CN107629028B - A method of furan derivatives are synthesized based on intermolecular ring-closure reaction - Google Patents
A method of furan derivatives are synthesized based on intermolecular ring-closure reaction Download PDFInfo
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Abstract
The invention discloses a kind of methods based on intermolecular ring-closure reaction synthesis furan derivatives, and this method is by acetophenone compounds and dimethyl sulfoxide, and one pot reaction in the presence of tetraalkylammonium iodides catalyst and potassium persulfate oxidation agent obtains furan derivatives；This method enriches furan derivatives type, provides more intermediates for pharmaceutical synthesis, and raw material sources are wide, step is simple, reaction condition is mild, high income, are conducive to industrialized production.
Description
Technical field
The present invention relates to a kind of synthetic methods of substituted furan, in particular to one kind is by acetophenone compounds and dimethyl
The method that sulfoxide generates furan derivatives by potassium persulfate oxidation single step reaction under tetraalkylammonium iodides catalytic action, belongs to
Pharmaceutical intermediate synthesizes field.
Background technique
Furan derivatives are organic or pharmaceutical synthesis a kind of important raw material or intermediate.In the prior art, relative complex
Furan derivatives drug class is often relied on to be extracted from natural plants, as Chinese patent (publication number: 101830871A) discloses
A method of it extracting furan derivatives from Snakegourd Fruit fruit, is specifically extracted, chromatographic isolation, be can be used for using ethyl alcohol
The furan derivatives drug of various diseases caused by complement system transition activation is treated, it is this to rely on extracted form natural plant furans
The method of derivative is at high cost, and yield is low, strong to natural resources dependent form.And simple furan derivatives can use furans original
Material mainly has aromatic ring property using furan nucleus, by carrying out the parental materials such as halogenation, nitrification, sulfonation, acylation to it to synthesize
Reaction, obtains different substitution products, as (" synthesis of 2- acetyl furan ", petrochemical industry, 2008, volume 37 increased document
Periodical, 328-330) disclose a kind of 2- acetyl furan that can be used for pharmaceutical intermediate and food additives, mainly using iodine,
Phosphoric acid etc. is used as catalyst, synthesizes 2- acetyl furan by acetic anhydride and furans.And it can also be with by simple furan derivatives
Further progress modification, it is hereby achieved that relative complex furan derivatives, as document (" grind by the synthesis of 2- furan boronic acid
Study carefully ", Hebei University of Science and Technology's journal, in April, 2012, the 2nd phase of volume 33,103-106 pages) it discloses by 2- bromine furans and boric acid three
Butyl ester is raw material, has synthesized 2- furan boronic acid using n-BuLi method, 2- furan boronic acid can be anti-by Suzuki cross-coupling
SP should be constructed2Type C-C singly-bound, it is hereby achieved that the furan derivatives of the substituent groups such as various aromatic rings.These pass through in furan
The method for directly synthesizing furan derivatives on ring by the methods of substitution reaction of muttering is influenced by furan nucleus electronic effect, is replaced
The quantity of base group modification and position are limited.Currently, also have the synthesis that furan derivatives are realized by directly synthesizing furan nucleus, and
Complicated substituent group can be directly introduced from raw material, more classical is that Paal-Knorr reaction is derivative for synthesizing furans
Object generates Furan and its derivatives if Isosorbide-5-Nitrae-dicarbonyl compound is dehydrated under anhydrous acid condition, and reaction equation is as follows:Wherein, tert-butyl can also be replaced using other groups, it is hereby achieved that 2
The furan derivatives of position and 5 substitutions.But this method is difficult to obtain using Isosorbide-5-Nitrae-cyclohexadione compounds itself, limits the party
The application of method.
Summary of the invention
For it is existing synthesis furan derivatives method there are the shortcomings that, the purpose of the invention is to provide one kind by
Acetophenone compounds and dimethyl sulfoxide are raw by potassium persulfate oxidation single step reaction under tetraalkylammonium iodides catalytic action
At the method for furan derivatives, this method enriches furan derivatives type, provides more intermediates, and raw material for pharmaceutical synthesis
Source is wide, step is simple, reaction condition is mild, high income, is conducive to industrialized production.
