CN111454226B - Method for synthesizing 2,4, 6-trisubstituted 1,3,5-triazine compound by aromatic aldehyde and ammonium iodide - Google Patents

Method for synthesizing 2,4, 6-trisubstituted 1,3,5-triazine compound by aromatic aldehyde and ammonium iodide Download PDF

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CN111454226B
CN111454226B CN202010438414.8A CN202010438414A CN111454226B CN 111454226 B CN111454226 B CN 111454226B CN 202010438414 A CN202010438414 A CN 202010438414A CN 111454226 B CN111454226 B CN 111454226B
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刘强
肖江
郭欣
郭灿城
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Yuanjiang Hualong Catalyst Technology Co ltd
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    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
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Abstract

The invention discloses a method for synthesizing a 2,4, 6-trisubstituted 1,3,5-triazine compound by aromatic aldehyde and ammonium iodide, belonging to the field of organic synthesis. The method comprises the step of carrying out one-pot reaction on aromatic aldehyde and ammonium iodide under the catalysis of ferric salt to obtain the 2,4, 6-trisubstituted 1,3,5-triazine compound. The method adopts micromolecular aryl aldehyde raw materials and an iron salt catalyst, has low cost and mild reaction conditions, can obtain the symmetrical 2,4, 6-trisubstituted 1,3,5-triazine compounds with high selectivity, and provides a brand new synthesis idea for the construction of triazine rings.

Description

Method for synthesizing 2,4, 6-trisubstituted 1,3,5-triazine compound by aromatic aldehyde and ammonium iodide
Technical Field
The invention relates to a synthesis method of a 1,3,5-triazine compound, in particular to a method for obtaining a 2,4, 6-trisubstituted 1,3,5-triazine compound with a symmetrical structure by utilizing the one-step reaction of aromatic aldehyde and ammonium iodide micromolecules under the catalysis of trivalent ferric salt, belonging to the technical field of organic synthesis.
Background
The nitrogen heterocyclic compound is one of important structural units universally existing in a plurality of natural products, synthetic drugs and advanced functional materials, and is also an important organic synthesis intermediate. The 1,3,5-triazine compound in the nitrogen heterocyclic compound is widely applied to liquid crystal, transition metal catalysts, supermolecules, reactive dyes, organic light-emitting diodes, selective conversion reagents and the like, and has very important position.
In the prior art, methods for synthesizing 1,3,5-triazine compounds generally include cyclization of nitrile and amidine compounds under the catalytic action, coupling of halogenated compounds and boric acid or organometallic compounds, and the like. In recent years, the construction of C ═ N bonds by transition metal or metal-free catalysis has become an important method for the construction of complex nitrogen-containing compounds, which not only improves the atom utilization rate, but also improves the energy efficiency. These methods mainly use nitriles, benzamidine derivatives, benzamidine hydrochloride, amides, and the like as nitrogen sources to synthesize 1,3,5-triazine compounds, as follows:
1) the newly reported method for synthesizing the 1,3,5-triazine compound by using the nitrile compound as a nitrogen-containing source comprises the following steps: in 2017, (Bai J, Wang P, Cao W, et al, tau-selective derivatives of enolate, ketone and amine by addition reaction of pigment-type associations with nitriles [ J ]. Journal of Molecular Structure,2017,1128(645-52.) reported a reaction method for synthesizing 1,3,5-triazine compounds using butyl lithium as a catalyst, in which not all nitrogen sources were from nitriles but one was from pyridine, the substrate range of the method was very limited, and only a few substrates were reacted to obtain 1,3,5-triazine compounds.
Figure BDA0002503169230000011
2) The most recently reported method for synthesizing 1,3,5-triazine compounds using amidine salts as nitrogen-containing sources: 2019, (Zhang Y, Liu Y, Zhang J, et al. An alternativelymethyl-free Synthesis of 1,3,5-triazines or 1,2,4-thiadiazoles from benzyl chlorides and benzylamines mediated by elementary sulphur, J]Tetrahedron Letters,2019,60(49)) report by S8Dehydrogenation and coupling of the system, then successfully obtaining an imine intermediate, continuing to react with one molecule of benzamidine to close the ring, and oxidizing to obtain the 1, 35-triazine compound, wherein the reaction route is as follows. The method takes the benzyl chloride and the benzamidine hydrochloride as substrates, has simple conditions, can avoid the use of metal catalysts and ligands, and provides a new feasible method for synthesizing other N-containing heterocyclic compounds.
Figure BDA0002503169230000021
3) The newly reported method for synthesizing the 1,3,5-triazine compound by using benzamidine and derivatives thereof as nitrogen sources comprises the following steps: 2019, (Shen J, Meng X.base-free Synthesis of 1,3,5-triazine via aerobic oxidation of alcohols and benzamidine over a recyclable OMS-2catalyst [ J]Catalysis Communications,2019,127(58-63).)2SO4·2H2O2NaCl is used as a reducing agent to prepare manganese oxide octahedral molecular sieve (OMS-2), and the aerobic oxidation of OMS-2 to benzyl alcohol and benzamidine to synthesize 1,3,5-triazine has excellent catalytic capability, and the reaction route is as follows. The method has the advantages of wide substrate range, high chemical selectivity, simple operation, recoverable catalyst and O2The green oxidant is characterized by being used as a green oxidant.
