CN111454226A - 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 PDFInfo
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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
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, ketoneamino by addition reaction of picolinyl-type derivatives with nitriles [ J ]. Journal of Molecular Structure,2017,1128(645-52.) reported a reaction method for synthesizing 1,3,5-triazine compounds using butyllithium 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.
2) A method for synthesizing 1,3,5-triazine compound by using amidine salt as nitrogen source is reported recently in 2019, (Zhang Y, &lTtTtransfer = L "&gTt L &/T &gTt iu Y, Zhang J, et al, an alternative metal-free synthesis of 1,3,5-triazine or 1,2,4-thiadiazoles from benzyl chloride and benzaminesminded by elementary sulfur [ J ] J].Tetrahedron Letters,2019,60(49)) reported passing 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.
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 aerobication 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.
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 ClCF2COONafor 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 in the absence of transition metal and external oxidantA series of 1,3,5-triazine and quinazolinone can be synthesized with a yield of up to 96%. The process avoids the use of transition metals and oxidants and produces inorganic waste of low toxicity.
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.
5) The most recently reported method for synthesizing 1,3,5-triazine compounds by coupling Suzuki-Miyaura type, 2019, (Chen T, L i W-Q, Hu W-B, et al.direct synthesis of synergistic triazine-based Structures (CTFs) through organic triazine reactive reactions [ J ]. RSC Advances,2019,9(31):18008-12.) reported the framework of various triazine compounds obtained by coupling organometallic lithium and halogenated triazine compounds.
In the same year, (Niakan M, Asadi Z, Masteri-Farahani M.Encapsulated of aPalladium Schiff-Base Complex inter the Nanocages of MeOporous SBA-16as and effective hetereogenous catalysts Catalyst for the synthesis of 1,3,5-triazine compounds using palladium Schiff Base complexes to catalyze the Reaction of halotriazine compounds with phenylboronic acid [ J ]. chemistry select,2019,4(5):1766-75.) is reported, and this Catalyst can catalyze the Reaction of various aryl halides with arylboronic acids under mild aqueous conditions to give aryl-substituted 1,3,5-triazine compounds, as shown in the following Reaction scheme.
6) The newly reported methods for the synthesis of 1,3,5-triazine compounds by oxidation or ring closure reactions: in 2013, (ZhaoF, 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 Nitriles 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.
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
The 2,4, 6-trisubstituted 1,3,5-triazine compound has the structure of formula 2:
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 is very reactive towards a variety of functional group substituents, including halogen, AOxy, ethoxy, trifluoromethyl and the like. Wherein, the yield of the target product is not greatly different from that of the substrate with electron withdrawing groups such as halogen, trifluoromethyl and the like relative to that of the substrate with electron donating groups such as methyl, methoxy and the like, which shows that the electronic effect of the substituent does not greatly influence the application range of the aromatic aldehyde substrate. 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;
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.
TABLE 1 Effect of different catalysts on the reaction
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5 m)mol), catalyst (0.1mmol), toluene (2m L), 130 ℃, under the atmosphere of air for 15 h.
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.
TABLE 2 influence of the amount of catalyst used on the experiment
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5mmol), FeCl3(X mmol%), toluene (2m L), 130 ℃ under an air atmosphere 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.
TABLE 3 influence of the type of inorganic ammonium salt on the reaction
aThe reaction conditions were benzaldehyde (0.5mmol), inorganic ammonium salt (0.5mmol), FeCl3(0.1mmol), toluene (2m L), 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.
TABLE 4 Effect of solvent on the reaction
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5mmol), FeCl3(0.1mmol), solvent (2m L), 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 O2Increase of contentAnd then remains substantially 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.
TABLE 5 Effect of the gas atmosphere on the reaction
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5mmol), FeCl3(0.1mmol), toluene (2m L), 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.
TABLE 6 influence of temperature on the reaction
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5mmol), FeCl3(0.1mmol), toluene (2m L), reacted for 15h under an air atmosphere [ b ]]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.
TABLE 7 Effect of time on the reaction
aThe reaction conditions were benzaldehyde (0.5mmol), ammonium iodide (0.5mmol), FeCl3(0.1mmol), toluene (2m L), 130 ℃, reacted under an atmosphere of air.
