CN109020935A - A kind of dibenzofuran derivative and preparation method thereof - Google Patents

A kind of dibenzofuran derivative and preparation method thereof Download PDF

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CN109020935A
CN109020935A CN201811183093.0A CN201811183093A CN109020935A CN 109020935 A CN109020935 A CN 109020935A CN 201811183093 A CN201811183093 A CN 201811183093A CN 109020935 A CN109020935 A CN 109020935A
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derivative
preparation
dibenzofuran derivative
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dibenzofurans
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郭旺军
刘英哲
张�杰
刘亚东
刘建群
伍致生
宋新潮
王户生
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Xian Modern Chemistry Research Institute
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention belongs to organic photoelectrical material technical fields, and in particular to a kind of dibenzofuran derivative and preparation method thereof.O-dibromobenzene and fortified phenol are dissolved in organic solvent by the present invention using one kettle way, back flow reaction 10 hours, inner molecular reaction then occur under the action of catalyst, it can 80% yield obtains substituted diphenylamine benzofuran derivs.The present invention has the advantages that raw material sources are extensive, economic, simple to operate, the easily separated purifying of product.In addition, substituted diphenylamine benzofuran derivs according to the present invention, can simply obtain polyfunctional group substitution product, it can be carried out next step derivative, synthesis series is the material of parent based on dibenzofurans, such material is electron-donating and conjugacy is strong, is expected to be used as organic photoelectrical material field.

