CN108752284A - Two amido-s- compound in triazine class of one kind and its preparation method and application - Google Patents
Two amido-s- compound in triazine class of one kind and its preparation method and application Download PDFInfo
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- CN108752284A CN108752284A CN201810701309.1A CN201810701309A CN108752284A CN 108752284 A CN108752284 A CN 108752284A CN 201810701309 A CN201810701309 A CN 201810701309A CN 108752284 A CN108752284 A CN 108752284A
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- 0 CN(C)c1[n+]c(N)nc(CC*)n1 Chemical compound CN(C)c1[n+]c(N)nc(CC*)n1 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
Abstract
It is an object of the invention to disclose one kind two amido-s- compound in triazine class, preparation method of the compound as shown in formula (II) to be：Alcohol compound shown in formula (I) is mixed with Metformin and is added in organic solvent, under the action of metallic catalyst, in the presence of alkaline matter, it is stirred to react 5~30 hours at a temperature of 80~140 DEG C, after reaction, obtain reaction solution, two amido-s- compound in triazine class method reaction conditions of the present invention shown in post-treated obtained formula (II) are mild, and raw material is easy to get, easy to operate, it is at low cost, there is extensive prospects for commercial application.Two amidos-s- compound in triazine class provided by the present invention shows certain anti-human lung carcinoma cell activity, lays a good foundation for new medicament screen and exploitation, has preferable practical value.
Description
(1) technical field
The present invention relates to a kind of two amido-s- compound in triazine class and its preparation method and application.
(2) background technology
Compound in triazine class is a kind of important heterocycle compound, has a variety of biologies such as anticancer, antimalarial, weeding living
Property, it is widely used and the fields such as medicine, pesticide.Therefore, compound in triazine class is gradual in organic chemistry and medicinal chemistry art
As the emphasis of people's research.
(3) invention content
The object of the present invention is to provide a kind of two amido-s- compound in triazine class and its preparation method and application.
The present invention adopts the following technical scheme that：
One kind two amido-s- compound in triazine class as shown in formula (II)：
In formula (II),
R is C6~C10Aryl, the aryl are phenyl or substituted-phenyl, and the substituent group is C1~4Alkyl, C1~4
Alkoxy or halogen.
Further, the preferably described substituent group is methyl, methoxyl group, 3,4- methylenes dimethoxy, fluorine, chlorine or bromine substitution
Phenyl.
The specific preparation method of two amidos-s- compound in triazine class of the present invention is as follows：
Alcohol compound shown in formula (I) is mixed with Metformin and is added in organic solvent, in metal catalytic
Under the action of agent, in the presence of alkaline matter, it is stirred to react 5~30 hours at a temperature of 80~140 DEG C, after reaction,
Obtain reaction solution, two amido-s- compound in triazine class shown in post-treated obtained formula (II)；Alcohols shown in the formula (I)
The ratio between compound and the amount of substance of Metformin, metallic catalyst, alkaline matter are 1：0.5~1.5：0.01~
0.04：1.0~3.0；The organic solvent is ethers；The metallic catalyst is ruthenium catalyst；
R in formula (I)1、R2It is such as above-mentioned.
Further, the organic solvent is preferably Isosorbide-5-Nitrae-dioxane, tetrahydrofuran or 2- methyltetrahydrofurans.Again
Further, the volumetric usage of the organic solvent be usually calculated as 5 with the amount of the substance of alcohol compound shown in formula (I)~
20mL/mmol。
Further, the metallic catalyst is preferably three (triphenylphosphine) ruthenous chlorides, ten dicarbapentaborane rutheniums, two (triphenyls
Phosphine) cyclopentadiene ruthenic chloride, dichloro (p -Methylisopropylbenzene base) ruthenium dimer or ruthenium-oxide.
Further, the alkaline matter is inorganic base or organic base；Preferably potassium tert-butoxide, sodium methoxide, triethylamine, hydrogen
Sodium oxide molybdena or potassium hydroxide.
