CN108586372A - A kind of synthetic method of 2- Fang oxazolin amide compounds - Google Patents
A kind of synthetic method of 2- Fang oxazolin amide compounds Download PDFInfo
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- CN108586372A CN108586372A CN201810416209.4A CN201810416209A CN108586372A CN 108586372 A CN108586372 A CN 108586372A CN 201810416209 A CN201810416209 A CN 201810416209A CN 108586372 A CN108586372 A CN 108586372A
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- amide compounds
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- oxazolin
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- FDLSEUGNQNFTFX-UHFFFAOYSA-N Nc(cccc1)c1C1=NCCO1 Chemical compound Nc(cccc1)c1C1=NCCO1 FDLSEUGNQNFTFX-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of synthetic methods of 2 Fang oxazolin amide compounds, include the following steps：2 oxazolinyl aniline, aryl iodide, alkali, metal palladium compound, organic solvent are sequentially added into reaction vessel, it is stirred at room temperature down and is passed through 10~15min of CO gases, then it is reacted 10~15 hours after reaction system sealing being warming up to 80~100 DEG C, concentrated by rotary evaporation and chromatographic isolation obtain 2 Fang oxazolin amide compounds after reaction.2 Fang oxazolin amide compounds are compound shown in general formula I：R is hydrogen, alkyl, OMe, CF in general formula3Or halogen.Synthesis step of the present invention is easy, CO is cheap and easy to get as starting material and has preferable yield and substrate universality, and in most cases yield is both greater than 90%.The inertia C H bond activations field that the 2 Fang oxazolins amide compounds that this method provides are oriented to base strategy auxiliary in organic synthesis especially bidentate has a very wide range of applications.
Description
Technical field：
The present invention relates to a kind of synthetic methods of compound, more particularly to a kind of 2- Fang oxazolin amide compounds
Synthetic method belongs to metal catalytic technical field.
Background technology：
In recent years, to be reacted to structure C-C keys, C-X keys by transition metal-catalyzed c h bond function dough most effective
One of strategy is a kind of environmental-friendly " Green Chemistry " building-up process.Wherein, 2- Fang oxazolins amide compound is as one
Class N, N- bidentate is oriented to the inertia c h bond function dough reaction that base participates in and achieves a series of progress.Such as：Yu Jinquan etc.
People reports the inertia C (sp of Cu (II) catalysis in succession using 2- Fang oxazolins amides as reaction substrate2)-H keys amidation and
Aryl amination reaction, trifluoromethylation reaction, alkynylation reaction, hydroxylating, coupling reaction etc.
(J.Am.Chem.Soc.2014,136,11590；Angew.Chem.Int.Ed.2014,53,10439；
J.Am.Chem.Soc.2014,136,3354；Org.Lett.2014,16,5666；J.Org.Chem.2015,80,8843；
Org.Lett.2015,17,1228).Chen Guoshu et al. reports the 2- virtue oxazolin amides and 2- mercaptoimidazoles of copper catalysis
Cascade reaction, simplicity have synthesized biologically active polycyclic condensed imidazole simultaneously [2,1-b] [1,3] thiazine ketone compounds
(Adv.Synth.Catal.2016,358,3694).Guo Kai et al. has developed is with noncorrosive nitrite tert-butyl (TBN)
Nitro source, the 2- Fang oxazolin amide regioselectivity C (sp of nickel catalysis2)-H key list nitros and dinitro glycosylation reaction
(Adv.Synth.Catal.2017,359,2596).However using raw material of industry CO simple and easy to get as carbonyl source, single step reaction
The synthesis 2- Fang oxazolins amide compounds of simple and effective also lack corresponding method.
It is used as one kind N in view of 2- virtue oxazolin amide compounds, it is anti-in inertia c h bond function dough that N- bidentates are oriented to base
It answers field to have a wide range of applications, therefore further explores a kind of simple and effective, free of contamination green syt 2- Fang Ji Evil
The method of oxazoline amide compound not only has academic significance, it may have very high practical value.
Invention content：
The technical problem to be solved by the present invention is to：A kind of synthetic method of 2- Fang oxazolin amide compounds is provided,
It is catalyzed reaction by a step efficiently to prepare 2- Fang oxazolin amide compounds.
The present invention is that technical scheme applied to solve the technical problem is as follows：
A kind of synthetic method of 2- Fang oxazolin amide compounds, which is characterized in that include the following steps：Hold to reaction
2- oxazolinyls aniline, aryl iodide, alkali, metal palladium compound, organic solvent are sequentially added in device, are stirred at room temperature down and are passed through
CO 10~15min of gas react 10~15 hours, after reaction after reaction system sealing is then warming up to 80~100 DEG C
Concentrated by rotary evaporation and chromatographic isolation obtain 2- Fang oxazolin amide compounds.2- Fang oxazolins amide compounds are general formula I institutes
The compound shown：
R is hydrogen, alkyl ,-OMe ,-CF in general formula3Or halogen.
