CN102603660A - Preparation method of 1H-1,2,3-triazole compound - Google Patents
Preparation method of 1H-1,2,3-triazole compound Download PDFInfo
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- CN102603660A CN102603660A CN2012100294082A CN201210029408A CN102603660A CN 102603660 A CN102603660 A CN 102603660A CN 2012100294082 A CN2012100294082 A CN 2012100294082A CN 201210029408 A CN201210029408 A CN 201210029408A CN 102603660 A CN102603660 A CN 102603660A
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- KRKLBJRYAJTCLR-UHFFFAOYSA-N C(c1ccccc1)[n]1nnc(-c2ccncc2)c1 Chemical compound C(c1ccccc1)[n]1nnc(-c2ccncc2)c1 KRKLBJRYAJTCLR-UHFFFAOYSA-N 0.000 description 1
- YGQCEDGIWRCCBM-UHFFFAOYSA-N CCCC[n]1nnc(-c2ccccc2)c1 Chemical compound CCCC[n]1nnc(-c2ccccc2)c1 YGQCEDGIWRCCBM-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a preparation method of a 1H-1,2,3-triazole compound as shown in a formula (I), which comprises the following steps: mixing halide as shown in a formula (III) with alkyne-terminated compound as shown in a formula (II) and sodium azide, reacting for 5-85 hours at 25-80 DEG C in a reaction solvent under the catalytic action of porous copper; after finishing the reaction, performing after-treatment of the reaction solution to obtain the 1H-1,2,3-triazole compound as shown in the formula (I), wherein the solvent is de-ionized water, acetonitrile, anhydrous ethanol, toluene, acetone, N,N-dimethylformamide, tetrahydrofuran or dioxane. The preparation method provided by the invention adopts one-pot operation, the catalyst can be reused for multiple times, the reaction condition is mild, and the operation is easy and simple.
Description
(1) technical field
The present invention relates to a kind of 1H-1,2, the preparation method of 3-triazole compounds.
(2) background technology
1H-1,2, the 3-triazole class compounds is widely used in synthetic fields such as agricultural chemicals, medicine as important industrial chemicals midbody.About 1H-1,2, up to the present the compound method of 3-triazole class compounds is reported less: 1. through PS sulfonyl hydrazide and 1; The effect of 1-Dichloro acetone obtains the chloroformyl sulphonyl hydrazone of α-two, prepares (Makam S.Raghavendra and Yulin Lam with amine through cyclic action again; Tetrahedron Letters; 2004,45,6129-6132).2. carry out 1 through copper catalysis alkynes/trinitride; The click reaction of 3-dipole cycloaddition (CuACC) prepares (Christian W.
Caspar Christensen; And Morten Melda.J.Org.Chem; 2002,67,3057-3064).3. with aniline raw material, through the diazo transfer of copper (II) catalysis, then under the reductive action of sodium ascorbate; 1 of the copper that obtains (I) catalysis alkynes/nitrine; The cycloaddition of 3-dipole (Henning S.G.Beckmann and Valentin Wittmann.Org.Lett.2007,9 (1), 1-4).But still there are a lot of defectives in above-mentioned preparation method: expensive like catalyzer, be difficult to obtain, generate by product easily, and yield is not high, and the scope of application is wideless, and limitation is bigger, and condition is harsh, has therefore limited its applicability.
(3) summary of the invention
The present invention seeks to improve the various defectives of prior art, provide be easy to get the repeatedly recycling, mild condition, one kettle way easy and simple to handle of a kind of catalyzer to prepare 1H-1,2, the method for 3-triazole class compounds.
For realizing the foregoing invention purpose, the technical scheme that the present invention adopts is:
1H-1 shown in a kind of formula (I), 2, the preparation method of 3-triazole class compounds; Described preparation method is: the halides shown in the formula (III) is mixed with end-group alkyne compounds and the sodiumazide shown in the formula (II); In reaction solvent under the katalysis of porous copper in 25～80 ℃ of reaction 5～85h, after reaction finished, the reaction solution aftertreatment made the 1H-1 shown in the formula (I); 2, the 3-triazole class compounds; Described reaction solvent is deionized water, acetonitrile, absolute ethyl alcohol, toluene, acetone, N, dinethylformamide, THF or dioxane;
In formula (I), formula (II) or the formula (III), X is halogen, OAc, OMs (methylsulfonic acid base) or OTf (trifluoromethanesulfonic acid base); R
1Be C1 to C13 alkyl, benzyl, substituted benzyl or ethyl acetate base, the substituting group on the said substituted benzyl phenyl ring is single halogen or the single C1 to C5 of replacement alkyl of replacing; R
2Be C6 to C13 alkyl, 5 yuan to 9 yuan cycloalkenyl groups, phenyl, substituted-phenyl, phthalimide methyl or pyridyl, the substituting group of said substituted-phenyl is single C1 to C5 alkoxyl group or single halogen that replaces of replacing.