In preparation method of the present invention, following method can be used in the post-processing of the reaction solution：After reaction, to institute
Add water in the reaction solution stated, be extracted with ethyl acetate, merge organic layer, dried with anhydrous sodium sulfate, filter, concentrates filtrate, warp
Column chromatography for separation, with volume ratio for 100:1 dichloromethane and the mixed liquor of methanol are eluant, eluent, are collected containing target compound
Eluent, vacuum distillation, is dried to obtain two amido-s- compound in triazine class shown in target compounds of formula (II).
Two amidos-s- compound in triazine class of the present invention can be used for preparing antitumor drug.
Further, the tumour is preferably human lung cancer.
Compared with prior art, the beneficial effects of the present invention are：
The present invention develops a kind of two amido-s- compound in triazine class and preparation method thereof, the technological reaction mild condition,
Raw material is easy to get, easy to operate, at low cost, there is extensive prospects for commercial application.Two amidos-s- triazines provided by the present invention
Compound shows certain anti-human lung carcinoma cell activity, lays a good foundation for new medicament screen and exploitation, has preferable practical valence
Value.
Specific implementation mode
Below will by embodiment, the present invention is further illustrated, but the scope of the present invention is not limited thereto.
Embodiment 1：The preparation of compound (II -1)
In the reaction vessel plus Metformin (82.8mg, 0.50mmol), cinnamyl alcohol (67.2mg,
0.50mmol), three (triphenylphosphine) ruthenous chloride (9.0mg, 0.01mmol), potassium tert-butoxide (115.4mg, 1.03mmol),
Mixing, is stirred to react 22 hours in 120 DEG C of oil baths in Isosorbide-5-Nitrae-dioxane (4mL)；After reaction, add methanol and dichloromethane
Alkane dissolves, and filtering concentrates filtrate, column chromatography (dichloromethane:Methanol=100:1) R, is collectedfThe eluent of value 0.3~0.35,
Vacuum distillation, is dried to obtain target compound (II -1), 93.0mg, yield 73%.
1H NMR(500MHz,CDCl3)δ7.32-7.25(m,4H),7.20(tt,6.8Hz,2.0Hz1H),5.24(br,
2H),3.18(s,3H),3.11(s,3H),3.08-3.03(m,2H),2.86-2.79(m,2H)。
Embodiment 2：
Temperature is reduced to 80 DEG C, other operations are the same as embodiment 1,35.1mg, yield 30%.
Embodiment 3：
140 DEG C are raised the temperature to, other operations are the same as embodiment 1,75.4mg, yield 62%.
Embodiment 4：
By time lengthening to 30h, Isosorbide-5-Nitrae-dioxane is changed to the same implementation of other operations of 2- methyltetrahydrofurans (2.5mL)
Example 1,83.3mg, yield 70%.
Embodiment 5：
The amount of Metformin is changed to (41.4mg, 0.25mmol), the reaction time is changed to 5 hours, other operations
With embodiment 1,83.3mg, yield 68%.
Embodiment 6：
The amount of melbine is changed to (124.2mg, 0.75mmol), Isosorbide-5-Nitrae-dioxane is changed to tetrahydrofuran (10mL)
Other operations are the same as embodiment Isosorbide-5-Nitrae 7.6mg, yield 38%.
Embodiment 7：
Three (triphenylphosphine) ruthenous chlorides are changed to two (triphenylphosphine) cyclopentadiene ruthenic chlorides (7.5mg, 0.01mmol),
Other operations are the same as embodiment Isosorbide-5-Nitrae 4.2mg, yield 36%.
Embodiment 8：
Three (triphenylphosphine) ruthenous chlorides are changed to ten dicarbapentaborane rutheniums (6.0mg, 0.01mmol), other operate same embodiment
1,68.7mg, yield 57%.
Embodiment 9：
Three (triphenylphosphine) ruthenous chlorides are changed to ruthenium-oxide (1.3mg, 0.01mmol), other are operated with embodiment 1,
67.5mg, yield 57%.
Embodiment 10：
By three (triphenylphosphine) ruthenous chlorides be changed to dichloro (p -Methylisopropylbenzene base) ruthenium dimer (6.8mg,
0.01mmol), other operations are the same as embodiment 1,13.7mg, yield 10%.
Embodiment 11：
The amount of potassium tert-butoxide is changed to (56.8mg, 0.50mmol), other operations are hardly reacted with embodiment 1.
