CN117720479A - Preparation method of 2-substituted benzothiazole compound - Google Patents
Preparation method of 2-substituted benzothiazole compound Download PDFInfo
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- CN117720479A CN117720479A CN202311696915.6A CN202311696915A CN117720479A CN 117720479 A CN117720479 A CN 117720479A CN 202311696915 A CN202311696915 A CN 202311696915A CN 117720479 A CN117720479 A CN 117720479A
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- -1 2-substituted benzothiazole compound Chemical class 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000004440 column chromatography Methods 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 239000002841 Lewis acid Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 6
- 239000011941 photocatalyst Substances 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 238000004821 distillation Methods 0.000 claims abstract description 5
- 230000001678 irradiating effect Effects 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
- 239000004471 Glycine Substances 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- 229930187593 rose bengal Natural products 0.000 claims description 5
- 229940081623 rose bengal Drugs 0.000 claims description 5
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- VYXSBFYARXAAKO-WTKGSRSZSA-N chembl402140 Chemical compound Cl.C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-WTKGSRSZSA-N 0.000 claims description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 3
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 9
- PYKAUMRUGSSBEP-UHFFFAOYSA-N 2-phenyl-2-(sulfanylamino)acetic acid Chemical class SNC(C1=CC=CC=C1)C(=O)O PYKAUMRUGSSBEP-UHFFFAOYSA-N 0.000 claims 1
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- VLQLCEXNNGQELL-UHFFFAOYSA-N ethyl 1,3-benzothiazole-2-carboxylate Chemical compound C1=CC=C2SC(C(=O)OCC)=NC2=C1 VLQLCEXNNGQELL-UHFFFAOYSA-N 0.000 description 5
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- UHIPSWQNPNQBQY-UHFFFAOYSA-K 2-pyridin-2-ylpyridine trichlororuthenium hexahydrate Chemical group O.O.O.O.O.O.Cl[Ru](Cl)Cl.N1=CC=CC=C1C1=CC=CC=N1.N1=CC=CC=C1C1=CC=CC=N1.N1=CC=CC=C1C1=CC=CC=N1 UHIPSWQNPNQBQY-UHFFFAOYSA-K 0.000 description 1
- SIDCPPUYOKZTEY-UHFFFAOYSA-K 2-pyridin-2-ylpyridine;ruthenium(3+);trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3].N1=CC=CC=C1C1=CC=CC=N1.N1=CC=CC=C1C1=CC=CC=N1.N1=CC=CC=C1C1=CC=CC=N1 SIDCPPUYOKZTEY-UHFFFAOYSA-K 0.000 description 1
- DKRUVYQMSDURHJ-UHFFFAOYSA-K O.O.O.O.O.O.[Ru](Cl)(Cl)Cl.N1=C(C=CC=C1)C1=NC=CC=C1 Chemical compound O.O.O.O.O.O.[Ru](Cl)(Cl)Cl.N1=C(C=CC=C1)C1=NC=CC=C1 DKRUVYQMSDURHJ-UHFFFAOYSA-K 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GDJYIXGPYCKDOV-UHFFFAOYSA-N n-phenylthiohydroxylamine Chemical compound SNC1=CC=CC=C1 GDJYIXGPYCKDOV-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The invention discloses a preparation method of a 2-substituted benzothiazole compound, which comprises the following steps: firstly, according to the mol ratio of 1:0.2:0.02, sequentially adding a sulfhydryl phenylglycine derivative, lewis acid and a photocatalyst into an organic solvent, irradiating with visible light, stirring in air at room temperature to fully react, removing the organic solvent by reduced pressure distillation, and obtaining the 2-substituted benzothiazole compound by column chromatography. The method has the advantages of mild reaction conditions, greenness, low cost and high efficiency.
Description
Technical Field
The invention belongs to the technical field of preparation of organic compounds, and particularly relates to a preparation method of a 2-substituted benzothiazole compound.