In order to achieve the above technical purposes, the present invention provides one kind synthesizes furan derivatives based on intermolecular ring-closure reaction
Method, 1 acetophenone compounds of formula and dimethyl sulfoxide, one pot in the presence of tetraalkylammonium iodides and potassium persulfate oxidation agent
Reaction, obtains 2 furan derivatives of formula；
Wherein, R is hydrogen, halogenic substituent, trifluoromethyl, nitro, alkyl, alkoxy or methyl mercapto.
Preferred scheme, substituted-phenyl in acetophenone compounds is for example adjacent// p-bromophenyl, neighbour// to chlorobenzene
Base, neighbour/to trifluoromethyl, neighbour// p-methylphenyl, neighbour/m-nitro base, neighbour/to methoxyl group, to methyl mercapto, to tert-butyl benzene
Base etc..Acetophenone compounds containing these substituent groups can obtain higher receipts during synthesizing corresponding furan derivatives
Rate.
Preferred scheme, concentration of the acetophenone compounds in dimethyl sulfoxide are 0.2~0.9mol/L；It is more excellent
It is selected as 0.2~0.3mol/L.
Preferred scheme, the mole of the tetraalkylammonium iodides are the 20~40% of acetophenone compounds mole；
More preferably 25~35%.
More preferably scheme, the tetraalkylammonium iodides include tetrabutylammonium iodide, tetraethyl ammonium iodide, tetramethyl iodate
At least one of ammonium；More preferably tetrabutylammonium iodide.
Preferred scheme, the mole of the potassium persulfate oxidation agent are 2~3 times of acetophenone compounds mole.
It is more preferably 2~2.5 times.
Preferred scheme, the condition of the reaction: reaction temperature is 90~140 DEG C, and the reaction time is 5~11h.Further
Preferred condition: reaction temperature is 100~130 DEG C, and the reaction time is 6~10h.
Tetraalkylammonium iodides are used as catalyst in technical solution of the present invention, and potassium peroxydisulfate is made as oxidant
With.Furan derivatives are passed through by two molecule acetophenone compounds and a molecule dimethyl sulfoxide to be cyclized, wherein a molecule
The methyl of the acetyl group of acetophenone compounds, the methyl of a molecule acetophenone compounds and a molecule dimethyl sulfoxide exists
It is cyclized under tetraalkylammonium iodides catalyst and potassium persulfate oxidation agent effect, so that acquisition 2,3 and 5 is simultaneously-substituted
Furan derivatives.There are two important roles for dimethyl sulfoxide tool in technical solution of the present invention, on the one hand good as dissolubility
Reaction efficiency can be improved in organic solvent, is on the other hand used as reaction substrate, one methyl participates in cyclisation, another methyl
Modification is on the furan nucleus of formation in the form of methyl mercapto.
Compared with the prior art, technical solution of the present invention bring advantageous effects:
1) technical solution of the present invention realizes that carrying out oxidative cyclization with dimethyl sulfoxide by acetophenone compounds obtains for the first time
Furan derivatives provide a kind of new thought for synthesis furan derivatives.
2) technical solution of the present invention uses conventional acetophenone compounds and dimethyl sulfoxide as raw material, relatively existing
Some 1,4- cyclohexadione compounds raw materials have the advantages that at low cost.
3) technical solution of the present invention step is simple, reaction condition is mild, and furan derivatives may be implemented by one kettle way
Synthesis, and reaction yield is high, is conducive to be mass produced.
4) aryl and methyl mercapto that the furan derivatives of technical solution of the present invention synthesis include are easy modification group again,
There is apparent advantage as nitrofurans synthetic intermediate.
Detailed description of the invention
[Fig. 1] is the 1H NMR spectra of furan derivatives in embodiment 1；
[Fig. 2] is the 13C NMR spectra of furan derivatives in embodiment 1；
[Fig. 3] is the 1H NMR spectra of furan derivatives in embodiment 2；
[Fig. 4] is the 13C NMR spectra of furan derivatives in embodiment 2.
Specific embodiment
Following embodiment is intended to further illustrate the content of present invention, rather than limits the protection model of the claims in the present invention
It encloses.
Substrate raw material and solvent etc. involved in following embodiment are commercially available commercial product (analytical reagents), and
And it is not further purified.
Product separation uses chromatography, chromatographic column silica gel (300-400 mesh).
1H NMR (400MHz), 13C NMR (100MHz), with CDCl3For solvent, using TMS as internal standard.