Figure BDA0002503169230000022
4) The newly reported method for constructing the triazine compound by utilizing the organic small molecule as the C1 base comprises the following steps: 2019, (Yan Y, Cui C, Wang J, et al. transition metal-free C-F/C-Cl/C-C clean of ClCF2COONa for the synthesis of heterocycles [ J]Org Biomol Chem,2019,17(35):8071-4.) proposes the use of small molecules (ClCF)2COONa) as a carbon source, reacting with aromatic amidine hydrochloride to construct a C ═ N bond, and synthesizing the ═ azacyclic compound, specifically adopting the following reaction route. The method realizes a substrate with two nitrogen nucleophilic sites and ClCF2COONa can synthesize a series of 1,3,5-triazine and quinazolinone under the conditions of no transition metal and no external oxidant, and the yield is up to 96%. The process avoids the use of transition metals and oxidants and produces inorganic waste of low toxicity.
Figure BDA0002503169230000023
In the same year, (Yu X, Zhou Y, Ma X, et al. transition metal-free assembly of 1,3,5-triazine using ethyl bromodifuoroacetate as C1 source [ J ]. Chem Commun (Camb),2019,55(56):8079-82.) bromodifluoroacetate was developed as a carbon source for the synthesis of 1,3,5-triazine compounds with aromatic amidines, in particular the following synthetic route. The method does not need a metal catalyst and an oxidant, is simpler to operate, and only generates low-toxicity inorganic waste in the reaction.
Figure BDA0002503169230000031
5) The most recently reported method for the coupled synthesis of 1,3,5-triazine compounds of the Suzuki-Miyaura type: in 2019, (Chen T, Li W-Q, Hu W-B, et al direct synthesis of synergistic triazine-based Structures (CTFs) through aromatic nuclear catalysis reactions [ J ]. RSC Advances,2019,9(31):18008-12.) reported the use of organometallic lithium and halotriazine compounds to couple and obtain frameworks of various triazine compounds. The method can be carried out at room temperature, does not need any catalyst, only needs to be refluxed in toluene, and has simple operation and mild condition. However, the method can only synthesize some triazine large frameworks, has no effect on some triazine compounds with small molecules, and simultaneously, organic metal lithium is not easy to obtain, thereby increasing the difficulty for the application of the method.
Figure BDA0002503169230000032
In the same year, (Niakan M, Asadi Z, Masteri-Farahani M.Encapsulated of a Palladium Schiff-Base Complex inter the Nanocages of Mesoporous SBA-16as an effective hetereogenous catalysts Catalyst for the synthesis of 1,3,5-triazine compounds with phenyl boronic acid using a Palladium Schiff Base Complex to catalyze the Reaction of a variety of aryl halides with aryl boronic acids under mild aqueous conditions to give aryl substituted 1,3,5-triazine compounds is reported, in particular, the following Reaction scheme.
Figure BDA0002503169230000033
6) The newly reported methods for the synthesis of 1,3,5-triazine compounds by oxidation or ring closure reactions: in 2013, (ZHao F, ZHan M, ZHang W-X, et al DFT students on the Reaction Mechanisms of 1,4-Dilithio 1,3-Dienes with Nitriles [ J ]. Organometallics,2013,32(7):2059-68.) reported the Reaction of organometallic lithium with nitrile followed by the removal of the organometallic lithium to synthesize 1,3,5-triazine compounds, as shown in the following Reaction scheme. The method has mild reaction conditions, can also synthesize other nitrogen-containing heterocyclic compounds, but is difficult to obtain the required target 1,3,5-triazine compounds in a targeted manner.
Figure BDA0002503169230000041
In the methods reported in the prior art, mainly nitrile or amidine compounds are used as single nitrogen-containing sources, cyclization is carried out under the action of a catalyst, and halogenated compounds and boric acid or organic metal compounds are coupled. However, most of these methods are complicated to operate, have severe reaction conditions and are expensive in materials.
Disclosure of Invention
Aiming at the defects of the triazine compound synthesis method in the prior art, the invention aims to provide the method for synthesizing the symmetrical 2,4, 6-trisubstituted 1,3,5-triazine compound by catalyzing aromatic aldehyde and ammonium iodide to react by ferric iron in one pot, the method has the advantages of low cost of raw materials and catalysts, mild reaction conditions and high selectivity, and the symmetrical 2,4, 6-trisubstituted 1,3,5-triazine compound can be obtained.
