CN105566198A - 3-dicarbonyl substitution indole compound and preparation method thereof - Google Patents
3-dicarbonyl substitution indole compound and preparation method thereof Download PDFInfo
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- CN105566198A CN105566198A CN201610093946.6A CN201610093946A CN105566198A CN 105566198 A CN105566198 A CN 105566198A CN 201610093946 A CN201610093946 A CN 201610093946A CN 105566198 A CN105566198 A CN 105566198A
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- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Abstract
The invention discloses a 3-dicarbonyl substitution indole compound and a preparation method thereof, and belongs to the technical field of synthesis of indole derivatives. According to the technical scheme, the 3-dicarbonyl substitution indole compound is characterized by being of the structural formula specified in the description. The invention further discloses the preparation method of the 3-dicarbonyl substitution indole compound. Indole 3 double carbonylation is achieved through a one-step cascade reaction, a series of multi-functionalization 3-dicarbonyl substitution indole compounds are synthetized, and a foundation is laid for further derivation research and synthesis of medicine molecules containing an indole structure.
Description
Technical field
The invention belongs to the synthesis technical field of indole derivatives, be specifically related to a kind of 3 dicarbapentaborane substituent indole compounds and preparation method thereof.
Background technology
Indoles heterocycle is extensively present in bioactive natural product and drug molecular structure, and it is functionalized is one of organic compound and pharmaceutical chemical priority research areas.The multiple biological activitys such as the Benzazole compounds that 3 dicarbapentaborane replace is the important bioactive natural product of a class and drug molecule, has parasiticide, atherosclerosis, anticancer, antiviral.Up to now, its preparation method reacts primarily of Fu-Ke of indoles and oxalyl chloride, and the oxidative coupling reaction of indoles 3 and α-amido ketone, fragrant methyl ketone and α-one aldehyde, reaction substrate is limited to.β-carbonyl nitrile compounds and indoles are prepared 3 dicarbapentaborane substituent indole compounds by cascade reaction and are had no report, and this compounds has broad application prospects in the diversity synthesis of the complete synthesis of bioactive natural product and drug molecule.
Summary of the invention
The technical problem that the present invention solves there is provided a kind of 3 dicarbapentaborane substituent indole compounds.
Another technical problem that the present invention solves there is provided a kind of preparation method of 3 dicarbapentaborane substituent indole compounds, the method is at 4-oxygen-2 by substituent indole compound and β-carbonyl nitrile compounds, 2,3 dicarbapentaborane substituent indole compounds are synthesized by cascade reaction under the effect of 6,6-tetramethyl piperidine oxide compound (4-oxo-TEMPO).
The present invention adopts following technical scheme for solving the problems of the technologies described above: a kind of 3 dicarbapentaborane substituent indole compounds, is characterized in that having following general structure:
Wherein R
1for alkyl, phenyl, substituted-phenyl, furyl or thienyl;
R
2for hydrogen, alkyl or benzyl;
R
3for hydrogen, alkyl or phenyl;
R
4for hydrogen, alkyl, halogen, hydroxyl or alkoxyl group.
Further restriction, 3 described dicarbapentaborane substituent indole compounds are one of following compounds:
。
The preparation method of 3 dicarbapentaborane substituent indole compounds of the present invention, it is characterized in that concrete steps are: by substituent indole compound 1, β-carbonyl nitrile compounds 2 and 4-oxo-2,2,6,6-tetramethyl piperidine oxide compound 4-oxo-TEMPO is under the effect of copper salt, by obtained 3 the dicarbapentaborane substituent indole compounds 3 of one kettle way polycomponent cascade reaction in acid solvent, the equation of reaction process is:
。
Further restriction, the mol ratio of described substituent indole compound, β-carbonyl nitrile compounds, 4-oxo-2,2,6,6-tetramethyl piperidine oxide compound and copper salt is 1:1-1.5:2-3:0.05-0.2.
Further restriction, described copper salt is CuCl, CuCl
2, CuBr, CuBr
2or Cu (OTf)
2.