Multiplicity is defined as follows: s (unimodal)；D (doublet)；T (triplet)；Q (quartet) and m (multiplet).Coupling
Constant J (hertz).
Condition optimizing experiment: optimum reaction condition is found by following control experiment group: with acetophenone and dimethyl sulfoxide
For reaction raw materials, while excess dimethyl sulfoxide is illustrated as reaction dissolvent, and specific reaction is as follows:
It weighs catalyst, acetophenone, oxidant to be placed in the reaction tube of 25mL, dimethyl sulfoxide (DMSO) is added as molten
Agent, mixed liquor are heated under the conditions of certain temperature in air atmosphere, are stirred to react.Reaction solution is cooled to room temperature, using acetic acid
Ethyl ester (10mL) is diluted reaction solution, washes (5mL), is extracted using ethyl acetate (5mL × 3) to reaction solution, extracts
Organic phase after taking is dried using anhydrous sodium sulfate, then solvent is spin-dried for by filtering with Rotary Evaporators.Object after concentration
Matter carries out separating-purifying (eluant, eluent is petrol ether/ethyl acetate) using silica gel column chromatography, obtains final product.
1~12 reaction condition of control experiment group: acetophenone (0.5mmol), DMSO (2.0mL), catalyst (30mol%),
Oxidant (1.0mmol), reaction time 8h.
The DMSO (1.0mL) of control experiment group 13, other conditions are identical as experimental group 1.
The DMSO (3.0mL) of control experiment group 14, other conditions are identical as experimental group 1.
The TBAI (10mol%) of control experiment group 15, other conditions are identical as experimental group 1.
The TBAI (50mol%) of control experiment group 16, other conditions are identical as experimental group 1.
React equal under the catalysis such as TBAI, TEAI, TBAB, TBAC, KI from can be seen that in control experiment group 1~5 in table
It can go on smoothly, but tetrabutylammonium iodide is compared TBAB, TBAC etc. and potassium iodide with tetraethyl ammonium iodide and had preferably
Catalytic activity, the furan derivatives yield accordingly obtained are higher.
It is carried out from can be seen that in control experiment group 1 and 6~10 in table in addition to persulfate can make to react, other routines
Oxidant such as hydrogen peroxide, oxygen, peroxide TBHP etc. all cannot achieve the synthesis of furan derivatives, and in persulfate,
It is best with the effect of potassium peroxydisulfate, it can obtain ideal yield, and (NH4)2S2O8、KHSO5Although reaction can be made to carry out, receive
Rate is unsatisfactory.
From can be seen that in control experiment group 1 and 11~12 in table, reaction temperature is too high or too low, and yield all can accordingly drop
It is low, optimal reaction effect can be reached at 120 DEG C or so.
To sum up control experiment group 1~16 can obtain optimal reaction condition: acetophenone (0.5mmol), and methyl sulfoxide
(2mL), TBAI (0.15mmol), K2S2O8(1.0mmol), 120 DEG C, 8h.
It is reacted according to the optimum reaction condition after above-mentioned optimization following example 1~18:
Embodiment 1
Raw material: acetophenone；
Target product:
Yield: 83%；
1H NMR(400MHz,CDCl3): δ 8.05 (dd, J=13.7,7.6Hz, 1H), 7.65-7.59 (m, 1H), 7.53
(t, J=7.1Hz, 1H), 7.48 (t, J=7.1Hz, 1H), 7.43-7.37 (m, 1H), 7.35 (s, 1H), 2.48 (s, 1H)
13C NMR(101MHz,CDCl3):δ181.8,153.8,150.3,137.2,132.6,129.5,129.3,
129.1,128.7,128.5,126.5,124.1,118.1,18.1.
Embodiment 2
Raw material: 2- bromoacetophenone；
Target product:
Yield: 62%；
1H NMR(400MHz,CDCl3): δ 7.67 (t, J=7.7Hz, 1H), 7.52 (d, J=7.3Hz, 1H), 7.36
(ddd, J=26.3,15.5,7.6Hz, 2H), 7.22 (s, 1H), 2.34 (s, 1H)
13C NMR(100MHz,CDCl3):δ182.4,155.4,150.8,139.1,133.4,133.4,132.3,
131.7,131.3,130.1,129.4,127.1,127.1,123.6,123.4,120.9,120.0,18.1.