Description

A kind of dibenzofuran derivative and preparation method thereof
Technical field
The invention belongs to organic photoelectric technical fields, and in particular to a kind of dibenzofuran derivative and preparation method thereof.
Background technique
Benzofuran derivatives are widely present in natural products, drug, bioactive molecule and organic functional material, Many natural products with dibenzofurans ring skeleton have good physiological activity, are a kind of important organic compounds Object, while dibenzofurans and its derivative are also important organic synthesis intermediate, can be used to synthetic compound, jeterocyclic chemistry Close object, drug molecule and a variety of materials molecule.Therefore, the synthesis of benzofuran derivatives is all weight in organic synthesis all the time One of research field wanted.Substituted dibenzofurans is important benzofuran derivatives, about their synthesis side Method is broadly divided into traditional synthetic method and transition metal-catalyzed method two types.
Traditional synthetic method usually requires longer reaction step, harsh reaction condition, and to the appearance of functional group Degree of bearing is limited, limits its scope of application.Transition metal-catalyzed reaction has easy to operate, mild condition, high efficiency mostly The advantages that with extensive substrate spectrum, causes the concern of vast chemist gradually.According to the difference of substrate, transition metal The synthetic method for being catalyzed dibenzofurans mainly includes o-phenyl phenol class and diaryl ether compound object inner molecular reaction method. Early in 1974, the palladium acetate that Itatuni etc. reports equivalent promoted diaryl ether intramolecular cyclization synthesis dibenzofurans to spread out Biology, but this method is expensive, product yield is lower, reaction selectivity it is uncontrollable (Angew.Chem.Int.Ed, 1974,13,471).2006, Fagnou synthesized dibenzofurans using the halogenated diaryl ether of palladium chtalyst, worked well, but bottom Object range is relatively narrow, and universality is poor (J.Am.Chem.Soc., 2006,128,581).It is blue relative to transition metal-catalyzed method State university Pan Xin second mining prepared after diazotising with o-nitrodiphenyl ether dibenzofuran derivative (applied chemistry, 2004,21, 20), this method substrate spectrum is narrow, expensive raw material price, and functional group's tolerance is poor.
Currently, the synthetic method for dibenzofurans focuses mostly in transition metal-catalyzed diaryl ether compound object molecule Intramolecular cyclization obtains, such method efficiency is higher, and condition is more mild, and substrate spectrum is wider, but there is still a need for synthesis with special How the diaryl ether compound object of structure more economically efficiently synthesizes to obtain dibenzofurans compound as urgently to be resolved Problem.
Summary of the invention
The deficiencies of in order to overcome cumbersome existing dibenzofurans compound route, at high cost, poor selectivity, the present invention provide A kind of one kettle way prepares dibenzofurans compound, synthesizes two virtues with phenol analog derivative by simple o-dibromobenzene derivative Then pyridyl ethers compound obtains dibenzofurans compound under conditions of metal catalytic.This method is easy to operate, it is efficient, Raw material sources are extensive, product it is easily separated purifying, be easy to modification, organic photoelectrical material and drug molecule synthesis have compared with Good application prospect.
Inventive concept: diphenyl ether is synthesized using from a wealth of sources, cheap o-dibromobenzene derivative and phenol derivatives Derivative prepares dibenzofuran derivative using metal catalytic cyclisation is crossed, and reduces cost, expands substrate reactions range.Base In the above thinking, the present invention using one kettle way by after o-dibromobenzene derivative and phenol derivatives synthesis diphenyl ether derivative by Metal catalytic cyclisation is crossed, the synthetic route that one kettle way prepares dibenzofuran derivative is had devised, in organic photoelectric material The fields such as material, drug are applied.
A kind of dibenzofuran derivative, structural formula are as follows:
Wherein R1, R2For hydrogen atom, fluorine atom, chlorine atom, C1~C8Alkyl, C1~C8Alkoxy, nitro, cyano, Ester group, trifluoromethyl, the derivative using one kettle way prepare, specific steps are as follows: by o-dibromobenzene derivative, phenol derivatives, Potassium carbonate and copper oxide (molar ratio is 1:1~1.2:0.5~3:1~5) are dissolved in organic solvent (optional N, N- dimethyl formyl One of amine, toluene, Isosorbide-5-Nitrae-dioxane, dimethyl sulfoxide are a variety of) in, it is back flow reaction 3~12 hours, cooling, it filters.Nitrogen Under gas shielded, by above-mentioned filtrate, inorganic base, (one of optional potassium carbonate, potassium hydroxide, potassium tert-butoxide, sodium hydroxide are more Kind), catalyst (optional Pd (OAc)2、PdCl2(PPh3)2、Pd(PPh3)4、Pd2(dba)3It is one or more) and ligand it is (optional PCy3·HBF4、PBut 3·HBF4、PPh3, DPPF it is one or more) (molar ratio be 1:1~3:0.01~0.1:0.01~ 0.2) be mixed in reaction flask, 80~140 DEG C are reacted 10~12 hours, it is cooling after through extraction, drying, concentration, column chromatography or again Crystallization purifying, it can the separation yield of 80%-92% obtains dibenzofuran derivative.
Main advantages of the present invention:
1. one pot process dibenzofuran derivative route has easy to operate, convenient post-treatment, low in cost, yield It is high.
2. the dibenzofuran derivative of synthesis has the wide substrate scope of application, good regioselectivity.
3. the dibenzofuran derivative functional group compatibility of synthesis is good, can further be modified by chemical reaction, Obtain other derivatives.
Specific embodiment
Below by specific embodiment the present invention will be further explained explanation.
The preparation route of dibenzofuran derivative is as follows, is starting with o-dibromobenzene derivative and phenol derivatives Raw material, is substituted reaction and ring closure reaction process obtains, and ultimately generates dibenzofurans bioxindol derivative, detailed in Example 1- 6。
Embodiment 1
3- methoxyl group dibenzofurans synthetic route is as follows:
O-dibromobenzene (0.235g, 1mmol) is added in 25mL single necked round bottom flask, meta-methoxy phenol (0.148g, 1.2mmol), potassium carbonate (0.069g, 0.5mmol) and copper oxide (0.079g, 1mmol) are dissolved in 5mL DMF, according to adding under stirring Hot back flow reaction 3 hours, is cooled to room temperature, and filters, and collects filtrate.Under nitrogen protection, by filtrate, Pd (OAc)2(0.011g, 5%mmol), PCy3·HBF4(0.0368g, 10%mmol) and potassium carbonate (0.345g, 2.5mmol) are added to 25mL there-necked flask In, reaction system is heated to 130 DEG C, is reacted 12 hours.Reaction terminates, and is cooled to room temperature, and suitable quantity of water is added, and ether extracts, Anhydrous sodium sulfate is dry, and rotation removes solvent, and crystallizing from ether obtains 0.18 gram of white solid, yield 91%.1H NMR(500MHz,CDCl3) δ7.89-7.66(m,3H),7.38-6.98(m,4H),3.83(s,3H).13C NMR(126MHz,CDCl3)δ,160.7, 157.6,147,134,123.3,120.9,96.3,55.8.
Embodiment 2
The fluoro- 7- methoxyl group dibenzofurans synthetic route of 2- is as follows:
O-dibromobenzene (0.253g, 1mmol) is added in 25mL single necked round bottom flask, meta-methoxy phenol (0.148g, 1.2mmol), potassium carbonate (0.069g, 0.5mmol) and copper oxide (0.079g, 1mmol) are dissolved in 5mL DMF, according to adding under stirring Hot back flow reaction 3 hours, is cooled to room temperature, and filters, and collects filtrate.Under nitrogen protection, by filtrate, Pd (OAc)2(0.011g, 5%mmol), PCy3·HBF4(0.0368g, 10%mmol) and potassium carbonate (0.345g, 2.5mmol) are added to 25mL there-necked flask In, reaction system is heated to 130 DEG C, is reacted 12 hours.Reaction terminates, and is cooled to room temperature, and suitable quantity of water is added, and ether extracts, Anhydrous sodium sulfate is dry, and rotation removes solvent, and crystallizing from ether obtains 0.18 gram of white solid, yield 83%.1H NMR(500MHz,CDCl3) δ7.78-7.64(m,2H),7.52-7.35(m,2H),7.22-6.90(m,2H),3.73(s,3H).13C NMR(126MHz, CDCl3)δ,162.4,158.3,157.4,147.3,133.2,123.0,122.3,99.7,60.3.
Embodiment 3
5- dibenzofurans methyl formate synthetic route is as follows:
O-dibromobenzene (0.235g, 1mmol) is added in 25mL flask, NSC 40536 (0.182g, 1.2mmol), potassium carbonate (0.069g, 0.5mmol) and copper oxide (0.079g, 1mmol) are dissolved in 5mL DMF, according to adding under stirring Hot back flow reaction 3 hours, is cooled to room temperature, and filters, and collects filtrate.Under nitrogen protection, by filtrate, Pd (OAc)2(0.011g, 5%mmol), PCy3·HBF4(0.0368g, 10%mmol) and potassium carbonate (0.345g, 2.5mmol) are added to 25mL there-necked flask In, reaction system is heated to 130 DEG C, is reacted 12 hours.Reaction terminates, and is cooled to room temperature, and suitable quantity of water is added, and ether extracts, Anhydrous sodium sulfate is dry, and rotation removes solvent, and crystallizing from ether obtains 0.19 gram of colorless oil, yield 85%.1H NMR(500MHz, CDCl3) δ 8.19 (d, J=7.5Hz, 1H), 7.89-7.87 (m, 2H), 7.66-7.49 (m, 2H), 7.38-7.32 (m, 2H), 3.90(s,3H).13C NMR(126MHz,CDCl3)δ,165.9,156.5,148.2,126.1,123.8,120.9,115.3, 51.5.
Embodiment 4
2- nitro dibenzofurans synthetic route is as follows:
O-dibromobenzene (0.235g, 1mmol) is added in 25mL flask, o-nitrophenol (0.167g, 1.2mmol), carbon Sour potassium (0.069g, 0.5mmol) and copper oxide (0.079g, 1mmol) are dissolved in 5mL DMF, according to heating reflux reaction 3 under stirring Hour, it is cooled to room temperature, filters, collect filtrate.Under nitrogen protection, by filtrate, Pd (OAc)2(0.011g, 5%mmol), PCy3·HBF4(0.0368g, 10%mmol) and potassium carbonate (0.345g, 2.5mmol) are added in 25mL there-necked flask, will be reacted System is heated to 130 DEG C, reacts 12 hours.Reaction terminates, and is cooled to room temperature, and suitable quantity of water, ether extraction, anhydrous sodium sulfate is added Dry, rotation removes solvent, and crystallizing from ether obtains 0.17 gram of white solid, yield 80%.1H NMR(500MHz,CDCl3)δ8.28(d,J =7.5Hz, 1H), 8.12 (d, J=7.5Hz, 1H), 7.89 (d, J=7.5Hz, 1H), 7.66-7.59 (m, 2H), 7.45-7.30 (m,2H).13C NMR(126MHz,CDCl3)δ,156.5,138.5,134.2,131.2,127.1,124.6,120.9,120.2.
Embodiment 5
4- trifluoromethyl dibenzofurans synthetic route is as follows:
O-dibromobenzene (0.235g, 1mmol) is added in 25mL single necked round bottom flask, 4- trifloro methyl phenol (0.194g, 1.2mmol), potassium carbonate (0.069g, 0.5mmol) and copper oxide (0.079g, 1mmol) are dissolved in 5mL DMF, according to adding under stirring Hot back flow reaction 3 hours, is cooled to room temperature, and filters, and collects filtrate.Under nitrogen protection, by filtrate, Pd (OAc)2(0.011g, 5%mmol), PCy3·HBF4(0.0368g, 10%mmol) and potassium carbonate (0.345g, 2.5mmol) are added to 25mL there-necked flask In, reaction system is heated to 130 DEG C, is reacted 12 hours.Reaction terminates, and is cooled to room temperature, and suitable quantity of water is added, and ether extracts, Anhydrous sodium sulfate is dry, and rotation removes solvent, and crystallizing from ether obtains 0.194 gram of white solid, yield 82%.1H NMR(500MHz, CDCl3) δ 7.92 (d, J=7.5Hz, 1H), 7.69-7.53 (m, 3H), 7.48-7.28 (m, 3H)13C NMR(126MHz, CDCl3)δ160.7,146.0,135.3,133.5,125.8(m),123.1,122.3,110.6,106.4.
Embodiment 6
3- butyl dibenzofurans synthetic route is as follows:
O-dibromobenzene (0.235g, 1mmol) is added in 25mL single necked round bottom flask, butylphenol (0.180g, 1.2mmol), potassium carbonate (0.069g, 0.5mmol) and copper oxide (0.079g, 1mmol) are dissolved in 5mL DMF, according to adding under stirring Hot back flow reaction 3 hours, is cooled to room temperature, and filters, and collects filtrate.Under nitrogen protection, by filtrate, Pd (OAc)2(0.011g, 5%mmol), PCy3·HBF4(0.0368g, 10%mmol) and potassium carbonate (0.345g, 2.5mmol) are added to 25mL there-necked flask In, reaction system is heated to 130 DEG C, is reacted 12 hours.Reaction terminates, and is cooled to room temperature, and suitable quantity of water is added, and ether extracts, Anhydrous sodium sulfate is dry, and rotation removes solvent, and crystallizing from ether obtains 0.186 gram of white solid, yield 83%.1H NMR(500MHz, CDCl3) δ 7.89-7.80 (m, 2H), 7.66 (d, J=7.5Hz, 1H), 7.40-7.30 (m, 2H), 7.23 (s, 1H), 6.99 (d, J=7.5Hz, 1H), 2.62 (t, J=7.5Hz, 2H), 1.59-1.31 (m, 4H), 0.92 (t, J=7.5Hz, 3H)13C NMR (126MHz,CDCl3)δ160.9,146.2,135.2,134.2,128.6,120.6,115.9,113.6,35.8,33.6, 22.3,14.3.

