CN115197124B - Method for synthesizing polysubstituted pyridine derivative based on alpha, beta-unsaturated oxime ester under catalysis of ammonium iodide - Google Patents
Method for synthesizing polysubstituted pyridine derivative based on alpha, beta-unsaturated oxime ester under catalysis of ammonium iodide Download PDFInfo
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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Abstract
The invention provides a method for synthesizing polysubstituted pyridine derivatives based on alpha, beta-unsaturated oxime ester under the catalysis of ammonium iodide, which comprises the steps of adding alpha, beta-unsaturated ketoxime acetate, ethyl pyruvate and ammonium iodide into an organic solvent, uniformly mixing, and heating for reaction. Compared with the prior art, the method has the advantages of mild reaction conditions, simple and rapid method, wide substrate applicability and more complex and various prepared structures.
Description
Technical Field
The invention relates to the field of organic compounds, in particular to a method for synthesizing a polysubstituted pyridine derivative based on alpha, beta-unsaturated oxime ester under the catalysis of ammonium iodide.
Background
Pyridine derivatives are important fine chemical intermediates and are widely applied to the fields of pesticides, medicines, tires, daily chemicals and daily chemical industry. Along with the development of economy in China, the demand for pyridine derivatives is also sharply increased, so that the research of a novel and simple synthesis method beneficial to industrialization is also necessary, and better economic benefits are also generated. Some methods for synthesizing pyridine derivatives are as follows:
in 2015, xu Xuefeng reported the synthesis of pyridine derivatives from the reaction of amine compounds and ketone compounds in the presence of trifluoromethanesulfonic acid (CN 105237466 a).
In 2020, miao Chunbao found that oxime acetate and a, beta-unsaturated ketone can react under the catalysis of ferric salt and high temperature without solvent to obtain polysubstituted pyridine derivative. The reaction has the advantages of simple raw material synthesis route, good reaction yield of different substituent groups, low price and easy acquisition of catalyst, no solvent reaction, acetic acid and water as reaction byproducts, environmental friendliness and the like (CN 111138345A).
Fu yajie reports that a highly efficient and simple method for synthesizing polysubstituted pyridine is realized by copper-catalyzed coupling reaction of oxime acetate and toluene derivatives (J.org.chem.2016, 81,23,11671-11677).
Forrester oxidizes iminooxyacetic acid by using tert-butyl hydroperoxide to obtain imine free radicals, and the imine free radicals further react with formaldehyde to obtain imine, wherein the generated imine can be converted into polysubstituted pyridine in the presence of persulfate oxidant. The disadvantage of this finding is the cumbersome operation, poor substrate expansibility and low yields, and the products obtained are often mixtures of I, II, III. (J.C.S. Perkin I,1979, 616-620).
Makoto nitta reports the use of a catalyst [ Mo (CO) under heating in a protic solvent 6 ]2,4, 6-triphenylphosphine can be synthesized by catalyzing (1E, 2E) -1,3-diphenylprop-2-en-1-one O-acetyl oxime. The disadvantage of this finding is that the metal catalysts are expensive, the reaction solvents are required, and the authors have only one substrate. (Bull. Chem. Soc. Jpn.1986,59,2365-2367)
Disclosure of Invention
The invention aims to provide a method for synthesizing a polysubstituted pyridine derivative based on alpha, beta-unsaturated oxime ester under the catalysis of ammonium iodide, which has the advantages of mild reaction conditions, simple and quick method, wide substrate applicability and more complex and various prepared structures.
The specific technical scheme of the invention is as follows:
the method for synthesizing the polysubstituted pyridine derivative based on the alpha, beta-unsaturated oxime ester under the catalysis of ammonium iodide specifically comprises the following steps: adding alpha, beta-unsaturated ketoxime acetate, ethyl pyruvate and ammonium iodide into an organic solvent, uniformly mixing, and heating for reaction to obtain the product.
The structural formula of the alpha, beta-unsaturated acetic ketoxime is as follows:
wherein R is 1 Hydrogen, halogen, nitro, cyano, methyl or methoxy;
R 2 hydrogen, halogen, nitro, cyano, methyl or methoxy;
preferably, the alpha, beta-unsaturated acetic acid ketoxime has the structural formula
The molar ratio of the alpha, beta-unsaturated acetic ketoxime, the ethyl pyruvate and the ammonium iodide is 0.2-0.6:0.02-0.06:0.1-0.3.
The concentration of the alpha, beta-unsaturated acetic ketoxime in the organic solvent is 0.1-0.6mol/L.
The organic solvent is toluene, acetonitrile, tetrahydrofuran or 1, 2-dichloroethane.
The heating reaction temperature is 80-140 ℃ and the reaction time is 8-12h.
