N- (3- oxos -3- phenyl-propyl group)-benzsulfamide.Propilolic alcohol, solvent, acid and amine sample-adding situation are benzene Propilolic alcohol (2mmol), dioxane (15mL), TFMS iron (0.4mmol) and TsNH2(4mmol)；Yield：94%.1H NMR(500MHz,CDCl3) δ 2.42 (s, 3H), 3.24 (t, J=6.0Hz, 2H), 3.37-3.34 (m, 2H), 5.27 (t, J= 6.5Hz, 1H), 7.31 (d, J=7.5Hz, 2H), 7.48 (t, J=8.0Hz, 2H), 7.60 (t, J=7.5Hz, 1H), 7.78 (d, J=8.0Hz, 2H), 7.89 (d, J=7.5Hz, 2H)
Embodiment 2
N- [3- (4- methoxyl groups-phenyl) -3- oxo-propylls] -4- methyl-benzene sulphonamides.Propilolic alcohol, solvent, acid and amine Sample-adding situation is to methoxybenzene propilolic alcohol (1mmol), dichloroethanes (5mL), Bismuth triflate (0.15mmol) and TsNH2 (1.95mmol；Yield：93%.1H NMR(500MHz,CDCl3) δ 2.42 (s, 3H), 3.18 (t, J=5.5Hz, 2H), 3.36- 3.32 (m, 2H), 3.89 (s, 3H), 5.31 (t, J=6.0Hz, 1H), 6.94 (d, J=8.5Hz, 2H), 7.31 (d, J= 7.5Hz, 2H), 7.78 (d, J=7.5,2H), 7.87 (d, J=8.5,2H)
Embodiment 3
N- (3- oxos -3- phenyl-propyl group)-Methanesulfomide.Propilolic alcohol, solvent, acid and amine sample-adding situation are phenylpropyl alcohol alkynol (2mmol), benzotrifluoride (15mL), copper trifluoromethanesulfcomposite (0.5mmol) and CH3SO2NH2(4.1mmol；Yield：81%.1H NMR(500MHz,CDCl3)δ3.01(s,3H),3.36-3.32(m,2H),3.37-3.34(m,2H),3.57-3.54(m,2H), (d, J=7.5Hz, the 2H) of 5.12 (br, NH, 1H), 7.50 (t, J=7.5Hz, 2H), 7.62 (t, J=7.5Hz, 1H), 7.96
Embodiment 4
N- (3- oxos -3- phenyl-propyl group)-benzamide.Propilolic alcohol, solvent, acid and amine sample-adding situation are phenylpropyl alcohol alkynol (3mmol), toluene (15mL), silver trifluoromethanesulfonate (0.45mmol) and benzamide (6mmol；Yield：8%.1H NMR (500MHz,CDCl3) δ 3.39-3.35 (m, 2H), 3.93-3.90 (m, 2H), 6.98 (br, NH, 1H), 7.43 (t, J= 7.5Hz, 2H), 7.51-7.48 (m, 3H), 7.61 (t, J=7.5Hz, 1H), 7.78 (d, J=7.5Hz, 2H), 7.99 (d, J= 7.5Hz,2H).
Embodiment 5
4- methyl-N- (1- methyl -3- oxos -3- phenyl-propyl group)-benzsulfamide.Propilolic alcohol, solvent, acid and amine sample-adding Situation is phenylpropyl alcohol alkynol (2mmol), benzene (13mL), TFMS scandium (0.35mmol) and TsNH2(4.05mmol；Yield： 30%.1H NMR(500MHz,CDCl3)δ2.39(s,3H),3.10-3.05(m,1H),3.24-3.20(m,1H),3.87-3.82 (m, 1H), 5.32-5.30 (m, 1H), 7.26 (d, J=8.0Hz, 2H), 7.45 (t, J=7.5Hz, 2H), 7.60-7.57 (m, 1H), 7.76 (d, J=8.0Hz, 2H), 7.84 (d, J=7.5Hz, 2H)
Embodiment 6
N, 4- dimethyl-N-(3- oxo -3- phenyl propyls)-benzsulfamide.Propilolic alcohol, solvent, acid and amine are loaded situation It is phenylpropyl alcohol alkynol (2mmol), tetrahydrofuran (15mL), TFMS iron (0.4mmol) and TsNH2(4mmol；Yield： 92%.1H NMR(500MHz,CDCl3)δ2.45(s,3H),2.83(s,3H),3.37-3.34(m,2H),3.48-3.45(m, 2H), 3.87-3.82 (m, 1H), 7.34 (t, J=8.5Hz, 2H), 7.49 (t, J=7.5Hz, 1H), 7.60 (t, J=7.5Hz, 1H), (d, J=7.5Hz, the 2H) of 7.62 (t, J=7.5Hz, 1H), 7.71 (d, J=8.5Hz, 2H), 7.96
Embodiment 7
4- methyl-N- (3- (2- naphthyls) -3- oxopropyls)-benzsulfamide.Propilolic alcohol, solvent, acid and amine are loaded situation It is naphthalene propilolic alcohol (2mmol), glycol dimethyl ether (15mL), TFMS (0.4mmol) and TsNH2(4mmol；Yield： 84%.1H NMR(500MHz,CDCl3) δ 2.38 (s, 3H), 3.38 (t, J=5.5Hz, 2H), 3.42 (t, J=5.5Hz, 2H), 5.29 (t, J=6.0Hz, 1H), 7.30 (d, J=8.5Hz, 2H), 7.63-7.59 (m, 1H), 7.66-7.64 (m, 1H), 7.85 (d, J=8.5Hz, 2H), 7.92-7.89 (m, 2H), 7.98-7.95 (m, 2H), 8.39 (s, 1H)
