CN112624998A - Azacyclolactone compound and preparation method thereof - Google Patents
Azacyclolactone compound and preparation method thereof Download PDFInfo
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- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/01—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having one nitrogen atom
Abstract
A aza-cyclolactone compound and a preparation method thereof, belonging to the technical field of compound preparation. The invention constructs the (5 + 6) cycloaddition reaction of vinyl ethylene carbonate and isatoic anhydride for the first time, and efficiently and simply realizes the chemical synthesis of azacyclolactone. Specifically, vinyl ethylene carbonate and isatoic anhydride are used as synthetic building blocks, and a target product is obtained by adding a metal palladium catalyst and a phosphorus-containing ligand and reacting under the heating condition of 50-70 ℃. The preparation method has the advantages of simple operation, quick reaction, high product yield, simple post-treatment and wide applicable substrate range. The method is a novel and efficient synthesis method of the azalide compound with potential biological activity and medicinal value.
Description
Technical Field
The invention particularly relates to a preparation method of a aza-cyclolactone compound, belonging to the technical field of compound preparation.
Background
The azalide compound is a heterocyclic compound with a unique chemical structure, is used as an advantageous drug skeleton structure, and widely exists in active natural products and drug molecular structures, such as anti-inflammatory, antifungal, antitumor, antiviral, antiparasitic and the like. At present, the synthesis of azalide compounds is reported more. In contrast, azalide compounds face great difficulties in their construction, primarily due to the need to overcome adverse entropy effects and trans-ring interactions in the construction of azalide compounds. At present, few reports are provided about the synthesis method of azacyclolactone compounds, and a large development space still exists. Therefore, the novel, efficient, environment-friendly and simple-to-operate organic synthesis method is designed and developed to construct the azacyclolactone compound with a novel structure, so that the research on the organic synthesis methodology of the azacyclolactone compound is greatly enriched, and the method has very important significance for developing and developing candidate drugs of the azacyclolactone compound.
Vinyl ethylene carbonate is an important synthetic building block and is widely applied to construction of various heterocyclic systems with complex and various structures. Under the action of a palladium catalyst, vinyl ethylene carbonate is decarboxylated to form a high-activity pi-allyl palladium zwitterion intermediate. The intermediate can be used as a 3 or 5 atom synthon to perform a [3+2], [5+2] or [5+4] cycloaddition reaction with olefin, aldehyde, imine, oxazolone, vinyl benzoxazinone and the like, so as to construct various heterocyclic skeleton structures with complex and various structures. In contrast, vinyl ethylene carbonate is currently not commonly studied as an organic building block for the construction of azacyclolactone-type compounds. The invention selects vinyl ethylene carbonate and isatoic anhydride as organic synthesis building blocks, and realizes the chemical synthesis of aza-cyclolactone compounds by constructing efficient and simple [5+6] cycloaddition reaction. The aza-cyclolactone obtained by the organic synthesis method has a novel and unique skeleton structure, a strong drug property of a chemical structure, and potential biological activity and medicinal development value.
Disclosure of Invention
The invention aims to provide a preparation method of aza-cyclolactone compounds.
In order to achieve the purpose of the invention, the technical scheme adopted by the invention is as follows:
a preparation method of an azacyclolactone compound comprises the following steps: vinyl ethylene carbonate and isatoic anhydride are used as synthesis building blocks, metal palladium catalyst and phosphorus-containing ligand are added, and the mixture is heated and stirred in organic solvent at 50-70 ℃ to react to obtain the product aza-cyclolactone compound. Preferably, the molar ratio of vinyl ethylene carbonate to isatoic anhydride is 2: 1.
The structural formula of the aza-cyclic lactone compound is as follows:
wherein R is1Is aryl; r2Is hydrogen or alkyl; r3One of hydrogen, fluorine, chlorine, bromine, alkyl and alkoxy; r4Is alkyl, benzyl, allyl or phenyl.
The aryl group is a phenyl group or a phenyl group having 1 to 2 substituents. For example: mono-substituted phenyl and di-substituted phenyl.
The substituents on the above phenyl groups are selected from: one or two of methyl, methoxy, fluorine, chlorine and bromine.
In the above technical scheme, the organic solvent is toluene, dichloromethane, acetone, ethyl acetate, ethyl propionate, cyclohexane or tetrahydrofuran.