Embodiment 12：
The amount of potassium tert-butoxide is changed to (168.9mg, 1.50mmol), other operations are the same as embodiment 1,56.4mg, yield
45%.
Embodiment 13：
Potassium tert-butoxide is changed to potassium hydroxide (57.5mg, 1.00mmol), other operations are the same as embodiment Isosorbide-5-Nitrae 9.4mg, yield
41%.
Embodiment 14：
Potassium tert-butoxide is changed to sodium hydroxide (45.3mg, 1.02mmol), other operations are the same as embodiment 1,38.6mg, yield
28%.
Embodiment 15：
Potassium tert-butoxide is changed to triethylamine (98.3mg, 1.00mmol), other operations are the same as embodiment 1,7.5mg, yield
6%.
Embodiment 16：
Potassium tert-butoxide is changed to sodium methoxide (51.5mg, 1.00mmol), other operations are the same as embodiment 1,16.2mg, yield
14%.
Embodiment 17：The preparation of compound (II -2)
Cinnamyl alcohol is only changed into methyl cinnamyl alcohol (90.6mg, 0.61mmol) with embodiment 1, target is made by operation
Compound (II -2), 106.1mg, yield 79%.
1H NMR(500MHz,CDCl3) δ 7.16 (d, J=8.0Hz, 2H), 7.10 (d, J=8.0Hz, 2H), 5.21 (br,
2H),3.18(s,3H),3.11(s,3H),3.04-3.01(m,2H),2.84-2.75(m,2H)
Embodiment 18：The preparation of compound (II -3)
Operation only changes cinnamyl alcohol into 3,4- bis- methylene oxygroup cinnamyl alcohols (81.1mg, 0.51mmol) with embodiment 1,
Target compound (II -3), 80.1mg, yield 61% is made.
1H NMR(500MHz,CDCl3) δ 6.76 (d, J=1.3Hz, 1H), 6.73 (d, J=8.0Hz, 1H), 6.70 (dd, J
=8.0,1.3Hz, 1H), 5.92 (s, 2H), 5.17 (br, 2H), 3.18 (s, 3H), 3.11 (s, 3H), 3.00-2.97 (m, 2H),
2.82-2.71(m,2H).
Embodiment 19：The preparation of compound (II -4)
Operation only changes cinnamyl alcohol into 4- methoxycinnamates alcohol (85.1mg, 0.51mmol) with embodiment 1, and mesh is made
Mark compound (II -2), 83.0mg, yield 61%.
1H NMR(500MHz,CDCl3) δ 7.18 (d, J=8.6Hz, 2H), 6.80 (d, J=8.6Hz, 2H), 5.14 (br,
2H),3.18(s,3H),3.11(s,3H),3.02-2.99(m,2H),2.83-2.71(m,2H)。
Embodiment 20：The preparation of compound (II -5)
Operation only changes cinnamyl alcohol into 3- methoxycinnamates alcohol (80.2mg, 0.50mmol) with embodiment 1, and mesh is made
Mark compound (II -5), 76.8mg, yield 57%.
1H NMR(500MHz,CDCl3) δ 7.20 (t, J=7.9Hz, 1H), 6.86 (d, J=7.9Hz, 1H), 6.82 (t, J
=2.2Hz, 1H), 6.74 (dd, J=7.9,2.2Hz, 1H), 5.20 (s, 2H), 3.80 (s, 3H), 3.19 (s, 3H), 3.11 (s,
3H),3.06-3.03(m,2H),2.84-2.80(m,2H)。
Embodiment 21：The preparation of compound (II -6)
Operation only changes cinnamyl alcohol into 2- methoxycinnamates alcohol (89.1mg, 0.52mmol) with embodiment 1, and mesh is made
Mark compound (II -6), 113.1mg, yield 83%.
1H NMR(500MHz,CDCl3)1H NMR(500MHz,CDCl3) δ 7.21 (dd, J=7.3Hz, 1.8Hz, 1H),
7.18 (td, J=7.8,1.8Hz, 1H), 6.89 (td, J=7.4,1.0Hz, 1H), 6.86 (d, J=8.3Hz, 1H), 5.26
(br,2H),3.85(s,2H),3.18(s,3H),3.11(s,3H),3.07-2.98(m,2H),2.84-2.77(m,2H)。
Embodiment 22：The preparation of compound (II -7)
Operation only changes cinnamyl alcohol into 4- fluorine cinnamyl alcohol (74.2mg, 0.51mmol) with embodiment 1, and targeted is made
Close object (II -7), 72.9mg, yield 57%.