Embodiment 8
4- methyl-N- (3- oxos -3- (3- thienyls)-propyl group)-benzsulfamide.Propilolic alcohol, solvent, acid and amine are loaded feelings Condition is thiophene propilolic alcohol (2mmol), dioxane (15mL), trifluoroacetic acid (0.4mmol) and TsNH2(4mmol；Yield： 91%.1H NMR(500MHz,CDCl3) δ 2.43 (s, 3H), 3.15 (t, J=6.0Hz, 2H), 3.36-3.32 (m, 2H), 5.24 (t, J=6.5Hz, 1H), 7.32 (d, J=8.0Hz, 2H), 7.36-7.33 (m, 1H), 7.50-7.49 (m, 1H), 7.78 (d, J =8.0Hz, 2H), 8.02 (s, 1H)
Embodiment 9
4- methyl-N- (3- oxo -1,3- diphenylpropyls)-benzsulfamide.Phenylpropyl alcohol alkynol, solvent, acid and amine are loaded situation It is 1- phenyl phenyl-allylene -1- alcohol (2mmol), dioxane (15mL), TFMS iron (0.4mmol) and TsNH2(4mmol； Yield：10%.1H NMR(500MHz,CDCl3)δ2.38(s,3H),3.50-3.45(m,1H),3.63-3.58(m,1H), 4.90-4.85 (m, 1H), 5.72-5.71 (m, 1H), 7.19-7.17 (m, 6H), 7.36 (s, 1H), 7.43 (t, J=7.0Hz, 2H), (d, J=7.5Hz, the 2H) of 7.56 (t, J=7.0Hz, 1H), 7.63 (d, J=7.5Hz, 2H), 7.82
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, on the premise of the technology of the present invention principle is not departed from, 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 preparation method of beta-amino ketones, it is characterised in that, backflow by fragrant cyclosubstituted propilolic alcohol 1 and amine 2 in a solvent Under the conditions of, obtain beta-amino ketones 3 through acid effect；Its reaction equation is as follows：
Wherein：
R1It is phenyl, substituted-phenyl, naphthyl, thienyl, pyridine radicals, furyl or pyrrole radicals；
R2It is hydrogen, methyl, ethyl, propyl group or phenyl；
R3It is sulfonyl or acyl group；
R4It is hydrogen, methyl, ethyl or propyl group.
2. preparation method according to claim 1, it is characterised in that R1Selected from 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. preparation method according to claim 1, it is characterised in that to MethOxybenzenesulfonyl, to Methyl benzenesulfonyl base, Benzenesulfonyl, brosyl, to chlorobenzenesulfonyl, to fluorophenylsulphonyl, mesyl or ethylsulfonyl.
4. preparation method according to claim 1, it is characterised in that solvent is dioxane, dichloroethanes, fluoroform In benzene, toluene, benzene, tetrahydrofuran or glycol dimethyl ether any one.
5. preparation method according to claim 1, it is characterised in that acid is TFMS, trifluoroacetic acid, fluoroform sulphur In sour iron, Bismuth triflate, copper trifluoromethanesulfcomposite, silver trifluoromethanesulfonate, TFMS scandium or ferric trichloride any one.
6. preparation method according to claim 1, it is characterised in that fragrant cyclosubstituted propilolic alcohol 1, amine 2 and acid mole Than being 1:(1.95~2.05):(0.15~0.25).
7. preparation method according to claim 1, it is characterised in that the ratio of fragrant cyclosubstituted propilolic alcohol 1 and solvent is 1:5~1:10mol/L.
CN201710224079.XA 2017-04-07 2017-04-07 A kind of preparation method of β amino ketones Pending CN106883152A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710224079.XA CN106883152A (en) 2017-04-07 2017-04-07 A kind of preparation method of β amino ketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710224079.XA CN106883152A (en) 2017-04-07 2017-04-07 A kind of preparation method of β amino ketones