In the above technical scheme, the palladium catalyst is selected from tetrakis (triphenylphosphine) palladium, palladium acetate, bis (triphenylphosphine) palladium dichloride, tris (dibenzylideneacetone) dipalladium or tris (dibenzylideneacetone) dipalladium-chloroform adduct.
In the above technical solution, the phosphorus-containing ligand is selected from: one or more of tricyclohexylphosphine, triphenylphosphine, 1' -bis (diphenylphosphino) ferrocene, 1, 4-bis (diphenylphosphino) butane, 1, 3-bis (diphenylphosphino) propane and 1, 2-bis (diphenylphosphino) benzene.
In the technical scheme, the reaction time is 1-10 hours.
In the technical scheme, the dosage of the palladium catalyst is 2.5-10% of the molar weight of the isatoic anhydride compound.
In the technical scheme, the dosage of the phosphorus-containing ligand is 10-40% of the molar weight of the isatoic anhydride compound.
In the technical scheme, the reaction process comprises the steps of adding a vinyl ethylene carbonate compound, an isatoic anhydride compound, a palladium catalyst, a phosphorus-containing ligand and an organic solvent into a reaction bottle, heating and stirring at 60 ℃, detecting the reaction process by using TLC (thin layer chromatography), and after the reaction is finished, obtaining a target product from a crude product by using simple column chromatography.
The preparation method of the vinyl ethylene carbonate compound belongs to the prior art, and the structural formula is as follows:
the preparation method of isatoic anhydride belongs to the prior art, and the structural formula of the isatoic anhydride is as follows:
The reaction process disclosed by the invention is as follows:
due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
1. the invention constructs the (5 + 6) cycloaddition reaction of vinyl ethylene carbonate and isatoic anhydride for the first time, and efficiently and simply realizes the chemical synthesis of azacyclolactone.
2. The method has the advantages of simple operation, short reaction time and high product yield.
3. The preparation method disclosed by the invention has the advantages of small catalyst consumption and simple post-treatment.
4. The method disclosed by the invention has wide substrate application range.
5. The raw materials related by the invention are convenient and easy to obtain, and have no pollution.
Detailed Description
The present invention will be further described with reference to the following examples, but the present invention is not limited to the following examples.
Example 1:
1a (38.0mg, 0.2mmol), 2a (17.7mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh were weighed out3(2.6mg, 0.01mmol) is dissolved in 1mL ethyl acetate, heated and stirred at 60 ℃ for 5 hours (detection reaction by TLC), after the reaction is completed, the crude product is subjected to column chromatography to obtain the target product 3aa (31.8mg), and the yield is 98%.
Characterization and analysis of the target:
3 aa: a white solid, a solid which is,1H NMR(400MHz,CDCl3):δ7.58(d,J＝7.2Hz,1H),7.51-7.47(m,3H),7.41-7.33(m,3H),7.27-7.25(m,2H),6.11(t,J＝6.8Hz,1H),5.26(s,2H),4.69(d,J＝6.0Hz,2H),3.45(s,3H)ppm；13C NMR(100MHz,CDCl3):δ167.9,154.2,145.8,141.1,140.8,131.3,130.0,128.6,128.2,127.5,126.8,125.4,124.6,124.5,64.1,61.6,38.1ppm；HRMS(ESI)m/z:C19H17NO4[M+H]+theoretical calculation 324.1230, found 324.1218.
Example 2:
1a (38.0mg, 0.2mmol), 2b (21.2mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh were weighed out3(2.6mg, 0.01mmol) was dissolved in 1mL of ethyl acetate and stirred at 60 ℃ for 4 hours (using TLC, detection reaction), after the reaction is completed, performing column chromatography on the crude product to obtain a target product 3ab (31.1mg), wherein the yield is 87%.
Characterization and analysis of the target:
3ab of a white solid, and (c) a white solid,1H NMR(400MHz,CDCl3):δ7.55(s,1H),7.49(d,6.4Hz,2H),7.45-7.36(m,4H),7.20(d,J＝8.8Hz,1H),6.13(t,J＝8.0Hz,1H),5.26(s,2H),4.68(d,J＝4.8Hz,2H),3.42(s,3H)ppm；13C NMR(100MHz,CDCl3):δ166.6,153.9,145.9,140.8,139.4,131.4,131.2,131.0,128.6,128.3,127.5,126.8,125.9,124.4,64.3,61.6,38.1ppm；HRMS(ESI)m/z:C19H16ClNO4[M+H]+theoretical calculation 358.0841, found 358.0827.
