CN110590636A - 4-sulfonyl pyrrolidone compound and synthesis method thereof - Google Patents
4-sulfonyl pyrrolidone compound and synthesis method thereof Download PDFInfo
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
Abstract
The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of a 4-sulfonyl pyrrolidone compound. The structure of the compound is shown in the specification1H NMR、13C NMR and the like. The method takes 1, 2-dichloroethane as a solvent, does not need a metal catalyst, and aryl diazonium salt reacts with a sulfur dioxide solid substitute at 30 ℃ to obtain sulfonyl free radical, and then cyclizes with 2, 3-dienamide to obtain the 4-sulfonyl pyrrolidone compound. The preparation method of the 4-sulfonyl pyrrolidone compound has the advantages of mild conditions, simplicity, high efficiency, high reaction yield, wide application range of substrates, good product purity, convenience for separation and purification and good application value.
Description
Technical Field
The invention belongs to the technical field of organic chemistry, and particularly relates to a 4-sulfonyl pyrrolidone compound and a synthesis method thereof.
Background
1, 5-dihydro-2H-pyrrol-2-one (γ -lactam) is an important class of compounds, widely found in natural products and biological compounds, especially in clinical therapeutics, e.g. (R) -Rolipram is an antidepressant [ (a) J.Zhu, E.mix, B.Winblad, CNS Drug Rev.2001, 7, 387; (b) garcia, m.j.s.cards, a.c.b.m.de Oca, m.a.g.dos Santos, c.c.santana, c.r.d.coreia, j.org.chem.2005, 70, 1050](ii) a Brivaracetam is an antiepileptic drug (m.a. rogawski, Epilepsy res.2006, 69, 273). In addition, of gamma-lactamsThe ring-opened product gamma-amino acid is a key intermediate in organic synthesis and is used for synthesizing various natural products and drug molecules [ (a) M).C.Cativiela，I.Romero-Estudillo，Tetrahedron：Asymmetry2016，27，999；(b)M.C.Cativiela，Tetrahedron：Asymmetry2007，18，3；(c)A.Trabocchi，F.Guama，A.Guarna，Curr.Org.Chem.2005，9，1127.]. More recently, the strategy of constructing compounds containing sulfonyl moieties by direct insertion of sulfur dioxide has attracted attention from chemists. The sulfonyl compounds are widely present in natural products and drug molecular frameworks, and the compounds have good biological activity. In recent years, a series of commercially available drugs containing sulfonyl moieties have also been developed, for example bicalutamide is a non-steroidal antiandrogen drug for the treatment of prostate cancer [ (a) Tucker, h; crook, j.w.; chesterson, g.j.j.med.chem.1988, 31, 954.USP 463605; (b) huo, c.; wang, y.; yuan, y.; chen, f.; tang, j.chem.commun.2016, 52, 7233, Xi, h.; deng, b.; zong, z.; lu, s.; li, z.org.lett.2015, 17, 1180, Wang, y.; jiang, w.; hum, c.j.org.chem.2017, 82, 10628]. Sulfur dioxide insertion is a simple, efficient, clean organic synthesis strategy [ (a) p.bisselet, n.blanchard, org.biomol.chem.2013, 11, 5393; (b) a.s.Deeming, E.j.emmett, C.s.Richards-Taylor, M.c.Willis, Synthesis2014, 2701; (c) liu, c.fan, j.wu, org.biomol.chem.2015, 13, 1592; d]E.J.Emmett，M.C.Willis，Asian J.Org.Chem.2015，4，602；(e)G.Qiu，K.Zhou，L.Gao，J.Wu，Org.Chem.Front.2018，5，691；(f)K.Hofman，N.-W.Liu，G.Manolikakes，Chem.Eur.J.2018，24，11852；(g)J.Zhu，W.-C.Yang，X.-D.Wang，L.Wu，Adv.Synth.Catal.2018，360，386.]. The synthesis of biologically active compounds by radical-initiated sulfur dioxide insertion in such reaction systems has developed particularly rapidly in recent years. But of the traditional sulphonyl groupThe synthesis of compounds requires the use of strongly acidic raw materials, which are difficult to use for large-scale industrial preparation.
Disclosure of Invention
The invention aims to provide a simple and efficient synthesis method of 4-sulfonyl pyrrolidone compounds. In the invention, sulfur dioxide is attacked by aryl radicals obtained by aryl diazonium salt to obtain aryl sulfonyl radicals, and the synthesis of a series of 4-sulfonyl pyrrolidone compounds is realized through subsequent free radical addition, cyclization reaction and single electron transfer.
