CN110437167A - A kind of compound in triazine class and the preparation method and application thereof that aromatic ethylene base replaces - Google Patents

A kind of compound in triazine class and the preparation method and application thereof that aromatic ethylene base replaces Download PDF

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CN110437167A
CN110437167A CN201910574184.5A CN201910574184A CN110437167A CN 110437167 A CN110437167 A CN 110437167A CN 201910574184 A CN201910574184 A CN 201910574184A CN 110437167 A CN110437167 A CN 110437167A
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preparation
compound
triazine
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CN110437167B (en
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崔冬梅
苏承武
邵雷
潘泽西
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Zhejiang University of Technology ZJUT
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • 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 compound in triazine class that one kind aromatic ethylene base as shown in formula (III) replaces, preparation method are as follows: mix alcohol compound shown in triazine shown in formula (I), formula (II), metallic catalyst, alkaline matter, organic solvent, it is warming up to 90~120 DEG C and is stirred to react 5~30h, reaction solution is post-treated later, product shown in formula (III) is obtained, compound (III) can be used for synthesizing the polysubstituted Striazine derivative with antibacterial and anti-tumor biological；Preparation process reaction condition of the present invention is mild, and raw material is easy to get, easy to operate, at low cost, there is preferable prospects for commercial application；

Description

A kind of compound in triazine class and the preparation method and application thereof that aromatic ethylene base replaces
(1) technical field
The present invention relates to the compound in triazine class and the preparation method and application thereof that a kind of aromatic ethylene base replaces.
(2) background technique
Pyrrolotriazine derivatives have the multiple biological activities such as antibacterial, anti-inflammatory, anti-malarial, anticancer, it has also become medical personal One of hot spot of research.Compound in triazine class is replaced to pass through the substitution reaction of three chlorotriazines or mainly with dicyanodiamine and nitrile Close the methods of cyclization reaction preparation of object, but traditional preparation process have reaction raw materials toxicity it is high, it is unstable, not easy to maintain and The disadvantages of condition is harsh.Therefore, research replaces compound in triazine class preparation method to have important practical application value.
(3) summary of the invention
The purpose of the present invention is to provide the compound in triazine class and the preparation method and application thereof that a kind of aromatic ethylene base replaces.
Technical scheme is as follows:
The compound in triazine class that one kind aromatic ethylene base as shown in formula (III) replaces:
In formula (III),
R1For hydrogen or C8~C15 aralkyl, preferably hydrogen or benzyl；
R2、R3Respectively stand alone as C1~C10 alkyl or R3、R4N between the two combines to be formed containing N or containing N, O C4~C8 heterocycle；It is preferred that R3、R4Respectively stand alone as methyl or R3、R4N between the two combines to form piperidine ring or morpholine Ring；
R4For sulfur-bearing heteroaromatic, C5~C10 aryl or the C5~C10 aryl being substituted by one or more substituents, institute Stating substituent group is C1~C4 alkyl, C1~C4 alkoxy or halogen；It is preferred that R4Replace for thiophene, phenyl or by one or two The phenyl that base replaces, the substituent group are methyl, methoxyl group or chlorine.
The compound in triazine class that the aromatic ethylene base of the present invention as shown in formula (III) replaces the preparation method comprises the following steps:
Alcohol compound shown in triazine shown in formula (I), formula (II), metallic catalyst, alkaline matter, organic solvent is mixed It closes, is warming up to 90~120 DEG C (preferably 120 DEG C) and is stirred to react 5~30h (preferably 16h), reaction solution is post-treated later, obtains The compound in triazine class that aromatic ethylene base shown in formula (III) replaces；
Triazine shown in the formula (I), alcohol compound, metallic catalyst shown in formula (II), alkaline matter substance amount The ratio between be 1:0.5~4:0.01~0.05:1~3, preferably 1:2:0.02:1；
The volumetric usage of the organic solvent is calculated as 4~20mL/mmol, preferably 8 with the amount of the substance of triazine shown in formula (I) ~10mL/mmol；
The metallic catalyst is metal Ru catalyst, such as: ruthenic oxide or ruthenium trichloride, preferably ruthenium trichloride；
The alkaline matter is organic base, preferably potassium tert-butoxide；
The organic solvent is ethers or aromatic hydrocarbons, preferably Isosorbide-5-Nitrae-dioxane or toluene；
The method of the post-processing are as follows: after reaction, be cooled to room temperature (20~30 DEG C) to reaction solution, methanol is added (solubilized target product), filtering carry out column chromatography for separation after taking filtrate to be concentrated, with ethyl acetate/petroleum ether volume ratio 1:10's Mixed liquor is eluant, eluent, collects the eluent containing target compound, solvent and drying is evaporated off, obtains product shown in formula (III)；
In formula (I) or (II), R1、R2、R3、R4Definition it is identical with formula (III).
