CN106699739A - Preparation method and application of 3-indole-4-indazole maleimide compounds - Google Patents
Preparation method and application of 3-indole-4-indazole maleimide compounds Download PDFInfo
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Abstract
The invention relates to a preparation method and an application of 3-indole-4-indazole maleimide compounds. The compounds are prepared from various substituted 3-chloro-4-indolylmaleimide compounds (1) and 1-methyl-3-(tributylstannyl)-1H-indazole (2) by Stille coupling under the action of a palladium catalyst as well as N-alkylation, aminolysis and other reactions. The operation method is simple, equipment requirement is low, product post-processing is simple, yield is high, the prepared 3-indole-4-indazole maleimide compounds can show fluorescent property in an organic solvent, Stokes shift exceeds 100, and the fluorescence quantum efficiency ranges from 0.23 to 0.52; the compounds have strong fluorescent property in a solid state and have aggregation-induced emission enhancement effect in a system containing organic solvents and water in different proportions.
Description
Technical field
The present invention relates to 3- indoles -4- indazole maleimide compounds and its preparation method and application.
Background technology
The application of luminous organic material is more and more extensive, and people are to this demand also more and more higher, and design and synthesis are novel
And the luminous organic material with excellent fluorescence property is the direction of the joint efforts of numerous researchers.
Bisindole maleimide class compound is after being transformed as lead compound with natural products staurosporine
The class compound for obtaining, because its structure is novel and with stronger bioactivity, causes the broad interest of researcher.This
Seminar finds 3- indoles -4- indazole maleimide compounds during GSK-3 inhibitor is developed
With very strong solid and solution fluorescence, and have aggregation inducing glimmering in the organic solvent of different proportion and the mixed solvent of water
Photo-enhancement effect, has good application prospect as fluorchrome.
The content of the invention
It is an object of the invention to provide the 3- indoles -4- indazole maleimide fluorchromes with novel structure, change
The general structure of compound is as follows：
Described 3- indoles -4- indazole maleimide compounds, it is characterised in that with such as formula（5）Shown structure is led to
Formula：
（5）,
Wherein R1It is hydrogen, halogen or alkoxy； R2It is hydrogen or alkyl；R3It is hydrogen, methyl or phenyl.
Described 3- indoles -4- indazole maleimide compounds, it is characterised in that R1It is hydrogen, fluorine or methoxyl group；R2It is
Hydrogen, methyl, normal-butyl or n-octyl；R3It is hydrogen, methyl or phenyl.
The preparation method of described 3- indoles -4- indazole maleimide compounds, it is characterised in that with such as formula（1）Institute
The chloro- 4- indolylmaleimides class compounds of 3- that show and such as formula（2）Shown 1- methyl -3- (tributyl tin) -1H- indazoles exist
In the presence of palladium catalyst occur stille coupling reactions, product successively with R2X carries out N- alkylated reactions and R3NH2 ammonia
The reaction such as solution is obtained, the structure of the chloro- 4- indolylmaleimides class compounds of 3- and 1- methyl -3- (tributyl tin) -1H- indazoles
Formula such as formula（1）, formula（2）It is shown：
；
Wherein R1It is hydrogen, halogen or alkoxy；R2It is hydrogen or alkyl；R3It is hydrogen, methyl or phenyl.
The preparation method of described 3- indoles -4- indazole maleimide compounds, it is characterised in that：
1）During the chloro- 4- indolylmaleimides class compounds of 3- and 1- methyl -3- (tributyl tin) indazole added into organic solvent,
In the presence of palladium catalyst and anhydrous Lithium chloride, nitrogen is protected in 90-110 DEG C of reaction 1-2h, and water is added after completion of the reaction, uses second
Acetoacetic ester is extracted, organic phase saturated common salt water washing, anhydrous sodium sulfate drying, is concentrated under reduced pressure, residue over silica gel column chromatography
Purification is evaporated and obtains such as formula（3）Shown intermediate 3；
2）By step 1）The intermediate 3 for obtaining is dissolved in stirring and dissolving in dry DMF, is cooled to -5~5 DEG C, adds 60% NaH,
Reaction 25-35 min are warmed to room temperature after adding, R is added dropwise2The solution of X and dry DMF composition, is warmed to room temperature reaction 1.5- after dripping off
2.5h, after reaction terminates, reaction solution is poured into frozen water, ethyl acetate extraction, merges organic phase, successively through saturated aqueous common salt
Wash, anhydrous sodium sulfate drying, concentrated under reduced pressure, residue over silica gel column chromatography（Petroleum ether：Ethyl acetate=1：5）Purification, obtain as
Formula（4）Shown intermediate 4；
3）Under nitrogen protection, by step 2）The intermediate 4 and sour ammonium for obtaining are 140 DEG C of reaction 5-8h, after completion of the reaction will be anti-
Answer liquid to be poured into water, be extracted with ethyl acetate, merge organic layer, with saturated common salt water washing, anhydrous sodium sulfate drying, depressurize dense
Contracting, residue is obtained such as formula through column chromatography purification（5）Shown target product 3- indoles -4- indazole maleimide chemical combination
Thing；
Its chemical equation is as follows：
。
The preparation method of described 3- indoles -4- indazole maleimide compounds, it is characterised in that step 1）Middle institute
Organic solvent is stated for toluene.