Further restriction, described acid solvent is acetic acid, propionic acid or butyric acid.
Further restriction, the temperature of reaction in reaction process is 25-100 DEG C.
The present invention has synthesized 3 two carbonyl Benzazole compounds by substituent indole compound and β-carbonyl nitrile compounds by cascade reaction, and be its further derivatize research, synthesis is laid a good foundation containing the drug molecule of indole structure.
Embodiment
Be described in further details foregoing of the present invention by the following examples, but this should be interpreted as that the scope of the above-mentioned theme of the present invention is only limitted to following embodiment, all technology realized based on foregoing of the present invention all belong to scope of the present invention.
Analytical instrument and reagent: proton nmr spectra BrukerASCEND400 type nuclear magnetic resonance analyser record, the unit of chemical shift d is ppm.All reaction solvents all conventionally carry out purifying.Column chromatography silica gel (200-300 order) is the production of Qingdao Haiyang chemical industry subsidiary factory.Thin-layer chromatography uses the efficient plate of GF254, for Yantai chemical institute is produced.Preparative thin layer chromatography board is prepared by oneself; stationary phase adopts GF254(HG/T2354-92) silica gel and Xylo-Mucine (800-1200) preparation, be respectively Qingdao Marine Chemical Co., Ltd. and China Medicine (Group) Shanghai Chemical Reagent Co., and produce.All solvents are analytical reagent, and agents useful for same is all purchased from Chemical Reagent Co., Ltd., Sinopharm Group.Adopt the colour developing of the method such as iodine, Ultraluminescence.Remove organic solvent under reduced pressure to carry out in Rotary Evaporators.
Embodiment 1
By starting compound indoles 58.5mg(0.5mmol), benzoyl acetonitrile 109mg(0.75mmol), 4-oxo-2,2,6,6-tetramethyl piperidine oxide compound 255mg(1.5mmol) and CuCl5mg(0.05mmol) be dissolved in 3mL Glacial acetic acid, by uncovered for reaction system 25 DEG C of reactions 3 hours, boil off acetic acid 50mL, add acetic acid ethyl dissolution resistates, wash twice (10mL × 2) with saturated sodium bicarbonate solution, be separated organic layer, anhydrous sodium sulfate drying, filter, revolve and steam except desolventizing, pillar layer separation obtains compound 3-1 sterling 108mg(yield 87%).
1HNMR(400MHz,Acetone-D
6)δ11.38(s,1H),8.41–8.34(m,1H),8.13(d,J=3.2Hz,1H),8.06(dt,J=8.5,1.5Hz,2H),7.75–7.68(m,1H),7.64–7.54(m,3H),7.37–7.30(m,2H)。
Embodiment 2
Replace except using 2-chlorobenzoylacetonitrile, except benzoyl acetonitrile, preparing compound 3-2 with the method identical with preparing compound 3-1.
1HNMR(400MHz,DMSO-D
6)δ12.45(s,1H),8.36(d,J=3.2Hz,1H),8.21–8.13(m,1H),7.81(dd,J=7.6,1.5Hz,1H),7.67(td,J=7.8,1.6Hz,1H),7.62–7.49(m,3H),7.35–7.25(m,2H)。
Embodiment 3
Except using 3-chlorobenzoylacetonitrile to replace benzoyl acetonitrile, CuBr replaces, beyond CuCl, preparing compound 3-3 with the method identical with preparing compound 3-1.
1HNMR(400MHz,DMSO-D
6)δ12.48(s,1H),8.24(s,2H),7.95(s,1H),7.92(d,J=7.6Hz,1H),7.82(d,J=7.6Hz,1H),7.63(t,J=7.8Hz,1H),7.56(d,J=4.7Hz,1H),7.37–7.27(m,2H)。
Embodiment 4
Benzoyl acetonitrile is replaced, CuBr except using 4-chlorobenzoylacetonitrile
2replace, beyond CuCl, preparing compound 3-4 with the method identical with preparing compound 3-1.