In order to realize the technical purpose, the invention provides a method for synthesizing a 2,4, 6-trisubstituted 1,3,5-triazine compound by aromatic aldehyde and ammonium iodide, which comprises the steps of carrying out one-pot reaction on the aromatic aldehyde and the ammonium iodide under the catalysis of ferric salt to obtain the 2,4, 6-trisubstituted 1,3,5-triazine compound;
the aromatic aldehyde has the structure of formula 1:
Ar-CHO
formula 1
The 2,4, 6-trisubstituted 1,3,5-triazine compound has the structure of formula 2:
Figure BDA0002503169230000042
wherein the content of the first and second substances,
ar is aryl or aromatic heterocyclic radical.
As a preferred scheme, Ar is a common aromatic group, and different 1,3,5-triazine compounds can be obtained by adopting different aromatic groups. Ar can be aryl or aromatic heterocyclic group, and the aryl can be selected from phenyl or substituted phenyl; the substituted phenyl group is generally a phenyl group having 1 to 2 substituents, and the position of the substituent on the phenyl ring is not limited, and preferably, the substituent is a para-position. The substituents being conventional organic radicals, e.g. C1～C5Alkyl of (C)1～C5Alkoxy, halogen substituent or trifluoromethyl. In general, the alkyl group may be a straight chain alkyl group or a branched chain alkyl group, preferably a straight chain alkyl group such as methyl, ethyl, propyl, and the like. The alkoxy group is mainly an alkoxy group containing a straight chain alkyl group such as methoxy group, ethoxy group and the like. Halogen substituents are often fluorine substituents or chlorine substituents. The aromatic heterocyclic group is mainly a five-membered aromatic heterocyclic group, such as thienyl, furyl or pyrrolyl. When Ar is a selectively substituted phenyl group, the position of the substituent on the phenyl ring has an influence on the reaction, and the yield of the target product finally obtained is high for a substrate having substituents at the para-position and the meta-position relative to a substrate having the same substituent at the ortho-position, probably because the steric hindrance of the substrate having substituents at the para-position and the meta-position is small relative to that of the substrate having substituents at the ortho-position. In addition, the reaction has good reactivity to various functional group substituents, including halogen, methoxy, ethoxy, trifluoromethyl and other substituents. Wherein, the yield of the target product is not greatly different between the substrate with electron withdrawing groups such as halogen, trifluoromethyl and the like and the substrate with electron donating groups such as methyl, methoxy and the like, which indicates that the substituent groupThe electron effect of (a) does not have a great influence on the applicability of aromatic aldehyde substrates. Meanwhile, when benzaldehyde containing one methyl group, two methyl groups and three methyl groups is used for reaction, the influence of steric hindrance on the reaction is relatively large. The product yields were 69%, 41%, and 0%, respectively. For heterocyclic aldehyde compounds, such as 2-thiophenecarboxaldehyde and 3-thiophenecarboxaldehyde, better conversion can be realized under the system, and the yield of the product is respectively 64 percent and 65 percent. However, pyridine aldehyde compounds such as 4-pyridinecarboxaldehyde, 2-pyridinecarboxaldehyde and 3-pyridinecarboxaldehyde are difficult to react in the system, and the reaction yield is low (<5%). Condensed ring aldehydes and other aldehyde compounds with larger steric hindrance basically do not react, but fatty aldehydes can react better under the system but are difficult to separate.
In a preferred embodiment, the amount of ammonium iodide is 0.8 to 1.2 times the molar amount of the aromatic aldehyde, and in a most preferred embodiment, the ammonium iodide is reacted with the aromatic aldehyde in an equimolar amount.
Preferably, the amount of the ferric salt is 10-30% of the molar amount of the aromatic aldehyde. In a more preferable scheme, the dosage of the ferric iron salt is 15-25% of the molar weight of the aromatic aldehyde.
In a preferred embodiment, the ferric salt is at least one of ferric chloride, ferric bromide and ferric sulfate. The ferric salt mainly plays a role in active catalysis and is ferric ion, so compounds capable of ionizing the ferric ion are theoretically suitable for the technical scheme of the invention, and the most preferable ferric salt is ferric chloride.
As a preferred embodiment, the one-pot reaction is carried out in a benzene-based solvent. The benzene solvent is chlorobenzene and/or toluene. Toluene is most preferred.
As a preferred scheme, the one-pot reaction conditions are as follows: reacting for 14-18 hours at 130-150 ℃ in an oxygen-containing atmosphere.
As a preferred embodiment, the oxygen-containing atmosphere is oxygen or air. If the reaction is carried out in an oxygen-free atmosphere, the reaction is difficult to proceed smoothly. It is therefore particularly suitable for carrying out the reaction in conventional open systems.
The reaction mechanism of the invention for synthesizing the 2,4, 6-trisubstituted-1, 3,5-triazine compound by the aromatic aldehyde and the ammonium iodide is as follows: wherein R is aryl or arylheterocyclyl;
Figure BDA0002503169230000061
in the reaction formula, in the first step of reaction, the aromatic aldehyde raw material 1 and ammonium iodide undergo a nucleophilic addition reaction to generate an intermediate A, H is removed from the intermediate A under the action of iodide ions to generate an intermediate B, meanwhile, the iodide ions lose electrons under the oxidation action of ferric ions to obtain iodine simple substances and ferrous ions and undergo redox cycling, then lone pair electrons on nitrogen of the generated intermediate A attack carbon atoms on imine on the intermediate B to obtain an intermediate C, finally, the intermediate C is attacked by the intermediate A again to obtain an intermediate D, the intermediate D undergoes self-cyclization to obtain an intermediate E, and the intermediate E finally obtains a target product 2 under the action of oxygen.