The 2- oxazolinyl aniline is general formula II compounds represented；
The aryl iodide is general formula III compound represented；
R is hydrogen, alkyl ,-OMe ,-CF in general formula III3Or any one of halogen；The halogen is in fluorine, chlorine or bromine
It is any.
The alkali is appointing in cesium carbonate, sodium carbonate, sodium bicarbonate, sodium tert-butoxide, potassium phosphate, potassium carbonate or triethylamine
It is a kind of.
The metal palladium compound is PdCl2(CH3CN)2、Pd2(dba)3、Pd(PPh3)4、Pd(OAc)2Or PdCl2。
The organic solvent is any one of toluene, dimethylbenzene or dimethyl sulfoxide (DMSO).
The 2- oxazolinyls aniline, aryl iodide, alkali, metal palladium compound molar ratio be 2- oxazolinyl benzene
Amine, aryl iodide, alkali, metal palladium compound=1.0：(1.0~1.5)：(1.5~3.0)：(0.05~0.1).
The positive effect of the present invention is：
The present invention provides a kind of using raw material of industry CO simple and easy to get as carbonyl source, using Metal Palladium as catalysis
Agent, the new method for being prepared for 2- Fang oxazolin amide compounds of single step reaction convenience and high-efficiency are 2- Fang oxazolin amides
The preparation of compound provides a kind of new path.Simultaneously the catalysts dosage is few, CO is cheap and easy to get as starting material, one
Step reacts and has preferable yield and substrate universality, and in most cases yield is both greater than 90%, has very high reality
With value.
Specific implementation mode：
The technical solution that the invention will now be further described with reference to specific embodiments, by following embodiments contribute into
One step understands the present invention, but does not limit the scope of the invention.
Embodiment 1：
Metal palladium catalyst screening test：By different Metal Palladium compound for catalysis reactions, different yields is obtained.
2- oxazolinyls aniline (32.4mg, 0.20mmol), potassium phosphate are sequentially added into dry Schlenk reaction tubes
(127.0mg, 0.60mmol), iodobenzene (61.2mg, 0.30mmol), metal palladium catalyst (0.02mmol) and dry toluene
(2.0mL), is passed through CO gas 30min under stirring later, and sealing makes reaction system be warming up to 100 DEG C of reaction 15h.Reaction
After, solvent, pillar layer separation (solvent is removed under reduced pressure：Dichloromethane) obtain target compound 1.
Different Metal Palladium compound for catalysis reactions, obtains different reaction results, as shown in table 1 below.
The reaction result of the different Metal Palladium compound for catalysis reaction of table 1
| Entry | Catalyst | Yield (%) |
| 1 | PdCl2(CH3CN)2 | 99 |
| 2 | PdCl2(PPh3)2 | 83 |
| 3 | PdCl2(dppf) | 84 |
| 4 | Pd2(dba)3 | 81 |
| 5 | PdCl2 | 66 |
Embodiment 2：
The preparation method of the following 2- Fang oxazolins amide compound 1 of structural formula：
2- oxazolinyls aniline (32.4mg, 0.20mmol), potassium phosphate are sequentially added into dry Schlenk reaction tubes
(127.0mg, 0.60mmol), iodobenzene (61.2mg, 0.30mmol), PdCl2(CH3CN)2(5.2mg, 0.02mmol) and without water beetle
Benzene (2.0mL), is passed through CO gas 30min under stirring later, and sealing makes reaction system be warming up to 100 DEG C of reaction 15h.Instead
After answering, solvent, pillar layer separation (solvent is removed under reduced pressure：Dichloromethane) obtain target compound 1 (52.7mg, 99%
yield)。1H NMR(400MHz,CDCl3) δ 13.01 (s, 1H), 8.98 (d, J=8.4Hz, 1H), 8.14-8.02 (m, 2H),
7.89 (dd, J=7.9,1.7Hz, 1H), 7.57-7.42 (m, 4H), 7.10 (t, J=7.6Hz, 1H), 4.39 (t, J=9.3Hz,
2H), 4.16 (t, J=9.6Hz, 2H)；13C NMR(100MHz,CDCl3)δ165.9,164.8,140.1,135.2,132.5,
131.6,129.2,128.5,127.7,122.3,119.8,113.5,66.2,54.6。
Embodiment 3：
The preparation method of the following 2- Fang oxazolins amide compound 2 of structural formula：