Background
Benzothiazole skeletons widely exist in various active compounds and existing medicines, and usually, the benzothiazole derivatives are modified by introducing different substituents on benzene rings or introducing different active groups on 2-positions, so that the biological activity of the benzothiazole derivatives can be obviously influenced, wherein the 2-position substituent has the greatest influence on the activity of benzothiazole, and the 2-substituted benzothiazole has various pharmacological activities such as antibiosis, antivirus, anticancer and the like, and the application is very wide.
At present, the 2-substituted benzothiazole compound is synthesized mainly through condensation reaction of mercaptoaniline and aldehyde compound or functionalization reaction of benzothiazole compound, and the problems of high reaction temperature, no water, strong acid addition and substrate pre-functionalization need exist generally, the conditions are harsh, the cost is high, and the application of the 2-substituted benzothiazole compound is limited. Thus, there is a need to develop a simple, inexpensive and efficient method for synthesizing 2-substituted benzothiazole compounds.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide a preparation method of a 2-substituted benzothiazole compound, which has the advantages of mild reaction condition, greenness, low cost and high efficiency.
In order to achieve the above purpose, the invention is realized by adopting the following technical scheme:
a method for preparing a 2-substituted benzothiazole compound, comprising the steps of:
firstly, according to the mol ratio of 1:0.2:0.02, sequentially adding a sulfhydryl phenylglycine derivative, lewis acid and a photocatalyst into an organic solvent, irradiating with visible light, stirring in air at room temperature to fully react, removing the organic solvent by reduced pressure distillation, and obtaining a 2-substituted benzothiazole compound by column chromatography, wherein the chemical reaction formula is as follows:
wherein: r is R 1 The substituent is electron-pushing group or electron-withdrawing group, R 2 The substituent is alkyl, alkoxy, aryl or substituted amino.
Further, the electron-donating group is an alkyl group, an ether group, an aryl group or an amino group; the electron withdrawing group is halogen, trifluoromethyl or nitro.
Further, the mercaptophenyl glycine derivative is any one of ethyl (2-mercaptophenyl) glycine, (2-mercapto-5-chlorophenyl) glycine methyl ester or tertiary ethyl (2-mercapto-5-trifluoromethyl) glycine.
Further, the Lewis acid is Cu (OTf) 2 、Cu(OAc) 2 、Fe(OTf) 2 、Ce(OTf) 3 、CuSO 4 Or FeSO 4 。
Further, the photocatalyst is tris (2, 2-bipyridine) ruthenium chloride hexahydrate, rhodamine 6G or rose bengal.
Further, the organic solvent is any one of dichloromethane, toluene, 1, 2-dichloroethane, acetonitrile, ethyl acetate or tetrahydrofuran.
Further, the light source adopted by the visible light irradiation is an energy-saving lamp, sunlight or a blue LED lamp.
Further, the stirring time is 10-24 hours.
Further, the eluent adopted by the column chromatography is a mixture of petroleum ether and ethyl acetate, and the volume ratio of petroleum ether to ethyl acetate is 8:1.
compared with the prior art, the invention has the following technical effects:
in the invention, under the condition of visible light catalysis, the 2-substituted benzothiazole compound is synthesized by utilizing the oxidative cyclization reaction of the sulfhydryl phenylglycine derivative, the catalysis is performed by using cheap, rich and green visible light, no photosensitizer is needed, oxygen in the air is used as a green oxidant, and no additional strong oxidant is needed to be added; the invention has the advantages of cheap and easily obtained raw materials, mild reaction condition, environment-friendly, simple and convenient operation, rich product types and the like, and the yield of the 2-substituted benzothiazole compounds is as high as 85 to 92 percent.
Drawings
Fig. 1: 1, 3-benzothiazole-2-carboxylic acid ethyl ester prepared in example 1Esters of 1 H NMR spectrum;
fig. 2: ethyl 1, 3-benzothiazole-2-carboxylate prepared in example 1 13 C NMR spectrum.
Detailed Description
The following examples illustrate the invention in further detail.