Further, after the completion of the heating reaction, the reaction solution was filtered, the obtained filtrate was dried by spin, and the residue was separated by column chromatography using a mixed solvent of petroleum ether and ethyl acetate as an eluent to obtain a pyridine compound.
The polysubstituted pyridine derivative prepared by the method has the structural formula:
wherein R is 1 Hydrogen, halogen, nitro, cyano, methyl or methoxy;
R 2 hydrogen, halogen, nitro, cyano, methyl or methoxy;
preferably, said R 1 Is hydrogen or methoxy;
R 2 hydrogen, chloro, methyl or methoxy;
preferably, the pyridine compound has the structural formula:
compared with the prior art, the method has the advantages of mild reaction conditions, simple and rapid method, wide substrate applicability, contribution to industrial production, and more complex and diversified structures of the prepared pyridine compound.
Drawings
FIG. 1 is a hydrogen spectrum of a pyridine compound prepared in example 1;
FIG. 2 is a carbon spectrum of the pyridine compound prepared in example 1;
FIG. 3 is a hydrogen spectrum of the pyridine compound prepared in example 2;
FIG. 4 is a carbon spectrum of the pyridine compound prepared in example 2;
FIG. 5 is a hydrogen spectrum of the pyridine compound prepared in example 3;
FIG. 6 is a carbon spectrum of the pyridine compound prepared in example 3;
FIG. 7 is a hydrogen spectrum of the pyridine compound prepared in example 4;
FIG. 8 is a carbon spectrum of the pyridine compound prepared in example 4;
FIG. 9 is a hydrogen spectrum of the pyridine compound prepared in example 5;
FIG. 10 is a carbon spectrum of the pyridine compound prepared in example 5;
FIG. 11 is a single crystal view of the pyridine compound prepared in example 4;
FIG. 12 illustrates the reaction mechanism of the present invention using the compound of example 1 as an example.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions in the embodiments of the present invention will be clearly and completely described in the following in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The test materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
Those of skill in the art, without any particular mention of the techniques or conditions, may follow the techniques or conditions described in the literature in this field or follow the product specifications.
Example 1
The method for synthesizing the polysubstituted pyridine derivative based on the alpha, beta-unsaturated oxime ester under the catalysis of ammonium iodide specifically comprises the following steps: sequentially adding 1mmol of alpha, beta-unsaturated acetic ketoxime with the structural formula of0.1mmol of ethyl pyruvate and 0.5mmol of ammonium iodide are uniformly mixed in 2mL of toluene; heating the reaction system to 100 ℃, reacting for 8 hours, filtering the reaction solution after the reaction is completed, spin-drying the obtained filtrate, and separating the residue by column chromatography by using a mixed solvent of petroleum ether and ethyl acetate as eluent (the volume ratio of petroleum ether to ethyl acetate is 40:1) to obtain the pyridine compound.
The reaction formula is as follows:
the compound prepared in example 1 is subjected to nuclear magnetic characterization, the hydrogen spectrum is shown in fig. 1, the C spectrum is shown in fig. 2, and nuclear magnetic data are as follows:
1 H NMR(600MHz,CDCl 3 )δ8.21(d,J＝7.8Hz,4H),7.89(s,2H),7.75(d,J＝7.8Hz,2H),7.55-7.51(m,6H),7.49-7.44(m,3H)；
13 C NMR(125MHz,CDCl 3 )δ157.5,150.3,139.5,139.1,129.2,129.1,129.0,128.8,127.2,127.2,117.2。
the preparation mechanism of example 1 is shown in fig. 12, the N-O bond of the chalcone oxime ester is firstly cut off under the catalysis of ammonium iodide to form ketimine compound, the ketimine compound is further dimerized, and the obtained dimer is oxidized by elemental iodine to generate a target product.
Example 2
The method for synthesizing the polysubstituted pyridine derivative based on the alpha, beta-unsaturated oxime ester under the catalysis of ammonium iodide specifically comprises the following steps: sequentially adding 1mmol of alpha, beta-unsaturated acetic ketoxime with the structural formula of0.1mmol of ethyl pyruvate and 0.5mmol of ammonium iodide are uniformly mixed in 2mL of toluene; heating the reaction system to 100 ℃, reacting for 8 hours, filtering the reaction solution after the reaction is completed, spin-drying the obtained filtrate, and separating the residue by column chromatography by using a mixed solvent of petroleum ether and ethyl acetate as eluent (the volume ratio of petroleum ether to ethyl acetate is 40:1) to obtain the pyridine compound.