1H NMR(500MHz,CDCl3)δ7.22-7.11(m,2H),7.01-6.90(m,2H),5.03(br,2H),3.17
(s,3H),3.11(s,3H),3.06-2.98(m,2H),2.80-2.75(m,2H)。
Embodiment 23：The preparation of compound (II -8)
Operation only changes cinnamyl alcohol into 3- chlorine cinnamyl alcohol (84.3mg, 0.50mmol) with embodiment 1, and targeted is made
Close object (II -8), 46.3mg, yield 33%.
1H NMR(500MHz,CDCl3) δ 7.27 (d, J=1.8Hz, 1H), 7.21 (t, J=7.9Hz, 1H), 7.16 (dt, J
=7.9Hz, 1.8Hz, 1H), 7.13 (d, J=7.9Hz, 1H), 5.01 (br, 2H), 3.17 (s, 3H), 3.11 (s, 3H), 3.06-
3.04(m,2H),2.84-2.80(m,2H)。
Embodiment 24：The preparation of compound (II -9)
Operation only changes cinnamyl alcohol into 4- chlorine cinnamyl alcohol (78.7mg, 0.61mmol) with embodiment 1, and targeted is made
Close object (II -9), 39.6mg, yield 28%.
1H NMR(500MHz,CDCl3) δ 7.24 (d, J=8.4Hz, 2H), 7.18 (d, J=8.4Hz, 2H), 5.05 (br,
2H),3.17(s,3H),3.11(s,3H),3.05-3.02(m,2H),2.81-2.79(m,2H)。
Embodiment 25：The preparation of compound (II -10)
Operation only changes cinnamyl alcohol into 4- cinnamyl bromides alcohol (103.8mg, 0.50mmol) with embodiment 1, and targeted is made
Close object (II -10), 98.1mg, yield 61%.
1H NMR(500MHz,CDCl3) δ 7.39 (d, J=8.4Hz, 2H), 7.13 (d, J=8.4Hz, 2H), 5.04 (br,
2H),3.16(s,3H),3.11(s,3H),3.05-3.00(m,2H),2.84-2.72(m,2H)。
Embodiment 26：The preparation of compound (II -11)
Operation only changes cinnamyl alcohol into 2,3- dimethoxys cinnamyl alcohol (115.1mg, 0.59mmol) with embodiment 1, makes
Obtain target compound (II -11), 118.8mg, yield 74%.
1H NMR(500MHz,CDCl3) δ 6.98 (t, J=7.9Hz, 1H), 6.85 (dd, J=7.9,1.3Hz, 1H), 6.79
(dd, J=7.9,1.3Hz, 1H), 5.39 (br, 2H), 3.87 (s, 3H), 3.86 (s, 3H), 3.17 (s, 3H), 3.14-3.02
(m,5H),2.86-2.70(m,2H)。
Embodiment 27：The preparation of compound (II -12)
Operation only changes cinnamyl alcohol into 3- methyl cinnamyls alcohol (68.8mg, 0.50mmol) with embodiment 1, and target is made
Compound (II -12), 74.7mg, yield 63%.
1H NMR(500MHz,CDCl3) δ 7.18 (t, J=7.5Hz, 1H), 7.10 (s, 1H), 7.07 (d, J=7.5Hz,
1H), 7.01 (d, J=7.5Hz, 1H), 5.13 (br, 2H), 3.19 (s, 3H), 3.12 (s, 3H), 3.06-3.00 (m, 2H),
2.86-2.77(m,2H),2.34(s,3H)。
Embodiment 28：Anti-lung cancer cell NCI-H460 biological activity tests
External anti-lung cancer cell NCI-H460 activity test methods：Mtt assay
Experimental procedure：
1) preparation of sample：For solvable sample, per 1mg with 20 μ L DMSO dissolvings, take 2uL dilute with 1000 μ L culture solutions
It releases, makes a concentration of 100 μ g/mL, then concentration is extremely used with culture solution serial dilution.