Example 3:
1b (53.8mg, 0.2mmol), 2a (17.7mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh were weighed out3(2.6mg, 0.01mmol) is dissolved in 1mL ethyl acetate, heated and stirred at 60 ℃ for 2 hours (detection reaction by TLC), after the reaction is completed, the crude product is subjected to column chromatography to obtain the target product 3ba (34.9mg), and the yield is 87%.
Characterization and analysis of the target:
3ba of white solid, and the white solid,1H NMR(400MHz,CDCl3):δ7.57(d,J＝7.2Hz,1H),7.51-7.47(m,3H),7.36(d,J＝8.0Hz,2H),7.27-7.25(m,2H),6.09(t,J＝6.4Hz,1H),5.19(s,2H),4.67(d,J＝4.8Hz,2H),3.43(s,3H)ppm；13C NMR(100MHz,CDCl3):δ167.8,154.1,144.5,140.9,140.1,131.7,131.3,130.0,128.5,127.5,125.5,125.0,124.6,122.3,64.1,61.3,38.1ppm；HRMS(ESI)m/z:C19H16BrNO4[M+H]+theoretical calculation 402.0336, found 402.0321.
Example 4:
1b (53.8mg, 0.2mmol), 2b (21.2mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh were weighed out3(2.6mg, 0.01mmol) was dissolved in 1mL of ethyl acetate, heated and stirred at 60 ℃ for 2 hours (detection by TLC), and the crude product was subjected to column chromatography to give the desired product 3bb (40.7mg) in 93% yield.
Characterization and analysis of the target:
3bb of a white solid, wherein the white solid is,1H NMR(400MHz,CDCl3):δ7.53-7.50(m,3H),7.44(d,J＝8.4Hz,1H),7.36(d,J＝8.4Hz,2H),7.20(d,J＝8.8Hz,1H),6.10(t,J＝6.8Hz,1H),5.20(s,2H),4.66(d,J＝6.0Hz,2H),3.40(s,3H)ppm；13C NMR(100MHz,CDCl3):δ166.5,153.8,144.6,139.8,139.4,131.7,131.3,131.2,131.0,128.5,127.5,125.9,124.9,122.5,64.3,61.4,38.0ppm；HRMS(ESI)m/z:C19H15BrClNO4[M+H]+theoretical calculation 435.9946, found 435.9925.
Example 5:
1b (53.8mg, 0.2mmol), 2c (19.1mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh were weighed out3(2.6mg, 0.01mmol) was dissolved in 1mL of ethyl acetate, heated and stirred at 60 ℃ for 7 hours (reaction detected by TLC), and the crude product was subjected to column chromatography to obtain the target product 3bc (40.1mg) in a yield of 95%.
Characterization and analysis of the target:
3bc is a white solid, and the white solid,1H NMR(400MHz,CDCl3):δ7.51-7.49(m,2H),7.37(d,J＝8.8Hz,3H),7.28(d,J＝8.0Hz,1H),7.15(d,J＝8.4Hz,1H),6.08(t,J＝6.4Hz,1H),5.18(s,2H),4.66(d,J＝5.6Hz,2H),3.40(s,3H),2.38(s,3H)ppm；13C NMR(100MHz,CDCl3):δ167.8,154.2,144.4,140.1,138.4,135.5,132.0,131.7,129.7,128.6,128.0,125.2,124.6,122.3,64.0,61.3,38.1,20.8ppm；HRMS(ESI)m/z:C20H18BrNO4[M+H]+theoretical calculation 416.0492, found 416.0479.
Example 6:
1c (44.9mg, 0.2mmol), 2a (17.7mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh were weighed out3(2.6mg, 0.01mmol) is dissolved in 1mL ethyl acetate, heated and stirred at 60 ℃ for 2 hours (detection reaction by TLC), after the reaction is completed, the crude product is subjected to column chromatography to obtain the target product 3ca (34.7mg), and the yield is 97%.
Characterization and analysis of the target:
3ca of a white solid, wherein the white solid is,1H NMR(400MHz,CDCl3):δ7.57(d,J＝7.2Hz,1H),7.49(t,J＝7.2Hz,1H),7.43(d,J＝8.0Hz,2H),7.35(d,J＝8.8Hz,2H),7.28-7.26(m,2H),6.09(t,J＝6.8Hz,1H),5.20(s,2H),4.68(d,J＝5.6Hz,2H),3.44(s,3H)ppm；13C NMR(100MHz,CDCl3):δ167.8,154.1,144.5,140.8,139.6,134.1,131.3,130.0,128.7,128.2,127.5,125.5,124.9,124.6,64.1,61.3,38.1ppm；HRMS(ESI)m/z:C19H16ClNO4[M+H]+theoretical calculation 358.0841, found 358.0827.