The preparation method of described 3- indoles -4- indazole maleimide compounds, it is characterised in that step 1）Middle institute
Palladium catalyst is stated for Pd (Ph3)2Cl2。
Described 3- indoles -4- indazole maleimide compounds as fluorchrome application.
Described 3- indoles -4- indazole maleimide compounds include it in solid-like as the application of fluorchrome
The application of state.
Described 3- indoles -4- indazole maleimide compounds include it organic molten as the application of fluorchrome
The aggregation inducing enhancement effect of fluorescence and related application having in the mixed solvent of agent and water.
Described 3- indoles -4- indazole maleimide compounds as fluorchrome application, it is characterised in that institute
State organic solvent and be included in toluene, tetrahydrofuran, chloroform, ether or N,N-dimethylformamide.
By using above-mentioned technology, compared with prior art, beneficial effects of the present invention are as follows：
1）3- indoles -4- indazole maleimide compounds of the invention are by the chloro- 4- indoles Malaysia acyls of various substituted 3-
Imine compound（1）There is stille in the presence of palladium catalyst with 1- methyl -3- (tributyl tin) -1H- indazoles (2)
Coupling, is then obtained through reactions such as N- alkylations and ammonolysis, and its operating method is simple, low for equipment requirements, product post processing letter
Just, high income；
2）3- indoles -4- indazole maleimide compounds of the invention are in toluene, tetrahydrofuran, chloroform, ether, N, N-
Photoluminescent property can be showed in the organic solvents such as dimethylformamide, more than 100, fluorescence quantum efficiency is 0.23 for Stokes shift values
To between 0.52；
3）3- indoles -4- indazole maleimides compound of the invention has very strong photoluminescent property in the solid state,
For example there is strong solid fluorescence in the case where wavelength is for the ultraviolet light of 365nm；
4）3- indoles -4- indazole maleimide compounds of the invention are in the organic solvent of different proportion and the system of water
With aggregation inducing enhancement effect of fluorescence, for example：Described Fluorescent dye material is in tetrahydrofuran：Ratio is in tetrahydrochysene in the system of water
Stronger fluorescence intensity can be showed in tetrahydrofuran solution, can be used as fluorchrome.
Brief description of the drawings
Fig. 1 is absorbance figure of the 3- indoles -4- indazole maleimide compounds in organic solvent toluene；
Fig. 2 is fluorescence intensity figure of the 3- indoles -4- indazole maleimide compounds in organic solvent toluene；
Fig. 3 is 3- indoles -4- indazole maleimides compound fluorescence intensity figure in the solid state；
Fig. 4 is the solid fluorescence figure of 3- indoles -4- indazole maleimide compounds；
Fig. 5 is 3- indoles -4- indazole maleimide compounds in the solvent that different proportion water and tetrahydrofuran are constituted
Fluorescence assembles enhancement effect figure；
Fig. 6 is 3- indoles -4- indazole maleimide fluorchromes in the solvent that different proportion water and tetrahydrofuran are constituted
Absorbance change figure；
Fig. 7 is 3- indoles -4- indazole maleimide fluorchromes in the solvent that different proportion water and tetrahydrofuran are constituted
Figure of fluorescence intensity changes.
Specific embodiment
The present invention be further described in conjunction with the embodiments, embodiment below is illustrate of the invention, rather than with times
Where formula limitation is of the invention.
