CN111235596A - Preparation method of thiazoline compound containing selenium - Google Patents
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- -1 thiazoline compound Chemical class 0.000 title claims abstract description 15
- 239000011669 selenium Substances 0.000 title claims abstract description 12
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 229910052711 selenium Inorganic materials 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003792 electrolyte Substances 0.000 claims abstract description 4
- 230000035484 reaction time Effects 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 4
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000005611 electricity Effects 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000741 silica gel Substances 0.000 abstract description 2
- 229910002027 silica gel Inorganic materials 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000013375 chromatographic separation Methods 0.000 abstract 1
- XIMIGUBYDJDCKI-UHFFFAOYSA-N diselenium Chemical compound [Se]=[Se] XIMIGUBYDJDCKI-UHFFFAOYSA-N 0.000 abstract 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 239000002994 raw material Substances 0.000 description 4
- 150000003549 thiazolines Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- QMGHHBHPDDAGGO-IIWOMYBWSA-N (2S,4R)-1-[(2S)-2-[[2-[3-[4-[3-[4-[[5-bromo-4-[3-[cyclobutanecarbonyl(methyl)amino]propylamino]pyrimidin-2-yl]amino]phenoxy]propoxy]butoxy]propoxy]acetyl]amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide Chemical compound CN(CCCNC1=NC(NC2=CC=C(OCCCOCCCCOCCCOCC(=O)N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)NCC3=CC=C(C=C3)C3=C(C)N=CS3)C(C)(C)C)C=C2)=NC=C1Br)C(=O)C1CCC1 QMGHHBHPDDAGGO-IIWOMYBWSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- YWWZCHLUQSHMCL-UHFFFAOYSA-N diphenyl diselenide Chemical compound C=1C=CC=CC=1[Se][Se]C1=CC=CC=C1 YWWZCHLUQSHMCL-UHFFFAOYSA-N 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MUTCAPXLKRYEPR-ITWZMISCSA-N methyl (e,3r,5s)-7-[4-bromo-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyhept-6-enoate Chemical compound COC(=O)C[C@H](O)C[C@H](O)\C=C\N1C(C(C)C)=C(Br)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 MUTCAPXLKRYEPR-ITWZMISCSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003342 selenium Chemical class 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
Abstract
The invention discloses a preparation method of a thiazoline compound containing selenium, belonging to the technical field of organic synthesis. The method comprises the following steps: adding thioamide, diselenide, solvent and electrolyte into a reactor, reacting under the action of electrification, and after the reaction is finished, carrying out chromatographic separation by using a silica gel column to obtain a pure target product. The preparation method of the thiazoline compound containing selenium provided by the invention has the characteristics of simple operation, mild condition, short reaction time and the like. The reaction equation is as follows:
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of a thiazoline compound containing selenium.
Background
Thiazolines and their derivatives are an important class of compounds, widely present in natural products, with diverse biological activities, such as anticancer (j.am. chem. soc.1990,112,8195), anti-HIV (Drugs2010,70,1885), etc. Meanwhile, the organic selenide is an important molecule with high pharmacological value and widely exists in bioactive molecules. Such as antitumor activity (j.med. chem.2017,60,7300), inhibition of herpes virus (j.med. chem.2015,58,8734), and the like. Therefore, the development of a new green and efficient method for synthesizing the seleno-thiazoline compound has very important significance.
The preparation method of the thiazoline compound comprises the following steps:
1) pan subjects produced thiazolines from NBS and thioamide as raw materials using chloroform as a solvent at high temperature (Tetrahedron Lett.2015,56,4128).
2) The Li project group uses olefin and thioamide as raw materials, and thiazoline compounds (org. Lett.2017,19,930) are prepared through two-step reaction at the temperature of 80 ℃.
3) The Cazin subject group takes nitrile and cysteamine hydrochloride as raw materials to synthesize thiazoline compounds (Green chem.2015,17,3090) at 80 ℃.