Examples 1-3 in the column chromatography process, the eluent used was petroleum ether and ethyl acetate in a volume ratio of 8:1, and mixing.
The rose bengal used in example 3 has a CAS number of 63183-44-8 and a molecular number of C 28 H 31 ClN 2 O 3 。
Example 1
Firstly, 10mmol (2-mercaptophenyl) glycine ethyl ester and 2mmol Cu (OTf) are weighed 2 And 0.2mmol of rhodamine 6G are sequentially added into 30mL of dichloromethane, irradiated by an energy-saving lamp with the weight of 26W, stirred for 10 hours at room temperature, distilled under reduced pressure to remove the dichloromethane, and purified by column chromatography to obtain light yellow solid 1, 3-benzothiazole-2-carboxylic acid ethyl ester, wherein the structural formula is as follows:
the ethyl 1, 3-benzothiazole-2-carboxylate prepared in example 1 was 92% yield and melting point 68.1-72.7 ℃ referring to fig. 1 and 2, and the ethyl 1, 3-benzothiazole-2-carboxylate prepared in example 1 was measured by nuclear magnetic resonance spectrometer, resulting in: IR (KBr, cm) -1 )1750； 1 H NMR(400MHz,CDCl 3 )δ＝1.4(t,J＝6.4,3H),4.4(q,J＝6.4,2H),7.3-7.5(m,2H),7.9-8.0(m,2H)； 13 C NMR(100MHz,CDCl 3 )δ＝14.0,62.5,122.5,124.5,126.7,126.9,135.4,152.2,156.5,160.8.HRMS(ESI)calcd for C 11 H 12 NO 2 S(M+H + )208.0427,found 208.0425。
Example 2
Firstly, 10mmol (2-mercapto-5-chlorophenyl) glycine methyl ester and 2mmol Cu (OTf) are weighed 2 And 0.2mmol of hexahydrateSequentially adding tris (2, 2-bipyridine) ruthenium chloride into 30mL of 1, 2-dichloroethane, using sunlight irradiation, stirring for 24h at room temperature in the air, removing the 1, 2-dichloroethane by reduced pressure distillation, and purifying by column chromatography to obtain a brown solid compound of 1, 3-benzothiazole-5-chloro-2-carboxylic acid ethyl ester, wherein the structural formula is as follows:
the compound ethyl 1, 3-benzothiazole-5-chloro-2-carboxylate prepared in example 2 was produced in 85% yield with a melting point of 91-93.1 ℃ and the compound ethyl 1, 3-benzothiazole-5-chloro-2-carboxylate prepared in example 2 was measured using a nuclear magnetic resonance spectrometer, resulting in: IR (KBr, cm) -1 )3334,1743,1583,1330,1164； 1 H NMR(400MHz,CDCl 3 )δ8.24(d,J＝1.9Hz,1H),7.91(d,J＝8.7Hz,1H),7.53(dd,J＝8.6,1.96Hz),4.57(q,J＝7.2Hz,2H),1.50(t,J＝7.1Hz,3H)； 13 C NMR(100MHz,CDCl 3 )δ160.3,160.3,154.0,135.0,133.3,128.3,125.1,123.0,63.4,14.3。
Example 3
Firstly, 10mmol (2-mercapto-5-trifluoromethyl) glycine tertiary ethyl ester and 2mmol Fe (OTf) are weighed 2 And 0.2mmol of rose bengal are sequentially added into 30mL of toluene, the mixture is irradiated by a blue LED lamp with the concentration of 18W, stirred in the air for 18h at room temperature, the toluene is removed by reduced pressure distillation, and then the yellow solid 1, 3-benzothiazole-5-trifluoromethyl-2-carboxylic acid ethyl ester is obtained by column chromatography purification, wherein the structural formula is as follows:
the ethyl 1, 3-benzothiazole-5-trifluoromethyl-2-carboxylate compound prepared in example 3 was produced in a yield of 90% and a melting point of 73-75 ℃, and the ethyl 1, 3-benzothiazole-5-trifluoromethyl-2-carboxylate compound prepared in example 3 was measured by nuclear magnetic resonance spectroscopy, resulting in: mp 73-75 ℃; IR (KBr, cm) -1 )3078,2989,1736,1493,1344,1114； 1 H NMR(400MHz,CDCl 3 )δ8.53(s,1H),8.13(d,J＝8.5Hz,1H),7.79(dd,J＝8.5,1.3Hz,1H),4.60(q,J＝7.1Hz,2H),1.52(t,J＝7.1Hz,3H)； 13 C NMR(100MHz,CDCl 3 )δ160.8,160.0,152.9,139.9,130.2,129.9,123.6,122.8,122.5,63.2,14.1。
The Lewis acids selected for use in the present invention are other than Cu (OTf) used in examples 1 to 3 2 And Fe (OTf) 2 In addition to, for example, cu (OAc) 2 、Ce(OTf) 3 、CuSO 4 Or FeSO 4 And other metal salts having the same catalytic function.
