CN116621766A - Preparation method of 3, 3-dichloro oxindole and derivative thereof - Google Patents
Preparation method of 3, 3-dichloro oxindole and derivative thereof Download PDFInfo
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- CN116621766A CN116621766A CN202310617639.3A CN202310617639A CN116621766A CN 116621766 A CN116621766 A CN 116621766A CN 202310617639 A CN202310617639 A CN 202310617639A CN 116621766 A CN116621766 A CN 116621766A
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- WGGLCBPNOIWKDL-UHFFFAOYSA-N 3,3-dichloro-1h-indol-2-one Chemical compound C1=CC=C2C(Cl)(Cl)C(=O)NC2=C1 WGGLCBPNOIWKDL-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000004440 column chromatography Methods 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000002475 indoles Chemical class 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- -1 indole compound Chemical class 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 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
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004185 ester 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
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000002390 rotary evaporation Methods 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 239000000758 substrate Substances 0.000 abstract description 5
- 229930014626 natural product Natural products 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000001704 evaporation Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- PZNYKBLADPHGMI-UHFFFAOYSA-N 1,5-dimethylindole Chemical compound CC1=CC=C2N(C)C=CC2=C1 PZNYKBLADPHGMI-UHFFFAOYSA-N 0.000 description 1
- YHYLDEVWYOFIJK-UHFFFAOYSA-N 1h-indole-5-carbonitrile Chemical compound N#CC1=CC=C2NC=CC2=C1 YHYLDEVWYOFIJK-UHFFFAOYSA-N 0.000 description 1
- IIBUEDXYXZEZMP-UHFFFAOYSA-N 1h-indole;methyl acetate Chemical compound COC(C)=O.C1=CC=C2NC=CC2=C1 IIBUEDXYXZEZMP-UHFFFAOYSA-N 0.000 description 1
- TVQLYTUWUQMGMP-UHFFFAOYSA-N 5-iodo-1h-indole Chemical compound IC1=CC=C2NC=CC2=C1 TVQLYTUWUQMGMP-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229930005303 indole alkaloid Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000005623 oxindoles Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940126680 traditional chinese medicines Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention discloses a preparation method of 3, 3-dichloro oxindole and derivatives thereof, belonging to the technical field of chemical synthesis, comprising the following steps: sequentially adding indole compounds, water and tetrahydrofuran into a pre-dried bottle, then adding chlorofluorosulfonyl, stirring at 300-600 rpm at room temperature, after the reaction is finished, rotationally evaporating and concentrating a reaction solution, and separating by column chromatography to obtain a target product; the invention discloses a preparation method of 3, 3-dichloro oxindole and derivatives thereof; the method has the advantages of wide substrate application, low cost of raw materials required by the reaction, mild reaction conditions and simple operation; the product can be used for further synthesis of various natural product skeleton molecules, and has good application prospect.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a preparation method of 3, 3-dichloro oxindole and a derivative thereof.
Background
Alkaloid is a kind of organic compound which mainly exists in plants and contains nitrogen and is alkaline, and is one of important effective components of some traditional Chinese medicines. Among these, indole alkaloids are one of the most recently discovered types, including 4100 many known compounds. Oxindoles and derivatives thereof are widely found in natural products, pharmaceuticals and agrochemicals. Wherein, the 3, 3-dichloro oxindole derivative can be used as an important synthesis intermediate for constructing helix Xin Yin, and some 3, 3-dichloro oxindole derivatives have shown good anticancer activity and good application prospect in the treatment of cardiovascular diseases, diabetes and the like. For the synthesis of 3, 3-dichloro-2-oxindole, a number of processes have been found which use isatin as starting material for the reaction with various chlorinating agents. However, the technology of preparing 3, 3-dichloro-2-oxindole by direct chlorination oxidation of simple indole to obtain 3, 3-dichloro-2-oxindole is still to be solved, which requires functionalized indole derivatives or N-protected indole.
The synthesis of 3, 3-dichloro oxindole compounds in the dichloro oxindole literature at home and abroad mainly has the following problems: 1. most of the synthesis is carried out by indole with a protective group connected to N, and the applicability of the substrate is not wide; 2. chlorination and oxidation involve multi-step transformations, limited substrate expansion and low yields; 3. some methods have harsh synthesis conditions.