Compared with the prior art, the technical scheme of the invention has the following beneficial technical effects:
the technical scheme of the invention adopts the micromolecular aldehyde compound as a carbon source and the inorganic ammonium salt as a nitrogen source, and has the advantages of wide raw material source and low cost;
according to the technical scheme, a pollution-free transition metal is not required to be used as a catalyst, and a pollution-free iron salt with low cost is used as a catalyst;
the technical scheme of the invention has mild reaction conditions, can obtain the target product by one-pot reaction in one step, has simple steps and operation, and is beneficial to expanding production;
the technical scheme of the invention has high reaction selectivity and relatively high yield of target products;
the technical scheme of the invention has wide adaptability to substrates, and can obtain corresponding symmetrical 2,4, 6-trisubstituted 1,3,5-triazine compounds through different substituted aromatic aldehydes.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of compound 2,4,6-triphenyl-1,3, 5-triazine;
FIG. 2 is a nuclear magnetic carbon spectrum of compound 2,4,6-triphenyl-1,3, 5-triazine;
FIG. 3 is a nuclear magnetic hydrogen spectrum of the compound 2,4,6-tri (thiophen-2-yl) -1,3, 5-triazine;
FIG. 4 is a nuclear magnetic carbon spectrum of the compound 2,4,6-tri (thiophen-2-yl) -1,3, 5-triazine.
Detailed Description
The following examples are intended to further illustrate the present disclosure, but not to limit the scope of the claims.
Condition-optimized reaction experiments:
taking benzaldehyde and ammonium iodide as reaction substrates as examples, various conditions (type and amount of catalyst, type of inorganic ammonium salt, oxidizing agent, reaction solvent, reaction temperature, reaction time, etc.) were systematically screened.
1. Optimizing the catalyst:
the experimental group mainly studied the influence of the kind of catalyst on the reaction of benzaldehyde and ammonium iodide. The results are shown in Table 1. Wherein, the ferric salt shows better catalytic effect, and the copper salt, the ferric salt and the cobalt salt can promote the reaction. However, when DMSO or other non-metallic oxidant is used as the catalyst, the reaction yield is low. Wherein, selecting FeCl3As a catalyst, the yield is highest (72%), so FeCl3Is the best catalyst.
Figure BDA0002503169230000071
TABLE 1 Effect of different catalysts on the reaction
Figure BDA0002503169230000072
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5mmol), catalyst (0.1mmol), toluene (2mL), 130 ℃ and air atmosphere for 15 hours.
2. Optimizing the using amount of the catalyst:
in the determination of FeCl3After optimizing the catalyst, the influence of the amount of the catalyst on the reaction yield was further screened. The results are shown in Table 2. As can be seen from Table 2, when the amount of the catalyst was increased gradually from 0% to 20%, the yield of the target molecule was increased, and when the amount of the catalyst was increased further to 30%, the yield of the product was decreased. Thus, FeCl3When the dosage of the catalyst reaches 20 percent, the catalytic effect on the reaction is optimal.
Figure BDA0002503169230000081
TABLE 2 influence of the amount of catalyst used on the experiment
Figure BDA0002503169230000082
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5mmol), FeCl3(X mmol%), toluene (2mL), 130 ℃, under an atmosphere of air for 15 h.
3. Optimizing the type of inorganic ammonium salt:
this set of experiments was performed in a series of studies on the selection of the type of inorganic ammonium salt, and the results are shown in table 3. From table 3 it can be concluded that: the reaction did not proceed in the absence of iodide ion, but most of the inorganic ammonium salt reacted when iodide ion (0.5equiv) was added. When inorganic ammonium salts such as: NH (NH)4Cl、NH4Br、NH4SCN、CH3COONH4The reaction can all occur, but the reaction yield is obviously different. Wherein NH4The yield of I is highest.
Figure BDA0002503169230000083
TABLE 3 influence of the type of inorganic ammonium salt on the reaction
Figure BDA0002503169230000084
Figure BDA0002503169230000091
aThe reaction conditions were benzaldehyde (0.5mmol), inorganic ammonium salt (0.5mmol), FeCl3(0.1mmol), toluene (2mL), 130 ℃ under an oxygen atmosphere for 15 h.
In addition, organic amine (such as methylamine, ethylamine and triethylamine) does not react under the system.