Example 7:
1c (44.9mg, 0.2mmol), 2b (21.2mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh were weighed out3(2.6mg, 0.01mmol) was dissolved in 1mL of ethyl acetate, heated and stirred at 60 ℃ for 2 hours (detection by TLC), and the crude product was subjected to column chromatography to give the desired product 3cb (33.4mg) in 85% yield.
Characterization and analysis of the target:
3cb of a white solid, and 3cb of a white solid,1H NMR(400MHz,CDCl3):δ7.54(s,1H),7.45-7.41(m,3H),7.36(d,J＝8.4Hz,2H),7.20(d,J＝8.8Hz,1H),6.10(t,J＝6.8Hz,1H),5.20(s,2H),4.66(d,J＝6.0Hz,2H),3.40(s,3H)ppm；13C NMR(100MHz,CDCl3):δ166.6,153.8,144.6,139.4,139.3,134.3,131.3,131.2,131.0,128.8,128.2,127.5,125.9,124.8,64.3,61.4,38.0ppm；HRMS(ESI)m/z:C19H15Cl2NO4[M+H]+theoretical calculation 392.0451, found 392.0433.
Example 8:
1c (44.9mg, 0.2mmol), 2c (19.1mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh were weighed out3(2.6mg, 0.01mmol) was dissolved in 1mL of ethyl acetate, heated and stirred at 60 ℃ for 2 hours (reaction detected by TLC), and the crude product was subjected to column chromatography to obtain 3cc (35.9mg) of the objective product, with a yield of 97%.
Characterization and analysis of the target:
3cc of white solid, wherein the white solid is,1H NMR(400MHz,CDCl3):δ7.44(d,J＝8.4Hz,2H),7.38-7.34(m,3H),7.29(s,1H),7.15(d,J＝8.0Hz,1H),6.09(t,J＝6.8Hz,1H),5.19(s,2H),4.67(d,J＝6.0Hz,2H),3.41(s,3H),2.38(s,3H)ppm；13C NMR(100MHz,CDCl3):δ167.8,154.2,144.3,139.6,138.3,135.5,134.1,131.9,129.6,128.7,128.2,127.9,125.1,124.6,64.0,61.2,38.0,20.7ppm；HRMS(ESI)m/z:C20H18ClNO4[M+H]+theoretical calculation 372.0997, found 372.0985.
Example 9:
1d (44.0mg, 0.2mmol), 2b (21.2mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh were weighed out3Dissolving (2.6mg, 0.01mmol) in 1mL ethyl acetate, heating and stirring at 60 deg.C for 6 hr (detecting reaction by TLC), and subjecting the crude product to column chromatography to obtain target product 3db (33.0mg) with yieldThe content was 85%.
Characterization and analysis of the target:
3db of white solid, wherein the white solid is,1H NMR(400MHz,CDCl3):δ7.53(s,1H),7.43(d,J＝8.0Hz3H),7.19(d,J＝8.4Hz,1H),6.92(d,J＝8.8Hz,2H),6.07(t,J＝6.4Hz,1H),5.24(s,2H),4.66(d,J＝6.0Hz,2H),3.85(s,3H),3.41(s,3H)ppm；13C NMR(100MHz,CDCl3):δ166.7,159.8,153.9,145.6,139.4,133.2,131.4,131.1,130.9,128.0,127.5,125.9,122.8,114.0,64.3,61.8,55.4,38.1ppm；HRMS(ESI)m/z:C20H18ClNO5[M+H]+theoretical calculation 388.0946, found 388.0933.
Example 10:
1d (44.0mg, 0.2mmol), 2d (25.3mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh were weighed out3(2.6mg, 0.01mmol) was dissolved in 1mL of ethyl acetate, heated and stirred at 60 ℃ for 4 hours (reaction detected by TLC), and the crude product was subjected to column chromatography to give the desired product 3dd (23.6mg) in 55% yield.