The compound in triazine class (III) that aromatic ethylene base of the present invention replaces under Pd carbon and hydrogen effect, by debenzylation and Double bond reduction reaction can synthesize the polysubstituted Striazine derivative (IV) (equal three with antibacterial and the bioactivity such as antitumor The relevant biological activity data of oxazine derivatives can be found in Org.Biomol.Chem., and 2018,16,6140-6145, CN201810701310.4, CN201810701309.1, CN201810700670.2), therefore aromatic ethylene base of the present invention substitution Compound in triazine class (III) can be used as the important intermediate of a variety of biologically active substances, have a wide range of applications.
In formula (IV), R2、R3、R4Definition it is identical with formula (III).
Compared with prior art, the beneficial effects of the present invention are three that: the present invention develops that a kind of aromatic ethylene base replaces Piperazine class compound and the preparation method and application thereof, preparation process reaction condition of the present invention is mild, and raw material is easy to get, easy to operate, at This is low, there is preferable prospects for commercial application.
(4) specific embodiment
Below by specific embodiment, the present invention is further illustrated, but protection scope of the present invention is not limited in This.
Embodiment 1: the preparation of compound (III-1)
In the reaction vessel plus N2Benzyl-N4,N4, 6- trimethyl -1,3,5-triazines (60.8mg, 0.250mmol), benzylalcohol (63.7mg, 0.50mmol), ruthenium trichloride (1.9mg, 0.005mmol), potassium tert-butoxide (28.0mg, 0.25mmol), in Isosorbide-5-Nitrae- It mixes in dioxane (2mL), is stirred to react 16 hours in 120 DEG C of oil baths；After reaction, add methanol, filter, concentration filter Liquid, column chromatograph (ethyl acetate: petroleum ether=1:10), collect RfThe eluent of value 0.3~0.35, vacuum distillation, is dried to obtain Target compound (III-1), 63.7mg, yield 77%.
1H NMR(500MHz,CDCl3) δ 7.95 (d, J=15.4Hz, 1H), 7.59 (d, J=6.0Hz, 2H), 7.44- 7.32 (m, 7H), 7.30-7.21 (m, 1H), 6.84 (d, J=15.4Hz, 1H), 5.73 (br, 1H), 4.84-4.59 (m, 2H), 3.25(s,3H),3.17(s,3H)。
Embodiment 2:
Ruthenium trichloride is changed to three (triphenylphosphine) ruthenous chlorides (5.2mg, 0.005mmol), other operate same embodiment 1, reaction does not obtain target product.
Embodiment 3:
Ruthenium trichloride is changed to ruthenic oxide (1.5mg, 0.005mmol), other operations obtain targeted with embodiment 1 Close object 18.8mg, yield 23%.
Embodiment 4:
The amount of benzylalcohol is changed to (108.2mg, 1.00mmol), other operations obtain target compound with embodiment 1 42.8mg, yield 50%.
Embodiment 5:
Time 30h will be extended to, other operations obtain target compound 62.4mg, yield 75% with embodiment 1.
Embodiment 6:
The amount of benzylalcohol is changed to (28.6mg, 0.25mmol), other operations obtain target compound with embodiment 1 26.9mg, yield 33%.
Embodiment 7:
The amount of ruthenium trichloride is changed to (1mg, 0.0025mmol), the amount of solvent is changed to 1mL, other are operated with embodiment 1, Obtain target compound 4.8mg, yield 6%.
Embodiment 8:
The amount of ruthenium trichloride is changed to (4.8mg, 0.0125mmol), other operations obtain target compound with embodiment 1 53.8mg, yield 65%.
Embodiment 9:
Dioxane solvent is changed to toluene (5mL), other operations obtain target compound 28.1mg with embodiment 1, receive Rate is 34%.