4. Optimization of reaction solvent:
the set of experiments was studied on the influence of the reaction solvent on the target product and its yield, from which the optimum solvent for the reaction was selected, and the results are shown in table 4. When using CH3When CN, DMF, DMSO, 1, 2-dichloroethane are used as solvents, the reaction can not occur, when toluene and chlorobenzene are used as solvents, the reaction can occur, the reaction yield is 72 percent and 62 percent respectively, and comparison shows that the best reaction effect is achieved when toluene is used as the solvent. Toluene is used as the best solvent for the reaction.
Figure BDA0002503169230000092
TABLE 4 Effect of solvent on the reaction
Figure BDA0002503169230000093
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5mmol), FeCl3(0.1mmol), solvent (2mL), 130 ℃ under an oxygen atmosphere for 15 h.
5. Influence of the gas atmosphere on the reaction:
the experimental group systematically investigated the effect of gas atmosphere on the reaction, and the results are shown in table 5. As can be seen from the table, the yield of the product in the reaction system is dependent on O2The content is increased and then is basically kept unchanged. When using N2As an atmosphere condition for the reaction, the reaction occurs but the yield is low; when the reaction is in an air atmosphere and completely in O2The yield of the atmosphere remained essentially the same (72%). Thus, an air atmosphere was selected as the atmospheric condition for the reaction.
Figure BDA0002503169230000101
TABLE 5 Effect of the gas atmosphere on the reaction
Figure BDA0002503169230000102
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5mmol), FeCl3(0.1mmol) and toluene (2mL) at 130 ℃ for 15 h.
6. Optimization of reaction temperature:
the effect of temperature on the reaction was studied in detail in this experimental group. As can be seen from table 6: the higher the temperature at the start, the higher the yield of the desired product. The yield of the product is best (72%) when the temperature is 130 ℃. When the temperature was raised further, the product yield was almost unchanged. Thus, 130 ℃ was chosen as the optimum temperature for the experiment.
Figure BDA0002503169230000103
TABLE 6 influence of temperature on the reaction
Figure BDA0002503169230000104
Figure BDA0002503169230000111
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide(0.5mmol),FeCl3(0.1mmol) and toluene (2mL) were reacted under an air atmosphere for 15 h. [ b ] a]The yield achieved after 24h of reaction.
7. Optimization of reaction time:
the experimental group investigated the effect of time on the reaction products and the results are shown in table 7. The yield of the desired product increased gradually with increasing reaction time, with a product yield (72%) of 15h at the highest time. When the time is increased further, the yield of the product remains substantially unchanged. Therefore, 15h was chosen as the optimal time for the reaction.
Figure BDA0002503169230000112
TABLE 7 Effect of time on the reaction
Figure BDA0002503169230000113
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5mmol), FeCl3(0.1mmol), toluene (2mL), 130 ℃, under an air atmosphere.
The following specific examples were carried out under the following preferred reaction conditions:
Figure BDA0002503169230000114
according to optimized reaction conditions of aromatic aldehyde (0.5mmol), ammonium salt (0.5mmol), toluene (2.0mL), ferric chloride (20 mmol%), 130 ℃, 15h and air atmosphere, different aldehyde substitutes, ammonium iodide and toluene are firstly used as substrates, and the experimental operation process is as follows:
example 1
Figure BDA0002503169230000121
The specific experimental procedure for synthesis of 2a is as follows: weighing53mg (0.5mmol) of benzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25mL of a stoppered tube with a stirrer and 2mL of toluene were added. The reaction was sealed and heated in an oil bath at 130 c and the reaction was stopped after 15h under magnetic stirring. After the reaction solution was cooled and washed with 6mL of a saturated NaCl solution, EtOAc (10 mL. times.3) was added to extract the reaction solution, and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Then adding silica gel powder, uniformly mixing the mixture with a sample, and then filling the mixture into filled silica gel for column chromatography separation and purification to obtain 111.24mg of white 2,4,6-triphenyl-1,3,5-triazine solid, wherein the yield is 72%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.80-8.78(dd,J＝8.0Hz,6H),8.17-7.42(m,9H).13C NMR(100MHz,CDCl3)δ171.66,136.26,132.49,128.96,128.63.HRMS(EI):calcd for C21H15N3:309.1266；found:309.1272。
example 2
Figure BDA0002503169230000122
The specific experimental procedure for synthesis of 2a is as follows: 60.5mg (0.5mmol) of 4-methylbenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride were weighed into a 25mL closed tube with a stirrer, and 2mL of toluene was added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column chromatography, and separating and purifying to obtain white 2,4,6-tri-p-tolyl-1,3,5-triazine solid 122.13mg with yield of 69%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.66-8.64(d,J＝8.0Hz,6H),7.37-7.35(d,J＝8.0Hz,6H),2.48(s,9H)13C NMR(100MHz,CDCl3)δ171.37,142.82,133.76,129.30,128.90,21.70.HRMS(EI):calcd for C24H21N3:351.17335；found:351.1738。