The following specific examples were carried out under the following preferred reaction conditions:
according to optimized reaction conditions of aromatic aldehyde (0.5mmol), ammonium salt (0.5mmol), toluene (2.0m L), 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
The specific experimental procedure for the synthesis of 2a was carried out by weighing 53mg (0.5mmol) benzaldehyde, 72.5mg (0.5mmol) ammonium iodide, 16.25mg (0.1mmol) anhydrous ferric chloride in 25m L sealed tube with stirrer and adding 2m L toluene, sealing the sealed tube and heating in an oil bath at 130 deg.C, reacting for 15h under magnetic stirringAfter the reaction solution was cooled, it was washed with 6m L saturated NaCl solution, and then EtOAc (10m L× 3) was added to extract the reaction solution, and the supernatant was collected and dried over anhydrous sodium sulfate to remove water therefrom, the resulting mixture was placed in a rotary evaporator and then 4m L CH was added thereto2Cl2Then 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)8.80-8.78(dd,J＝8.0Hz,6H),8.17-7.42(m,9H).13C NMR(100MHz,CDCl3)171.66,136.26,132.49,128.96,128.63.HRMS(EI):calcdfor C21H15N3:309.1266；found:309.1272。
example 2
The specific experimental procedure for the synthesis of 2a was 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 25m L sealed tube with a stirrer and 2m L of toluene was added, the sealed tube was sealed and placed in a 130 ℃ oil bath and heated and reacted for 15 hours with magnetic stirring to stop the reaction, the cooled reaction solution was washed with 6m L of saturated NaCl solution and then EtOAc (10m L× 3) was added to extract the reaction solution, the supernatant was collected and dried with anhydrous sodium sulfate and the water was removed, the resulting mixture was placed in a rotary evaporator and dried and 4m L CH was added2Cl2Adding 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)8.66-8.64(d,J＝8.0Hz,6H),7.37-7.35(d,J＝8.0Hz,6H),2.48(s,9H)13C NMR(100MHz,CDCl3)171.37,142.82,133.76,129.30,128.90,21.70.HRMS(EI):calcd for C24H21N3:351.17335；found:351.1738。
example 3
Synthesis of 2c A specific experimental procedure was carried out by weighing 60.5mg (0.5mmol) of 3-methylbenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25m L sealed tube with stirrer and 2m L of toluene, heating the sealed tube in a 130 ℃ oil bath under magnetic stirring for 15h, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) to extract the reaction solution, collecting the supernatant and drying it with anhydrous sodium sulfate to remove water, placing the resulting mixture in a rotary evaporator and drying it, adding 4m L 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)8.60-8.58(d,J＝9.2Hz,6H),7.96–6.85(m,6H),2.54(s,9H).13C NMR(100MHz,CDCl3)171.68,138.25,136.27,133.22,129.38,128.50,126.20,77.32,77.00,76.68,21.55.HRMS(EI):calcd for C24H21N3:351.1735；found:351.1742。
example 4
The specific experimental procedure for the synthesis of 2d was as follows, 60.5mg (0.5mmol) of 2-methylbenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride were weighed into a 25m L sealed tube with a stirrer and 2m L of toluene was added, the sealed tube was sealed in a 130 ℃ oil bath and heated and reacted for 15h under magnetic stirring, the cooled reaction solution was washed with 6m L of saturated NaCl solution and then EtOAc (10m L× 3) was added to extract the reaction solution, the supernatant was collected and dried over anhydrous sodium sulfate and removedDrying the obtained mixture in a rotary evaporator, adding 4m L 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)8.25-8.23(d,J＝7.6Hz,3H),7.71–7.23(m,9H),2.80(d,J＝13.6Hz,9H).13C NMR(100MHz,CDCl3)173.81,138.91,136.16,131.79,131.28,130.84,126.03,22.26.HRMS(EI):calcd for C24H21N3:351.1735；found:351.1731。
example 5
The specific experimental procedure for the synthesis of 2e was carried out by weighing 56mg (0.5mmol) of 2-thiophenecarboxaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25m L sealed tube with stirrer and 2m L of toluene, sealing the sealed tube in a 130 ℃ oil bath and heating and reacting under magnetic stirring for 15h, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) and extracting the reaction solution, collecting the supernatant and drying it with anhydrous sodium sulfate and removing water, placing the resulting mixture in a rotary evaporator and adding 4m L CH 3532Cl2Adding 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)8.28-8.27(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)167.69,141.43,132.28,131.66,128.38.HRMS(EI):calcd for C15H9N3S3:326.9959.1263；found:326.9965.