2) culture of cell
2.1) preparation of culture medium:Contain 800,000 units of Penicillin, 1.0g streptomysins, 10% inactivation in per 1000mL culture mediums
Fetal calf serum.
2.2) culture of cell：By tumor cell inoculation in culture medium, 37 DEG C are set, 5%CO2It is cultivated in incubator, 3~
5d is passed on.
3) inhibiting effect of the determination sample to growth of tumour cell
Cell EDTA- pancreatin digestive juices are digested, culture medium is used in combination to be diluted to 1 × 105/ mL is added to 96 hole cell trainings
It supports in plate, per hole 100uL, sets 37 DEG C, 5%CO2It is cultivated in incubator.After inoculation for 24 hours, the diluted sample of addition culture medium,
Per 100 μ L of hole, each concentration adds 3 holes, sets 37 DEG C, 5%CO2It is cultivated in incubator, 5mg/ is added after 72h in cell culture well
The MTT of mL sets 37 DEG C of incubation 4h, DMSO is added, per 150 μ L of hole, is vibrated with oscillator per 10 μ L of hole, and Shi Jia Za is completely dissolved,
With microplate reader under 570nm wavelength colorimetric.With similarity condition use be free of sample, the medium culture containing same concentration DMSO it is thin
Born of the same parents as a contrast, calculate sample to the inhibiting rate of growth of tumour cell, the results are shown in Table 1.
Using lung carcinoma cell NCI-H460 as model, the two amido-s- compound in triazine class samples prepared in embodiment are determined
Product are in vitro to the inhibiting effect of lung cancer cell growth (the results detailed in Table 1).
Inhibiting rate of the 1 each compound of table to lung carcinoma cell NCI-H460
| Compound | Inhibiting rate % | Compound | Inhibiting rate % |
| (II-1) | 17 | (II-6) | 55 |
| (II-2) | 47 | (II-7) | 55 |
| (II-3) | 43 | (II-8) | 25 |
| (II-4) | 29 | (II-9) | 32 |
| (II-5) | 57 | (II-10) | 50 |
| (II-11) | 48 | (II-12) | 35 |
Claims (10)
1. a kind of two amido-s- compound in triazine class as shown in formula (II)：
In formula (II),
R is C6~C10Aryl, the aryl are phenyl or substituted-phenyl, and the substituent group is C1~4Alkyl, C1~4Alkane
Oxygroup or halogen.
2. two amidos-s- compound in triazine class as described in claim 1, it is characterised in that：The substituent group is methyl, first
The phenyl that oxygroup, 3,4- methylenes dimethoxy, fluorine, chlorine or bromine replace.
3. two amidos-s- compound in triazine class as described in claim 1, it is characterised in that：The method is specifically according to such as
Lower step carries out：
Alcohol compound shown in formula (I) is mixed with Metformin and is added in organic solvent, in metallic catalyst
Under effect, in the presence of alkaline matter, it is stirred to react at a temperature of 80~140 DEG C 5~30 hours, after reaction, obtains
Reaction solution, two amido-s- compound in triazine class shown in post-treated obtained formula (II)；Alcohols chemical combination shown in the formula (I)
The ratio between object and the amount of substance of Metformin, metallic catalyst, alkaline matter are 1：0.5~1.5：0.01~0.04：
1.0~3.0；The organic solvent is ethers；The metallic catalyst is ruthenium catalyst；
4. method as claimed in claim 3, it is characterised in that：The organic solvent is Isosorbide-5-Nitrae-dioxane, tetrahydrofuran
Or 2- methyltetrahydrofurans.
5. method as claimed in claim 3, it is characterised in that：The volumetric usage of the organic solvent is with shown in formula (I)
The amount of the substance of alcohol compound is calculated as 5~20mL/mmol.
6. method as claimed in claim 3, it is characterised in that：The metallic catalyst be three (triphenylphosphine) ruthenous chlorides,
Ten dicarbapentaborane rutheniums, two (triphenylphosphine) cyclopentadiene ruthenic chlorides, dichloro (p -Methylisopropylbenzene base) ruthenium dimer or ruthenium-oxide.