The above methods have significant disadvantages or shortcomings: high temperature heating, use of toxic solvents, and cumbersome operation.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a method for synthesizing a selenothiazoline compound by utilizing a diselenide compound.
A preparation method of a selenium-containing thiazoline compound, wherein the selenium-containing thiazoline compound has a structure shown in a formula I:
in the formula I, wherein R1Is selected from 2-thienyl, phenyl and substituted phenyl, wherein the substituent of the substituted phenyl is 4-chlorine, 4-bromine, 4-trifluoromethyl, 4-methoxyl and 4-methyl; r2Selected from hydrogen atoms, cyclopropyl; r3Selected from phenyl, methyl, benzyl. Characterized in that the molar ratio of 1: 0.6 of thioamide and diselenide compound, adding acetonitrile as a solvent, taking a graphite felt as an electrode, taking lithium perchlorate as an electrolyte, stirring and reacting for 4 hours at room temperature under the action of constant current of 2mA, wherein the reaction equation is as follows:
the invention has the beneficial effects that: the synthetic method of the selenium-containing thiazoline compound provided by the invention is scientific and reasonable, is green and environment-friendly, and establishes a new method for synthesizing the polysubstituted selenium-containing thiazoline compound; the method has the advantages of easily available raw materials, simple operation, mild reaction conditions and the like.
Drawings
FIG. 1 is an NMR spectrum of Compound 3a prepared in example 1;
FIG. 2 is an NMR spectrum of compound 3h prepared in example 7;
FIG. 3 is an NMR spectrum of compound 3i prepared in example 9.
Detailed Description
The invention is described in further detail below with reference to the following figures and specific examples:
the test methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
Preparation of thiazoline compound 3a containing selenium
Into a 10mL two-necked flask were charged N-allylbenzene-methionine amide 1a (0.20mmol,36mg), diphenyl diselenide 2a (0.12mmol,38mg), LiClO4(0.3mmol,32mg) and acetonitrile (4 mL). Graphite felt electrodes were used as a cathode and an anode, respectively, and electrolysis was carried out at room temperature for 4 hours at a constant current of 2 mA. After completion of the reaction, the solvent was distilled off using a rotary evaporator, and the product was purified by silica gel flash column chromatography (petroleum ether: ethyl acetate) to obtain the product 3a in 67% yield.
1H NMR(DMSO-d6,500MHz):δ7.74(d,J＝7.6Hz,2H),7.48(dt,J＝28.3,7.3Hz,5H),7.33–7.22(m,3H),4.42(dd,J＝16.3,3.3Hz,1H),4.30(dd,J＝16.3,8.1Hz,1H),4.22–4.14(m,1H),3.18(d,J＝7.3Hz,2H).13C NMR(DMSO-d6,125MHz):δ165.5,133.3,132.4,131.8,129.8,129.8,129.2,128.4,127.5,69.7,51.3,33.2.HRMS(ESI-TOF,[M+H+]):calcd forC16H16NSSe,334.0169,found334.0170.
example 2
1a in example 1 is replaced by 1b, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3b:
1H NMR(DMSO-d6,500MHz):δ7.64–7.60(m,2H),7.54–7.48(m,2H),7.32–7.23(m,5H),4.39(dd,J＝16.3,3.6Hz,1H),4.28(dd,J＝16.3,8.0Hz,1H),4.20–4.13(m,1H),3.17(d,J＝7.3Hz,2H),2.33(s,3H).13C NMR(DMSO-d6,125MHz):δ165.3,141.8,132.4,130.6,129.8,129.8,128.4,127.5,69.6,51.2,33.2,21.5.HRMS(ESI-TOF,[M+H+]):calcd forC17H18NSSe,348.0325,found 348.0330.
example 3
1a in example 1 was replaced by 1c, and the experimental results are shown in Table 1, except that the conditions were the same as in example 1.