Embodiment 1：3- (1H- indol-3-yls) -4- (1- methyl-indazol -3- bases) -1- phenyl maleimides（3a）'s
Prepare
1.13 g are added in there-necked flask（3.5 mmol）The chloro- 4- of 3- (1H- indol-3-yls) -1- phenyl maleimides,
1.47g（3.5 mmol）1- methyl -3- (tributyl tin) indazole, 0.1g anhydrous Lithium chlorides, 0.1g Pd (Ph3)2Cl2With 100 mL
Dry toluene, then reacts 1.5h in 100 DEG C under nitrogen protection, and 100 mL water are added after completion of the reaction, is extracted with ethyl acetate
Take（100 mL × 3）, saturated common salt water washing is used after organic layer merging（300 mL）, anhydrous sodium sulfate drying, be concentrated under reduced pressure,
The purification of residue over silica gel column chromatography is evaporated and obtains 1.28g yellow solid 3a, yield 77.1%, fusing point：258-259℃.1H
NMR (500 MHz, CDCl3) δ 9.12 (s, 1H), 8.06 (d, J = 2.9 Hz, 1H), 7.75 (d, J =
8.2 Hz, 1H), 7.60 –7.50 (m, 4H), 7.47 – 7.37 (m, 3H), 7.32 (d, J = 8.1Hz,
1H), 7.17–7.05 (m, 2H), 6.74 (t, J = 7.6 Hz, 1H), 6.37 (d, J = 8.1 Hz, 1H),
4.02 (s, 3H).
Embodiment 2：3- (the fluoro- 1- Methvl-indoles -3- bases of 5-) -4- (1- methyl-indazol -3- bases) -1- phenyl maleimides
（3b）Preparation
Synthetic method is simply replaced with implementing 1 with the chloro- 4- of 3- (the fluoro- 1- Methvl-indoles -3- bases of 5-) -1- phenyl maleimides
The chloro- 4- of 3- (1H- indol-3-yls) -1- phenyl maleimides, obtain orange solids 3b, yield：80.0%, fusing point：223-
224℃。1H NMR (500 MHz, CDCl3) δ 8.20 (s, 1H), 7.73 (d, J = 8.2 Hz, 1H), 7.61-
7.51 (m, 4H), 7.51 – 7.36 (m, 3H), 7.25-7.18 (m, 1H), 7.13 (t, J = 7.4 Hz,
1H), 6.90 (t, J = 8.7 Hz, 1H), 5.92 (d, J = 10.3 Hz, 1H), 4.04 (s, 3H), 3.88
(s, 3H).
Embodiment 3：3- (5- methoxyl group -1- Methvl-indole -3- bases -4- (1- methyl-indazol -3- bases) -1- benzyl maleimides
Amine（3c）Preparation
Synthetic method is same to implement 1, simply with the chloro- 4- of 3- (5- methoxyl group -1- Methvl-indole -3- bases) -1- phenyl maleimides
3- chloro- 4- (1H- indol-3-yls) -1- phenyl maleimides are replaced, orange solids 3c, yield is obtained：71.7%, 217-
218℃。1H NMR (500 MHz, CDCl3) δ 8.13 (s, 1H), 7.76 (d, J = 8.2 Hz, 1H), 7.57 –
7.50 (m, 4H), 7.45 – 7.36 (m, 3H), 7.17 (d, J = 8.8 Hz, 1H), 7.14-7.10 (m,
1H), 6.74 (dd, J = 8.8, 2.4 Hz, 1H), 5.66 (d, J = 2.4 Hz, 1H), 4.01 (s, 3H),
3.88 (s, 3H), 2.93 (s, 3H).
Embodiment 4：3- (1- Methvl-indole -3- bases) -4- (1- methyl-indazol -3- bases) -1- phenyl maleimides（4a）
Preparation
105 mg are added in there-necked flask（0.25 mmol）3a and 20 mL dry DMFs, stirring and dissolving are cooled to 00C or so,
Add 10.8 mg（0.26 mmol）60% NaH, is warmed to room temperature 30 min of reaction after adding, 71mg (0.5 mmol) iodine is added dropwise
The solution of methane and 5Ml dry DMFs composition, is warmed to room temperature reaction 2h after dripping off, after reaction terminates, reaction solution is poured into 100
In mL frozen water, ethyl acetate extraction（3 × 100 mL）, merge organic phase, saturated common salt washing（3 ×300 mL）, anhydrous sulphur
Sour sodium is dried, and is concentrated under reduced pressure, residue over silica gel column chromatography（Petroleum ether：Ethyl acetate=1：5）Purification, obtains 80mg orange solid
Body 4a, yield：73.6%, fusing point：292-293℃.1H NMR (500 MHz, CDCl3) δ 8.17 (s, 1H), 7.79
(d, J = 8.3 Hz, 1H), 7.58 – 7.50 (m, 4H), 7.47 – 7.37 (m, 3H), 7.31 (d,J =
8.2 Hz, 1H), 7.18 – 7.10 (m, 2H), 6.75 (t, J = 7.9 Hz , 1H), 6.31 (d, J = 8.1
Hz, 1H), 4.00 (s, 3H), 3.90 (s, 3H).