The synthesis method of the pyrrolidone sulfone compounds provided by the invention utilizes 2, 3-diene amide or 2, 3-diene amide derivatives, sulfur dioxide solid substitutes and aryl diazonium salts, does not need a catalytic free radical reaction of a catalyst in an oil bath kettle at 30 ℃, and efficiently constructs the 4-sulfonyl pyrrolidone compounds.
Specifically, the method of the invention is that in an organic solvent, in an oil bath kettle at 30 ℃, without a catalyst, aryl diazonium salt and sulfur dioxide generate aryl sulfonyl free radical, the aryl sulfonyl free radical attacks the 2-position of 2, 3-diene amide or 2, 3-diene amide derivative, and then cyclization is carried out to obtain the target product. The reaction formula is as follows:
in the formula, Ar1、Ar2The substituted group is an aromatic ring substituent group for electron withdrawing or electron supplying, the electron withdrawing group has a fluorine substituent group, and the electron supplying group is an alkyl group or a methoxyl group; r is aromatic ring substituent or alkyl.
The method comprises the following specific steps:
(1) adding 0.2mmol of 2, 3-diene amide or 2, 3-diene amide derivative, 0.2mmol of sulfur dioxide solid substitute and 0.3mmol of aryl diazonium salt into a reaction tube in sequence, plugging the reaction tube by a plug, placing the reaction tube in high-purity nitrogen or argon for ventilation, adding 2mL of organic solvent after the system is in an anaerobic condition, placing the system in a 30 ℃ oil bath kettle, and stirring until complete reaction;
(2) after TLC monitoring complete reaction, directly decompressing and concentrating the reaction liquid, carrying out column chromatography separation, and adopting a mixed liquid of petroleum ether and ethyl acetate (the volume ratio is 4: 1-2: 1) as a mobile phase to obtain the corresponding 4-sulfonyl pyrrolidone compound.
The reaction yield of the method reaches 46-77%. The sulfur dioxide solid substitute in the invention is DABCO (SO)2)2The 2, 3-dienamide derivative is N, 4-diphenylpenta-2, 3-dienamide, N- (4- (tert-butyl) phenyl) -4-phenyl-penta-2, 3-dienamide, N-butyl-4-phenyl-penta-2, 3-dienamide, N-phenyl-4- (p-tolyl) penta-2, 3-dienamide or 4- (4-fluorophenyl) -N-phenylpenta-2, 3-dienamide.
The structure of the compound synthesized by the method of the invention is shown in the specification1H NMR、13C NMR and the like.
In the present invention, the organic solvent used in the reaction system is 1, 2-Dichloroethane (DCE).
In the present invention, the amount of the sulfur dioxide solid substitute is 1.0 equivalent and the amount of the aryl diazonium salt is 1.5 equivalents based on 1.0 equivalent of the 2, 3-dienamide.
In the invention, the reaction temperature of the reaction system is 30 ℃; the reaction time was 12 hours.
The reaction of the invention is carried out under very mild and simple conditions, a catalyst is not needed, aryl diazonium salt and sulfur dioxide generate aryl sulfonyl free radical, the aryl sulfonyl free radical attacks and cyclizes the 2-position of the allenamide, and then single electron transfer is carried out to obtain the target product. The method constructs a series of 4-sulfonyl pyrrolidone compounds; the sulfur dioxide solid substitutes required by the reaction are all abundant and easily-obtained chemical raw materials, the reaction avoids the use of strong acid raw materials in the synthesis of the traditional sulfonyl compounds, can be used for large-scale industrial preparation, and have good guiding significance and application prospect in the fields of scientific research and industry.
Detailed Description
The invention is further described below by means of specific examples.
Example 1
0.2mmol of N, 4-diphenylpenta-2, 3-dienamide and 0.2mmol of DABCO (SO) were added to the reaction tube in this order2)2And 0.3mmol of p-tolyl diazonium salt, plugging the reaction tube by a plug, placing the reaction tube in high-purity nitrogen or argon for ventilation, adding 2mL of 1, 2-dichloroethane after the system is in an anaerobic condition, and placing the mixture in an oil bath kettle at the temperature of 30 ℃ for stirring until the reaction is completed. The reaction solution is directly decompressed and concentrated, column chromatography separation is carried out, and the corresponding 5-methyl-1, 5-diphenyl-4-tosyl-1, 5-dihydro-2H-pyrrole-2-ketone compound example 1 can be obtained by adopting the mixed solution of petroleum ether and ethyl acetate as a mobile phase.