Embodiment 3
Raw material: 2- trifluoromethyl acetophenone；
Target product:
Yield: 50%；
1H NMR(400MHz,CDCl3): δ 7.79-7.74 (m, 1H), 7.67-7.60 (m, 2H), 7.57 (t, J=6.4Hz,
1H),7.30(s,1H),2.33(s,1H).
13C NMR(100MHz,CDCl3):δ182.4,153.6,151.3,136.4,132.2,131.5,131.3,
(130.3,130.0,129.6,129.3,128.4,127.0 q, J=5.1Hz), 126.7,126.7 (dd, J=8.7,3.9Hz),
124.9,124.7,122.7,120.8,18.0.
Embodiment 4
Raw material: 2- methyl acetophenone；
Target product:
Yield: 74%；
1H NMR(400MHz,CDCl3): δ 7.53 (d, J=7.5Hz, 1H), 7.40 (t, J=7.4Hz, 1H), 7.37-
7.27(m,2H),7.15(s,1H),2.43(s,2H),2.40(s,1H),2.32(s,1H).
13C NMR(100MHz,CDCl3):δ184.5,156.8,151.4,137.8,137.3,137.2,131.2,
130.9,130.7,130.2,129.8,128.4,128.3,125.5,125.1,123.7,119.,20.7,19.8,18.1.
Embodiment 5
Raw material: 2- chloro-acetophenone；
Target product:
Yield: 65%；
1H NMR(400MHz,CDCl3): δ 7.55 (t, J=8.4Hz, 1H), 7.46 (dd, J=19.9,8.6Hz, 1H),
7.42–7.32(m,1H),7.23(s,1H),2.35(s,1H).
13C NMR(100MHz,CDCl3):δ181.6,154.0,151.2,137.1,133.9,131.9,131.8,
131.7,131.3,131.1,130.3,130.3,129.4,128.0,126.5,123.4,121.1,18.0。
Embodiment 6
Raw material: 2- nitro-acetophenone；
Target product:
Yield: 64%；
1H NMR(400MHz,CDCl3): δ 8.21 (d, J=8.2Hz, 1H), 7.92 (d, J=8.1Hz, 1H), 7.82 (t, J
=7.5Hz, 1H), 7.72 (dd, J=21.5,7.4Hz, 3H), 7.59 (dd, J=15.5,7.6Hz,
2H),7.40(s,1H),2.41(s,3H).
13C NMR(100MHz,CDCl3):δ180.5,151.2,150.6,148.1,146.8,134.2,
133.9,132.7,131.4,131.2,130.4,129.2,124.7,124.4,123.0,121.6,121.4,
17.9.
Embodiment 7
Raw material: 2- methoxyl group benzoylformaldoxime；
Target product:
Yield: 70%；
1H NMR(400MHz,CDCl3): δ 7.53 (d, J=7.5Hz, 1H), 7.47 (t, J=8.9Hz, 2H), 7.39 (dd,
J=14.8,6.8Hz, 1H), 7.14 (s, 1H), 7.06-6.94 (m, 4H), 3.86 (s, 3H), 3.83 (s, 3H), 2.32 (s,
3H).
13C NMR(100MHz,CDCl3):δ182.3,157.5,157.2,153.4,151.6,132.2,131.2,
130.7,129.69,127.8,123.1,120.4,120.2,120.2,118.4,111.6,111.3,55.8,55.5,17.8.
Embodiment 8
Raw material: 3- bromoacetophenone；
Target product:
Yield: 84%；
1H NMR(400MHz,CDCl3): δ 8.19 (s, 1H), 8.17 (s, 1H), 7.96 (dd, J=15.7,7.8Hz, 2H),
7.74 (d, J=7.9Hz, 1H), 7.52 (t, J=9.6Hz, 1H), 7.41 (t, J=7.9Hz, 1H), 7.38-7.30 (m, 2H),
2.49(s,3H).
13C NMR(100MHz,CDCl3):δ179.9,152.0,150.1,138.7,135.6,132.3,132.0,
131.1,130.2,130.1,129.1,127.8,124.9,123.9,122.9,122.8,119.6,17.9.