The reaction formula is as follows:
the compound prepared in example 2 was subjected to nuclear magnetic characterization, the hydrogen spectrum is shown in fig. 3, the C spectrum is shown in fig. 4, and the nuclear magnetic data are as follows:
1 H NMR(600MHz,CDCl 3 )δ8.20(d,J＝7.8Hz,4H),7.88(s,2H),7.66(d,J＝7.8Hz,2H),7.53-7.50(m,4H),7.46-7.44(m,2H),7.33(d,J＝7.8Hz,2H),2.44(s,3H)；
13 C NMR(125MHz,CDCl 3 )δ157.5,150.2,139.6,139.2,136.1,129.9,129.1,128.7,127.2,127.1,117.0,21.3。
example 3
The method for synthesizing the polysubstituted pyridine derivative based on the alpha, beta-unsaturated oxime ester under the catalysis of ammonium iodide specifically comprises the following steps: sequentially adding 1mmol of alpha, beta-unsaturated acetic ketoxime with the structural formula of0.1mmol of ethyl pyruvate and 0.5mmol of ammonium iodide are uniformly mixed in 2mL of toluene; heating the reaction system to 100 ℃, reacting for 8 hours, filtering the reaction liquid after the reaction is completed, spin-drying the obtained filtrate,the residue was subjected to column chromatography using a mixed solvent of petroleum ether and ethyl acetate as an eluent (the volume ratio of petroleum ether to ethyl acetate is 40:1) to obtain a pyridine compound.
The reaction formula is as follows:
the compound prepared in example 3 was subjected to nuclear magnetic characterization, the hydrogen spectrum is shown in fig. 5, the C spectrum is shown in fig. 6, and the nuclear magnetic data are as follows:
1 H NMR(600MHz,CDCl 3 )δ8.19(d,J＝7.8Hz,4H),7.83(s,2H),7.67(d,J＝8.4Hz,2H),7.53-7.44(m,8H)；
13 C NMR(125MHz,CDCl 3 )δ157.7,149.0,139.3,137.5,135.3,129.4,129.2,128.8,128.5,127.2,116.9。
example 4
The method for synthesizing the polysubstituted pyridine derivative based on the alpha, beta-unsaturated oxime ester under the catalysis of ammonium iodide specifically comprises the following steps: sequentially adding 1mmol of alpha, beta-unsaturated acetic ketoxime with the structural formula of0.1mmol of ethyl pyruvate and 0.5mmol of ammonium iodide are uniformly mixed in 2mL of toluene; heating the reaction system to 100 ℃, reacting for 8 hours, filtering the reaction solution after the reaction is completed, spin-drying the obtained filtrate, and separating the residue by column chromatography by using a mixed solvent of petroleum ether and ethyl acetate as eluent (the volume ratio of petroleum ether to ethyl acetate is 40:1) to obtain the pyridine compound.
The reaction formula is as follows:
the compound prepared in example 4 was subjected to nuclear magnetic characterization, the hydrogen spectrum is shown in fig. 7, the C spectrum is shown in fig. 8, and the nuclear magnetic data are as follows:
1 H NMR(600MHz,CDCl 3 )δ8.20(d,J＝7.8Hz,4H),7.87(s,2H),7.53-7.50(m,4H),7.46-7.42(m,3H),7.33-7.32(m,1H),7.26-7.24(m,1H),7.02-7.00(m,1H),3.89(s,3H)；
13 C NMR(125MHz,CDCl 3 )δ160.2,157.5,150.2,140.6,139.5,130.2,129.1,128.8,127.2,119.7,117.3,114.3,113.1,55.5。
example 5
The method for synthesizing the polysubstituted pyridine derivative based on the alpha, beta-unsaturated oxime ester under the catalysis of ammonium iodide specifically comprises the following steps: sequentially adding 1mmol of alpha, beta-unsaturated acetic ketoxime with the structural formula of0.1mmol of ethyl pyruvate and 0.5mmol of ammonium iodide are uniformly mixed in 2mL of toluene; heating the reaction system to 100 ℃, reacting for 8 hours, filtering the reaction solution after the reaction is completed, spin-drying the obtained filtrate, and separating the residue by column chromatography by using a mixed solvent of petroleum ether and ethyl acetate as eluent (the volume ratio of petroleum ether to ethyl acetate is 40:1) to obtain the pyridine compound.
The reaction formula is as follows:
the compound prepared in example 5 was subjected to nuclear magnetic characterization, the hydrogen spectrum is shown in fig. 9, the C spectrum is shown in fig. 10, and the nuclear magnetic data are as follows:
1 H NMR(600MHz,CDCl 3 )δ8.15(d,J＝8.4Hz,4H),7.77(s,2H),7.73-7.72(m,2H),7.53-7.50(m,2H),7.47-7.45(m,1H),7.04-7.02(m,4H),3.88(s,6H)；
13 C NMR(125MHz,CDCl 3 )δ160.5,156.9,150.1,139.3,132.2,129.1,128.9,128.4,127.2,115.8,114.0,55.4。
the above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present invention.
