CN104262273A - Synthesis method of 1,3,5-triazine derivatives - Google Patents

Synthesis method of 1,3,5-triazine derivatives Download PDF

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CN104262273A
CN104262273A CN201410458244.4A CN201410458244A CN104262273A CN 104262273 A CN104262273 A CN 104262273A CN 201410458244 A CN201410458244 A CN 201410458244A CN 104262273 A CN104262273 A CN 104262273A
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synthetic method
triazines
amidine
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hydrochloride
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CN104262273B (en
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张武
尤青
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Anhui Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms

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  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to a synthesis method of 1,3,5-triazine derivatives. The synthesis method comprises the steps of mixing amidine hydrochloride, alcohol, hydrated copper acetate and sodium carbonate, adding a solvent, reacting for 12 hours-24 hours in air at the temperature of 110 DEG C-120 DEG C to obtain a product, purifying the product, extracting, drying, concentrating and separating by virtue of column chromatography to obtain the 1,3,5-triazine derivatives. The synthesis method of the 1,3,5-triazine derivatives, which is disclosed by the invention has the advantages of low cost, available raw materials, high synthesis efficiency and wide application range and is suitable for reaction of a plurality of substrates.

Description

A kind of synthetic method of 1,3,5-triazines analog derivative
Technical field
The invention belongs to technical field of organic synthesis, particularly a kind of synthetic method of triazine derivative.
Background technology
The research of triazine derivative starts from mid-term the 1950's, develops first triazine herbicide simazine at that time and makes farm crop obtain large-scale harvest.After this abroad develop tens of kinds of such compound in triazine class, be mainly used in weeding, desinsection, sterilization and antiviral etc., as triaziflam, 1,3,5-triazines-2,4-diketone, prometryn and terbuthylazine etc.This kind of toxicity of compound is low, residual short, and mechanism of action is unique, is subject to the extensive concern of domestic and international researchist in recent years especially.In addition, triaizine compounds ring strain is less, and stability is fine, nitrogen content high (51.83%), there is higher Enthalpies of Formation, and this compounds has the advantage such as high-density, Heat stability is good, therefore can as gas-evolution agent, solid propellant fuel and pyrotechnics composition.If 2,4,6-tri-chloro-1,3,5-triazines (TCT), 2,4,6-triazidos-1,3,5-triazines (TAT) and 2,4,6-trinitro--1,3,5-triazines (TNTA) etc. are all good energetic materials.Therefore, synthesis, the biological activity of exploring 1,3,5-triazines analog derivative are one of research topics of most vitality in organic chemistry.
The method of the synthesis of triazine compound reported in document mainly contains following several:
(1) under microwave, 1,3,5-triazines compounds is obtained by reacting with isosulfocyanate compound and amidine.
This method employs microwave condition, and the alkali used is the highly basic such as NaOH, and productive rate is not high, and industrial enforcement is more difficult.
(2) in THF solvent, react 24h under room temperature with isosulfocyanate compound and N, N-diethyl amidine compound and obtain intermediate product, then with HgCl 2for catalyzer, trolamine is alkali, at room temperature reacts 4h obtain 1,3,5-triazines analog derivative with the hydrochloride of amidine.
Although the method is at room temperature carried out, use this hypertoxic class material of HgCl2 and make catalyzer, and the products collection efficiency obtained is all not ideal.
(3) utilize Ru title complex to make catalyzer, amidine is obtained by reacting 1,3,5-triazines with alcohol.
This reaction makees catalyzer with precious metal Ru title complex, and the alkali used is Cs 2cO 3, reaction cost is high, is unfavorable for industrial mass production.
(4) 1,3,5-triazines compounds is obtained by reacting with the hydrochloride of amidine and DMF.
The method use pyridine and do part, and need the O of 1atm 2condition, reaction is comparatively harsh, and the suitability of substrate is not high, and productive rate is also undesirable.
(5) carry out three components with 1,2,4-triazole and cyanamide and triethyl orthoformate and be obtained by reacting material containing 1,3,5-triazines structure.
This reaction employs microwave reaction, and temperature of reaction is higher, and productive rate is general, is unfavorable for industrial production.
(6) utilize p-nitrophenyl carbonate resin to carry out polystep reaction and obtain 1,3,5-triazines analog derivative.
(i) S-methyl-isourea (6equiv, 0.1M), Cs 2cO 3(12equiv, 0.2M), DMF, room temperature, 48h.(ii) R 1nCO (6equiv, 0.1M), DCM, room temperature, a night.(iii) R 2nH 2(6equiv, 0.1M), THF, 50 DEG C, a night.(iv) KOEt (3equiv, 0.1M), EtOH, 60 DEG C, a night.(v)TFA/DCM(1:1)，1h。The method is polystep reaction, and it is not high that this also determines final product productive rate.