Embodiment 9
Raw material: 3- methyl acetophenone；
Target product:
Yield: 79%；
1H NMR(400MHz,CDCl3): δ 7.88 (d, J=8.9Hz, 1H), 7.82 (s, 1H), 7.43 (s, 1H), 7.36
(t, J=7.7Hz, 1H), 7.32 (s, 1H), 7.21 (d, J=7.1Hz, 1H), 2.46 (s, 3H), 2.43 (s, 2H)
13C NMR(100MHz,CDCl3):δ182.0,154.0,150.1,138.4,138.4,137.3,133.4,
129.9,129.8,129.4,128.6,128.3,127.1,126.5,124.1,123.8,117.8,21.5,21.4,18.1.
Embodiment 10
Raw material: 3- chloro-acetophenone；
Target product:
Yield 80%；
1H NMR(400MHz,CDCl3): δ 8.04 (s, 1H), 8.00 (s, 1H), 7.91 (dd, J=13.3,7.7Hz, 2H),
7.66 (s, 1H), 7.59 (d, J=8.0Hz, 1H), 7.48 (t, J=7.7Hz, 1H), 7.41 (t, J=7.7Hz, 1H), 7.36
(d, J=7.5Hz, 2H), 2.49 (s, 3H)
13C NMR(100MHz,CDCl3):δ180.1,152.1,150.1,138.5,134.8,134.8,132.7,
130.9,130.0,129.9,129.4,129.1,127.4,126.3,124.5,124.0,119.6,17.9.
Embodiment 11
Raw material: 3- nitro-acetophenone；
Target product:
Yield: 88%；
1H NMR(400MHz,CDCl3): δ 9.00 (s, 1H), 8.95 (s, 1H), 8.51 (d, J=8.2Hz, 1H), 8.38
(dd, J=13.2,7.8Hz, 2H), 8.25 (d, J=8.2Hz, 1H), 7.78 (t, J=8.0Hz, 1H), 7.69 (t, J=
8.0Hz, 1H), 7.51 (d, J=13.0Hz, 1H), 2.57 (s, 4H)
13C NMR(100MHz,CDCl3):δ178.7,151.0,150.4,148.6,148.2,137.8,134.9,
131.6,130.6,130.0,130.0,127.3,124.4,123.8,123.5,121.4,121.1,17.8.
Embodiment 12
Raw material: 4- bromoacetophenone；
Target product:
Yield: 80%；
1H NMR(400MHz,CDCl3): δ 7.90 (t, J=8.4Hz, 1H), 7.68 (d, J=7.7Hz, 1H), 7.60 (d, J
=7.9Hz, 1H), 7.34 (s, 1H), 2.48 (s, 1H)
13C NMR(100MHz,CDCl3):δ180.5,152.7,150.2,135.7,132.0,131.8,130.8,
128.2,127.8,123.9,123.4,119.0,18.0.
Embodiment 13
Raw material: 4- trifluoromethyl acetophenone；
Target product:
Yield 78%；
(4-(methylthio)-5-(4-(trifluoromethyl)phenyl)furan-2-yl)(4-
(trifluoromethyl)phenyl)methanone
1H NMR(400MHz,CDCl3): δ 8.14 (t, J=9.4Hz, 1H), 7.82 (d, J=7.9Hz, 1H), 7.74 (d, J
=8.0Hz, 1H), 7.39 (s, 1H), 2.52 (s, 1H)
13C NMR(100MHz,CDCl3):δ180.5,151.9,150.4,139.8,134.3,132.4,129.6,
(129.1,128.3,126.6,126.5,125.7 dd, J=7.5,3.7Hz), 125.6 (q, J=3.7Hz), 123.8,120.8,
17.8.
Embodiment 14
Raw material: 4- methyl acetophenone；
Target product:
Yield: 73%
1H NMR(400MHz,CDCl3): δ 7.99-7.92 (m, 1H), 7.32 (d, J=6.6Hz, 1H), 7.27 (d, J=
8.0Hz,1H),2.45(s,2H),2.40(s,1H).
13C NMR(100MHz,CDCl3):δ181.4,154.12,150.2,143.4,139.2,134.6,129.5,
129.4,129.2,126.8,126.5,124.0,117.2,21.7,21.5,18.1.
Embodiment 15
Raw material: 4- chloro-acetophenone；
Target product:
Yield: 80%；
1H NMR(400MHz,CDCl3): δ 8.03-7.93 (m, 1H), 7.51 (d, J=8.2Hz, 1H), 7.45 (d, J=
8.3Hz,1H),7.35(s,1H),2.48(s,1H).