Therefore, the method for obtaining the 3, 3-dichloro oxindole compound with wide application of the development substrate, simple and easily obtained raw materials, high yield and high selectivity is very significant.
Disclosure of Invention
The present invention is directed to a method for preparing 3, 3-dichloro oxindole and derivatives thereof, which solves the problems set forth in the background art.
In order to achieve the above purpose, the present invention provides the following technical solutions:
a preparation method of 3, 3-dichloro oxindole and derivatives thereof comprises the following steps:
sequentially adding indole compounds, water and tetrahydrofuran into a pre-dried bottle, then adding chlorofluorosulfonyl, stirring at the room temperature at 300-600 rpm, after the reaction is finished, concentrating the reaction liquid by rotary evaporation, and separating by column chromatography to obtain a target product.
Preferably, the molar ratio of the indole compound to water is 1:1, the molar ratio of indole compounds to chlorofluorosulfonyl is 1:4, tetrahydrofuran is used as a solvent, the reaction temperature is room temperature, and the reaction time is 1.5-14h h.
Preferably, the rotary steaming temperature can be selected between 36-40deg.C, the vacuum degree can be selected between 0.08-0.12Mpa, the chromatography adopts 200-300 mesh column chromatography silica gel, and the developing agent is petroleum ether: ethyl acetate, polarity can be at 4:1 to 20: 1.
Preferably, the structure of the indole compound is shown as a formula I:
formula I:
wherein, in the formula I, R1 groups are halogen, alkyl, alkoxy, cyano and nitro, and R2 groups are alkyl, benzyl, p-toluenesulfonyl and ester groups.
Preferably, the structure of the 3, 3-dichloro oxindole and the derivative thereof is shown as a formula II:
formula II:
preferably, the structure of the chlorofluorosulfonyl is shown in a formula III:
formula III:
compared with the prior art, the invention has the beneficial effects that:
(1) The invention discloses a preparation method of 3, 3-dichloro oxindole and a derivative thereof.
(2) The method has the advantages of wide substrate application, low cost of raw materials required by the reaction, mild reaction conditions and simple operation.
(3) The product can be used for further synthesis of various natural product skeleton molecules, and has good application prospect.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum H of the target compound of example 1.
FIG. 2 is a nuclear magnetic resonance spectrum C of the target compound of example 1.
FIG. 3 is a nuclear magnetic resonance spectrum H of the target compound of example 2.
FIG. 4 is a nuclear magnetic resonance spectrum C of the target compound of example 2.
FIG. 5 is a nuclear magnetic resonance spectrum H of the target compound of example 3.
FIG. 6 is a nuclear magnetic resonance spectrum C of the target compound of example 3.
FIG. 7 is a nuclear magnetic resonance spectrum H of the target compound of example 4.
FIG. 8 is a nuclear magnetic resonance spectrum C of the target compound of example 4.
Detailed Description
The technical scheme of the patent is further described in detail below with reference to the specific embodiments.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways other than those described herein, and persons skilled in the art will readily appreciate that the present invention is not limited to the specific embodiments disclosed below.
Further, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic can be included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
Example 1
To a previously dried 4mL bottle, 5-iodoindole (49.6 mg,0.2 mmol), water (3.6. Mu.L, 1 eq), tetrahydrofuran (2 mL, 0.1M) and chlorofluorosulfonyl (0.8mmol,4eq,1M in anhydrous PhCF3) were successively added, and the bottle was sealed and stirred at room temperature for 14h. After the reaction mixture was stirred, quenched with water, extracted with ethyl acetate and the organic phase was dried over Na2SO 4. Then using a Heidolph rotary evaporator, rotating at 100-200 rpm, at 38-40 ℃ and 0.08-0.12Mpa, treating for 3-5 min, removing solvent, and then using 200 mesh column chromatography silica gel for column chromatography, wherein the developing agent is petroleum ether: ethyl acetate = 20:1 to 4:1, separating to obtain the target compound. (61.6 mg, yield: 94%, which reflects extremely high purity of the product in terms of nuclear magnetic pattern profile, signal, noise, etc.).