1HNMR(400MHz,DMSO-D6)δ12.45(s,1H),8.22(t,J=4.9Hz,2H),7.98(d,J=8.5Hz,2H),7.67(d,J=8.4Hz,2H),7.59–7.52(m,1H),7.36–7.27(m,2H)。
Embodiment 5
Benzoyl acetonitrile is replaced, Cu (OTf) except using 4-toluyl acetonitrile
2replace, beyond CuCl, preparing compound 3-5 with the method identical with preparing compound 3-1.
1HNMR(400MHz,DMSO-D
6)δ12.40(s,1H),8.26–8.18(m,1H),8.15(s,1H),7.86(d,J=8.1Hz,2H),7.59–7.51(m,1H),7.40(d,J=8.0Hz,2H),7.31(p,J=6.5Hz,2H),2.40(s,3H)。
Embodiment 6
Except 4-methoxybenzoyl acetonitrile replaces benzoyl acetonitrile, propionic acid replaces, beyond acetic acid, preparing compound 3-6 with the method identical with preparing compound 3-1.
1HNMR(400MHz,DMSO-D
6)δ12.36(s,1H),8.25–8.16(m,1H),8.12(s,1H),7.97–7.88(m,2H),7.59–7.50(m,1H),7.30(dt,J=6.7,3.6Hz,2H),7.16–7.06(m,2H),3.86(s,3H)。
Embodiment 7
Except using 4-fluorobenzoyl acetonitrile to replace benzoyl acetonitrile, butyric acid replaces, beyond acetic acid, preparing compound 3-7 with the method identical with preparing compound 3-1.
1HNMR(500MHz,DMSO-D
6)δ:12.44(s,1H),8.24(s,1H),8.20(d,J=3.5Hz,1H),8.08-8.05(m,2H),7.58-7.56(m,1H),7.41(t,J=9.0Hz,2H),7.34-7.29(m,2H)。
Embodiment 8
Replace except using 3-Bromophenacyl acetonitrile, except benzoyl acetonitrile, preparing compound 3-8 with the method identical with preparing compound 3-1.
1HNMR(400MHz,DMSO-D
6)δ12.48(s,1H),8.23(dd,J=8.6,3.7Hz,2H),8.09(t,J=1.7Hz,1H),7.96(dd,J=7.9,1.8Hz,2H),7.59–7.54(m,2H),7.35–7.30(m,2H)。
Embodiment 9
Replace except using 2-furoyl acetonitrile, except benzoyl acetonitrile, preparing compound 3-9 with the method identical with preparing compound 3-1.
1HNMR(400MHz,DMSO-D
6)δ12.42(s,1H),8.29(d,J=3.2Hz,1H),8.25–8.16(m,2H),7.56(ddd,J=7.7,6.1,3.4Hz,2H),7.36–7.25(m,2H),6.81(dd,J=3.6,1.6Hz,1H)。
Embodiment 10
Replace except using 2-thenoyl acetonitrile, except benzoyl acetonitrile, preparing compound 3-10 with the method identical with preparing compound 3-1.
1HNMR(400MHz,DMSO-D
6)δ12.44(s,1H),8.33(s,1H),8.23(dd,J=10.6,5.1Hz,2H),7.96(d,J=3.3Hz,1H),7.59–7.51(m,1H),7.36–7.25(m,3H)。
Embodiment 11
By raw material 5-methoxy-Indole (0.5mmol), benzoyl acetonitrile 109mg(0.75mmol), 4-oxo-2, 2, 6, 6-tetramethyl piperidine oxide compound 255mg(1.5mmol) and CuCl5mg(0.05mmol) be dissolved in 3mL Glacial acetic acid, by reaction system heating in the open to 100 DEG C reaction 2 hours, boil off acetic acid 50mL, add acetic acid ethyl dissolution resistates, wash twice (10mL × 2) with saturated sodium bicarbonate solution, be separated organic layer, anhydrous sodium sulfate drying, filter, revolve and steam except desolventizing, pillar layer separation obtains compound 3-11 sterling 124mg(yield 89%).