13C NMR(100MHz,CDCl3):δ180.3,152.7,150.2,139.2,135.3,135.1,130.7,
129.0,128.9,127.8,127.7,123.9,118.8,18.0.
Embodiment 16
Raw material: 4- methoxyacetophenone；
Target product:
Yield: 72%；
1H NMR(400MHz,CDCl3): δ 8.05 (dd, J=16.5,7.6Hz, 1H), 7.33 (s, 1H), 7.05-6.94
(m,2H),3.91(s,1H),3.88(s,1H),2.45(s,1H).
13C NMR(100MHz,CDCl3):δ193.5,163.2,160.1,154.0,150.1,132.3,131.7,
129.9,128.1,124.0,122.4,114.3,114.1,113.7,55.5,55.3,18.3.
Embodiment 17
Raw material: 4- methylthio phenyl ethyl ketone；
Target product:
Yield 63%；
1H NMR(400MHz,CDCl3): δ 7.98 (d, J=8.2Hz, 1H), 7.33 (t, J=6.4Hz, 1H), 7.26 (s,
1H),2.56(s,1H),2.53(s,1H),2.47(s,1H).
13C NMR(100MHz,CDCl3):δ180.5,153.4,150.2,145.5,140.3,133.3,129.8,
126.7,126.0,125.9,125.0,123.9,117.6,18.1,15.2,14.8.
Embodiment 18
Raw material: 4- tert-butylacetophenone；
Target product:
Yield: 58%；
1H NMR(400MHz,CDCl3): δ 8.01 (d, J=7.8Hz, 1H), 7.52 (dd, J=14.9,7.6Hz, 1H),
7.36(s,1H),2.47(s,1H),1.38(s,2H),1.36(s,2H).
13C NMR(100MHz,CDCl3):δ181.3,156.3,154.0,152.3,150.4,134.5,129.4,
126.8,126.3,125.6,125.4,124.0,117.3,35.1,34.8,31.2,31.1,18.2.
Claims (7)
1. a kind of method based on intermolecular ring-closure reaction synthesis furan derivatives, it is characterised in that: 1 acetophenone compounds of formula
And dimethyl sulfoxide, one pot reaction in the presence of tetraalkylammonium iodides catalyst and potassium persulfate oxidation agent, it obtains 2 furans of formula and spreads out
Biology；
Wherein, R is hydrogen, halogenic substituent, trifluoromethyl, nitro, alkyl, alkoxy or methyl mercapto.
2. a kind of method based on intermolecular ring-closure reaction synthesis furan derivatives according to claim 1, feature exist
In: concentration of the acetophenone compounds in dimethyl sulfoxide is 0.2~0.9mol/L.
3. a kind of method based on intermolecular ring-closure reaction synthesis furan derivatives according to claim 1, feature exist
In: the mole of the tetraalkylammonium iodides is the 20~40% of acetophenone compounds mole.
4. a kind of method based on intermolecular ring-closure reaction synthesis furan derivatives according to claim 3, feature exist
In: the tetraalkylammonium iodides include at least one of tetrabutylammonium iodide, tetraethyl ammonium iodide, tetramethyl-ammonium iodide.
5. a kind of method based on intermolecular ring-closure reaction synthesis furan derivatives according to claim 1, feature exist
In: the mole of the potassium persulfate oxidation agent is 2~3 times of acetophenone compounds mole.
6. a kind of described in any item methods based on intermolecular ring-closure reaction synthesis furan derivatives according to claim 1~5,
It is characterized by: the condition of the reaction: reaction temperature is 90~140 DEG C, and the reaction time is 5~11h.
7. a kind of method based on intermolecular ring-closure reaction synthesis furan derivatives according to claim 6, feature exist
In: the condition of the reaction: reaction temperature is 100~130 DEG C, and the reaction time is 6~10h.
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| CN108358877B (en) * | 2018-04-24 | 2020-06-02 | 沅江华龙催化科技有限公司 | Furyl o-diketone derivative and preparation method thereof |
| CN108383803B (en) * | 2018-05-08 | 2020-02-21 | 沅江华龙催化科技有限公司 | Synthetic method of 2, 4-disubstituted oxazole |
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| CN108440438B (en) * | 2018-05-08 | 2020-04-21 | 沅江华龙催化科技有限公司 | Method for constructing 2, 4-diaryl oxazole by acetophenone compounds, ammonium persulfate and dimethyl sulfoxide |
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