example 6
The specific experimental procedure for the synthesis of 2f was carried out by weighing 56mg (0.5mmol) of 3-thiophenecarboxaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25m L sealed tube with stirrer and 2m L of toluene, sealing the sealed tube in a 130 ℃ oil bath and heating and reacting under magnetic stirring for 15h, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) and extracting the reaction solution, collecting the supernatant and drying it with anhydrous sodium sulfate and removing water, placing the resulting mixture in a rotary evaporator and adding 4m L CH 3532Cl2Adding 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)8.61-8.60(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)168.34,140.40,131.00,127.62,126.21.HRMS(EI):calcd for C15H19N3S3:326.9959；found:326.9963.
example 7
The specific experimental procedure for the synthesis of 2g was carried out by weighing 61.5mg (0.5mmol) of 2-fluorobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25m L sealed tube with stirrer and 2m L of toluene, sealing the sealed tube in a 130 ℃ oil bath and heating and reacting for 15h under magnetic stirring, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) and extracting the reaction solution, collecting the supernatant and drying it with anhydrous sodium sulfate and removing water, placing the resulting mixture in a rotary evaporator and spin-drying it, adding 4m L CH2Cl2Adding silica gel powder, mixing, and fillingThe obtained product was purified by silica gel column chromatography to give 108.9mg of a white solid of 2,4,6-tris (2-fluorophenyl) -1,3,5-triazine in 60% yield.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)8.49-8.46(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)170.80,170.75,163.70,161.12,133.74,133.65,132.38,124.61,124.53,124.30,124.26,117.37,117.15.HRMS(EI):calcd for C21H12N3F3:363.0983；found:363.0976.
example 8
The experimental procedure for the synthesis of 2h was carried out by weighing 70.25mg (0.5mmol) of 2-chlorobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25m L sealed tube with stirrer, adding 2m L of toluene, sealing the sealed tube in a 130 ℃ oil bath, heating and reacting under magnetic stirring for 15h, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) to extract the reaction solution, collecting the supernatant, drying with anhydrous sodium sulfate and removing water, placing the resulting mixture in a rotary evaporator, spin-drying, adding 4m L 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)8.12-8.10(m,3H),7.58-7.55(m,1H),7.49-7.42(m,Hz,6H).13C NMR(100MHz,CDCl3)172.73,135.35,133.63,132.66,131.91,131.13,126.99.HRMS(EI):calcd for C21H12N3Cl3:411.0097；found:411.0103.
example 9
The specific experimental procedure for the synthesis of 2i was carried out by weighing 70.25mg (0.5mmol) of 4-ethylbenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in a 25m L sealed tube with stirrer and adding 2m L of toluene, sealing the sealed tube in a 130 ℃ oil bath and heating and reacting under magnetic stirring for 15h, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) and extracting the reaction solution, collecting the supernatant and drying it with anhydrous sodium sulfate and removing water, placing the resulting mixture in a rotary evaporator and adding 4m L 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)8.70-8.68(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)171.43,149.09,134.03,129.01,128.11,29.02,15.37.HRMS(EI):calcd forC27H27N3:393.2205；found:393.2213。
example 10
The specific experimental procedure for the synthesis of 2j was as follows, 92.5mg (0.5mmol) of 3-bromobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride were weighed into a 25m L sealed tube with a stirrer and 2m L of toluene was added, the sealed tube was sealed and placed in a 130 ℃ oil bath and heated and reacted for 15h under magnetic stirring, the cooled reaction solution was washed with 6m L of saturated NaCl solution and then added with EtOAc (10m L× 3) to extract the reaction solution, the supernatant was collected and dried with anhydrous sodium sulfate and the water was removed, the resulting mixture was placed in a rotary evaporator and then added with 4m L CH2Cl2Adding silica gel powder, mixing, loading into packed silica gel column chromatography, and separating and purifying to obtain white 2,4,6-tris (3-bromophenyl)182.91mg of a solid, 1,3,5-triazine, yield 67%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)8.76(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)170.58,137.59,135.72,131.79,130.21,127.58,122.98.HRMS(EI):calcd for C21H12N3Br3:544.8561；found:544.8566。