Characterization and analysis of the target:
3dd white solid, 1H NMR (400MHz, CDCl)3):δ7.57(d,J＝5.6Hz,1H),7.45-7.34(m,8H),7.23-7.16(m,2H),6.93(d,J＝8.4Hz,2H),6.07(t,J＝5.6Hz,1H),5.22(s,2H),5.06(s,2H),4.74(s,2H),3.85(s,3H)ppm；13C NMR(100MHz,CDCl3):δ167.8,159.7,154.6,145.5,140.0,137.6,133.5,131.1,129.9,128.5,128.0,127.8,127.6,127.3,125.5,124.3,123.0,113.9,63.8,62.0,55.4,54.5ppm；HRMS(ESI)m/z:C26H23NO5[M+H]+Theoretical calculation 430.1649, found 430.1633.
Example 11:
weighing 1a(38.0mg, 0.2mmol), 2d (25.3mg, 0.1mmol), Palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh3(2.6mg, 0.01mmol) was dissolved in 1mL of ethyl acetate, heated and stirred at 60 ℃ for 1.5 hours (reaction detected by TLC), and the crude product was subjected to column chromatography to obtain the desired product 3ad (32.8mg), with an yield of 82%.
Characterization and analysis of the target:
3ad (3) the white solid,1H NMR(400MHz,CDCl3):δ7.59(d,J＝7.2Hz,1H),7.51(d,J＝7.2Hz,2H),7.42-7.33(m,9H),7.24-7.17(m,2H),6.12(t,J＝6.8Hz,1H),5.25(s,2H),5.07(s,2H),4.76(s,2H)ppm；13C NMR(100MHz,CDCl3):δ167.7,154.6,145.8,141.1,140.0,137.6,131.2,129.9,128.6,128.5,128.2,127.9,127.6,127.3,126.8,125.5,124.5,124.3,63.9,61.8,54.5ppm；HRMS(ESI)m/z:C25H21NO4[M+H]+theoretical calculation 400.1543, found 400.1530.
The results show that the preparation method disclosed by the invention has the advantages of high reaction speed, high product yield and simple post-treatment.
Claims (9)
1. A aza-cyclolactone with the structural formula
Wherein R is1Is aryl; r2Is hydrogen or alkyl; r3Is one of hydrogen, fluorine, chlorine, bromine, alkyl and alkoxy; r4Is alkyl, benzyl, allyl or phenyl;
the aryl group is a phenyl group or a phenyl group having 1 to 2 substituents; the substituents on the above phenyl groups are selected from: one or two of methyl, methoxy, fluorine, chlorine and bromine.
2. The preparation method of azacyclolactone as claimed in claim 1, wherein the reaction process comprises adding vinyl ethylene carbonate compound, isatoic anhydride compound, palladium catalyst, phosphorus-containing ligand and organic solvent into a reaction flask, heating and stirring at 50-70 ℃, detecting the reaction progress by TLC, after the reaction is finished, obtaining the target product from the crude product by simple column chromatography, and the eluent is selected from the group consisting of 10: 1 of a petroleum ether/ethyl acetate mixed solution.
3. A method of preparing an azacyclolactone according to claim 2, wherein the molar ratio of vinyl ethylene carbonate to isatoic anhydride compound is 2: 1.
4. A method of preparing an azacyclolactone according to claim 2, wherein the organic solvent is toluene, dichloromethane, acetone, ethyl acetate, ethyl propionate, cyclohexane or tetrahydrofuran.
5. A process according to claim 2, wherein said palladium catalyst is selected from the group consisting of tetrakis (triphenylphosphine) palladium, palladium acetate, bis (triphenylphosphine) palladium dichloride, tris (dibenzylideneacetone) dipalladium, and tris (dibenzylideneacetone) dipalladium-chloroform adduct.
6. A process according to claim 2, wherein said phosphorus-containing ligand is selected from the group consisting of: one or more of tricyclohexylphosphine, triphenylphosphine, 1' -bis (diphenylphosphino) ferrocene, 1, 4-bis (diphenylphosphino) butane, 1, 3-bis (diphenylphosphino) propane and 1, 2-bis (diphenylphosphino) benzene.
7. A method of preparing azacyclolactone according to claim 2, wherein the reaction time is 1 to 10 hours.
8. A method for preparing azacyclolactone according to claim 2, wherein the amount of said palladium catalyst is 2.5-10% by mole of the isatin anhydride compound; the dosage of the phosphorus-containing ligand is 10 to 40 percent of the molar weight of the isatoic anhydride compound.
9. A method of producing an azacyclolactone according to claim 2, wherein the vinyl ethylene carbonate compound has the following structural formula:
the structure formula of the isatin acid anhydride compound is shown as follows:
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