The method of prior art synthesis 1,3,5-triazines compounds is a lot, but some needs of these methods are through complicated synthesis step, and side reaction is more, and most of productivity ratio is lower; Some uses highly toxic substrate or organic solvent easily to cause environmental pollution, and some uses rare earth metal etc. to be catalyzer, and cost costly, is not suitable for industrial production.Therefore, provide a kind of novel green synthesis method synthesizing 1,3,5-triazines compounds necessary.
Summary of the invention
For the deficiencies in the prior art, the object of this invention is to provide a kind of 1, the synthetic method of 3,5-triazine derivative, the present invention utilizes air for oxygenant, neutralized verdigris catalysis amidine and alcohol direct reaction, synthetic method cost of the present invention is low, and raw material is easy to get, and efficiency is high, use range is wide, is applicable to multiple substrate reactions.
The technical solution used in the present invention is:
A synthetic method for 1,3,5-triazines derivative, step comprises:
A, the hydrochloride of amidine, alcohol are mixed with a hydration neutralized verdigris, sodium carbonate after, add solvent, under the condition of 110 DEG C-120 DEG C, react 12h-24h in air;
B, by product purification, through extraction, dry, concentrated after obtain 1,3,5-triazines analog derivative by column chromatography for separation.
The structural formula of the hydrochloride of described amidine is:
Wherein R is H, Br, CH 3;
The structural formula of described alcohol is:
Wherein R is selected from H, CH 3, CH 3cH 2cH 2, (CH 3) 2cH, Ph, 2-CH 3-C 6h 4, 3-CH 3-C 6h 4, 4-CH 3-C 6h 4, 4-OCH 3-C 6h 4, 2-Cl-C 6h 4, 3-Cl-C 6h 4, 4-Cl-C 6h 4, 4-Br-C 6h 4, 4-F-C 6h 4, 4-CF 3-C 6h 4, 2-NO 2-C 6h 4, 3-NO 2-C 6h 4, 4-NO 2-C 6h 4, 4-(CH 3) 2cH-C 6h 4in one;
The amount of substance ratio of the hydrochloride of described amidine, alcohol, a hydration neutralized verdigris, sodium carbonate is: 2:(1-1.5): 0.2:2;
The hydrochloride concentration in a solvent of described amidine is: 0.40-0.67mol/L;
Described solvent is toluene;
In described step B, purifying is specially: be extracted with ethyl acetate by products therefrom, anhydrous sodium sulfate drying, concentrating under reduced pressure, obtaining crude product, take volume ratio as sherwood oil: the mixed solvent of ethyl acetate=80-100:1 is developping agent, obtains 1 by column chromatography for separation, 3,5-compound in triazine class.
The synthetic method of a kind of 1,3,5-triazines derivative provided by the invention, compared with prior art, has following advantage: (1) carries out in air atmosphere, and cost is low; (2) do not use precious metal, highly basic and organic oxidizing agent, but utilize a hydration neutralized verdigris to make catalyzer, cost-saving; (3) utilize amidine and alcohol to be reaction raw materials, raw material is easy to get; (4) this synthetic method efficiency is high, and use range is wide, is applicable to multiple substrate reactions.
Embodiment
Embodiment 1
The synthesis of 2,4,6-triphenyl-1,3,5-triazines, comprises the following steps:
Get 20mmol benzamidine hydrochlorid and 12mmol phenylcarbinol in the round-bottomed flask of 100mL, then add 2mmolCu (OAc) toward it 2h 2o, 20mmol Na 2cO 3and 30mL toluene, at 110 DEG C, stirring reaction is after 24 hours, product ethyl acetate extracted, drying obtains crude product, and by crude product purified by silica gel column chromatography, (solvent volume is than for sherwood oil: ethyl acetate=100:1) purifying obtains white solid that is 2,4,6-triphenyl-1,3,5-triazines, productive rate 88%, fusing point is 238 DEG C.