Structural characterization of compound example 1:1H NMR(400MHz，CDCl3)δ7.34-7.24(m，5H)，7.21-7.11(m，5H)，7.10-7.02(m，3H)，6.96(s，1H)，6.67(s，1H)，2.36(s，3H)，2.20(s，3H)；13C NMR(101MHz，CDCl3)δ(ppm)162.2，157.0，145.0，136.8，135.7，132.2，129.5，128.6，128.3，127.9，126.0，125.3，124.1，121.8，92.6，24.2，23.7，21.5.HRMS calcd for C24H21N1O3S(M+H+)：404.1315.Found：404.1318.
example 2
0.2mmol of N, 4-diphenylpenta-2, 3-dienamide and 0.2mmol of DABCO (SO) were added to the reaction tube in this order2)2And 0.3mmol of phenyl diazonium salt, plugging the reaction tube by a plug, placing the reaction tube in high-purity nitrogen or argon for ventilation, adding 2mL of 1, 2-dichloroethane after the system is in an anaerobic condition, and placing the mixture in an oil bath kettle at the temperature of 30 ℃ for stirring until the reaction is completed. The reaction liquid is directly decompressed and concentrated, column chromatography separation is carried out, and the corresponding 5-methyl can be obtained by adopting the mixed liquid of petroleum ether and ethyl acetate as a mobile phase-1, 5-Diphenyl-4- (phenylsulfonyl) -1, 5-dihydro-2H-pyrrol-2-one Compound example 2.
Structural characterization of compound example 2:1H NMR(400MHz，CDCl3)δ(ppm)7.55-7.47(m，4H)，7.42-7.36(m，4H)，7.27(d，J＝6.5Hz，3H)，7.14-7.09(m，3H)，7.00-6.92(m，1H)，4.96(s，1H)，2.03(s，3H)；13C NMR(101MHz，CDCl3)δ(ppm)168.8，157.0，143.3，140.7，137.6，133.8，132.86，129.0，128.8，128.6，128.0，127.3，126.0，124.1，120.7，52.9，24.8.HRMS calcdfor C23H19N1O3S(M+H+)：390.1158.Found：390.1156.
example 3
0.2mmol of N, 4-diphenylpenta-2, 3-dienamide and 0.2mmol of DABCO (SO) were added to the reaction tube in this order2)2And 0.3mmol of 4-methoxyphenyl diazonium salt, plugging the reaction tube by a plug, placing the reaction tube in high-purity nitrogen or argon for ventilation, adding 2mL of 1, 2-dichloroethane after the system is in an anaerobic condition, and placing the mixture in an oil bath kettle at the temperature of 30 ℃ for stirring until the reaction is completed. The reaction solution was directly concentrated under reduced pressure, and column chromatography was performed using a mixture of petroleum ether and ethyl acetate as the mobile phase to obtain the corresponding 4- ((4-methoxyphenyl) sulfonyl) -5-methyl-1, 5-diphenyl-1, 5-dihydro-2H-pyrrol-2-one compound example 3.
Structural characterization of compound example 3:1H NMR(400MHz，CDCl3)δ(ppm)7.36-7.29(m，3H)，7.26(d，J＝5.9Hz，2H)，7.22-7.13(m，5H)，7.12-7.05(m，2H)，6.94(s，1H)，6.68(t，J＝7.7Hz，2H)，3.80(d，J＝3.1Hz，3H)，2.17(d，J＝5.3Hz，3H)；13C NMR(101MHz，CDCl3)δ(ppm)163.9，131.8，130.5，130.3，129.1，128.7，128.7，128.6，128.4，126.1，125.4，124.1，120.6，114.5，114.3，55.7，24.3，23.7.HRMS calcd for C24H21N1O45(M+H+)：420.1264.Found：420.1278.
example 4
0.2mmol of N- (4- (tert-butyl) phenyl) -4-phenyl-penta-2, 3-dienamide and 0.2mmol of DABCO (SO) were added to the reaction tube in this order2)2And 0.3mmol of p-tolyl diazonium salt, plugging the reaction tube by a plug, placing the reaction tube in high-purity nitrogen or argon for ventilation, adding 2mL of 1, 2-dichloroethane after the system is in an anaerobic condition, and placing the mixture in an oil bath kettle at the temperature of 30 ℃ for stirring until the reaction is completed. The reaction mixture was directly concentrated under reduced pressure, and column chromatography was carried out using a mixture of petroleum ether and ethyl acetate as the mobile phase to give 1- (4- (tert-butyl) phenyl) -5-methyl-5-phenyl-4-tosyl-1, 5-dihydro-2H-pyrrol-2-one compound example 4.