The structure of the 3, 3-dichloro oxindole compound obtained in this example is shown below:
the structural characterization data of the product are:
1 H NMR(600MHz,DMSO-d 6 )δ11.44(br,s,1H),7.96(d,J＝1.6Hz,1H),7.74(dd,J＝8.2,1.8Hz,1H),6.81(d,J＝8.2Hz,1H).
13 C NMR(150MHz,DMSO-d 6 )δ168.5,140.9,138.9,132.9,130.9,113.7,86.1,74.1.
HRMS-ESI m/z:[M+Na] + Calcd for C 8 H 4 Cl 2 INONa 349.8607；Found 349.8619.
example 2
To a previously dried 4mL bottle, 5-cyanoindole (29.3 mg,0.2 mmol), water (3.6. Mu.L, 1 eq), tetrahydrofuran (2 mL, 0.1M) and chlorofluorosulfonyl (0.8mmol,4eq,1M in anhydrous PhCF3) were successively added, and the bottle was sealed and stirred at room temperature for 10 hours. After the reaction mixture was stirred, quenched with water, extracted with ethyl acetate and the organic phase was dried over Na2SO 4. Then using a Heidolph rotary evaporator, rotating at 100-200 rpm, at 38-40 ℃ and 0.08-0.12Mpa, treating for 3-5 min, removing solvent, and then using 200 mesh column chromatography silica gel for column chromatography, wherein the developing agent is petroleum ether: ethyl acetate = 20:1 to 4:1, separating to obtain the target compound. (40.7 mg, yield 90%, and extremely high purity of the product can be reflected in nuclear magnetic pattern appearance, signal, noise, etc.).
The structure of the 3, 3-dichloro oxindole compound obtained in this example is shown below:
the structural characterization data of the product are:
1 H NMR(600MHz,DMSO-d 6 )δ11.85(br,s,1H),8.27(d,J＝1.5Hz,1H),7.88(dd,J＝8.2,1.6Hz,1H),7.13(d,J＝8.2Hz,1H).
13 C NMR(150MHz,DMSO-d 6 )δ169.0,143.3,137.3,129.7,129.0,118.2,112.4,106.0,73.5.
HRMS-ESI m/z:[M+H] + Calcd for C 9 H 5 Cl 2 N 2 O 226.9773；Found 226.9770.
example 3
To a previously dried 4mL bottle, 1-methyl acetate indole a (37.8 mg,0.2 mmol), water (3.6. Mu.L, 1 eq), tetrahydrofuran (2 mL, 0.1M) and chlorofluorosulfonyl (0.8mmol,4eq,1M in anhydrous PhCF3) were successively added, and the bottle was sealed and stirred at room temperature for 5 hours. After the reaction mixture was stirred, quenched with water, extracted with ethyl acetate and the organic phase was dried over Na2SO 4. Then using a Heidolph rotary evaporator, rotating at 100-200 rpm, at 38-40 ℃ and 0.08-0.12Mpa, treating for 3-5 min, removing solvent, and then using 200 mesh column chromatography silica gel for column chromatography, wherein the developing agent is petroleum ether: ethyl acetate = 20:1 to 4:1, separating to obtain the target compound. (44.2 mg, yield of 81%), which reflects extremely high purity of the product in terms of nuclear magnetic pattern profile, signal, noise, etc.
The structure of the 3, 3-dichloro oxindole compound obtained in this example is shown below:
the structural characterization data of the product are:
1 H NMR(600MHz,CDCl 3 )δ7.65(d,J＝7.6Hz,1H),7.38(dd,J＝11.3,4.3Hz,1H),7.20(t,J＝7.6Hz,1H),6.76(d,J＝7.9Hz,1H),4.49(s,2H),3.77(s,3H).
13 C NMR(150MHz,CDCl 3 )δ169.1,167.1,139.5,132.0,129.1,125.2,124.7,109.3,74.0,53.0,41.9.
HRMS-ESI m/z:[M+Na] + Calcd for C 11 H 9 Cl 2 NO 3 Na 295.9852；Found 295.9851.
example 4
To a previously dried 4mL bottle, 1, 5-dimethylindole (29.1 mg,0.2 mmol), water (3.6. Mu.L, 1 eq), tetrahydrofuran (2 mL, 0.1M) and chlorofluorosulfonyl (0.8mmol,4eq,1M in anhydrous PhCF3) were successively added, and the bottle was sealed and stirred at room temperature for 1.5 hours. After the reaction mixture was stirred, quenched with water, extracted with ethyl acetate and the organic phase was dried over Na2SO 4. Then using a Heidolph rotary evaporator, rotating at 100-200 rpm, at 38-40 ℃ and 0.08-0.12Mpa, treating for 3-5 min, removing solvent, and then using 200 mesh column chromatography silica gel for column chromatography, wherein the developing agent is petroleum ether: ethyl acetate = 20:1 to 4:1, separating to obtain the target compound. (43.4 mg, yield: 94%), which reflects extremely high purity of the product in terms of nuclear magnetic pattern profile, signal, noise, etc.