example 11
The specific experimental procedure for the synthesis of 2k was carried out by weighing 70.25mg (0.5mmol) of 3-chlorobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in a 25m L sealed tube with stirrer and adding 2m L of toluene, sealing the sealed tube in a 130 ℃ oil bath and heating and reacting for 15h under magnetic stirring, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) and extracting the reaction solution, collecting the supernatant and drying it with anhydrous sodium sulfate and removing water, placing the resulting mixture in a rotary evaporator and adding 4m L 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)8.61(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)170.67,137.39,134.92,132.76,129.93,128.85,127.09.HRMS(EI):calcd forC21H12N3Cl3:411.0097；found:411.0092。
example 12
The specific experimental procedure for the synthesis of 2l was as follows: : weighing 62mg (0.5mmol) of 3-chlorobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25m L sealed tube with stirrer and 2m L of toluene are added, the sealed tube is sealed and placed in an oil bath kettle at 130 ℃ for heating and reacting for 15h under magnetic stirring to stop the reaction, the cooled reaction solution is washed by 6m L of saturated NaCl solution, then EtOAc (10m L× 3) is added to extract the reaction solution, the supernatant is collected and dried by using anhydrous sodium sulfate to remove the water, the obtained mixture is placed in a rotary evaporator for spin drying, and 4m L CH is added2Cl2Silica 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)8.56-8.54(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)170.96,164.39,161.94,138.16,138.08,130.33,130.25,124.70,124.67,119.87,119.66,115.86,115.62.HRMS(EI):calcd for C21H12N3F3:363.0983；found:363.0988。
example 13
The specific experimental procedure for the synthesis of 2m was carried out by weighing 68mg (0.5mmol) of 4-methoxybenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25m L closed tube with stirrer and adding 2m L of toluene, sealing the sealed tube in a 130 ℃ oil bath and heating and reacting under magnetic stirring for 15h, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) and extracting the reaction solution, collecting the supernatant and drying it with anhydrous sodium sulfate and removing water, placing the resulting mixture in a rotary evaporator and adding 4m L CH 3532Cl2Adding silica gel powder, mixing, loading into packed silica gel column, separating and purifying to obtain white 2,4,6-tris (4-methoxyphenyl) -1,3,5-triazine solid 83.79mg, yield 42%.
Nuclear magnetic characterization data:1H NMR(400MHz,CDCl3)8.71-8.69(d,J＝9.2Hz,6H),7.06-7.04(d,J＝9.6Hz,6H),3.91(s,9H).13C NMR(100MHz,CDCl3)170.68,163.08,130.68,129.13,113.82,55.41.HRMS(EI):calcd for C24H21N3O3:399.1583；found:399.1576。
example 14
The specific experimental procedure for the synthesis of 2n was carried out by weighing 68mg (0.5mmol) of 3-methoxybenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25m L closed tube with stirrer and adding 2m L of toluene, sealing the sealed tube in a 130 ℃ oil bath and heating and reacting under magnetic stirring for 15h, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) and extracting the reaction solution, collecting the supernatant and drying it with anhydrous sodium sulfate and removing water, placing the resulting mixture in a rotary evaporator and adding 4m L CH 3532Cl2Adding 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)8.37-8.35(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)171.42,159.91,137.61,129.63,121.52,118.44,113.88,55.44.HRMS(EI):calcdfor C24H21N3O3:399.1583；found:399.1589。
example 15