1H?NMR(300MHz,CDCl 3)δ8.80-8.78(m,6H),7.65-7.56(m,9H)；
13C?NMR(75MHz,d 6-DMSO)δ166.6,134.6,129.8,128.9。
Embodiment 2
The synthesis of 2-(4-chloro-phenyl-)-4,6-phenylbenzene-1,3,5-triazines, comprises the following steps:
Get 20mmol benzamidine hydrochlorid and 13mmol 4-chlorobenzene methanol in the round-bottomed flask of 100mL, then add 2mmolCu (OAc) toward it 2h 2o, 20mmol Na 2cO 3and 30mL toluene, at 110 DEG C, stirring reaction is after 12 hours, product ethyl acetate is extracted, drying obtains crude product, and by crude product purified by silica gel column chromatography, (solvent volume is than being sherwood oil: ethyl acetate=80:1) purifying obtains white solid and 2-(4-chloro-phenyl-)-4,6-phenylbenzene-1,3,5-triazine, productive rate 88%, fusing point is 198 DEG C.
1H?NMR(300MHz,CDCl 3)δ8.74-8.66(m,6H),7.59-7.50(m,8H)；
13C?NMR(75MHz,CDCl 3)δ172.0,171.0,139.1,136.4,135.1,133.0,130.6,129.3,129.3,129.0。
Embodiment 3
The synthesis of 2,4-phenylbenzene-6-p-methylphenyl-1,3,5-triazines, comprises the following steps:
Get 20mmol benzamidine hydrochlorid and 14mmol 4-methylbenzyl alcohol in the round-bottomed flask of 100mL, then add 2mmol Cu (OAc) toward it 2h 2o, 20mmol Na 2cO 3and 30mL toluene, at 110 DEG C, stirring reaction is after 24 hours, product ethyl acetate is extracted, drying obtains crude product, and by crude product purified by silica gel column chromatography, (solvent volume is than being sherwood oil: ethyl acetate=100:1) purifying obtains white solid i.e. 2,4-phenylbenzene-6-p-methylphenyls-1,3,5-triazine, productive rate 88%, fusing point is 196 DEG C.
1H?NMR(300MHz,CDCl 3)δ8.72(d,J＝6.0Hz,4H),8.60(d,J＝7.8Hz,2H),7.53(d,J＝6.6Hz,6H),7.3(d,J＝7.8Hz,2H)；
13C?NMR(75MHz,d 6-DMSO)δ171.9,171.8,143.5,136.7,133.9,132.8,129.8,129.3,129.0,22.2。
Embodiment 4
The synthesis of 2,4-phenylbenzene-6-(4-trifluoromethyl)-1,3,5-triazines, comprises the following steps:
Get 20mmol benzamidine hydrochlorid and 12mmol4-trifluoromethyl benzyl alcohol in the round-bottomed flask of 100mL, then add 2mmol Cu (OAc) toward it 2h 2o, 20mmol Na 2cO 3and 30mL toluene, at 110 DEG C, stirring reaction is after 18 hours, product ethyl acetate is extracted, drying obtains crude product, and by crude product purified by silica gel column chromatography, (solvent volume is than being sherwood oil: ethyl acetate=90:1) purifying obtains white solid i.e. 2,4-phenylbenzene-6-(4-trifluoromethyl)-1,3,5-triazine, productive rate 87%, fusing point is 183 DEG C.
1H?NMR(300MHz,CDCl 3)δ8.84(d,J＝8.1Hz,2H),8.76-8.73(m,4H),7.81(d,J＝8.1Hz,2H),7.66-7.55(m,6H)；
13C?NMR(75MHz,CDCl 3)δ172.0,170.6,139.8,136.1,134.3,133.1,129.5,129.3,129.0,125.8,125.8。
Embodiment 5
The synthesis of 2-(4-p-methoxy-phenyl)-4,6-phenylbenzene-1,3,5-triazines, comprises the following steps:
Get 20mmol benzamidine hydrochlorid and 15mmol4-methoxy benzyl alcohol in the round-bottomed flask of 100mL, then add 2mmol Cu (OAc) toward it 2h 2o, 20mmol Na 2cO 3and 30mL toluene, at 110 DEG C, stirring reaction is after 24 hours, product ethyl acetate is extracted, drying obtains crude product, and by crude product purified by silica gel column chromatography, (solvent volume is than being sherwood oil: ethyl acetate=80:1) purifying obtains white solid and 2-(4-p-methoxy-phenyl)-4,6-phenylbenzene-1,3,5-triazine, productive rate 91%, fusing point is 160 DEG C.