1HNMR(400MHz,DMSO-D6)δ12.31(s,1H),8.09(d,J=2.6Hz,1H),7.97(d,J=7.4Hz,2H),7.78–7.70(m,2H),7.60(t,J=7.7Hz,2H),7.46(d,J=8.8Hz,1H),6.95(dd,J=8.8,2.5Hz,1H),3.83(s,3H)。
Embodiment 12
Replace except using 5-skatole, except 5-methoxy-Indole, preparing compound 3-12 with the method identical with preparing compound 3-11.
1HNMR(400MHz,DMSO-D6)δ12.31(s,1H),8.10(d,J=3.3Hz,1H),8.05(s,1H),7.96(d,J=7.3Hz,2H),7.74(t,J=7.4Hz,1H),7.59(t,J=7.7Hz,2H),7.43(d,J=8.3Hz,1H),7.14(d,J=8.3Hz,1H),2.45(s,3H)。
Embodiment 13
Replace except using 5-fluoro indole, except 5-methoxy-Indole, preparing compound 3-13 with the method identical with preparing compound 3-11.
1HNMR(400MHz,Acetone-D
6)δ11.46(s,1H),8.20(s,1H),8.07–8.01(m,3H),7.75–7.70(m,1H),7.65–7.56(m,3H),7.14(td,J=9.1,2.6Hz,1H)。
Embodiment 14
Replace except using 5-chloro-indole, except 5-methoxy-Indole, preparing compound 3-14 with the method identical with preparing compound 3-11.
1HNMR(400MHz,Acetone-D
6)δ11.51(s,1H),8.37(d,J=2.0Hz,1H),8.20(s,1H),8.09–8.03(m,2H),7.73(t,J=7.4Hz,1H),7.65–7.57(m,3H),7.34(dd,J=8.7,2.1Hz,1H)。
Embodiment 15
Replace except using 5-bromo indole, except 5-methoxy-Indole, preparing compound 3-15 with the method identical with preparing compound 3-1.
1HNMR(400MHz,DMSO-D
6)δ12.59(s,1H),8.36(d,J=1.6Hz,1H),8.25(s,1H),7.97(d,J=7.3Hz,2H),7.75(t,J=7.4Hz,1H),7.60(t,J=7.7Hz,2H),7.54(d,J=8.6Hz,1H),7.46(dd,J=8.6,1.9Hz,1H)。
Embodiment 16
Replace except using 5-OHi, except 5-methoxy-Indole, preparing compound 3-16 with the method identical with preparing compound 3-1.
1HNMR(400MHz,DMSO-D
6)δ12.18(s,1H),9.22(s,1H),8.01(d,J=3.3Hz,1H),7.98–7.91(m,2H),7.77–7.70(m,1H),7.59(dd,J=10.7,4.8Hz,3H),7.34(d,J=8.7Hz,1H),6.79(dd,J=8.7,2.4Hz,1H)。
Embodiment 17
Replace except using 6-fluoro indole, except 5-methoxy-Indole, preparing compound 3-17 with the method identical with preparing compound 3-11.
1HNMR(400MHz,DMSO-D
6)δ12.46(s,1H),8.25–8.17(m,2H),7.97(d,J=7.5Hz,2H),7.75(t,J=7.4Hz,1H),7.60(t,J=7.7Hz,2H),7.36(dd,J=9.5,2.1Hz,1H),7.23–7.14(m,1H)。
Embodiment 18
Replace except using 6-chloro-indole, except 5-methoxy-Indole, preparing compound 3-18 with the method identical with preparing compound 3-11.
1HNMR(400MHz,DMSO-D
6)δ12.50(s,1H),8.28–8.16(m,2H),7.97(d,J=7.4Hz,2H),7.75(t,J=7.1Hz,1H),7.65–7.55(m,3H),7.34(d,J=8.2Hz,1H)。
Embodiment 19
Replace except using 6-bromo indole, except 5-methoxy-Indole, preparing compound 3-19 with the method identical with preparing compound 3-11.