Publications (1)

Publication Number Publication Date
CN106883152A true CN106883152A (en) 2017-06-23

Family

ID=59182797

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710224079.XA Pending CN106883152A (en) 2017-04-07 2017-04-07 A kind of preparation method of β amino ketones

Country Status (1)

Country Link
CN (1) CN106883152A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107698469A (en) * 2017-10-13 2018-02-16 上海应用技术大学 A kind of preparation method of α halos β amino ketones
CN109836410A (en) * 2019-04-02 2019-06-04 上海应用技术大学 One kind (4,6- diaryl -3,4- dihydro -2H- sulphur pyrans -3- base)-aryl ketone and preparation
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
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
CN110467549A (en) * 2019-08-26 2019-11-19 上海应用技术大学 A kind of N substitution 2- aminomethyl-1,2, the preparation method of 3,5- triaryl pentane -1,5- diketone
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
CN111960961A (en) * 2020-09-17 2020-11-20 河南师范大学 Synthetic method of alpha-amidoketone compound
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

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009093269A1 (en) * 2008-01-24 2009-07-30 Panacea Biotec Limited Novel heterocyclic compounds
CN101784188A (en) * 2007-06-29 2010-07-21 奥克塞拉有限公司 alkynyl phenyl derivative compounds for treating ophthalmic diseases and disorders
CN103664674A (en) * 2013-11-25 2014-03-26 大连理工大学 Preparation method of multi-substituted fused ring compounds
CN106146359A (en) * 2016-07-29 2016-11-23 江西师范大学 The gentle efficient preparation method of α acyloxy acrylamide compound and the application in amide and Peptide systhesis thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101784188A (en) * 2007-06-29 2010-07-21 奥克塞拉有限公司 alkynyl phenyl derivative compounds for treating ophthalmic diseases and disorders
WO2009093269A1 (en) * 2008-01-24 2009-07-30 Panacea Biotec Limited Novel heterocyclic compounds
CN103664674A (en) * 2013-11-25 2014-03-26 大连理工大学 Preparation method of multi-substituted fused ring compounds
CN106146359A (en) * 2016-07-29 2016-11-23 江西师范大学 The gentle efficient preparation method of α acyloxy acrylamide compound and the application in amide and Peptide systhesis thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BHANUCHANDRA M ET AL: "A convenient approach to β-heteroarylated (C-N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles", 《ORGANIC & BIOMOLECULAR CHEMISTRY》 *
REISCH J ET AL: "Synthesis of β-aminopropiophenones from aromatic amines and phenylethylcarbinol", 《ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESELLSCHAFT》 *
TAO RUIHENG ET AL: "Fe(OTf)3-catalyzed tandem Meyer-Schuster rearrangement/intermolecular hydroamination of 3-aryl propargyl alcohols for the synthesis of acyclic b-Aminoketones", 《TETRAHEDRON》 *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107698469A (en) * 2017-10-13 2018-02-16 上海应用技术大学 A kind of preparation method of α halos β amino ketones
CN109836410A (en) * 2019-04-02 2019-06-04 上海应用技术大学 One kind (4,6- diaryl -3,4- dihydro -2H- sulphur pyrans -3- base)-aryl ketone and preparation