Spectrogram analysis data 3c:
1H NMR(DMSO-d6,500MHz):δ7.68(d,J＝8.6Hz,2H),7.51(d,J＝6.9Hz,2H),7.33–7.23(m,3H),6.99(d,J＝8.6Hz,2H),4.37(dd,J＝16.1,3.5Hz,1H),4.25(dd,J＝16.1,8.0Hz,1H),4.19–4.11(m,1H),3.78(s,3H),3.17(d,J＝7.3Hz,2H).13C NMR(DMSO-d6,125MHz):δ164.7,162.1,132.4,130.1,129.8,127.5,125.9,114.5,69.6,55.9,51.3,33.2.HRMS(ESI-TOF,[M+H+]):calcd for C17H18NOSSe,364.0274,found 364.0273.
example 4
1a in example 1 is replaced by 1d, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3d:
1H NMR(DMSO-d6,500MHz):δ7.76(d,J＝8.5Hz,2H),7.59–7.51(m,4H),7.37–7.25(m,3H),4.44(dd,J＝16.4,3.6Hz,1H),4.33(dd,J＝16.4,8.1Hz,1H),4.27–4.21(m,1H),3.22(d,J＝7.3Hz,2H).13C NMR(DMSO-d6,125MHz):δ164.0,136.0,131.9,131.5,129.6,129.5,129.3,129.2,128.8,127.0,69.2,51.3,32.6.HRMS(ESI-TOF,[M+H+]):calcd forC16H15ClNSSe,367.9779,found 367.9780.
example 5
1a in example 1 is replaced by 1e, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Spectrogram analysis data 3e:
1H NMR(DMSO-d6,500MHz):δ7.70(s,4H),7.59–7.51(m,2H),7.36–7.28(m,3H),4.45(dd,J＝16.4,3.5Hz,1H),4.33(dd,J＝16.3,8.1Hz,1H),4.28–4.22(m,1H),3.23(d,J＝7.3Hz,2H).13C NMR(DMSO-d6,125MHz):δ164.6,132.4,132.4,132.3,130.3,129.8,129.7,127.5,125.4,69.7,51.8,33.1.HRMS(ESI-TOF,[M+H+]):calcd for C16H15BrNSSe,411.9274,found 411.9270.
example 6
1a in example 1 was replaced by 1f, and the experimental results are shown in Table 1, except that the conditions were the same as in example 1.
Spectrogram analysis data 3f:
1H NMR(DMSO-d6,500MHz):δ7.97(d,J＝8.1Hz,2H),7.86(d,J＝7.9Hz,2H),7.56(d,J＝7.5Hz,2H),7.37–7.26(m,3H),4.51(dd,J＝16.6,3.5Hz,1H),4.39(dd,J＝16.5,8.2Hz,1H),4.34–4.25(m,1H),3.25(d,J＝7.3Hz,2H).13C NMR(DMSO-d6,125MHz):δ164.6,136.8,132.4,131.7,131.4,131.2,129.8,129.7,129.1,127.5,126.2,126.2,124.3(d,J＝272.6Hz),69.8,51.9,33.0.HRMS(ESI-TOF,[M+H+]):calcd for C17H15F3NSSe,402.0043,found 402.0041.
example 7
1a in example 1 was replaced by 1g, and the experimental results are shown in Table 1, except that the conditions were the same as in example 1.
3g of spectrogram analysis data:
1H NMR(DMSO-d6,500MHz):δ7.80(d,J＝5.0Hz,1H),7.56(d,J＝7.7Hz,2H),7.45(d,J＝3.4Hz,1H),7.37–7.28(m,3H),7.18–7.14(m,1H),4.40–4.33(m,1H),4.29(t,J＝7.5Hz,1H),4.25(d,J＝7.3Hz,1H),3.23(d,J＝6.7Hz,2H).13C NMR(DMSO-d6,125MHz):δ158.8,136.9,132.4,131.4,131.3,129.8,129.7,128.5,127.5,69.1,52.4,33.0.HRMS(ESI-TOF,[M+H+]):calcd for C14H14NS2Se,339.9733,found 339.9734.
example 8
1a in example 1 is replaced by 1h, other conditions are the same as example 1, and the experimental results are shown in Table 1.