7. method as claimed in claim 3, it is characterised in that：The alkaline matter is potassium tert-butoxide, sodium methoxide, three second
Amine, sodium hydroxide or potassium hydroxide.
8. method as claimed in claim 3, it is characterised in that：The post-processing approach of the reaction solution is：After reaction, to
Add water in the reaction solution, be extracted with ethyl acetate, merge organic layer, dried with anhydrous sodium sulfate, filter, concentrates filtrate,
Through column chromatography for separation, with volume ratio for 100:1 dichloromethane and the mixed liquor of methanol are eluant, eluent, collect and contain target compound
Eluent, vacuum distillation, be dried to obtain two amido-s- compound in triazine class shown in target compounds of formula (II).
9. two amidos-s- compound in triazine class as described in claim 1 is preparing the application in treating antitumor drug.
10. application as claimed in claim 9, it is characterised in that：The tumour is human lung cancer.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293589A (en) * | 2018-11-22 | 2019-02-01 | 辽宁大学 | A kind of 6- Polyfluoroalkyl -1,3,5- compound in triazine class and its synthetic method and application |
| CN110272395A (en) * | 2019-07-12 | 2019-09-24 | 赣南师范大学 | A kind of method of the asymmetric polysubstituted amino -1,3,5- compound in triazine class of photocatalysis preparation |
| CN110407761A (en) * | 2019-06-28 | 2019-11-05 | 浙江工业大学 | A kind of polysubstituted heterocyclic nitrogen compound and the preparation method and application thereof |
| CN112194637A (en) * | 2020-09-15 | 2021-01-08 | 浙江工业大学 | Aromatic methylamine substituted nitrogen heterocyclic compound and preparation method and application thereof |
| CN113387984A (en) * | 2020-03-13 | 2021-09-14 | 九江学院 | Symmetric binuclear ruthenium complex containing deprotonated metformin ligand and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105384702A (en) * | 2015-12-11 | 2016-03-09 | 浙江大学 | Tri-substituted sym-triazine compound and preparation method thereof |
| CN105399695A (en) * | 2015-12-11 | 2016-03-16 | 浙江大学 | Triazine-kind compounds, preparation method and applications |
| CN105753801A (en) * | 2016-03-25 | 2016-07-13 | 浙江工业大学 | Preparation method of s-triazine compound |
| CN105820133A (en) * | 2016-03-25 | 2016-08-03 | 浙江工业大学 | Polysubstitution s-triazine compound and preparing method and application thereof |
-
2018
- 2018-06-29 CN CN201810701309.1A patent/CN108752284A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105384702A (en) * | 2015-12-11 | 2016-03-09 | 浙江大学 | Tri-substituted sym-triazine compound and preparation method thereof |
| CN105399695A (en) * | 2015-12-11 | 2016-03-16 | 浙江大学 | Triazine-kind compounds, preparation method and applications |
| CN105753801A (en) * | 2016-03-25 | 2016-07-13 | 浙江工业大学 | Preparation method of s-triazine compound |
| CN105820133A (en) * | 2016-03-25 | 2016-08-03 | 浙江工业大学 | Polysubstitution s-triazine compound and preparing method and application thereof |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293589A (en) * | 2018-11-22 | 2019-02-01 | 辽宁大学 | A kind of 6- Polyfluoroalkyl -1,3,5- compound in triazine class and its synthetic method and application |
| CN109293589B (en) * | 2018-11-22 | 2022-04-05 | 辽宁大学 | 6-polyfluoroalkyl-1, 3, 5-triazine compound and synthetic method and application thereof |
| CN110407761A (en) * | 2019-06-28 | 2019-11-05 | 浙江工业大学 | A kind of polysubstituted heterocyclic nitrogen compound and the preparation method and application thereof |
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| CN113387984B (en) * | 2020-03-13 | 2023-05-23 | 九江学院 | Symmetric binuclear ruthenium complex containing deprotonated metformin ligand, and preparation method and application thereof |
| CN112194637A (en) * | 2020-09-15 | 2021-01-08 | 浙江工业大学 | Aromatic methylamine substituted nitrogen heterocyclic compound and preparation method and application thereof |
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