Embodiment 5：3- (1- butyl-indol-3-yl) -4- (1- methyl-indazol -3- bases) -1- phenyl maleimides（4b）'s
Prepare
Synthetic method simply replaces iodomethane with implementing 4 with NBB, obtains orange solids 4b, yield：73.3%, fusing point：
176-177℃。1H NMR (500 MHz, CDCl3) δ 8.19 (s, 1H), 7.70 (d, J = 8.2 Hz, 1H),
7.61–7.49 (m, 4H), 7.46 – 7.37 (m, 3H), 7.33 (d, J = 8.2 Hz, 1H), 7.13 (t, J
= 7.7 Hz, 1H), 7.08 (t, J = 7.6 Hz, 1H) ,6.75 (t, J = 7.5 Hz, 1H), 6.42 (d, J
= 8.1 Hz, 1H), 4.19 (t, J = 7.1 Hz, 2H), 4.03 (s, 3H), 1.97 – 1.79 (m, 2H),
1.50 – 1.16 (m, 2H), 0.98 (t, J = 7.4 Hz , 3H).
Embodiment 6：3- (1- octyl groups-indol-3-yl) -4- (1- methyl-indazol -3- bases) -1- phenyl maleimides（4c）
Preparation
Synthetic method simply replaces iodomethane with implementing 4 with bromooctane, obtains orange solids 4c, yield：56.8%, fusing point：
133-134℃。1H NMR (500 MHz, CDCl3) δ 8.20 (s, 1H), 7.69 (d, J = 8.2 Hz, 1H),
7.59 – 7.49 (m, 4H), 7.47 – 7.36 (m, 3H), 7.32 (d, J = 8.2 Hz, 1H), 7.13 (t,J
= 7.9 Hz, 1H), 7.08 (t,J = 7.9 Hz, 1H) ,6.74 (t, J = 7.5 Hz, 1H), 6.39 (d, J
= 8.1 Hz, 1H), 4.18 (t, J = 7.2 Hz,2H), 4.04 (s, 3H), 1.99 – 1.82 (m, 2H),
1.47 – 1.16 (m, 10H), 0.89 (t, J = 6.9 Hz, 3H).
Embodiment 7：1H-3- (1- Methvl-indole -3- bases) -4- (1- methyl-indazol -3- bases) maleimide（5a）Preparation
0.43g is added in there-necked flask（1mmol）Compound 4a and 2g ammonium acetate, reacts 6h, reaction in 140 DEG C under nitrogen protection
Reaction solution is poured into 100ml water after finishing, is extracted with ethyl acetate（100 mL×3）, merge organic layer, use saturated aqueous common salt
Washing（300 mL）, anhydrous sodium sulfate drying, be concentrated under reduced pressure, residue through column chromatography purification obtain 0.24g dark red solids
5a, yield 66.8%, fusing point：202-203℃.1H NMR (500 MHz, CDCl3) δ 8.10 (s, 1H), 7.65(d, J
= 8.2 Hz, 1H), 7.60 (s, 1H), 7.45 – 7.34 (m, 2H), 7.29 (d, J = 8.3 Hz, 1H),
7.18 – 7.03 (m, 2H), 6.71 (t, J = 7.6 Hz, 1H), 6.26 (d, J = 8.1 Hz, 1H), 4.01
(s, 3H), 3.89 (s, 3H).