1H NMR(DMSO-d6,500MHz):δ7.77(d,J＝7.6Hz,2H),7.69–7.63(m,2H),7.50(t,J＝7.3Hz,1H),7.44(t,J＝7.4Hz,2H),7.41–7.33(m,3H),4.23(dd,J＝17.0,3.4Hz,1H),3.94(dd,J＝17.0,7.9Hz,1H),3.81–3.73(m,1H),3.05(t,J＝8.8Hz,1H),1.18–1.09(m,1H),0.70–0.63(m,1H),0.63–0.56(m,1H),0.48–0.42(m,1H),0.38–0.30(m,1H).13C NMR(DMSO-d6,125MHz):δ157.8,138.6,134.5,131.1,129.8,128.9,128.2,126.3,53.7,51.1,41.4,17.9,7.1,4.1.HRMS(ESI-TOF,[M+H+]):calcd for C19H20NSSe,374.0482,found 374.0480.
example 9
2a in example 1 was replaced by 2b, and the experimental results are shown in Table 1, except that the conditions were the same as in example 1.
Spectrogram analysis data 3i:
1H NMR(DMSO-d6,500MHz):δ7.81–7.77(m,2H),7.55(t,J＝7.2Hz,1H),7.50(t,J＝7.3Hz,2H),4.46–4.40(m,1H),4.36(t,J＝5.8Hz,1H),4.34–4.30(m,1H),2.83–2.76(m,2H),2.06(s,3H).13C NMR(DMSO-d6,125MHz):δ165.6,133.4,131.8,129.2,128.3,69.8,51.5,31.0,4.6.HRMS(ESI-TOF,[M+H+]):calcd for C11H14NSSe,272.0012,found272.0014.
example 10
2a in example 1 was replaced with 2c, and the experimental results were shown in Table 1, except that the conditions were the same as in example 1.
Spectrogram analysis data 3j:
1H NMR(DMSO-d6,500MHz):δ7.78(d,J＝8.0Hz,2H),7.55(t,J＝7.2Hz,1H),7.49(t,J＝7.4Hz,2H),7.32(q,J＝8.25,7.8Hz,4H),7.23(t,J＝6.9Hz,1H),4.38(dd,J＝15.6,2.8Hz,1H),4.30(dd,J＝15.9,7.8Hz,1H),4.25(dt,J＝7.3,3.6Hz,1H),3.94(s,2H),2.75(d,J＝7.0Hz,2H).13C NMR(DMSO-d6,125MHz):δ165.5,134.0,133.3,131.8,129.3,129.2,128.9,128.4,127.0,69.9,51.5,29.7,27.1.HRMS(ESI-TOF,[M+H+]):calcd forC17H18NSSe,348.0325,found 348.0327.
TABLE 1
Claims (2)
1. A preparation method of a selenium-containing thiazoline compound, wherein the selenium-containing thiazoline compound has a structure shown in a formula I:
in the formula I, wherein R1Is selected from 2-thienyl, phenyl and substituted phenyl, wherein the substituent of the substituted phenyl is 4-chlorine, 4-bromine, 4-trifluoromethyl, 4-methoxyl and 4-methyl; r2Selected from hydrogen atoms, cyclopropyl; r3Selected from phenyl, methyl, benzyl. Characterized in that the molar ratio of 1: 0.6 of thioamide and diselenide compound, adding acetonitrile as a solvent, lithium perchlorate as an electrolyte, and stirring to react at room temperature under the action of electricity, wherein the reaction equation is as follows:
2. the method of claim 1, wherein: the electrode is graphite felt, the solvent is acetonitrile, the electrolyte is lithium perchlorate, the reaction time is 4h, and the constant current is 2 mA.
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