CN113234067B - 2, 5-disubstituted thiophene compounds and synthetic method thereof - Google Patents
2, 5-disubstituted thiophene compounds and synthetic method thereof Download PDFInfo
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- -1 2, 5-disubstituted thiophene compounds Chemical class 0.000 title claims abstract description 30
- 238000010189 synthetic method Methods 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 17
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 5
- 238000001308 synthesis method Methods 0.000 claims abstract 3
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 12
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 241001597008 Nomeidae Species 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical class O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 3
- 238000005580 one pot reaction Methods 0.000 abstract description 3
- 229910052723 transition metal Inorganic materials 0.000 abstract description 3
- 150000003624 transition metals Chemical class 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 239000008204 material by function Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 229930192474 thiophene Natural products 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- AXCXHFKZHDEKTP-NSCUHMNNSA-N 4-methoxycinnamaldehyde Chemical compound COC1=CC=C(\C=C\C=O)C=C1 AXCXHFKZHDEKTP-NSCUHMNNSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- ALGQVMMYDWQDEC-OWOJBTEDSA-N (e)-3-(4-nitrophenyl)prop-2-enal Chemical compound [O-][N+](=O)C1=CC=C(\C=C\C=O)C=C1 ALGQVMMYDWQDEC-OWOJBTEDSA-N 0.000 description 1
- SQRYQSKJZVQJAY-UHFFFAOYSA-N 6-bromo-2-methylquinoline Chemical compound C1=C(Br)C=CC2=NC(C)=CC=C21 SQRYQSKJZVQJAY-UHFFFAOYSA-N 0.000 description 1
- VTGXHCUQALWXCR-UHFFFAOYSA-N 6-ethoxy-2-methylquinoline Chemical compound N1=C(C)C=CC2=CC(OCC)=CC=C21 VTGXHCUQALWXCR-UHFFFAOYSA-N 0.000 description 1
- SLHCMPVPVQSTBV-UHFFFAOYSA-N C1=CNC2=C3C=CN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=CN=C3C=CC2=C1 SLHCMPVPVQSTBV-UHFFFAOYSA-N 0.000 description 1
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention mainly relates to a synthetic method of 2, 5-disubstituted thiophene. The invention realizes the one-pot reaction of 2-methylquinoline, cinnamaldehyde compounds and elemental sulfur in the air atmosphere under the action of acid, and uses the elemental sulfur as a sulfur source to efficiently obtain the 2, 5-disubstituted thiophene. The method does not need transition metal catalysis, and provides a new path for synthesizing the 2, 5-disubstituted thiophene compound. The method has the characteristics of simple reaction system, mild reaction conditions, less reaction equipment, simple and convenient experimental operation, wide material sources and the like. The 2, 5-disubstituted thiophene and the synthesis method thereof can be used in a plurality of industrial production fields of medicines, pesticides, organic functional materials and the like.
Description
Technical Field
The invention relates to a 2, 5-disubstituted thiophene compound and a synthetic method thereof, belonging to the field of organic synthesis.
Background
2, 5-diaryl thiophene compounds are an important class of sulfur-containing heterocyclic compounds and widely exist in natural products. 2, 5-diarylthiophenes have been reported as core structures for drugs, liquid crystals, organic light emitting diodes, and organic effect transistors. In addition, electron-rich 2, 5-diarylthiophene scaffolds have been well applied to perovskite solar hole transport layer units. The synthesis of 2, 5-diarylthiophene compounds typically requires highly functionalized starting materials, transition metal catalysts, multi-step reactions, and harsh reaction conditions, among others.
Disclosure of Invention
Therefore, the invention aims to provide 2, 5-diaryl thiophene and derivatives thereof.
The invention also aims to provide a synthetic method of the 2, 5-diaryl thiophene and the derivatives thereof, which has the advantages of simple reaction conditions, convenient operation and high yield.
Thus, the present invention provides 2, 5-diarylthiophenes and derivatives thereof having the general formula:
wherein
R1 is selected from hydrogen atom, alkyl and halogen radical;
r2 is selected from hydrogen atom, alkoxy, nitro and heterocyclic aryl.
The invention also provides a method for synthesizing 2, 5-diaryl thiophene and derivatives thereof, which is obtained by heating and stirring three components of 2-methyl quinoline compounds, cinnamaldehyde compounds and elemental sulfur under the reaction condition of acid, organic solvent and water.
Preferably, in the method of the present invention, the 2-methylquinoline compound has a general formula of formula ii:
wherein:
r1 is selected from hydrogen atom, alkyl and halogen radical.