Embodiment 10:
90 DEG C are cooled the temperature to, other operations obtain target compound 4.3mg, yield 5% with embodiment 1.
Embodiment 11:
The amount of potassium tert-butoxide is changed to (84mg, 0.75mmol), other operations obtain target compound with embodiment 1 51.6mg, yield 60%.
Embodiment 12: the preparation of compound (III-2)
Operation only changes benzylalcohol into 2,3- dimethoxy-benzyl alcohol (84.7mg, 0.50mmol) with embodiment 1, and mesh is made It marks compound (III-2), 40.4mg, yield 41%.
1H NMR(500MHz,CDCl3) δ 8.26 (d, J=15.7Hz, 1H), 7.38 (d, J=7.5Hz, 2H), 7.34 (t, J =7.5Hz, 2H), 7.31-7.23 (m, 2H), 7.06 (t, J=8.0Hz, 1H), 6.90 (dd, J=8.0,1.2Hz, 1H), 6.86 (d, J=15.7Hz, 1H), 5.56 (br, 1H), 4.78-4.60 (m, 2H), 3.89 (s, 3H), 3.88 (s, 3H), 3.25 (s, 3H),3.16(s,3H)。
Embodiment 13: the preparation of compound (III-3)
Operation only changes benzylalcohol into 4- xylyl alcohol (61.8mg, 0.50mmol) with embodiment 1, and target chemical combination is made Object (III-3), 60.0mg, yield 70%.
1H NMR(500MHz,CDCl3) δ 7.93 (d, J=15.5Hz, 1H), 7.48 (d, J=7.8Hz, 2H), 7.38 (d, J =7.0Hz, 2H), 7.34 (t, J=7.0Hz, 2H), 7.31-7.25 (m, 1H), 7.19 (d, J=7.8Hz, 2H), 6.80 (d, J =15.5Hz, 1H), 5.73 (br, 1H), 4.85-4.56 (m, 2H), 3.25 (s, 3H), 3.16 (s, 3H), 2.38 (s, 3H).
Embodiment 14: the preparation of compound (III-4)
Operation only changes benzylalcohol into 3- xylyl alcohol (61.8mg, 0.50mmol) with embodiment 1, and target chemical combination is made Object (III-4), 62.8mg, yield 73%.
1H NMR(500MHz,CDCl3) δ 7.90 (d, J=15.4Hz, 1H), 7.43-7.34 (m, 4H), 7.32 (t, J= 7.7Hz, 2H), 7.27-7.22 (m, 2H), 7.13 (d, J=7.5Hz, 1H), 6.81 (d, J=15.4Hz, 1H), 5.54 (br, 1H),4.85-4.56(m,2H),3.22(s,3H),3.14(s,3H),2.36(s,3H)。
Embodiment 15: the preparation of compound (III-5)
Operation only changes benzylalcohol into 4- methoxyl group benzylalcohol (70.3mg, 0.50mmol) with embodiment 1, and targeted is made It closes object (III-5), 72.2mg, yield 80%.
1H NMR(500MHz,CDCl3) δ 7.91 (d, J=15.2Hz, 1H), 7.54 (d, J=8.5Hz, 2H), 7.38 (d, J =7.5Hz, 2H), 7.34 (t, J=7.5Hz, 2H), 7.30-7.24 (m, 1H), 6.91 (d, J=8.5Hz, 2H), 6.72 (d, J =15.2Hz, 1H), 5.49 (br, 1H), 4.85-4.55 (m, 2H), 3.85 (s, 3H), 3.23 (s, 3H), 3.17 (s, 3H).
Embodiment 16: the preparation of compound (III-6)
Operation only changes benzylalcohol into 3- methoxyl group benzylalcohol (69.6mg, 0.50mmol) with embodiment 1, and targeted is made It closes object (III-6), 75.8mg, yield 85%.
1H NMR(500MHz,CDCl3) δ 7.92 (d, J=15.2Hz, 1H), 7.43-7.31 (m, 4H), 7.31-7.25 (m, 2H), 7.18 (d, J=7.4Hz, 1H), 7.16-7.11 (m, 1H), 6.91-6.87 (m, 1H), 6.83 (d, J=15.2Hz, 1H), 5.58(br,1H),4.87-4.54(m,2H),3.85(s,3H),3.24(s,3H),3.17(s,3H)。
Embodiment 17: the preparation of compound (III-7)
Operation only changes benzylalcohol into 2- methoxyl group benzylalcohol (103.8mg, 0.75mmol) with embodiment 1, and targeted is made It closes object (III-7), 84.2mg, yield 93%.
