CN113603653B - Synthesis method of selenooxazolidine-2, 4-dione promoted by visible light - Google Patents
Synthesis method of selenooxazolidine-2, 4-dione promoted by visible light Download PDFInfo
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- 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
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Abstract
The invention discloses a method for synthesizing seleno oxazolidine-2, 4-diketone promoted by visible light, which takes N-Boc protected acrylamide and diselenide as reaction raw materials, and carries out stirring reaction under the irradiation of a light source under the condition of a certain temperature to obtain a seleno oxazolidine-2, 4-diketone compound. The method has simple reaction conditions and high yield of the product, and realizes the preparation of the seleno oxazolidine-2, 4-diketone heterocyclic compound from the acrylamide raw material for the first time; the method also has the advantages of insensitivity to air, wide substrate range and the like, develops a new synthetic route and a new method for the seleno-oxazolidine-2, 4-diketone heterocyclic compound, and has good application potential and research value.
Description
Technical Field
The invention relates to the technical field of organic synthetic chemistry, in particular to a method for promoting synthesis of seleno oxazolidine-2.4-diketone by visible light.
Background
Oxazolidine-2, 4-dione compounds are important intermediates in organic synthesis and also important building blocks in bioactive molecules. The compounds have wide application in the fields of medicine and agriculture, such as antidiabetic, antiepileptic and anti-inflammatory activity, and can be used as bactericides, herbicides and the like. Therefore, development of a method for efficiently synthesizing oxazolidine-2, 4-diones has been receiving wide attention from organic chemists and medicinal chemists. The usual synthetic methods include the condensation of alpha-hydroxyamides with carbonates or the reaction of alpha-hydroxy esters with urea or isocyanates to give ((a) J.W.Clark-Lewis, chem.Rev.1958, 58, 63-99; (b) R.Maity, S.Naskar, K.Mal, S.Biswas, I.das, adv. Synth.Catal.2017,359, 4405-4410; (c) H.Huang, J.Fan, G.He, Z.Yang, X.jin, Q.Liu, H.Zhu, chem.Eur.J.2016,22, 2532-. However, these methods generally require the use of a pre-prepared substrate; the carbonate and isocyanate raw materials have high toxicity; the atom economy is not high; and the yield is generally not high. In addition, it has been reported that oxazolidine-2, 4-dione compounds are synthesized using carbon dioxide as a C1 resource ((a) G.Galliani, B.Rindone, F.Saliu Tetrahedron Lett.20095123-5125 (b) G.Chen, C.Fu, S.Ma, org.Biomol.Chem.2011, 9,105-one 110), but such reactions usually require high temperature and high pressure conditions or expensive transition metals as catalysts.
Selenium is a very important trace element in the human body, and its existence is closely related to human health. Selenium has the effects of resisting cancer, resisting oxidation, enhancing human immunity, antagonizing harmful heavy metals, regulating vitamin absorption, regulating protein synthesis and enhancing reproductive function, and has certain preventing and treating effects on diabetes, cataract and cardiovascular and cerebrovascular diseases (a), and also has certain preventing and treating effects on (a) Nogueira, C.W.; Zeni, G.G.; Rocha, J.B.T., chem.Rev.2004,104,6255-6286, and (b) Derek, W.J.; Risto, L., Selenium and Tellurium Chemistry: From Small bacteria to biologicals and materials, Springer-Verlag: Berlin, 2011). In addition, selenium-containing compounds have wide application in the fields of organic synthesis, medicine and material science. Accordingly, much effort has been devoted to developing various methods for introducing selenium groups into organic molecules. However, few research methods for introducing a selenium-based functional group into an oxazolidine-2, 4-dione skeleton have been reported, and there is still a need for continued research and exploration, which is the basis and motivation for the completion of the present invention.
Visible light is a clean and pollution-free energy source, and in recent years, organic synthesis reaction promoted by visible light is greatly developed. However, literature research indicates that a method for synthesizing seleno-oxazolidine-2, 4-diketone based on participation of visible light has not been reported so far. Here, we report a new synthesis method of a visible light-promoted selenooxazolidine-2.4-dione compound involving visible light.
Disclosure of Invention
The invention aims to provide a method for promoting the synthesis of seleno oxazolidine-2, 4-diketone by visible light so as to solve the problems in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme: a method for promoting the synthesis of seleno oxazolidine-2, 4-diketone by visible light comprises the following steps: in an organic solvent, taking N-Boc protected acrylamide with a structure shown in a formula (I) and diselenide with a structure shown in a formula (II) as reaction raw materials, carrying out reaction under the irradiation of visible light, after the reaction is finished, decompressing reaction liquid, removing the solvent to obtain a crude product, and purifying the crude product by column chromatography to obtain a selenooxazolidine-2.4-diketone compound with a structure shown in a formula (III);
the reaction equation is shown as follows:
wherein R in the compound of formula (I)1And R2Is H atom, alkyl and aryl, and the compound of formula (II) adopts diaryl diselenide and dialkyl diselenide.