Further, X is preferably Br, Cl or I.
Further, R
1Be preferably benzyl, C1 to C8 alkyl or ethyl acetate base.Further, preferred ethyl of the alkyl of described C1 to C8 or butyl.
Further, R
2Be preferably phenyl, p-methoxyphenyl, to ethoxyl phenenyl, rubigan, a fluorophenyl, 4-pyridyl, 1-cyclohexenyl, phthalimide methyl or C6 to C10 alkyl.Further, the preferred octyl group of said C6 to C10 alkyl.
Concrete, the end-group alkyne compounds shown in the preferred formula of the present invention (II) is phenylacetylene, 4-anisole acetylene, 4-phenetole acetylene, 4-chlorobenzene acetylene, 3-fluorobenzene acetylene, 1-phthalic imidine propine, 4-pyrrole heavy stone used as an anchor acetylene, 1-cyclohexenyl acetylene or 1-octyne.
Concrete, the halides shown in the preferred formula of the present invention (III) is benzyl bromine, benzyl chlorine, iodoethane, bromination of n-butane or 1-METHYL BROMOACETATE.
Among the present invention, described reaction solvent is preferably deionized water, has environmental protection, cost is low, reaction yield is high advantage.
Among the present invention, described catalyzer is a porous copper, and the aperture is preferably 5～150 μ m, and more preferably 5～50 μ m further are preferably 5～20 μ m, most preferably are 5 μ m.Porous copper uses the commercial goods among the present invention.
Among the present invention, described halides (III) is 1: 1.0～1.2: 1.2～2: 0.05～0.15 with the ratio of the amount of substance that feeds intake of end-group alkyne compounds (II), sodiumazide, copper catalyst, most preferably is 1: 1.1: 2: 0.05.
Among the present invention, the volumetric usage of said reaction solvent is counted 4～10ml/mmol with the mole number of halides (III), most preferably is 4ml/mmol.
Reaction conditions of the present invention is gentle, and preferable reaction temperature is at 55～60 ℃, and the preferred reaction time is 8～50h.
The present invention is after reaction finishes, and the gained reaction solution can obtain title product through conventional aftertreatment.The present invention recommends described post-treating method to be: after reaction finished, the gained reaction solution was used ethyl acetate extraction, the saturated sodium-chloride washing; Organic phase is dry, concentrates, and be that 5: 1 sherwood oil and ETHYLE ACETATE is as developping agent with volume ratio then; Carry out column chromatography, collect R
fThe elutriant of value 0.3～0.35, underpressure distillation, drying obtains 1H-1, and 2, the 3-triazole class compounds.
The described 1H-1 of the concrete recommendation of the present invention, 2, the preparation method of 3-triazole class compounds carries out according to following steps: the halides shown in the formula (III) is mixed with end-group alkyne compounds and the sodiumazide shown in the formula (II); In deionized water under the katalysis of porous copper in 55 ℃～60 ℃ reaction 8～50h, after reaction finished, the gained reaction solution was used ethyl acetate extraction; The saturated sodium-chloride washing; Organic phase is dry, concentrates, and be that 5: 1 sherwood oil and ETHYLE ACETATE is as developping agent with volume ratio then; Carry out column chromatography, collect R
fThe elutriant of value 0.3～0.35, underpressure distillation, drying obtains the 1H-1 shown in (I), and 2, the 3-triazole class compounds; Described halides (III) is 1: 1.1: 2 with the ratio of the amount of substance that feeds intake of end-group alkyne compounds (II), sodiumazide, porous copper: 0.05; The volumetric usage of described deionized water is counted 4ml/mmol with the mole number of halides (III).
Compared with prior art, 1H-1 provided by the invention, 2, the preparing method's of 3-triazole class compounds advantage is:
(1) the present invention has adopted the one kettle way method to prepare 1H-1, and 2, the 3-triazole class compounds, reaction conditions is gentle, and is easy to operate.