Embodiment 8：1- methyl -3- (1- Methvl-indole -3- bases) -4- (1- methyl-indazol -3- bases) maleimide（5b）
Preparation
0.43g is added in there-necked flask（1mmol）Compound 4a and 2g methylamine alcohol solution, normal-temperature reaction 2h after having reacted, subtracts
Pressure concentration, residue is evaporated through column chromatography purification, obtains 0.25g dark red solid 5b, yield 68.4%, fusing point：241-242
℃。1H NMR (500 MHz, CDCl3) δ 8.10 (s, 1H), 7.68 (d,J = 8.2, 2H), 7.48 – 7.36
(m, 2H), 7.29(d, J = 8.5, 1H), 7.18-7.04 (m, 2H), 6.71 (t, J = 7.6 Hz, 1H),
6.24 (d, J = 8.1 Hz, 1H), 3.99 (s, 3H), 3.87 (s, 3H), 3.23 (s, 3H) 。
Embodiment 9：Extinction of the 3- indoles -4- indazole maleimide compounds as fluorchrome in organic solvent
The measure of degree and fluorescence intensity
3- indoles -4- indazole maleimide fluorchromes 3a ~ 3c, 4a ~ 4c, 5a ~ 5b is dissolved in toluene respectively, is configured
Into 1.0 × 10-5The solution of mol/L.Determine the maximum absorption wavelength of these solution respectively with UV-2550 type ultraviolet spectrometry range meters
And absorbance（See accompanying drawing 1）；Their fluorescence emission wavelengths λ em (nm) and fluorescence intensity is determined with F-7000 type fluorescence photometers
（See accompanying drawing 2）；The data such as molar absorption coefficient ε, Stokes displacement to them, the fluorescence quantum efficiency Φ f for calculating are shown in Table 1.
The part 3- indoles -4- indazole maleimide fluorchromes of table 1 are in organic solvent toluene（10-5mol/L）'s
Fluorescence property table
Embodiment 10：The measure of 3- indoles -4- indazole maleimides fluorchrome fluorescence intensity in the solid state
3- indoles -4- indazole maleimide fluorchromes 3a ~ 3c, 4a ~ 4c, 5a ~ 5b is dissolved in dichloromethane respectively,
It is configured to 1.0 × 10-3The solution of mol/L, solution is dropped on glass slide, after dichloromethane volatilization is clean on glass flake
Form one layer of uniform lamella pigments；Their fluorescence emission wavelengths λ em (nm) and fluorescence is determined with F-7000 type fluorescence photometers
Intensity（See accompanying drawing 3）；Several 3- indoles -4- indazole maleimide fluorchromes have strong solid glimmering under 365nm irradiations
Light（See accompanying drawing 4）.
Embodiment 11：3- indoles -4- indazole maleimide fluorchromes are in different proportion water and tetrahydrofuran group
Into solvent in absorbance and fluorescence intensity measure
3- indoles -4- indazole maleimide fluorchromes 3b, 4b, 4c are dissolved in tetrahydrofuran respectively, 1.0 are configured to
×10-3The solution of mol/L is used as mother liquor；By every kind of mother liquor into 1.0 × 10-4The tetrahydrofuran of mol/L：Water=1:0/4:1/
2:1/1:1/1:2/1:4/1:9 solution；Tetrahydrofuran of the Fluorescent dye material in part：It is more molten than in tetrahydrofuran in aqueous systems
Stronger fluorescence intensity can be showed in liquid（See accompanying drawing 5）.These solution are determined respectively with UV-2550 type ultraviolet spectrometry range meters
Maximum absorption wavelength and absorbance（See accompanying drawing 6）；Their fluorescence emission wavelengths λ em (nm) is determined with F-7000 type fluorescence photometers
And fluorescence intensity（See accompanying drawing 7）.
Claims (10)
1.3- indoles -4- indazole maleimide compounds, it is characterised in that with such as formula（5）Shown general structure：
,
Wherein R1It is hydrogen, halogen or alkoxy； R2It is hydrogen or alkyl；R3It is hydrogen, methyl or phenyl.
2. 3- indoles -4- indazole maleimide compounds according to claim 1, it is characterised in that R1For hydrogen, fluorine or
Methoxyl group；R2It is hydrogen, methyl, normal-butyl or n-octyl；R3It is hydrogen, methyl or phenyl.
3. a kind of preparation method of 3- indoles -4- indazole maleimide compounds according to claim 1, its feature
It is with such as formula（1）Chloro- 4- indolylmaleimides class compounds of shown 3- and such as formula（2）Shown 1- methyl -3- (three fourths
Ji Xi) there is stille coupling reactions in -1H- indazoles in the presence of palladium catalyst, product successively with R2X carries out N- alkyl
Change reaction and R3The reaction such as NH2 ammonolysis is obtained, the chloro- 4- indolylmaleimides class compounds of 3- and 1- methyl -3- (tributyls
Tin) -1H- indazoles structural formula such as formula（1）, formula（2）It is shown：
Wherein R1It is hydrogen, halogen or alkoxy；R2It is hydrogen or alkyl；R3It is hydrogen, methyl or phenyl.