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
CN110467549A (en) * 2019-08-26 2019-11-19 上海应用技术大学 A kind of N substitution 2- aminomethyl-1,2, the preparation method of 3,5- triaryl pentane -1,5- diketone
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
CN110467549B (en) * 2019-08-26 2021-09-24 上海应用技术大学 Preparation method of N-substituted 2-aminomethyl-1, 3, 5-triarylpentane-1, 5-diketone
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
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
CN111960961A (en) * 2020-09-17 2020-11-20 河南师范大学 Synthetic method of alpha-amidoketone compound
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

Similar Documents

Publication Publication Date Title
CN106883152A (en) A kind of preparation method of β amino ketones
CN107698469A (en) A kind of preparation method of α halos β amino ketones
CN107903211B (en) Preparation method of 3-halogenated-2, 3-dihydro-4-quinolinone
JP7339677B2 (en) Fluorosulfonyl-containing compounds, intermediates, methods of preparation and uses thereof
CN106349147A (en) Synthetic method of pyrrole derivatives
CN105884663B (en) A kind of preparation method of (Z) sulfonyl olefin(e) acid ester
CN106986800A (en) A kind of preparation method of β carbonyls thioether
CN105712922B (en) The synthetic method of pyrrolin class and azoles
CN104326892A (en) Synthetic method of indanone by gold-catalysis
CN109705001A (en) The method that photocatalysis prepares 3- sulfonyl -1,2- dialin compound
CN108586302A (en) A kind of synthetic method preparing thiosulfonates based on sulfinic acid sodium salt disproportionated reaction
CN102260200A (en) Method for synthesizing phenylsulfone compounds
CN110117237B (en) Preparation method of aromatic nitrile or alkenyl nitrile compound
CN109851544A (en) A kind of preparation method of polysubstituted pyrrole compound
CN105906537A (en) One-pot synthesis method of (Z)-type sulfonyl olefine acid ester compound
CN105481624B (en) The catalysis oxidation synthetic method of Arneel SD
CN103804221B (en) A kind of Preparation Method And Their Intermediate of 4-(4-aminophenyl)-3-morpholone
CN102558046B (en) Solid-phase synthesis method of quinoline compound
JP4283043B2 (en) Process for producing stereoisomer-enriched 4-aryl-4-hydroxybutanoic acid derivatives
CN107056674A (en) A kind of method of suzuki cyclisation coupling one-step synthesis dihydro pyrrole derivates
CN102180794B (en) Method for synthesizing nitrobenzene compounds
Mao et al. A practical, chemoselective approach to O-methylation of carboxylic acids with dimethyl malonate
CN113603655B (en) Preparation method of 4-hydroxy-2-methyl-3- (benzenesulfonyl) thiazolidine-2-carboxylic acid methyl ester compound
CN103772229A (en) Preparation method for aromatic formamide derivative
CN108727323A (en) A kind of method that N-heterocyclic carbine catalyzes and synthesizes trifluoromethyl substitution homoisoflavone class 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
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20170623