Preferably, in the method of the present invention, the 2-methylquinoline compound is selected from: 2.4-dimethylquinoline, 2-methyl-6-bromoquinoline, 2-methyl-6-ethoxyquinoline.
Preferably, in the method of the present invention, the cinnamaldehyde compound has the formula iii:
wherein:
r2 is selected from hydrogen atom, methoxyl and nitryl.
Preferably, in the method of the present invention, the cinnamaldehyde-based compound is selected from: cinnamaldehyde, 4-methoxycinnamaldehyde, 4-nitrocinnamaldehyde.
Preferably, in the method of the present invention, the acid is: benzoic acid, salicylic acid, and p-nitrobenzoic acid.
Preferably, in the method of the present invention, the organic solvent is one selected from chlorobenzene and o-dichlorobenzene mixed with water, and the solvent is used in an amount of: 0-1.0 mL.
Preferably, in the method of the present invention, the molar ratio of the 2-methylquinoline compound, the cinnamaldehyde compound, the elemental sulfur, and the acid is 1.0: 1.0-2.0:3.0-5.0: 0.5-1.5; the reaction temperature is 130-150 ℃; the atmosphere in the reaction vessel was: an air atmosphere; the reaction time is 16-24 h.
The technical scheme of the invention has the following advantages:
(I) under the action of acid, in the air atmosphere, the technical scheme of realizing one-pot reaction of 2-methylquinoline compounds, cinnamaldehyde compounds and elemental sulfur, synthesizing a plurality of C-C and C-S compounds, and synthesizing 2, 5-diaryl thiophene and derivatives thereof in one step under the condition of no transition metal is adopted, so that the target product is directly and selectively synthesized in one step, the problem of huge waste of people, property and materials caused by the existing multi-step synthesis method needing a metal catalyst is solved, a large amount of research time is saved, and the production period is shortened; (II) the 2-methylquinoline compound, the cinnamaldehyde compound and the elemental sulfur are heated and stirred under the reaction condition of acid, organic solvent and water to selectively obtain the 2, 5-diaryl thiophene and the derivative thereof, and the method has the advantages of simple reaction system, mild reaction condition, wide material source, obvious increase of the added value of the product, high availability and foreseeable market commercialization prospect; (III) the technical scheme of converting the 2-methylquinoline compound, the cinnamaldehyde compound and the elemental sulfur into the 2, 5-diaryl thiophene and the derivatives thereof has the advantages of scientific and reasonable process, good group positioning and selectivity, wide material source, stable structure, easy experimental operation, obviously shortened reaction steps and less required instruments and equipment; (IV) the 2, 5-diaryl thiophene derivative and its synthetic method of the invention, can be used in a plurality of industrial production fields such as medicine, agricultural chemicals, organic functional material, etc.; is particularly suitable for scientific research, development and utilization of the high-efficiency selective synthesis of pyrroloquinoline compounds by a one-pot method.
Detailed Description
The present invention will now be described in further detail with reference to the reaction schemes. The basic structure of the present invention is described only in a schematic manner, and thus it shows only the constitution related to the present invention.
Examples 1 to 5
The method comprises the following steps:
the preparation method comprises the steps of adding a 2-methylquinoline compound, a cinnamic aldehyde compound, elemental sulfur, acid, an organic solvent and water into a reaction vessel;
heating after fully mixing the reactants;
and thirdly, purifying after the reaction to obtain the product.