1H?NMR(300MHz,CDCl 3)δ8.78-8.73(m,6H),7.62-7.55(m,6H),7.07(d,J＝8.7Hz,2H),3.92(s,3H)；
13C?NMR(75MHz,d 6-DMSO)δ171.5,164.1,136.3,133.8,131.5,129.8,129.4,128.4,115.2,56.4。
Embodiment 6
The synthesis of 2-(4-nitrophenyl)-4,6-phenylbenzene-1,3,5-triazines, comprises the following steps:
Get 20mmol benzamidine hydrochlorid and 14mmol 4-nitrobenzyl alcohol in the round-bottomed flask of 100ml, then add 2mmol Cu (OAc) toward it 2h 2o, 20mmol Na 2cO 3and 50mL toluene, at 110 DEG C, stirring reaction is after 12 hours, product ethyl acetate is extracted, drying obtains crude product, and by crude product purified by silica gel column chromatography, (solvent volume is than being sherwood oil: ethyl acetate=100:1) purifying obtains white solid and 2-(4-nitrophenyl)-4,6-phenylbenzene-1,3,5-triazine, productive rate 46%, fusing point is 217 DEG C.
1H?NMR(300MHz,CDCl 3)δ8.93(d,J＝8.7Hz,2H),8.78-8.75(m,4H),8.41(d,J＝9.0Hz,2H),7.68-7.57(m,6H)；
13C?NMR(75MHz,CDCl 3)δ172.4,170.3,136.0,133.4,130.2,129.4,129.2,124.1。
Embodiment 7
The synthesis of 2-phenyl-4,6-bis--p-methylphenyl-1,3,5-triazines, comprises the following steps:
Get 20mmol 4-methylbenzene amitraz hydrochloride and 13mmol phenylcarbinol in the round-bottomed flask of 100mL, then add 2mmol Cu (OAc) toward it 2h 2o, 20mmol Na 2cO 3and 30mL toluene, at 110 DEG C, stirring reaction is after 24 hours, product ethyl acetate is extracted, drying obtains crude product, and by crude product purified by silica gel column chromatography, (solvent volume is than being sherwood oil: ethyl acetate=100:1) purifying obtains white solid and 2-phenyl-4,6-bis--p-methylphenyl-1,3,5-triazine, productive rate 87%, fusing point is 233 DEG C.
1H?NMR(300MHz,CDCl 3)δ8.77(d,J＝6.0Hz,2H),8.66(d,J＝8.1Hz,4H),7.63-7.55(m,3H),7.37(d,J＝7.8Hz,4H)；
13C?NMR(75MHz,CDCl 3)δ171.9,171.8,143.4,136.8,134.0,132.7,129.7,129.3,129.3,128.9,22.1。
Embodiment 8
The synthesis of 2,4,6-, tri--p-methylphenyl-1,3,5-triazines, comprises the following steps:
Get 20mmol 4-methylbenzene amitraz hydrochloride and 12mmol 4-methylbenzyl alcohol in the round-bottomed flask of 100mL, then add 2mmol Cu (OAc) toward it 2h 2o, 20mmol Na 2cO 3and 30mL toluene, at 110 DEG C, stirring reaction is after 24 hours, product ethyl acetate extracted, drying obtains crude product, and by crude product purified by silica gel column chromatography, (solvent volume is than for sherwood oil: ethyl acetate=100:1) purifying obtains white solid that is 2,4,6-tri--p-methylphenyl-1,3,5-triazines, productive rate 86%, fusing point is 321 DEG C.
1H?NMR(300MHz,CDCl 3)δ8.65(d,J＝6.3Hz,6H),7.36(d,J＝6.3Hz,6H),2.47(s,9H)；
13C?NMR(75MHz,CDCl 3)δ171.7,143.2,134.1,129.7,129.3,22.1。
Embodiment 9
The synthesis of 2,4-dibromo phenyl-6-(4-isopropyl phenyl)-1,3,5-triazines, comprises the following steps:
Get 20mmol 4-bromobenzene amitraz hydrochloride and 14mmol 4-isopropylbenzyl alcohol in the round-bottomed flask of 100mL, then add 2mmol Cu (OAc) toward it 2h 2o, 20mmol Na 2cO 3and 30mL toluene, at 120 DEG C, stirring reaction is after 24 hours, product ethyl acetate is extracted, drying obtains crude product, and by crude product purified by silica gel column chromatography, (solvent volume is than being sherwood oil: ethyl acetate=100:1) purifying obtains white solid i.e. 2,4-dibromo phenyl-6-(4-isopropyl phenyl)-1,3,5-triazine, productive rate 66%, fusing point is 181 DEG C.