Structural characterization of compound example 4:1H NMR(400MHz，CDCl3)δ(ppm)7.32(d，J＝9.9Hz，6H)，7.22(d，J＝6.7Hz，1H)，7.20-7.14(m，4H)，7.05(d，J＝7.8Hz，2H)，6.95(s，1H)，2.35(s，3H)，2.19(s，3H)，1.28(s，9H)；13C NMR(101MHz，CDCl3)δ(ppm)161.8，148.6，145.0，142.2，137.1，132.5，129.6，128.6，128.4，128.0，126.1，126.1，125.6，124.2，121.5，92.6，34.4，31.3，24.4，21.5.HRMS calcd for C28H29N1O3S(M+H+)：460.1941.Found：460.1945.
example 5
0.2mmol of N-butyl-4-phenyl-penta-2, 3-dienamide, 0.2mmol of DABCO (SO) were added to the reaction tube in this order2)20.3mmol of p-methylphenyl diazonium salt, plugging the reaction tube by a plug, placing the reaction tube in high-purity nitrogen or argon for ventilation, adding 2mL of 1, 2-dichloroethane after the system is in an anaerobic condition,the mixture was stirred in an oil bath at 30 ℃ until the reaction was complete. The reaction solution was directly concentrated under reduced pressure, and column chromatography was performed using a mixture of petroleum ether and ethyl acetate as the mobile phase to obtain the corresponding 1-butyl-5-methyl-5-phenyl-4-tosyl-1, 5-dihydro-2H-pyrrol-2-one compound example 5.
Structural characterization of compound example 5:1H NMR(400MHz，CDCl3)δ(ppm)8.09(d，J＝7.7Hz，2H)，7.40(s，3H)，7.32(d，J＝6.9Hz，3H)，7.26(s，1H)，4.71(s，1H)，2.36(s，3H)，2.04(s，3H)，1.58(s，2H)，1.39-1.33(m，2H)，1.22-1.16(m，2H)，0.82(t，J＝7.1Hz，3H)；13C NMR(101MHz，CDCl3)δ(ppm)171.1，143.3，141.1，129.2，128.9，128.6，128.3，127.8，127.6，127.5，127.4，52.6，39.7，31.1，21.5，19.9，13.7.HRMS calcd for C22H25N1O3S(M+H+)：384.1628.Found：384.1630.
example 6
0.2mmol of N-phenyl-4- (p-tolyl) penta-2, 3-dienamide and 0.2mmol of DABCO (SO) were added to the reaction tube in this order2)2And 0.3mmol of p-methylphenyl diazonium salt, plugging the reaction tube by a plug, placing the reaction tube in high-purity nitrogen or argon for ventilation, adding 2mL of 1, 2-dichloroethane after the system is in an anaerobic condition, and placing the mixture in an oil bath kettle at the temperature of 30 ℃ for stirring until the reaction is completed. The reaction mixture was directly concentrated under reduced pressure and subjected to column chromatography, using a mixture of petroleum ether and ethyl acetate as a mobile phase, to give 5-methyl-1-phenyl-5- (p-tolyl) -4-toluenesulfonyl-1, 5-dihydro-2H-pyrrol-2-one compound example 6.
Structural characterization of compound example 6:1H NMR(400MHz，CDCl3)δ(ppm)7.33(d，J＝7.8Hz，2H)，7.29(s，3H)，7.11(d，J＝6.6Hz，1H)，7.06(d，J＝8.0Hz，2H)，7.02(d，J＝7.6Hz，3H)，6.95(d，J＝3.4Hz，2H)，6.93(s，1H)，2.37(s，3H)，2.29(s，3H)，2.15(s，3H)；13C NMR(101MHz，CDCl3)δ(ppm)162.4，144.9，138.8，133.8，132.1，129.5，129.3，129.0，128.9，128.7，128.1，125.9，125.3，124.2，121.9，92.6，24.1，21.6，21.0.HRMS calcd for C25H23N1O3S(M+H+)：418.1471.Found：418.1475.
example 7
0.2mmol of 4- (4-fluorophenyl) -N-phenylpenta-2, 3-dienamide and 0.2mmol of DABCO (SO) were added to the reaction tube in this order2)2And 0.3mmol of p-methylphenyl diazonium salt, plugging the reaction tube by a plug, placing the reaction tube in high-purity nitrogen or argon for ventilation, adding 2mL of 1, 2-dichloroethane after the system is in an anaerobic condition, and placing the mixture in an oil bath kettle at the temperature of 30 ℃ for stirring until the reaction is completed. The reaction mixture was directly concentrated under reduced pressure and subjected to column chromatography, using a mixture of petroleum ether and ethyl acetate as a mobile phase, to give 5- (4-fluorophenyl) -5-methyl-1-phenyl-4-tosyl-1, 5-dihydro-2H-pyrrol-2-one compound example 7.