1HNMR(400MHz,DMSO-D
6)δ12.52(s,1H),8.23(s,1H),8.15(d,J=8.4Hz,1H),7.96(d,J=7.5Hz,2H),7.74(d,J=7.2Hz,2H),7.60(t,J=7.6Hz,2H),7.46(dd,J=8.4,1.2Hz,1H)。
Embodiment 20
Replace except using 7-skatole, except 5-methoxy-Indole, preparing compound 3-20 with the method identical with preparing compound 3-11.
1HNMR(400MHz,DMSO-D
6)δ12.47(s,1H),8.17(d,J=3.3Hz,1H),8.06(d,J=7.8Hz,1H),8.01–7.93(m,2H),7.74(t,J=7.2Hz,1H),7.60(t,J=7.6Hz,2H),7.22(t,J=7.5Hz,1H),7.12(d,J=7.1Hz,1H),2.53(s,3H)。
Embodiment 21
Replace except using 2 methyl indole, except 5-methoxy-Indole, preparing compound 3-21 with the method identical with preparing compound 3-11.
1HNMR(400MHz,Acetone-D6)δ11.22(s,1H),8.03(d,J=7.4Hz,2H),7.98(d,J=7.4Hz,1H),7.72(d,J=7.5Hz,1H),7.60(t,J=7.7Hz,2H),7.45(d,J=7.1Hz,1H),7.22–7.15(m,2H),2.58(s,3H)。
Embodiment 22
Replace except using 1-skatole, except 5-methoxy-Indole, preparing compound 3-22 with the method identical with preparing compound 3-11.
1HNMR(400MHz,CDCl
3)δ8.58(d,J=4.1Hz,1H),8.20(d,J=7.4Hz,2H),7.88(s,1H),7.59(t,J=7.2Hz,2H),7.48(s,3H),3.90(s,3H)。
Embodiment 23
Replace except using 1-benzylindole, except 5-methoxy-Indole, preparing compound 3-23 with the method identical with preparing compound 3-11.
1HNMR(400MHz,CDCl
3)δ8.50(d,J=7.8Hz,1H),8.14–8.06(m,2H),7.91(s,1H),7.63(t,J=7.4Hz,1H),7.50(t,J=7.7Hz,2H),7.38(ddd,J=8.0,5.8,2.5Hz,1H),7.35–7.28(m,5H),7.19–7.11(m,2H)。
Embodiment 24
Except using 1-skatole to replace 5-methoxy-Indole, beyond pivalyl acetonitrile substituted benzene formyl acetonitrile, prepare compound 3-24 with the method identical with preparing compound 3-11.
1HNMR(400MHz,DMSO-D
6)δ8.16(d,J=7.2Hz,1H),8.08(s,1H),7.59(d,J=8.0Hz,1H),7.38–7.28(m,2H),3.89(s,3H),1.27(s,9H)。
Embodiment above describes ultimate principle of the present invention, principal character and advantage; the technician of the industry should understand; the present invention is not restricted to the described embodiments; what describe in above-described embodiment and specification sheets just illustrates principle of the present invention; under the scope not departing from the principle of the invention; the present invention also has various changes and modifications, and these changes and improvements all fall in the scope of protection of the invention.
Claims (7)
1. 3 dicarbapentaborane substituent indole compounds, is characterized in that having following general structure:
Wherein R
1for alkyl, phenyl, substituted-phenyl, furyl or thienyl;
R
2for hydrogen, alkyl or benzyl;
R
3for hydrogen, alkyl or phenyl;
R
4for hydrogen, alkyl, halogen, hydroxyl or alkoxyl group.