1H?NMR(300MHz,CDCl 3)δ8.59-8.52(m,6H),7.65(d,J＝8.1Hz,4H),7.40(d,J＝8.4Hz,2H),3.10-2.97(m,1H),1.34(d,J＝6.9Hz,6H)；
13C?NMR(75MHz,CDCl 3)δ172.1,170.0,154.6,135.4,133.8,132.2,130.7,129.5,127.9,127.2,34.7,24.2。
Embodiment 10
The synthesis of 2-methyl-4,6-phenylbenzene-1,3,5-triazines, comprises the following steps:
Get 20mmol benzamidine hydrochlorid and 14mmol ethanol in the round-bottomed flask of 100mL, then add 2mmolCu (OAc) toward it 2h 2o, 20mmol Na 2cO 3and 30mL toluene, at 110 DEG C, stirring reaction is after 24 hours, product ethyl acetate is extracted, drying obtains crude product, and by crude product purified by silica gel column chromatography, (solvent volume is than being sherwood oil: ethyl acetate=100:1) purifying white solid and 2-methyl-4,6-phenylbenzene-1,3,5-triazine, productive rate 63%, fusing point is 80 DEG C.
1H?NMR(300MHz,CDCl 3)δ8.58-8.55(m,4H),7.51-7.46(m,6H),2.71(s,3H)；
13C?NMR(75MHz,CDCl 3)δ177.4,171.6,136.3,132.9,129.3,129.2,26.5。
The above is only the preferred embodiment of the present invention; be noted that for a person skilled in the art, under the premise without departing from the principles of the invention, some improvements and modifications can also be made; these improvements and modifications, all should be considered as protection scope of the present invention.

Claims (7)

1. a synthetic method for 1,3,5-triazines derivative, step comprises:
A, the hydrochloride of amidine, alcohol are mixed with a hydration neutralized verdigris, sodium carbonate after, add solvent, under the condition of 110 DEG C-120 DEG C, react 12h-24h in air;
B, by product purification, through extraction, dry, concentrated after obtain 1,3,5-triazines analog derivative by column chromatography for separation.
2. synthetic method as claimed in claim 1, is characterized in that: the hydrochloride structural formula of described amidine is:
Wherein R is H, Br, CH 3.
3. synthetic method as claimed in claim 1, is characterized in that: the structural formula of described alcohol is:
Wherein: R is selected from H, CH 3, CH 3cH 2cH 2, (CH 3) 2cH, Ph, 2-CH 3-C 6h 4, 3-CH 3-C 6h 4, 4-CH 3-C 6h 4, 4-OCH 3-C 6h 4, 2-Cl-C 6h 4, 3-Cl-C 6h 4, 4-Cl-C 6h 4, 4-Br-C 6h 4, 4-F-C 6h 4, 4-CF 3-C 6h 4, 2-NO 2-C 6h 4, 3-NO 2-C 6h 4, 4-NO 2-C 6h 4, 4-(CH 3) 2cH-C 6h 4in one.
4. synthetic method as claimed in claim 1, is characterized in that: the amount of substance ratio of the hydrochloride of described amidine, alcohol, a hydration neutralized verdigris, sodium carbonate is: 2:(1-1.5): 0.2:2.
5. synthetic method as claimed in claim 1, is characterized in that: the hydrochloride concentration in a solvent of described amidine is: 0.40-0.67mol/L.
6. synthetic method as claimed in claim 1, is characterized in that: described solvent is toluene.
7. synthetic method as claimed in claim 1, it is characterized in that: in described step B, purifying is specially: be extracted with ethyl acetate by products therefrom, anhydrous sodium sulfate drying, concentrating under reduced pressure, obtaining crude product, take volume ratio as sherwood oil: the mixed solvent of ethyl acetate=80-100:1 is developping agent, obtains 1 by column chromatography for separation, 3,5-compound in triazine class.
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CN106866563A (en) * 2015-12-11 2017-06-20 中国科学院大连化学物理研究所 A kind of method for preparing the pyrrolotriazine derivatives of bis- substitutions of 2,4- -1,3,5
CN108409672A (en) * 2018-03-28 2018-08-17 安徽师范大学 A kind of method that mantoquita catalyzes and synthesizes polysubstituted pyrimidine
CN109810069A (en) * 2019-03-27 2019-05-28 郑州轻工业学院 A kind of preparation method of polysubstituted 1,3,5- triazine
CN109810069B (en) * 2019-03-27 2020-10-30 郑州轻工业学院 Preparation method of polysubstituted 1,3, 5-triazine
CN110054593A (en) * 2019-05-16 2019-07-26 南京工业大学 A method of synthesis 1,3,5- pyrrolotriazine derivatives
CN110054593B (en) * 2019-05-16 2022-07-08 南京工业大学 Method for synthesizing 1,3, 5-triazine derivative
CN110407759A (en) * 2019-07-04 2019-11-05 深圳市格物致欣化学技术有限公司 1,3,5 replace triaizine compounds and preparation method thereof

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