The 2-methylquinoline compound, the cinnamaldehyde compound, the elemental sulfur, the reaction conditions, the reaction products and the yield are shown in table 1:
table 1: reactants and reaction conditions in examples 1-5:
the nuclear magnetic data for the products of some of the examples are:
the nuclear magnetic data of the product of example 1 are as follows:
1H NMR(400MHz,Chloroform-d)δ8.15–8.04(m,2H),7.81–7.64(m,6H),7.50–7.29(m,5H).13C NMR (100MHz,Chloroform-d)δ152.2,148.1,147.2,144.3,136.5,134.2,129.8,129.1,128.9,127.9,127.5,127.1,126.7, 126.0,125.8,124.0,117.3。
the nuclear magnetic data of the product of example 2 are as follows:
1H NMR(400MHz,Chloroform-d)δ8.00(d,J＝8.7Hz,1H),7.96–7.87(m,2H),7.81–7.64(m,5H),7.46– 7.38(m,2H),7.37–7.29(m,2H).13C NMR(100MHz,Chloroform-d)δ152.5,147.6,146.7,143.8,135.4,134.0, 133.2,130.8,129.5,129.0,128.1,128.0,127.1,125.8,124.1,119.7,118.1。
the nuclear magnetic data of the product of example 3 are as follows:
1H NMR(400MHz,Chloroform-d)δ7.99(d,J＝8.9Hz,2H),7.76–7.67(m,3H),7.61(d,J＝3.9Hz,1H),7.44– 7.28(m,5H),7.02(d,J＝2.8Hz,1H),4.13(q,J＝7.0Hz,2H),1.48(t,J＝7.0Hz,3H).13C NMR(100MHz, Chloroform-d)δ156.9,149.9,146.3,144.6,144.0,135.2,134.3,130.6,128.9,128.1,127.8,125.9,125.7,123.9,122.6, 117.5,105.9,63.7,14.7。
the nuclear magnetic data of the product of example 4 are as follows:
1H NMR(400MHz,Chloroform-d)δ8.14–8.05(m,2H),7.80–7.73(m,2H),7.71–7.61(m,4H),7.49–7.44(m, 1H),7.25–7.23(m,1H),6.98–6.89(m,2H),3.84(s,3H).13C NMR(100MHz,Chloroform-d)δ159.5,152.3,148.1, 147.2,143.3,136.4,129.8,129.1,127.4,127.1,127.0,126.8,125.9,122.9,117.2,114.3,55.3。
the nuclear magnetic data of the product of example 5 are as follows:
1H NMR(400MHz,Chloroform-d)δ8.28–8.21(m,2H),8.16(d,J＝8.6Hz,1H),8.09(d,J＝8.5Hz,1H),7.85– 7.77(m,4H),7.75–7.69(m,2H),7.56–7.49(m,2H).13C NMR(100MHz,Chloroform-d)δ151.5,148.1,147.5, 146.8,143.8,140.4,136.8,130.1,129.3,127.6,127.4,126.9,126.6,125.9,124.5,117.2。
in light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (4)
1. A method for synthesizing 2, 5-disubstituted thiophene and its derivant, characterized by that, heat and stir to get under the reaction condition of acid, organic solvent and water 2-methyl quinoline compound, cinnamaldehyde compound and elementary substance sulphur three-component;
the structure of the 2-methylquinoline compound is as follows:
the structure of the cinnamaldehyde compound is
The 2, 5-disubstituted thiophene and the derivative thereof obtained by the reaction of the 2-methylquinoline compound and the cinnamaldehyde compound have the following structures:
wherein
R1 is selected from hydrogen atom, alkyl and halogen radical;
r2 is selected from hydrogen atom, alkoxy and nitro.
2. The method of synthesis according to claim 1, wherein the acid is: benzoic acid, salicylic acid, and p-nitrobenzoic acid.
3. The synthesis method as claimed in claim 1, wherein the organic solvent is selected from chlorobenzene and o-dichlorobenzene, and is mixed with water, and the total solvent is used in the following amount: 1.0 mL.
4. The synthesis method according to claim 1, wherein the molar ratio of the 2-methylquinoline compound to the cinnamaldehyde compound to the elemental sulfur to the acid is 1.0: 1.0-2.0:3.0-5.0: 0: 5-1.5; the reaction temperature is 130-150 ℃; the atmosphere in the reaction vessel was: an air or oxygen atmosphere; the reaction time was 24 h.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108409712A (en) * | 2018-04-16 | 2018-08-17 | 湘潭大学 | 3-（Methyl mercapto）- 2- phenyl benzo [b] thiophene derivant and its synthetic method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108409712A (en) * | 2018-04-16 | 2018-08-17 | 湘潭大学 | 3-（Methyl mercapto）- 2- phenyl benzo [b] thiophene derivant and its synthetic method |
Non-Patent Citations (4)
| Title |
|---|
| Steinkopf，Wilhelm et al..Thiophene series.LIII.2,2’-Bi-α-thiophanthrenequinonyl, the thiophene isolog of 2,2’-bianthraquinonyl.《Justus Liebigs Annalen der Chemie》.1940,第545卷第33-37页. * |
| Synthesis and in vitro antitumor activity of substituted quinazoline and quinoxaline derivatives:Search for anticancer agent;Malleshappa N.Noolvi et al.;《European Journal of Medicinal Chemistry》;20110315;第46卷;第2327-2346页 * |
| Thiophene series.LIII.2,2’-Bi-α-thiophanthrenequinonyl, the thiophene isolog of 2,2’-bianthraquinonyl;Steinkopf，Wilhelm et al.;《Justus Liebigs Annalen der Chemie》;19401231;第545卷;第33-37页 * |
| 利用无机硫化物构建含硫杂环化合物的研究;曾巍澜;《中国优秀博硕士学位论文全文数据库（硕士）工程科技I辑》;20160415(第04期);第B014-122页 * |
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