2- oxazolinyls aniline (32.4mg, 0.20mmol), potassium phosphate are sequentially added into dry Schlenk reaction tubes
(127.0mg, 0.60mmol), 4- methyl iodobenzene (65.4mg, 0.30mmol), PdCl2(CH3CN)2(5.2mg, 0.02mmol) and
Dry toluene (2.0mL), is passed through CO gas 30min under stirring later, and sealing makes reaction system be warming up to 100 DEG C of reactions
15h.After reaction, solvent, pillar layer separation (solvent is removed under reduced pressure：Dichloromethane) obtain target compound 2
(53.8mg, 96%yield).1H NMR(400MHz,CDCl3) δ 12.96 (s, 1H), 8.96 (d, J=9.0Hz, 1H), 7.99
(d, J=8.2Hz, 2H), 7.89 (dd, J=7.9,1.5Hz, 1H), 7.52 (t, J=8.6Hz, 1H), 7.29 (d, J=8.0Hz,
2H), 7.09 (t, J=8.1Hz, 1H), 4.39 (t, J=9.7Hz, 2H), 4.18 (t, J=9.7Hz, 2H), 2.42 (s, 3H)；13C
NMR(100MHz,CDCl3)δ166.1,164.9,142.1,140.3,132.6,132.5,129.2,127.7,122.2,
119.8,113.4,66.2,54.7,21.5。
Embodiment 4：
The preparation method of the following 2- Fang oxazolins amide compound 3 of structural formula：
2- oxazolinyls aniline (32.4mg, 0.20mmol), potassium phosphate are sequentially added into dry Schlenk reaction tubes
(127.0mg, 0.60mmol), 4- methoxyl groups iodobenzene (70.2mg, 0.30mmol), PdCl2(CH3CN)2(5.2mg,0.02mmol)
With dry toluene (2.0mL), CO gas 30min are passed through under stirring later, sealing makes reaction system be warming up to 100 DEG C instead
Answer 15h.After reaction, solvent, pillar layer separation (solvent is removed under reduced pressure：Dichloromethane) obtain target compound 3
(54.5mg, 92%yield).1H NMR(400MHz,CDCl3) δ 12.89 (s, 1H), 8.96 (d, J=8.4Hz, 1H), 8.12-
8.01 (m, 2H), 7.88 (dd, J=7.9,1.4Hz, 1H), 7.51 (t, J=8.6Hz, 1H), 7.08 (t, J=8.1Hz, 1H),
7.00-6.92 (m, 2H), 4.38 (t, J=9.7Hz, 2H), 4.17 (t, J=9.7Hz, 2H), 3.85 (s, 3H)；13C NMR
(100MHz,CDCl3)δ165.6,164.9,162.3,140.4,132.5,129.5,129.2,127.6,122.0,119.7,
113.7,113.3,66.2,55.3,54.6。
Embodiment 5：
The preparation method of the following 2- Fang oxazolins amide compound 4 of structural formula：
2- oxazolinyls aniline (32.4mg, 0.20mmol), potassium phosphate are sequentially added into dry Schlenk reaction tubes
(127.0mg, 0.60mmol), 4- bromo-iodobenzenes (84.9mg, 0.30mmol), PdCl2(CH3CN)2(5.2mg, 0.02mmol) and nothing
Water-toluene (2.0mL), is passed through CO gas 30min under stirring later, and sealing makes reaction system be warming up to 100 DEG C of reactions
15h.After reaction, solvent, pillar layer separation (solvent is removed under reduced pressure：Dichloromethane) obtain target compound 4
(59.4mg, 86%yield).1H NMR(400MHz,CDCl3) δ 13.05 (s, 1H), 8.92 (d, J=8.5Hz, 1H), 7.99-
7.92 (m, 2H), 7.89 (dd, J=7.9,1.5Hz, 1H), 7.67-7.59 (m, 2H), 7.52 (t, J=8.6Hz, 1H), 7.12
(t, J=8.1Hz, 1H), 4.41 (t, J=9.7Hz, 2H), 4.18 (t, J=9.7Hz, 2H)；13C NMR(100MHz,CDCl3)δ
165.0,139.9,134.2,132.7,131.8,129.3,126.4,122.6,119.8,113.5,66.3,54.6。
Embodiment 6：
The preparation method of the following 2- Fang oxazolins amide compound 5 of structural formula：
2- oxazolinyls aniline (32.4mg, 0.20mmol), potassium phosphate are sequentially added into dry Schlenk reaction tubes
(127.0mg, 0.60mmol), 4- trifluoromethyl iodobenzenes (81.6mg, 0.30mmol), PdCl2(CH3CN)2(5.2mg,
0.02mmol) with dry toluene (2.0mL), CO gas 30min are passed through under stirring later, sealing makes reaction system heat up
To 100 DEG C of reaction 15h.After reaction, solvent, pillar layer separation (solvent is removed under reduced pressure：Dichloromethane) obtain targeted
Close object 4 (55.5mg, 83%yield).1H NMR(400MHz,CDCl3) δ 13.16 (s, 1H), 8.93 (d, J=8.3Hz, 1H),
8.18 (d, J=8.2Hz, 2H), 7.89 (dd, J=7.9,1.4Hz, 1H), 7.75 (d, J=8.3Hz, 2H), 7.52 (t, J=
8.6Hz, 1H), 7.12 (t, J=8.1Hz, 1H), 4.41 (t, J=9.6Hz, 2H), 4.18 (t, J=9.4Hz, 2H)；13C NMR
(100MHz,CDCl3)δ165.0,164.5,139.8,138.5,133.2(q,JC-F=32.6Hz), 132.7,129.3,
128.1,125.6(q,JC-F=3.7Hz), 123.8 (q, JC-F=270.9Hz), 122.8,119.8,113.6,66.3,54.6.