1H NMR(500MHz,CDCl3) δ 8.28 (d, J=15.0Hz, 1H), 7.63 (d, J=7.2Hz, 1H), 7.42- 7.35 (m, 2H), 7.34 (t, J=7.3Hz, 2H), 7.31-7.25 (m, 2H), 6.97 (t, J=7.2Hz, 1H), 6.92 (d, J= 8.2Hz, 1H), 6.87 (d, J=15.0Hz, 1H), 5.53 (br, 1H), 4.78-4.60 (m, 2H), 3.90 (s, 3H), 3.25 (s, 3H),3.17(s,3H)。
Embodiment 18: the preparation of compound (III-8)
Operation only changes benzylalcohol into 4- chlorobenzyl alcohol (106.6mg, 0.75mmol) with embodiment 1, and target compound is made (III-8), 47.8mg, yield 52%.
1H NMR(500MHz,CDCl3) δ 7.88 (d, J=15.2Hz, 1H), 7.50 (d, J=6.7Hz, 2H), 7.41- 7.31 (m, 6H), 7.30-7.25 (m, 1H), 6.80 (d, J=15.2Hz, 1H), 5.65 (br, 1H), 4.87-4.51 (m, 2H), 3.24(s,3H),3.16(s,3H)。
Embodiment 19: the preparation of compound (III-9)
Operation only changes benzylalcohol into 3- chlorobenzyl alcohol (106.6mg, 0.75mmol) with embodiment 1, and target compound is made (III-9), 34.1mg, yield 37%.
1H NMR(500MHz,CDCl3) δ 7.85 (d, J=15.3Hz, 1H), 7.57 (s, 1H), 7.50-7.42 (m, 1H), 7.40-7.32 (m, 4H), 7.31-7.29 (m, 2H), 7.28-7.26 (m, 1H), 6.82 (d, J=15.3Hz, 1H), 5.52 (br, 1H),4.70-4.53(m,2H),3.24(s,3H),3.16(s,3H)。
Embodiment 20: the preparation of compound (III-10)
Operation only changes benzylalcohol into 2- thenyl alcohol (78.0mg, 0.75mmol) with embodiment 1, and target chemical combination is made Object (III-10), 30.5mg, yield 36%.
1H NMR(600MHz,CDCl3) δ 8.03 (d, J=13.5Hz, 1H), 7.38-7.31 (m, 4H), 7.29 (d, J= 5.0Hz, 1H), 7.28-7.24 (m, 1H), 7.21 (d, J=3.7Hz, 1H), 7.03 (dd, J=5.0,3.7Hz, 1H), 6.64 (d, J=13.5Hz, 1H), 5.41 (br, 1H), 4.80-4.57 (m, 2H), 3.22 (s, 3H), 3.15 (s, 3H).
Embodiment 21: the preparation of compound (III-11)
Operation is with embodiment 1, only by N2Benzyl-N4,N4, 6- trimethyl -1,3,5- triazine changes N into2,N2Dibenzyl- N2,N2, 6- trimethyl -1,3,5-triazines (84.0mg, 0.25mmol), obtained target compound (III-11), 60.1mg, yield It is 57%.
1H NMR(500MHz,CDCl3) δ 7.98 (d, J=15.9Hz, 1H), 7.38 (t, J=7.4Hz, 2H), 7.35- 7.26 (m, 11H), 6.92 (d, J=15.9Hz, 1H), 4.95 (s, 2H), 4.82 (s, 2H), 3.25 (s, 3H), 3.15 (s, 3H).
Embodiment 22: the preparation of compound (III-12)
Operation is with embodiment 1, only by N2Benzyl-N4,N4, 6- trimethyl -1,3,5- triazine changes N into2Benzyl -4- piperazine Pyridine -6- methyl-1,3,5- triazines (69.5mg, 0.25mmol) are made target compound (III-12), 61.2mg, and yield is 67%.