The photocatalyst selected by the invention comprises ruthenium chloride hexahydrate (2, 2-bipyridine) used in the examples 1-3, rhodamine 6G and rose bengal, and also comprises other Ru complexes, ir complexes or other organic dyes with photocatalytic activity.
The organic solvent used in the present invention may be acetonitrile, ethyl acetate or tetrahydrofuran in addition to the methylene chloride, toluene or 1, 2-dichloroethane used in examples 1 to 3.
Claims (9)
1. A method for producing a 2-substituted benzothiazole compound, comprising the steps of:
firstly, according to the mol ratio of 1:0.2:0.02, sequentially adding a sulfhydryl phenylglycine derivative, lewis acid and a photocatalyst into an organic solvent, irradiating with visible light, stirring in air at room temperature to fully react, removing the organic solvent by reduced pressure distillation, and obtaining a 2-substituted benzothiazole compound by column chromatography, wherein the chemical reaction formula is as follows:
wherein: r is R 1 The substituent is electron-pushing group or electron-withdrawing group, R 2 The substituent is alkyl, alkoxy, aryl or substituted amino.
2. The method for producing a 2-substituted benzothiazole compound according to claim 1, wherein said electron-donating group is an alkyl group, an ether group, an aryl group or an amino group; the electron withdrawing group is halogen, trifluoromethyl or nitro.
3. The method for producing a 2-substituted benzothiazole compound according to claim 1, characterized in that said mercaptophenylglycine derivative is any one of ethyl (2-mercaptophenyl) glycine, (2-mercapto-5-chlorophenyl) glycine methyl ester or tert-ethyl (2-mercapto-5-trifluoromethyl) glycine.
4. The method for producing a 2-substituted benzothiazole compound according to claim 1, characterized in that said Lewis acid is Cu (OTf) 2 、Cu(OAc) 2 、Fe(OTf) 2 、Ce(OTf) 3 、CuSO 4 Or FeSO 4 。
5. The method for producing a 2-substituted benzothiazole compound according to claim 1, characterized in that said photocatalyst is tris (2, 2-bipyridine) chloride hexahydrate, rhodamine 6G or rose bengal.
6. The method for producing a 2-substituted benzothiazole compound according to claim 1, characterized in that said organic solvent is any one of methylene chloride, toluene, 1, 2-dichloroethane, acetonitrile, ethyl acetate, or tetrahydrofuran.
7. The method for producing a 2-substituted benzothiazole compound according to claim 1, characterized in that said light source used for irradiation of visible light is an energy-saving lamp, sunlight or blue LED lamp.
8. The method for producing a 2-substituted benzothiazole compound according to claim 1, characterized in that said stirring time is 10 to 24 hours.
9. The method for producing a 2-substituted benzothiazole compound according to claim 1, characterized in that said eluent used for column chromatography is a mixture of petroleum ether and ethyl acetate, and the volume ratio of petroleum ether and ethyl acetate is 8:1.
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