Claims (7)
1. a kind of synthetic method of 2- Fang oxazolin amide compounds, which is characterized in that include the following steps：To reaction vessel
In sequentially add 2- oxazolinyls aniline, aryl iodide, alkali, metal palladium compound, organic solvent, be stirred at room temperature down and be passed through CO
10~15min of gas is reacted 10~15 hours after reaction system sealing is then warming up to 80~100 DEG C, is revolved after reaction
Inspissation contracts and chromatographic isolation obtains 2- Fang oxazolin amide compounds；2- Fang oxazolin amide compounds are shown in general formula I
Compound：
R is hydrogen, alkyl ,-OMe ,-CF in general formula3Or halogen.
2. the synthetic method of 2- Fang oxazolin amide compounds according to claim 1, it is characterised in that：The 2-
Oxazolinyl aniline is general formula II compounds represented.
3. the synthetic method of 2- Fang oxazolin amide compounds according to claim 1, it is characterised in that：The virtue
Base iodide are general formula III compound represented；
R is hydrogen, alkyl ,-OMe ,-CF in general formula III3Or any one of halogen；The halogen is any in fluorine, chlorine or bromine
Kind.
4. the synthetic method of 2- Fang oxazolin amide compounds according to claim 1, it is characterised in that：The alkali
For any one of cesium carbonate, sodium carbonate, sodium bicarbonate, sodium tert-butoxide, potassium phosphate, potassium carbonate or triethylamine.
5. the synthetic method of 2- Fang oxazolin amide compounds according to claim 1, it is characterised in that：The gold
Category palladium compound is PdCl2(CH3CN)2、Pd2(dba)3、Pd(PPh3)4、Pd(OAc)2Or PdCl2。
6. the synthetic method of 2- Fang oxazolin amide compounds according to claim 1, it is characterised in that：Described has
Solvent is any one of toluene, dimethylbenzene or dimethyl sulfoxide (DMSO).
7. the synthetic method of 2- Fang oxazolin amide compounds according to claim 1, it is characterised in that：The 2-
Oxazolinyl aniline, aryl iodide, alkali, metal palladium compound molar ratio be 2- oxazolinyls aniline, aryl iodide,
Alkali, metal palladium compound=1.0：(1.0~1.5)：(1.5~3.0)：(0.05~0.1).
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112441987A (en) * | 2019-08-31 | 2021-03-05 | 商丘师范学院 | Synthesis method of halogen oxazoline compound |
| CN115433141A (en) * | 2022-09-06 | 2022-12-06 | 贵州大学 | Alpha-oximido phenylacetamide compound, preparation method thereof and application thereof as agricultural bactericide |
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| CN102046577A (en) * | 2008-05-27 | 2011-05-04 | 巴斯夫欧洲公司 | Method for producing aromatic and heteroaromatic carboxylic acids, carboxylic acid esters and carboxylic acid amides |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112441987A (en) * | 2019-08-31 | 2021-03-05 | 商丘师范学院 | Synthesis method of halogen oxazoline compound |
| CN115433141A (en) * | 2022-09-06 | 2022-12-06 | 贵州大学 | Alpha-oximido phenylacetamide compound, preparation method thereof and application thereof as agricultural bactericide |
| CN115433141B (en) * | 2022-09-06 | 2023-08-22 | 贵州大学 | Alpha-oximino phenylacetamide compound, preparation method thereof and application thereof as agricultural bactericide |
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