1H NMR(500MHz,CDCl3) δ 7.93 (d, J=14.7Hz, 1H), 7.59 (d, J=7.2Hz, 2H), 7.43- 7.31 (m, 7H), 7.30-7.25 (m, 1H), 6.84 (d, J=14.7Hz, 1H), 5.57 (br, 1H), 4.82-4.50 (m, 2H), 4.02-3.71(m,4H),1.73-1.66(m,2H),1.65-1.54(m,4H)。
Embodiment 23: the preparation of compound (III-13)
Operation is with embodiment 1, only by N2Benzyl-N4,N4, 6- trimethyl -1,3,5- triazine changes N into2Benzyl -4- Quinoline -6- methyl-1,3,5- triazines (69.5mg, 0.25mmol) are made target compound (III-13), 61.2mg, and yield is 67%.
1H NMR(500MHz,CDCl3) δ 7.93 (d, J=15.6Hz, 1H), 7.64-7.55 (m, 2H), 7.42-7.32 (m, 7H), 7.31-7.26 (m, 1H), 6.82 (d, J=15.6Hz, 1H), 5.69 (br, 1H), 4.82-4.54 (m, 2H), 4.00- 3.80(m,4H),3.81-3.66(m,4H)。
Embodiment 24: the preparation of compound (IV)
1 gained compound (III) (1mmol) of embodiment and 10% palladium carbon (300mg) are added in 10mL methanol, in hydrogen Under the conditions of back flow reaction be down to room temperature until the reaction is complete, filter, concentration, target compound is obtained by column chromatography for separation (IV)。

Claims (10)

1. a kind of compound in triazine class that the aromatic ethylene base as shown in formula (III) replaces:
In formula (III),
R1For hydrogen or C8~C15 aralkyl；
R2、R3Respectively stand alone as C1~C10 alkyl or R3、R4N between the two combines to be formed containing N or containing C4~C8 of N, O Heterocycle；
R4For sulfur-bearing heteroaromatic, C5~C10 aryl or the C5~C10 aryl being substituted by one or more substituents, the substitution Base is C1~C4 alkyl, C1~C4 alkoxy or halogen.
2. the preparation method for the compound in triazine class that aromatic ethylene base shown in formula (III) as described in claim 1 replaces, feature It is, the preparation method is that:
Alcohol compound shown in triazine shown in formula (I), formula (II), metallic catalyst, alkaline matter, organic solvent are mixed, risen Temperature is stirred to react 5~30h to 90~120 DEG C, and reaction solution is post-treated later, obtains the substitution of aromatic ethylene base shown in formula (III) Compound in triazine class；
The ratio between triazine shown in the formula (I), alcohol compound, metallic catalyst, the amount of substance of alkaline matter shown in formula (II) For 1:0.5~4:0.01~0.05:1~3；
The metallic catalyst is metal Ru catalyst；
The alkaline matter is organic base；
The organic solvent is ethers or aromatic hydrocarbons；
In formula (I) or (II), R1、R2、R3、R4Definition it is identical with formula (III).
3. preparation method as claimed in claim 2, which is characterized in that reaction temperature is 120 DEG C.
4. preparation method as claimed in claim 2, which is characterized in that reaction time 16h.
5. preparation method as claimed in claim 2, which is characterized in that triazine shown in the formula (I), alcohols shown in formula (II) Closing the ratio between amount of substance of object, metallic catalyst, alkaline matter is 1:2:0.02:1.
6. preparation method as claimed in claim 2, which is characterized in that the volumetric usage of the organic solvent is shown in formula (I) The amount of the substance of triazine is calculated as 4~20mL/mmol.
7. preparation method as claimed in claim 2, which is characterized in that the metallic catalyst is ruthenic oxide or tri-chlorination Ruthenium.
8. preparation method as claimed in claim 2, which is characterized in that the alkaline matter is potassium tert-butoxide.
9. preparation method as claimed in claim 2, which is characterized in that the organic solvent is Isosorbide-5-Nitrae-dioxane or toluene.
10. aromatic ethylene base shown in formula (III) as described in claim 1 replace compound in triazine class synthesis have antibacterial and Application in the polysubstituted Striazine derivative (IV) of anti-tumor biological, the synthetic method are as follows: aromatic ethylene base replaces Compound in triazine class (III) Pd carbon and hydrogen effect under, by debenzylation and double bond reduction reaction, obtain polysubstituted equal three Oxazine derivatives (IV)；
In formula (IV), R2、R3、R4Definition it is identical with formula (III).
CN201910574184.5A 2019-06-28 2019-06-28 Aromatic vinyl substituted triazine compound and preparation method and application thereof Active CN110437167B (en)

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