Preferably, the mol ratio of the acrylamide with the structure shown in the formula (I) to the diselenide with the structure shown in the formula (II) is 1: 1-1: 2, preferably 1: 1.
Preferably, the organic solvent is at least one of N, N-dimethylformamide, dichloromethane, ethyl acetate, chloroform, N-hexane, acetonitrile, 1, 4-dioxane, toluene, tetrahydrofuran, diethyl ether and carbon tetrachloride, and is preferably acetonitrile.
Preferably, the irradiation light source for the reaction is one of sunlight, mercury lamp, fluorescent lamp, tungsten lamp, and LED lamp, preferably fluorescent lamp.
Preferably, the reaction time is 26h-36 h.
Preferably, after the reaction is finished, the reaction solution is decompressed and concentrated, and the concentrate is separated by column chromatography, and a mixed solution of petroleum ether and ethyl acetate is used as an eluent, wherein the ratio of petroleum ether: the volume ratio of ethyl acetate is (1-40): 1, collecting the eluent, and carrying out rotary evaporation on the solvent to obtain the seleno-oxazolidine-2, 4-diketone shown in the formula (III).
Compared with the prior art, the invention has the beneficial effects that:
(1) the method adopts cheap and easily-obtained acrylamide and diselenide as raw materials, the acrylamide can be obtained by coupling reaction of acryloyl chloride and corresponding amine through a carbon-nitrogen bond, and the diselenide is obtained through a commercial way.
(2) The method can be operated under the air condition, is not sensitive to water and oxygen, has relatively mild reaction condition and is simple to operate.
(3) The method adopts visible light as an agent, and has low cost and high reaction efficiency.
(4) The method can obtain the target product by only one step, and has the advantages of high yield, good functional group compatibility, simple post-treatment and good application potential.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides the following technical scheme: a method for promoting the synthesis of seleno oxazolidine-2, 4-diketone by visible light comprises the following steps: in an organic solvent, taking N-Boc protected acrylamide with a structure shown in a formula (I) and diselenide with a structure shown in a formula (II) as reaction raw materials, carrying out reaction under the irradiation of visible light, after the reaction is finished, decompressing reaction liquid, removing the solvent to obtain a crude product, and purifying the crude product by column chromatography to obtain a selenooxazolidine-2.4-diketone compound with a structure shown in a formula (III);
the reaction equation is shown as follows:
wherein R in the compound of formula (I)1And R2Is H atom, alkyl and aryl, and the compound of formula (II) adopts diaryl diselenide and dialkyl diselenide.
The first embodiment is as follows:
the reaction equation is shown as follows:
after the reaction was completed, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (200 to 300 mesh; eluent petroleum ether/ethyl acetate: 20:1) to obtain 93 mg of a white solid at a yield of 94%,
the nuclear magnetic spectrum data of the obtained product are as follows:11H NMR(400MHz，CDCl3)：δ7.56-7.52 (m，2H)，7.46(d，J＝8.8Hz，2H)，7.39(d，J＝8.8Hz，2H)，7.30- 7.25(m，3H)，3.46(d，J＝13.9 Hz，1H)，3.41(d，J＝13.9Hz，1H)， 1.77(s，3H).13C NMR(100MHz，CDCl3)：δ173.2，152.8，134.8，133.6， 129.5，129.42，129.40，128.7，128.1，126.8，85.4，34.4，22.9。
example two:
the reaction equation is shown as follows:
after the reaction was completed, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (200 to 300 mesh, eluent petroleum ether/ethyl acetate: 25:1) to obtain 104 mg of a white solid at a yield of 95%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz,CDCl3):δ7.54(d,J＝ 8.8Hz,2H),7.49–7.42(m,2H),7.25(d,J＝8.8Hz,2H),7.23– 7.16(m,3H),3.38(d,J＝13.9Hz,1H),3.33(d,J＝13.9Hz,1H), 1.69(s,3H).13C NMR(100MHz,CDCl3):δ172.1,151.7,132.5,131.5, 128.9,128.4,127.6,127.1,126.0,121.7,84.4,33.4,21.8.