Claims (6)

1. a kind of dibenzofuran derivative, it is characterised in that its structural formula are as follows:
Wherein R1、R2Respectively hydrogen atom, fluorine atom, chlorine atom, C1~C8Alkyl, C1~C8Alkoxy, nitro, cyano, Ester group or trifluoromethyl.
2. a kind of preparation method of dibenzofuran derivative described in claim 1, it is characterised in that step are as follows: be by molar ratio 1:1~1.2:0.5~3:1~5 o-dibromobenzene derivative, phenol derivatives, potassium carbonate and copper oxide are dissolved in organic solvent, It is back flow reaction 3~12 hours, cooling, it filters；Under nitrogen protection, above-mentioned filtrate, inorganic base, catalyst and ligand are mixed in instead It answers in bottle, molar ratio is 1:1~3:0.01~0.1:0.01~0.2, and 80~140 DEG C are reacted 10~12 hours, is passed through after cooling Extraction, dry, concentration, column chromatography or recrystallization purifying, it can it is derivative that the separation yield of 80%-92% obtains dibenzofurans Object.
3. the preparation method of dibenzofuran derivative as claimed in claim 2, it is characterised in that the organic solvent is One of N,N-dimethylformamide, toluene, 1,4- dioxane, dimethyl sulfoxide are a variety of.
4. the preparation method of dibenzofuran derivative as claimed in claim 2, it is characterised in that the inorganic base is carbon One of sour potassium, potassium hydroxide, potassium tert-butoxide are a variety of.
5. the preparation method of dibenzofuran derivative as claimed in claim 2, it is characterised in that the catalyst is Pd (OAc)2、PdCl2(PPh3)2、Pd(PPh3)4、Pd2(dba)3It is one or more.
6. the preparation method of dibenzofuran derivative as claimed in claim 2, it is characterised in that the ligand is PCy3· HBF4、PBut 3·HBF4、PPh3, one of DPPF or a variety of.
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CN115960062A (en) * 2023-01-31 2023-04-14 中钢集团南京新材料研究院有限公司 Preparation method of 9-chloronaphtho [2,3-b ] benzofuran

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