4. the preparation method of 3- indoles -4- indazole maleimide compounds according to claim 3, its feature exists
In：
1）During the chloro- 4- indolylmaleimides class compounds of 3- and 1- methyl -3- (tributyl tin) indazole added into organic solvent,
In the presence of palladium catalyst and anhydrous Lithium chloride, nitrogen is protected in 90-110 DEG C of reaction 1-2h, and water is added after completion of the reaction, uses second
Acetoacetic ester is extracted, organic phase saturated common salt water washing, anhydrous sodium sulfate drying, is concentrated under reduced pressure, residue over silica gel column chromatography
Purification is evaporated and obtains such as formula（3）Shown intermediate 3；
2）By step 1）The intermediate 3 for obtaining is dissolved in stirring and dissolving in dry DMF, is cooled to -5~5 DEG C, adds 60% NaH,
Reaction 25-35 min are warmed to room temperature after adding, R is added dropwise2The solution of X and dry DMF composition, is warmed to room temperature reaction 1.5- after dripping off
2.5h, after reaction terminates, reaction solution is poured into frozen water, ethyl acetate extraction, merges organic phase, successively through saturated aqueous common salt
Wash, anhydrous sodium sulfate drying, concentrated under reduced pressure, residue over silica gel column chromatography（Petroleum ether：Ethyl acetate=1：5）Purification, obtain as
Formula（4）Shown intermediate 4；
3）Under nitrogen protection, by step 2）The intermediate 4 and sour ammonium for obtaining are 140 DEG C of reaction 5-8h, after completion of the reaction will be anti-
Answer liquid to be poured into water, be extracted with ethyl acetate, merge organic layer, with saturated common salt water washing, anhydrous sodium sulfate drying, depressurize dense
Contracting, residue is obtained such as formula through column chromatography purification（5）Shown target product 3- indoles -4- indazole maleimide chemical combination
Thing；
Its chemical equation is as follows：
5. the preparation method of 3- indoles -4- indazole maleimide compounds according to claim 4, it is characterised in that
Step 1）Described in organic solvent be toluene.
6. the preparation method of 3- indoles -4- indazole maleimide compounds according to claim 4, it is characterised in that
Step 1）Described in palladium catalyst be Pd (Ph3)2Cl2。
7. a kind of 3- indoles -4- indazole maleimide compounds according to claim 1 as fluorchrome should
With.
8. 3- indoles -4- indazole maleimide compounds according to claim 7 are wrapped as the application of fluorchrome
Include its application in solid state.
9. 3- indoles -4- indazole maleimide compounds according to claim 7 are wrapped as the application of fluorchrome
Include aggregation inducing enhancement effect of fluorescence and related application that it has in the mixed solvent of organic solvent and water.
10. 3- indoles -4- indazole maleimide compounds according to claim 9 as fluorchrome application,
It is characterized in that the organic solvent is included in toluene, tetrahydrofuran, chloroform, ether or N,N-dimethylformamide.
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| CN107973785A (en) * | 2017-11-27 | 2018-05-01 | 浙江工业大学上虞研究院有限公司 | It is a kind of to be used to detect fluorescence probe of silver ion and its preparation method and application |
| CN107973785B (en) * | 2017-11-27 | 2019-12-31 | 浙江工业大学上虞研究院有限公司 | Fluorescent probe for detecting silver ions and preparation method and application thereof |
| CN110183450A (en) * | 2019-07-11 | 2019-08-30 | 河南师范大学 | A kind of synthetic method of 2- arylindazoles and maleimide fused-polycyclic compounds |
| CN110183450B (en) * | 2019-07-11 | 2020-05-12 | 河南师范大学 | Synthetic method of 2-arylindazolo maleimide fused polycyclic compound |
| CN110862396A (en) * | 2019-11-29 | 2020-03-06 | 浙江工业大学 | Synthesis method of pyrrolo [3,4-c ] carbazole-1, 3(2H,6H) -diketone compound |
| CN111978298A (en) * | 2020-09-05 | 2020-11-24 | 广东石油化工学院 | Bis-indole maleimide fluorescence sensor containing aromatic amide group |
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| CN106699739B (en) | 2019-03-12 |
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