example 3
Figure BDA0002503169230000131
The specific experimental procedure for synthesis of 2c is as follows: the specific experimental operations were as follows: 60.5mg (0.5mmol) of 3-methylbenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride were weighed into a 25mL closed tube with a stirrer, and 2mL of toluene was added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column, and separating and purifying to obtain white 2,4,6-tri-m-tolyl-1,3,5-triazine solid 125.67mg with yield of 71%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.60-8.58(d,J＝9.2Hz,6H),7.96–6.85(m,6H),2.54(s,9H).13C NMR(100MHz,CDCl3)δ171.68,138.25,136.27,133.22,129.38,128.50,126.20,77.32,77.00,76.68,21.55.HRMS(EI):calcd for C24H21N3:351.1735；found:351.1742。
example 4
Figure BDA0002503169230000141
The specific experimental procedure for synthesis of 2d is as follows: the specific experimental operations were as follows: 60.5mg (0.5mmol) of 2-methylbenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide and 16.25mg (0.1mmol) of methanolFerric chloride hydrate was placed in a 25mL stopcock with a stirrer and 2mL toluene was added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into silica gel column, separating and purifying to obtain light yellow oily 2,4,6-tri-o-tolyl-1,3,5-triazine liquid 92.04mg with yield of 52%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.25-8.23(d,J＝7.6Hz,3H),7.71–7.23(m,9H),2.80(d,J＝13.6Hz,9H).13C NMR(100MHz,CDCl3)δ173.81,138.91,136.16,131.79,131.28,130.84,126.03,22.26.HRMS(EI):calcd for C24H21N3:351.1735；found:351.1731。
example 5
Figure BDA0002503169230000142
The specific experimental procedure for the synthesis of 2e is as follows: 56mg (0.5mmol) of 2-thiophenecarboxaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride are weighed into a 25mL sealed tube with a stirrer and 2mL of toluene are added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column chromatography, and separating and purifying to obtain white 2,4,6-tri (thiophen-2-yl) -1,3,5-triazine solid 104.64mg with yield of 64%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.28-8.27(d,J＝3.6Hz,3H),7.63-7.61(d,J＝4.8Hz,3H),7.22-7.20(t,J＝4.4Hz,3H).13C NMR(100MHz,CDCl3)δ167.69,141.43,132.28,131.66,128.38.HRMS(EI):calcd for C15H9N3S3:326.9959.1263；found:326.9965.
example 6
Figure BDA0002503169230000151
The specific experimental procedure for synthesis of 2f is as follows: 56mg (0.5mmol) of 3-thiophenecarboxaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride are weighed into a 25mL sealed tube with a stirrer and 2mL of toluene are added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column chromatography, and separating and purifying to obtain white 2,4,6-tri (thiophen-3-yl) -1,3,5-triazine solid 106.27mg with yield of 65%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.61-8.60(dd,J＝3.0,1.0Hz,3H),8.07-8.05(dd,J＝4.8,1.2Hz,3H),7.44-7.42(dd,J＝5.2,3.2Hz,3H).13C NMR(100MHz,CDCl3)δ168.34,140.40,131.00,127.62,126.21.HRMS(EI):calcd for C15H19N3S3:326.9959；found:326.9963.
example 7
Figure BDA0002503169230000161
The specific experimental procedure for the synthesis of 2g is as follows: 61.5mg (0.5mmol) of 2-fluorobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride are weighed into a 25mL sealed tube with a stirrer, and 2mL of toluene are added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column chromatography, and separating and purifying to obtain white 2,4,6-tris (2-fluorophenyl) -1,3,5-triazine solid 108.9mg with yield of 60%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.49-8.46(t,J＝7.8Hz,3H),7.61-7.56(q,J＝6.8Hz,3H),7.38-7.34(t,J＝7.6Hz,3H),7.31–7.28(m,3H).13C NMR(100MHz,CDCl3)δ170.80,170.75,163.70,161.12,133.74,133.65,132.38,124.61,124.53,124.30,124.26,117.37,117.15.HRMS(EI):calcd for C21H12N3F3:363.0983；found:363.0976.
example 8
Figure BDA0002503169230000162
The specific experimental procedure for synthesis of 2h was as follows: 70.25mg (0.5mmol) of 2-chlorobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride are weighed into a 25mL sealed tube with a stirrer and 2mL of toluene are added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Silica gel powder was added thereto, and the mixture was subjected to silica gel column chromatography to obtain 82.5mg of a white 2,4,6-tris (2-fluorophenyl) -1,3,5-triazine solid with a yield of 42% by separation and purification.
Characterization data:1H NMR(400MHz,CDCl3)δ8.12-8.10(m,3H),7.58-7.55(m,1H),7.49-7.42(m,Hz,6H).13C NMR(100MHz,CDCl3)δ172.73,135.35,133.63,132.66,131.91,131.13,126.99.HRMS(EI):calcd for C21H12N3Cl3:411.0097；found:411.0103.
example 9
Figure BDA0002503169230000171
The specific experimental procedure for the synthesis of 2i is as follows: 70.25mg (0.5mmol) of 4-ethylbenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride were weighed into 25mL of a stoppered tube with a stirrer, and 2mL of toluene was added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column, and separating and purifying to obtain white 2,4,6-tris (4-ethylphenyl) -1,3,5-triazine solid 115.93mg with yield of 59%.