The specific experimental procedure for the synthesis of 2o is as follows: 67mg (0.5mmol) of 3, 4-dimethylbenzaldehyde and 72.5mg (0.5 m) of dimethylbenzaldehyde were weighed outmol) ammonium iodide, 16.25mg (0.1mmol) anhydrous ferric chloride in 25m L sealed tube with stirrer and 2m L toluene are added, the reaction sealed tube is sealed and placed in an oil bath kettle at 130 ℃ for heating and reacts for 15h under the condition of magnetic stirring to stop the reaction, the cooled reaction liquid is washed by 6m L saturated NaCl solution and then added with EtOAc (10m L× 3) to extract the reaction liquid, the supernatant is collected and dried by using anhydrous sodium sulfate and the water is removed, the obtained mixture is put in a rotary evaporator for spin drying and then 4m L CH is added2Cl2Adding 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)8.51-8.49(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)171.50,141.50,136.79,134.17,129.94,129.87,126.58,20.06,19.94.HRMS(EI):calcd forC27H27N3:393.2205；found:393.2201。
example 16
The specific experimental procedure for the synthesis of 2p was carried out by weighing 67mg (0.5mmol) of 4-fluorobenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25m L sealed tube with stirrer and 2m L of toluene, sealing the sealed tube in a 130 ℃ oil bath and heating and reacting under magnetic stirring for 15h, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) and extracting the reaction solution, collecting the supernatant and drying it with anhydrous sodium sulfate and removing water, placing the resulting mixture in a rotary evaporator and adding 4m L CH after spin-drying it2Cl2Adding 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)7.52(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).13CNMR(100MHz,CDCl3)181.29,155.95,151.23,148.71,148.35,128.43,122.33,122.30,121.56,112.76,37.41.HRMS(EI):calcd for C21H12N3F3:363.0983；found:363.0991。
example 17
The specific experimental procedure for the synthesis of 2q was carried out by weighing 87mg (0.5mmol) of 3-trifluoromethylbenzaldehyde, 72.5mg (0.5mmol) of ammonium iodide, 16.25mg (0.1mmol) of anhydrous ferric chloride in 25m L sealed tube with stirrer and 2m L of toluene, sealing the sealed tube in a 130 ℃ oil bath and heating and reacting under magnetic stirring for 15h, washing the cooled reaction solution with 6m L of saturated NaCl solution, adding EtOAc (10m L× 3) and extracting the reaction solution, collecting the supernatant and drying it with anhydrous sodium sulfate and removing water, placing the resulting mixture in a rotary evaporator and adding 4m L 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)8.97–8.92(m,6H),7.91-7.89(d,J＝7.8Hz,3H),7.76-7.72(t,J＝7.8Hz,3H)13C NMR170.98,136.32,132.21,131.63,131.30,129.43,125.82,125.79,125.29,122.58.HRMS(EI):calcd for C24H12N3F9:513.0888；found:513.0883。
Claims (10)
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:
wherein the content of the first and second substances,
ar aryl or aromatic heterocyclic group.
2. The method of synthesizing 2,4, 6-trisubstituted 1,3,5-triazine compound according to claim 1, wherein:
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.
3. 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.
4. 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.
5. The method of claim 4, wherein the aromatic aldehyde and ammonium iodide are used to synthesize 2,4, 6-trisubstituted 1,3,5-triazine compound, and the method comprises the following steps: the dosage of the trivalent ferric salt is 15-25% of the molar weight of the aromatic aldehyde.
6. The method of claim 5, wherein the aromatic aldehyde and ammonium iodide are used to synthesize 2,4, 6-trisubstituted 1,3,5-triazine compound, and the method comprises the following steps: the ferric salt is at least one of ferric chloride, ferric bromide and ferric sulfate.
7. The method of synthesizing 2,4, 6-trisubstituted 1,3,5-triazine compound according to claim 1, wherein: the one-pot reaction is carried out in a benzene solvent.
8. The method of claim 7, wherein the aromatic aldehyde and ammonium iodide are used to synthesize 2,4, 6-trisubstituted 1,3,5-triazine compound, and the method comprises the following steps: the benzene solvent is chlorobenzene and/or toluene.
9. The method for synthesizing a 2,4, 6-trisubstituted 1,3,5-triazine compound according to any one of claims 1 to 8, wherein: the one-pot reaction conditions are as follows: reacting for 14-18 hours at 130-150 ℃ in an oxygen-containing atmosphere.
10. The method of claim 9, wherein the aromatic aldehyde and ammonium iodide are used to synthesize 2,4, 6-trisubstituted 1,3,5-triazine compound, and the method comprises the following steps: the oxygen-containing atmosphere is oxygen or air.
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