2. 3 dicarbapentaborane substituent indole compounds according to claim 1, is characterized in that 3 described dicarbapentaborane substituent indole compounds are one of following compounds:
。
3. the preparation method of 3 dicarbapentaborane substituent indole compounds according to claim 1, it is characterized in that concrete steps are: by substituent indole compound 1, β-carbonyl nitrile compounds 2 and 4-oxo-2,2,6,6-tetramethyl piperidine oxide compound 4-oxo-TEMPO is under the effect of copper salt, by obtained 3 the dicarbapentaborane substituent indole compounds 3 of one kettle way polycomponent cascade reaction in acid solvent, the equation of reaction process is:
。
4. the preparation method of 3 dicarbapentaborane substituent indole compounds according to claim 3, it is characterized in that: described substituent indole compound, β-carbonyl nitrile compounds, 4-oxo-2,2, the mol ratio of 6,6-tetramethyl piperidine oxide compound and copper salt is 1:1-1.5:2-3:0.05-0.2.
5. the preparation method of 3 dicarbapentaborane substituent indole compounds according to claim 3, is characterized in that: described copper salt is CuCl, CuCl
2, CuBr, CuBr
2or Cu (OTf)
2.
6. the preparation method of 3 dicarbapentaborane substituent indole compounds according to claim 3, is characterized in that: described acid solvent is acetic acid, propionic acid or butyric acid.
7. the preparation method of 3 dicarbapentaborane substituent indole compounds according to claim 3, is characterized in that: the temperature of reaction in reaction process is 25-100 DEG C.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106478483A (en) * | 2016-10-14 | 2017-03-08 | 方美兰 | A kind of diaryl replaces the synthetic method of dicarbonyl compound |
| CN106496091A (en) * | 2016-10-08 | 2017-03-15 | 新乡医学院 | A kind of 2 dicarbapentaborane substituted azole class compounds and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103848774A (en) * | 2014-04-03 | 2014-06-11 | 辽宁科技大学 | Synthetic method of indolyl 1,2-ethanedione derivative |
| CN104557663A (en) * | 2015-01-13 | 2015-04-29 | 马良军 | Synthetic method of dicarbonyl substituted indole pharmaceutical intermediate compound |
| CN104817483A (en) * | 2015-03-10 | 2015-08-05 | 华东师范大学 | Bis carbonyl indole compound and synthesis method |
-
2016
- 2016-02-22 CN CN201610093946.6A patent/CN105566198B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103848774A (en) * | 2014-04-03 | 2014-06-11 | 辽宁科技大学 | Synthetic method of indolyl 1,2-ethanedione derivative |
| CN104557663A (en) * | 2015-01-13 | 2015-04-29 | 马良军 | Synthetic method of dicarbonyl substituted indole pharmaceutical intermediate compound |
| CN104817483A (en) * | 2015-03-10 | 2015-08-05 | 华东师范大学 | Bis carbonyl indole compound and synthesis method |
Non-Patent Citations (4)
| Title |
|---|
| JIANWEI YAN等: "Friedel–Crafts reaction of indoles with vicinal tricarbonyl compounds generated in situ from 1,3-dicarbonyl compounds and TEMPO: highly selective synthesis of tertiary alcohols", 《RSC ADVANCES》 * |
| JI-CHENG WU等: "Copper-Catalyzed C-H Oxidation/Cross-Coupling of α-Amino Carbonyl Compounds", 《ANGEWANDTE INTERNATIONAL EDITION CHEMIE》 * |
| NAGARAJU MUPPARAPU等: "Aminocatalytic Cross-Coupling Approach via Iminium Ions to Different C-C Bonds", 《CHEMISTRY-A EUROPEAN JOURNAL》 * |
| RI-YUAN TANG等: "Palladium-Catalyzed Synthesis of 3-Acylated Indoles Involving Oxidative Cross-Coupling of Indoles with α-Amino Carbonyl Compounds", 《THE JOURNAL OF ORGANIC CHEMISTRY》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496091A (en) * | 2016-10-08 | 2017-03-15 | 新乡医学院 | A kind of 2 dicarbapentaborane substituted azole class compounds and preparation method thereof |
| CN106496091B (en) * | 2016-10-08 | 2018-05-22 | 新乡医学院 | A kind of 2 dicarbapentaborane substituted azole class compounds and preparation method thereof |
| CN106478483A (en) * | 2016-10-14 | 2017-03-08 | 方美兰 | A kind of diaryl replaces the synthetic method of dicarbonyl compound |
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