Characterization data:1H NMR(400MHz,CDCl3)δ8.70-8.68(d,J＝7.6Hz,6H),7.41-7.39(d,J＝7.6Hz,6H),2.81-2.76(q,J＝7.4Hz,6H),1.35-1.31(t,J＝7.6Hz,9H).13C NMR(100MHz,CDCl3)δ171.43,149.09,134.03,129.01,128.11,29.02,15.37.HRMS(EI):calcd for C27H27N3:393.2205；found:393.2213。
example 10
Figure BDA0002503169230000181
The specific experimental procedure for the synthesis of 2j is as follows: 92.5mg (0.5mmol) of 3-bromobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride are weighed into a 25mL sealed tube with a stirrer, and 2m of ferric chloride are addedAnd L is toluene. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Silica gel powder was added thereto, and the mixture was subjected to silica gel column chromatography to obtain 182.91mg of a white 2,4,6-tris (3-bromophenyl) -1,3,5-triazine solid in 67% yield.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.76(s,3H),8.61-8.59(d,J＝8.0Hz,3H),7.74-7.72(d,J＝7.8Hz,3H),7.44-7.41(t,J＝8.0Hz,3H).13C NMR(100MHzCDCl3)δ170.58,137.59,135.72,131.79,130.21,127.58,122.98.HRMS(EI):calcd for C21H12N3Br3:544.8561；found:544.8566。
example 11
Figure BDA0002503169230000191
The specific experimental procedure for the synthesis of 2k is as follows: 70.25mg (0.5mmol) of 3-chlorobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride are weighed into a 25mL sealed tube with a stirrer and 2mL of toluene are added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column chromatography, and separating and purifying to obtain white 2,4,6-tris (3-chlorophenylyl) -1,3,5-triazine solid 135.06mg with yield of 65%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.61(s,3H),8.57-8.55(d,J＝8.0Hz,3H),7.58-7.56(d,J＝8.0Hz,3H),7.51-7.47(t,J＝7.8Hz,3H).13C NMR(100MHz,CDCl3)δ170.67,137.39,134.92,132.76,129.93,128.85,127.09.HRMS(EI):calcd for C21H12N3Cl3:411.0097；found:411.0092。
example 12
Figure BDA0002503169230000192
The specific experimental procedure for the synthesis of 2l was as follows: : 62mg (0.5mmol) of 3-chlorobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride are weighed into a 25mL sealed tube with a stirrer, and 2mL of toluene are added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Silica gel powder was added thereto, and the mixture was subjected to silica gel column chromatography to obtain 128.86mg of a white 2,4,6-tris (3-fluorophenyl) -1,3,5-triazine solid in a yield of 71%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.56-8.54(d,J＝8.0Hz,3H),8.50–8.33(m,3H),7.56(q,J＝7.8Hz,3H),7.46–7.27(m,3H).13C NMR(100MHz,CDCl3)δ170.96,164.39,161.94,138.16,138.08,130.33,130.25,124.70,124.67,119.87,119.66,115.86,115.62.HRMS(EI):calcd for C21H12N3F3:363.0983；found:363.0988。
example 13
Figure BDA0002503169230000201
The specific experimental procedure for the synthesis of 2m is as follows: 68mg (0.5mmol) of 4-methoxybenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide and 16.25mg (0.1mmol) of anhydrous chloride are weighed outIron was placed in a 25mL stopcock with a stirrer and 2mL toluene was added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column chromatography, and separating and purifying to obtain white 2,4,6-tris (4-methoxyphenyl) -1,3,5-triazine solid 83.79mg with yield of 42%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.71-8.69(d,J＝9.2Hz,6H),7.06-7.04(d,J＝9.6Hz,6H),3.91(s,9H).13C NMR(100MHz,CDCl3)δ170.68,163.08,130.68,129.13,113.82,55.41.HRMS(EI):calcd for C24H21N3O3:399.1583；found:399.1576。
example 14
Figure BDA0002503169230000211
The specific experimental procedure for the synthesis of 2n is as follows: 68mg (0.5mmol) of 3-methoxybenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride are weighed into 25mL of a stoppered tube with a stirrer, and 2mL of toluene are added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column chromatography, and separating and purifying to obtain white 2,4,6-tris (3-fluorophenyl) -1,3,5-triazine solid 89.77mg with yield of 45%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.37-8.35(d,J＝8.0Hz,3H),8.30-8.29(m,3H),7.50-7.46(t,J＝8.0Hz,3H),7.17–7.14(m,3H),3.96(s,9H).13C NMR(100MHz,CDCl3)δ171.42,159.91,137.61,129.63,121.52,118.44,113.88,55.44.HRMS(EI):calcd for C24H21N3O3:399.1583；found:399.1589。
example 15
Figure BDA0002503169230000221
The specific experimental procedure for the synthesis of 2o is as follows: 67mg (0.5mmol) of 3, 4-dimethylbenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride were weighed into a 25mL stoppered tube with a stirrer, and 2mL of toluene was added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column, and separating and purifying to obtain white 2,4,6-tris (3,4-dimethylphenyl) -1,3,5-triazine solid 80.56mg with yield of 41%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.51-8.49(d,J＝9.2Hz,6H),7.34-7.32(d,J＝7.6Hz,3H),2.44-2.39(d,J＝20.8Hz,18H).13C NMR(100MHz,CDCl3)δ171.50,141.50,136.79,134.17,129.94,129.87,126.58,20.06,19.94.HRMS(EI):calcd for C27H27N3:393.2205；found:393.2201。
example 16
Figure BDA0002503169230000222
The specific experimental procedure for the synthesis of 2p is as follows: 67mg (0.5mmol) of 4-fluorobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 2 are weighed out5mL of a stoppered tube with a stirrer and 2mL of toluene were added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column chromatography, and separating and purifying to obtain white 2,4,6-tris (4-fluorophenyl) -1,3,5-triazine solid 81.67mg with a yield of 45%.