Structural characterization of compound example 7:1H NMR(400MHz，CDCl3)δ(ppm)7.81-7.75(m，3H)，7.68-7.60(m，2H)，7.45(d，J＝5.8Hz，3H)，7.23(d，J＝7.1Hz，3H)，6.96(t，J＝8.3Hz，2H)，6.83(s，1H)，2.43(s，3H)，2.37(s，3H)；13C NMR(101MHz，CDCl3)δ(ppm)164.3，130.2(d，J＝8.0Hz)，129.9，129.8，129.6(d，J＝6.0Hz)，129.3，128.9，127.3，124.8(d，J＝29Hz)，124.0，122.8，122.5，122.3，120.8，119.9，55.0，21.5，20.8.HRMS calcd for C24H20F1N1O3S(M+H+)：422.1221.Found：422.1216.
it will be appreciated by persons skilled in the art that the above examples are illustrative only and not intended to be limiting of the invention, and that modifications to the above-described embodiments will fall within the scope of the appended claims provided they fall within the true spirit of the invention.
Claims (7)
1. A4-sulfonyl pyrrolidone compound is characterized in that the 4-position of pyrrolidone is substituted by aryl sulfonyl, and the molecular structure is as follows:
in the formula, Ar1、Ar2Is an electron-withdrawing or electron-supplying aromatic ring substituent, the electron-withdrawing group has a fluorine substituent group, and the electron-supplying group is an alkyl group or a methoxy group; r is aromatic ring substituent or alkyl.
2. The method for synthesizing 4-sulfonyl pyrrolidones as claimed in claim 1, wherein in an organic solvent, aryl diazonium salt and sulfur dioxide generate aryl sulfonyl radical, the aryl sulfonyl radical attacks and cyclizes 2, 3-dienamide or 2, 3-dienamide derivative at 2-position, and then single electron transfer occurs to obtain the target product, and the method comprises the following specific steps:
″SO2″＝DABCO·(SO)2
(1) at room temperature, sequentially adding 2, 3-diene amide or 2, 3-diene amide derivatives, sulfur dioxide solid substitutes and aryl diazonium salts into a reaction tube, plugging the reaction tube by using a plug, placing the reaction tube in high-purity nitrogen or argon for ventilation, adding a certain amount of organic solvent after the system is in an anaerobic condition, placing the system in a 30 ℃ oil bath kettle, and stirring until complete reaction;
(2) and after TLC monitoring complete reaction, directly carrying out reduced pressure concentration on the reaction liquid, carrying out column chromatography separation, and taking the mixed liquid of petroleum ether and ethyl acetate as a mobile phase to obtain the corresponding aryl sulfonyl substituted pyrrolidone compound.
3. The method for synthesizing 4-sulfonyl pyrrolidone compounds according to claim 2, wherein the organic solvent is 1, 2-dichloroethane.
4. The method for synthesizing 4-sulfonylpyrrolidones according to claim 2, wherein the amount of the sulfur dioxide solid substitute is 1.0 equivalent, the amount of the aryldiazonium salt is 1.5 equivalents, and the amount of the organic solvent is 2ml per 0.2mmol of 2, 3-dienamide or 2, 3-dienamide derivative, based on 1.0 equivalent of 2, 3-dienamide or 2, 3-dienamide derivative.
5. The method for synthesizing 4-sulfonyl pyrrolidone compounds according to claim 2, wherein the solid substitute of sulfur dioxide is DABCO (SO)2)2The 2, 3-dienamide derivative is N, 4-diphenylpenta-2, 3-dienamide, N- (4- (tert-butyl) phenyl) -4-phenyl-penta-2, 3-dienamide, N-butyl-4-phenyl-penta-2, 3-dienamide, N-phenyl-4- (p-tolyl) penta-2, 3-dienamide or 4- (4-fluorophenyl) -N-phenylpenta-2, 3-dienamide.
6. The method for synthesizing 4-sulfonyl pyrrolidone compound according to patent claim 2, wherein the volume ratio of petroleum ether to ethyl acetate in the mobile phase is: 4: 1-2: 1.
7. The method for synthesizing 4-sulfonyl pyrrolidone compound according to claim 2, wherein the reaction time is 10-12 h.
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Application publication date: 20191220 |