The structure of the 3, 3-dichloro oxindole compound obtained in this example is shown below:
the structural characterization data of the product are:
1 H NMR(600MHz,CDCl 3 )δ7.44(s,1H),7.20(dd,J＝8.0,0.8Hz,1H),6.75(d,J＝8.0Hz,1H),3.24(s,3H),2.38(s,3H).
13 C NMR(150MHz,CDCl 3 )δ169.0,138.4,134.3,132.4,129.3,125.5,109.0,74.7,27.2,21.1.
HRMS-ESI m/z:[M+Na] + Calcd for C 10 H 9 Cl 2 NONa 251.9953；Found 251.9951.
in view of the above, we have developed a process for the preparation of 3, 3-dichlorooxindole and derivatives thereof. The reaction condition is mild and convenient, the operation is simple, the compatibility of functional groups is good, and the product has good application prospect.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential characteristics thereof. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Furthermore, it should be understood that although the present disclosure describes embodiments, not every embodiment is provided with a separate embodiment, and that this description is provided for clarity only, and that the disclosure is not limited to the embodiments described in detail below, and that the embodiments described in the examples may be combined as appropriate to form other embodiments that will be apparent to those skilled in the art.
Claims (6)
1. A preparation method of 3, 3-dichloro oxindole and derivatives thereof, which is characterized by comprising the following steps:
sequentially adding indole compounds, water and tetrahydrofuran into a pre-dried bottle, then adding chlorofluorosulfonyl, stirring at the room temperature at 300-600 rpm, after the reaction is finished, concentrating the reaction liquid by rotary evaporation, and separating by column chromatography to obtain a target product.
2. The method for preparing 3, 3-dichloro oxindole and its derivative according to claim 1, wherein the molar ratio of indole compound to water is 1:1, the molar ratio of indole compounds to chlorofluorosulfonyl is 1:4, tetrahydrofuran is used as a solvent, the reaction temperature is room temperature, and the reaction time is 1.5-14h.
3. The method for preparing 3, 3-dichloro oxindole and its derivative according to claim 1, wherein the spin-steaming temperature is selected between 36-40 ℃, the vacuum degree is selected between 0.08-0.12Mpa, the chromatography adopts 200-300 mesh column chromatography silica gel, and the developing agent is petroleum ether: ethyl acetate, polarity can be at 4:1 to 20: 1.
4. The method for preparing 3, 3-dichloro oxindole and its derivatives according to claim 1, wherein the structure of the indole compound is shown in formula i:
formula I:
wherein, in the formula I, R1 groups are halogen, alkyl, alkoxy, cyano and nitro, and R2 groups are alkyl, benzyl, p-toluenesulfonyl and ester groups.
5. The method for preparing 3, 3-dichloro oxindole and its derivative according to claim 4, wherein the 3, 3-dichloro oxindole and its derivative has a structure represented by formula II:
formula II:
6. the method for preparing 3, 3-dichloro oxindole and its derivative according to claim 1, wherein the structure of the chlorofluorosulfonyl group is shown in formula iii:
formula III:
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| CN202310617639.3A CN116621766A (en) | 2023-05-30 | 2023-05-30 | Preparation method of 3, 3-dichloro oxindole and derivative thereof |
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- 2023-05-30 CN CN202310617639.3A patent/CN116621766A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| JIAN, YINXIANG等: "Controllable transformation of indoles using iodine(III) reagent", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 21, no. 1, pages 179 - 186 * |
| MA, TIANTING等: "SO2ClF: A Reagent for Controllable Chlorination and Chlorooxidation of Simple Unprotected Indoles", JOURNAL OF ORGANIC CHEMISTRY, vol. 88, no. 7, pages 4839 - 4847 * |
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