Characterization data:1H NMR(400MHz,CDCl3)δ7.52(s,1H),7.07(d,J＝2.0Hz,1H),7.04(t,J＝7.4Hz,2H),6.79(t,J＝7.4Hz,1H),6.72(d,J＝7.6Hz,2H),6.42(s,1H),3.01(s,6H).13C NMR(100MHz,CDCl3)δ181.29,155.95,151.23,148.71,148.35,128.43,122.33,122.30,121.56,112.76,37.41.HRMS(EI):calcd for C21H12N3F3:363.0983；found:363.0991。
example 17
Figure BDA0002503169230000231
The specific experimental procedure for the synthesis of 2q is as follows: 87mg (0.5mmol) of 3-trifluoromethylbenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride were weighed into 25mL of a stoppered tube with a stirrer, and 2mL of toluene was added. The reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ to be heated and reacted for 15h under the condition of magnetic stirring, and the reaction is stopped. The cooled reaction solution was washed with 6mL of a saturated NaCl solution, and then extracted with additional EtOAc (10 mL. times.3), and the supernatant was collected and dried over anhydrous sodium sulfate to remove water. The resulting mixture was placed in a rotary evaporator and dried by adding 4mL CH2Cl2Silica gel powder was added thereto, and the mixture was subjected to silica gel column chromatography to obtain 133.38mg of a white 2,4,6-tris (4-fluorophenyl) -1,3,5-triazine solid in 52% yield.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)δ8.97–8.92(m,6H),7.91-7.89(d,J＝7.8Hz,3H),7.76-7.72(t,J＝7.8Hz,3H)13C NMRδ170.98,136.32,132.21,131.63,131.30,129.43,125.82,125.79,125.29,122.58.HRMS(EI):calcd for C24H12N3F9:513.0888；found:513.0883。

Claims (5)

1. a method for synthesizing 2,4, 6-trisubstituted 1,3,5-triazine compound by aromatic aldehyde and ammonium iodide is characterized in that: aromatic aldehyde and ammonium iodide are subjected to one-pot reaction under the catalytic action of ferric salt to obtain a 2,4, 6-trisubstituted 1,3,5-triazine compound;
the aromatic aldehyde has the structure of formula 1:
Ar-CHO
formula 1
The 2,4, 6-trisubstituted 1,3,5-triazine compound has the structure of formula 2:
Figure FDA0003075374530000011
wherein the content of the first and second substances,
ar is aryl or aromatic heterocyclic radical; the aryl is phenyl or substituted phenyl; the substituted phenyl is phenyl containing 1-2 substituents, and the substituent is C1～C5Alkyl of (C)1～C5Alkoxy, halogen substituent or trifluoromethyl; the aromatic heterocyclic group is thienyl, furyl or pyrrolyl;
the dosage of the trivalent ferric salt is 15-25% of the molar weight of the aromatic aldehyde; the ferric iron salt is at least one of ferric chloride, ferric bromide and ferric sulfate; the one-pot reaction is carried out in a benzene solvent; the one-pot reaction conditions are as follows: reacting for 14-18 hours at 130-150 ℃ in an oxygen-containing atmosphere.
2. The method of synthesizing 2,4, 6-trisubstituted 1,3,5-triazine compound according to claim 1, wherein: the dosage of the ammonium iodide is 0.8 to 1.2 times of the molar weight of the aromatic aldehyde.
3. The method of synthesizing 2,4, 6-trisubstituted 1,3,5-triazine compound according to claim 1, wherein: the dosage of the trivalent ferric salt is 10-30% of the molar weight of the aromatic aldehyde.
4. The method of synthesizing 2,4, 6-trisubstituted 1,3,5-triazine compound according to claim 1, wherein: the benzene solvent is chlorobenzene and/or toluene.
5. The method of synthesizing 2,4, 6-trisubstituted 1,3,5-triazine compound according to claim 1, wherein: the oxygen-containing atmosphere is oxygen or air.
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