example 3
The reaction equation is shown as follows:
after the reaction was completed, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (200 to 300 mesh, eluent petroleum ether/ethyl acetate 20:1) to obtain 90 mg of an oily liquid at a yield of 96%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz,CDCl3):δ7.61–7.51 (m,2H),7.34–7.17(m,7H),3.45(d,J＝13.8Hz,1H),3.41(d, J＝13.8Hz,1H),2.40(s,3H),1.76(s,3H).13C NMR(100MHz,CDCl3): δ173.6,153.4,139.2,133.7,130.0,129.4,128.9,128.3,128.0, 125.6,85.3,34.5,22.9,21.2。
example 4
The reaction equation is shown as follows:
after the reaction was completed, the organic phase was removed by a rotary evaporator and the residue was purified by a silica gel column (200 to 300 mesh, eluent petroleum ether/ethyl acetate 15:1) to obtain 93 mg of a white solid at a yield of 91%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz,CDCl3):δ7.88(d,J＝ 8.8Hz,1H),7.84–7.78(m,3H),7.59–7.39(m,5H),7.26–7.09 (m,3H),3.44(d,J＝13.8Hz,1H),3.37(d,J＝13.9Hz,1H),1.73 (s,3H).13C NMR(100MHz,CDCl3):δ173.6,153.3,133.6,133.1,133.0, 129.4,129.4,128.9,128.3,128.1,127.8,127.2,126.7,124.9,122.9, 85.4,34.5,22.9。
example 5
The reaction equation is shown as follows:
after loading N-Boc-N- (3,4, 5-trimethoxy) -2-methacrylamide (0.25 mmol), diphenyl diselenide (0.25 mmol) and acetonitrile (2 ml) into a 25 ml reaction tube equipped with a magnetic stirrer at room temperature, placing a 23W white compact fluorescent lamp at a distance of 3 cm from the reaction tube, reacting at room temperature for 36 hours, passing the organic phase through a rotary evaporator to remove the solvent, purifying the residue with a silica gel column (the silica gel specification is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate 15:1) to obtain 102 mg of white solid with a yield of 91%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz,CDCl3):δ7.62–7.48 (m,2H),7.37–7.20(m,3H),6.64(s,2H),3.87(s,3H),3.85(s, 6H),3.47(d,J＝13.9Hz,1H),3.43(d,J＝13.9Hz,1H),1.78(s, 3H).13C NMR(100MHz,CDCl3):δ173.6,153.6,153.2,138.5,133.4, 129.4,128.9,128.0,126.4,103.5,85.2,60.9,56.3,34.4,22.8。
example 6
The reaction equation is shown as follows:
after the reaction was completed by placing a 23W white compact fluorescent lamp at a distance of 3 cm from the reaction tube and reacting at room temperature for 36 hours, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (silica gel specification: 200 to 300 mesh; eluent: petroleum ether/ethyl acetate ═ 20:1) to obtain 82 mg of colorless oil at a yield of 90%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz,CDCl3):δ7.39(dd,J ＝7.5,2.0Hz,2H),7.29(dd,J＝1.8,0.9Hz,1H),7.23–7.15(m, 3H),6.39–6.28(m,1H),6.25(dd,J＝3.3,1.9Hz,1H),4.65(d, J＝15.4Hz,1H),4.59(d,J＝15.4Hz,1H),3.24(s,2H),1.57(s, 3H).13C NMR(100MHz,CDCl3):δ173.8,153.8,147.5,142.9,133.7, 129.2,128.9,128.0,110.6,109.8,85.7,36.5,34.0,22.7。
example 7
The reaction equation is shown as follows:
after the reaction was completed by placing a 23-watt white compact fluorescent lamp at a distance of 3 cm from the reaction tube and reacting at room temperature for 36 hours, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (the silica gel specification was 200-300 mesh, and the eluent was petroleum ether/ethyl acetate: 30:1) to obtain 69 mg of colorless oil at a yield of 93%,
the nuclear magnetic spectrum data of the obtained product are as follows: :1H NMR(400MHz,CDCl3):δ77.44–7.29 (m,5H),3.44(d,J＝13.8Hz,1H),3.42(d,J＝13.8Hz,1H),3.13 (s,3H),1.76(s,3H).13C NMR(100MHz,CDCl3):δ173.9,153.1,133.6, 129.3,128.0,125.6,84.3,34.5,27.3,21.2。
example 8
The reaction equation is shown as follows:
after the reaction was completed, the organic phase was removed from the solvent by a rotary evaporator, and the residue was purified by a silica gel column (silica gel size: 200 to 300 mesh; eluent: petroleum ether/ethyl acetate: 25:1) to obtain 93 mg of an oily liquid with a yield of 94%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz,CDCl3):δ7.61–7.51 (m,2H),7.34–7.17(m,7H),5.70–5.62(m,1H),3.49–3.40(m, 2H),2.40(s,3H).13C NMR(100MHz,CDCl3):δ174.0,152.3,140.1, 133.5,129.8,128.4,127.9,127.2,126.5,124.9,86.1,35.4,21.9。
example 9
The reaction equation is shown as follows:
a 25 ml reaction tube equipped with a magnetic stirrer was charged with N-Boc-N- (4-methylphenyl) -2-methacrylamide (0.25 mmol), bis (4-methylphenyl) diselenide (0.25 mmol), acetonitrile (2 ml) at room temperature, after which a 23 w white compact fluorescent lamp was placed at a distance of 3 cm from the reaction tube and reacted at room temperature for 36 hours, after completion of the reaction, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified with a silica gel column (silica gel size 200-300 mesh, eluent petroleum ether/ethyl acetate 15:1) to obtain 93 mg of oily liquid at a yield of 92%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz,CDCl3):δ7.60–7.21 (m,8H),3.75(s,3H),3.44(d,J＝13.8Hz,1H),3.39(d,J＝13.8 Hz,1H),2.39(s,3H),1.77(s,3H).13C NMR(100MHz,CDCl3):δ173.6, 154.4,140.2,132.6,131.0,128.3,127.9,127.3,127.0,125.7,85.3, 55.6,34.5,22.9,21.2。
example 10
The reaction equation is shown as follows:
after the reaction was completed, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified by a silica gel column (200 to 300 mesh, eluent petroleum ether/ethyl acetate 15:1) to obtain 74 mg of an oily liquid at a yield of 95%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz,CDCl3):δ7.60–7.39(m, 4H),3.44(d,J＝13.8Hz,1H),3.39(d,J＝13.8Hz,1H),2.39(s,3H), 1.95(s,3H),1.69(s,3H).13C NMR(100MHz,CDCl3):δ173.5,154.4, 139.2,130.0,128.3,125.6,86.3,34.4,23.3,22.5.6.1。
in conclusion, the method adopts cheap and easily-obtained acrylamide and diselenide as raw materials, the acrylamide can be obtained by the coupling reaction of acryloyl chloride and corresponding amine through a carbon-nitrogen bond, and the diselenide is obtained by a commercial way; the method can be operated under the air condition, is not sensitive to water and oxygen, has relatively mild reaction condition and is simple to operate; the method adopts visible light as an agent, so that the cost is low and the reaction efficiency is high; the method can obtain the target product by only one step, and has the advantages of high yield, good functional group compatibility, simple post-treatment and good application potential.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (5)
1. A method for promoting the synthesis of seleno oxazolidine-2, 4-diketone by visible light is characterized by comprising the following steps: the method comprises the following steps: in an organic solvent, taking N-Boc protected acrylamide with a structure shown in a formula (I) and diselenide with a structure shown in a formula (II) as reaction raw materials, carrying out reaction under the irradiation of visible light, after the reaction is finished, decompressing reaction liquid, removing the solvent to obtain a crude product, and purifying the crude product by column chromatography to obtain a selenooxazolidine-2, 4-diketone compound with a structure shown in a formula (III);
the reaction equation is shown as follows:
wherein R in the compound of formula (I)1And R2Is H atom, alkyl and aryl, the compound of formula (II) adopts diaryl diselenide, dialkyl diselenide;
the organic solvent is acetonitrile; the irradiation light source for the reaction is a fluorescent lamp.
2. The method for synthesizing visible light promoted selenooxazolidine-2, 4-dione as claimed in claim 1, characterized in that: the mol ratio of the acrylamide with the structure shown in the formula (I) to the diselenide with the structure shown in the formula (II) is 1: 1-1: 2.
3. the method for synthesizing the visible light promoted selenooxazolidine-2, 4-dione as claimed in claim 2, characterized in that: the mol ratio of the acrylamide with the structure shown in the formula (I) to the diselenide with the structure shown in the formula (II) is 1: 1.
4. The method for synthesizing visible light promoted selenooxazolidine-2, 4-dione as claimed in claim 1, characterized in that: the reaction time is 26-36 h.
5. The method for synthesizing visible light promoted selenooxazolidine-2, 4-dione as claimed in claim 1, characterized in that: after the reaction is finished, concentrating the reaction solution under reduced pressure, separating the concentrate by column chromatography, and taking the mixed solution of petroleum ether and ethyl acetate as an eluent, wherein the ratio of petroleum ether: the volume ratio of ethyl acetate is (1-40): 1, collecting the eluent, and carrying out rotary evaporation on the solvent to obtain the seleno-oxazolidine-2, 4-diketone shown in the formula (III).
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