Claims (7)
1. A method for synthesizing a polysubstituted pyridine derivative based on alpha, beta-unsaturated oxime ester under the catalysis of ammonium iodide, which is characterized by comprising the following steps: adding alpha, beta-unsaturated ketoxime acetate, ethyl pyruvate and ammonium iodide into an organic solvent, uniformly mixing, and heating for reaction to obtain the alpha, beta-unsaturated ketoxime acetate;
the structural formula of the alpha, beta-unsaturated acetic ketoxime is as follows: ；
wherein R is 1 Hydrogen, halogen, nitro, cyano, methyl or methoxy;
R 2 hydrogen, halogen, nitro, cyano, methyl or methoxy;
the structural formula of the prepared polysubstituted pyridine derivative is as follows:；
wherein R is 1 Hydrogen, halogen, nitro, cyano, methyl or methoxy;
R 2 is hydrogen, halogen, nitro, cyano, methyl or methoxy.
2. The method according to claim 1, wherein the molar ratio of alpha, beta-unsaturated ketoxime acetate, ethyl pyruvate and ammonium iodide is 0.2-0.6:0.02-0.06:0.1-0.3.
3. The method of claim 2, wherein the α, β -unsaturated acetic acid ketoxime has the formula
、/>、/>、
、/>。
4. The method according to claim 1, wherein the concentration of the α, β -unsaturated ketoxime acetate in the organic solvent is 0.1 to 0.6mol/L.
5. The method according to claim 1, wherein the organic solvent is toluene, acetonitrile, tetrahydrofuran or 1, 2-dichloroethane.
6. The method according to claim 1, wherein the heating reaction temperature is 80-140 ℃ and the reaction time is 8-12h.
7. The method of claim 1, wherein the polysubstituted pyridine derivative has the structural formula:
、/>、/>、/>、。
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB881895A (en) * | 1957-05-27 | 1961-11-08 | Ciba Ltd | New pyridine compounds |
| GB1240160A (en) * | 1968-11-19 | 1971-07-21 | Shun-Ichi Naito | 4-(haloethylsulfonylamino)-antipyrine, and haloethylsulfonyl-p-phenetidine and their related compounds |
| CH554375A (en) * | 1971-03-02 | 1974-09-30 | Jenapharm Veb | METHOD FOR PRODUCING TRIMETHYLSILYL, CHLOROMETHYLDIMETHYLSILYL AND AETHYLDIMETHYLSILYL OXIMINOSTEROIDS. |
| JP2005126340A (en) * | 2003-10-22 | 2005-05-19 | Kureha Chem Ind Co Ltd | Method for producing substituted pyridone compounds, raw material compound thereof and method for producing the same |
| CN111138345A (en) * | 2020-01-15 | 2020-05-12 | 常州大学 | Method for synthesizing polysubstituted pyridine derivative based on oxime ester and unsaturated ketone under catalysis of iron salt |
| CN112358443A (en) * | 2020-11-09 | 2021-02-12 | 巢湖学院 | Pyridine compound and preparation method thereof |
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2022
- 2022-07-14 CN CN202210829929.XA patent/CN115197124B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB881895A (en) * | 1957-05-27 | 1961-11-08 | Ciba Ltd | New pyridine compounds |
| GB1240160A (en) * | 1968-11-19 | 1971-07-21 | Shun-Ichi Naito | 4-(haloethylsulfonylamino)-antipyrine, and haloethylsulfonyl-p-phenetidine and their related compounds |
| CH554375A (en) * | 1971-03-02 | 1974-09-30 | Jenapharm Veb | METHOD FOR PRODUCING TRIMETHYLSILYL, CHLOROMETHYLDIMETHYLSILYL AND AETHYLDIMETHYLSILYL OXIMINOSTEROIDS. |
| JP2005126340A (en) * | 2003-10-22 | 2005-05-19 | Kureha Chem Ind Co Ltd | Method for producing substituted pyridone compounds, raw material compound thereof and method for producing the same |
| CN111138345A (en) * | 2020-01-15 | 2020-05-12 | 常州大学 | Method for synthesizing polysubstituted pyridine derivative based on oxime ester and unsaturated ketone under catalysis of iron salt |
| CN112358443A (en) * | 2020-11-09 | 2021-02-12 | 巢湖学院 | Pyridine compound and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| Cheng Dong,et al..A-NH4I-Triggered [4 + 2] Annulation of α,β-Unsaturated Ketoxime Acetates with N-Acetyl Enamides for the Synthesis of Pyridines.《HETEROCYCLED》.2022,第104卷(第8期),第1435-1446页. * |
| Jindian Duan,et al..NH4I-Triggered [4 + 2] Annulation of α,β-Unsaturated Ketoxime Acetates with N-Acetyl Enamides for the Synthesis of Pyridines.《The Journal of Organic Chemistry》.2020,第85卷第8157-8165页. * |
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