(2) the present invention has selected for use the porous copper that cheaply is easy to get as catalyzer, and this catalyzer just need not handle and can reuse repeatedly, meets the atom economy principle; The present invention has simultaneously selected for use deionized water as solvent, and environmentally friendly, cost is low, and reaction yield is high, good product quality.
In view of 1H-1,2, the 3-triazole class compounds has stronger biological activity, as has antianaphylaxis, antibiotic, HIV-resistant activity, therefore in medicinal design, be widely used, so the present invention has the wide industrial application prospect.
(4) embodiment
To be further described the present invention through embodiment below, but protection scope of the present invention is not limited thereto.
The porous copper that the embodiment of the invention is used is produced by Changsha Liyuan New Material Co., Ltd..
Embodiment 1: the preparation of the 1-benzyl-4-phenyl-1,2,3-triazoles shown in the formula (I-1)
With the benzyl bromine shown in the formula (III-1) (171.0mg, 1mmol), sodiumazide (130mg; 2mmol), and the phenylacetylene shown in the formula (II-1) (112.3mg, 1.1mmol); (5 μ m apertures, 3.2mg 0.05mmol) mix in deionized water (4ml) porous copper; Stirring reaction 29h in 55 ℃ of oil baths, TLC follows the tracks of reaction.After reaction finished, with ETHYLE ACETATE (10mL * 3) extraction, the saturated common salt water washing merged organic phase, and anhydrous sodium sulfate drying filters, and concentrated column chromatography (sherwood oil: ETHYLE ACETATE=5: 1), collect R
fThe elutriant of value 0.3～0.35, underpressure distillation, drying obtains target compound 224.6mg, and yield is 95.47%, white needle-like crystals.
1HNMR(CDCl
3)：δ＝7.81-7.83(m，2H)，7.68(s，1H)，7.39-7.43(m，5H)，7.32-7.34(m，3H)，5.59(s，2H)
Embodiment 2:
The amount of porous copper is increased to 6.4mg (0.10mmol), and the reaction times is 10 hours, and other are operated with embodiment 1, and yield is 94.9%.
Embodiment 3:
The amount of porous copper is increased to 9.6mg (0.15mmol), and the reaction times is 29 hours, and other are operated with embodiment 1, and yield is 94.81%.
Embodiment 4:
The amount of porous copper is increased to 12.8mg (0.20mmol), and the reaction times is 27.5 hours, and other are operated with embodiment 1, and yield is 94.25%.
Embodiment 5:
Change porous copper (5 μ m) into porous copper (20 μ m), the reaction times is 28 hours, and other are operated with embodiment 1, and yield is 87.20%.
Embodiment 6:
Change porous copper (5 μ m) into porous copper (50 μ m), the reaction times is 43.5 hours, and other are operated with embodiment 1, and yield is 65.76%.
Embodiment 7:
Change porous copper (5 μ m) into porous copper (150 μ m), the reaction times is 85 hours, and other are operated with embodiment 1, and yield is 27.30%.
Embodiment 8:
Temperature of reaction is brought up to 80 ℃, and the reaction times is 11 hours, and other are operated with embodiment 1, and yield is 94.99%.
Embodiment 9:
Change solvent deionized water into acetonitrile, the reaction times is 22.5 hours, and other are operated with embodiment 1, and yield is 10.20%.
Embodiment 10:
Change solvent deionized water into absolute ethyl alcohol, the reaction times is 34 hours, and other are operated with embodiment 1, and yield is 44.17%.
Embodiment 11:
Change solvent deionized water into toluene, the reaction times is 28.5 hours, and other are operated with embodiment 1, and yield is a trace.
Embodiment 12:
Change solvent deionized water into acetone, the reaction times is 24.5 hours, and other are operated with embodiment 1, and yield is 58.78%.
Embodiment 13:
Change solvent deionized water into N, dinethylformamide, the reaction times is 52.5 hours, and other are operated with embodiment 1, and yield is 28.10%.
Embodiment 14:
Change solvent deionized water into THF, the reaction times is 54.5 hours, and other are operated with embodiment 1, and yield is 4.50%.
Embodiment 15:
Change solvent deionized water into dioxane, the reaction times is 69 hours, and other are operated with embodiment 1, and yield is 5.30%.
Embodiment 16: the preparation of the 1-benzyl-4-p-methoxyphenyl-1,2,3-triazoles shown in the formula (I-2)
Substitute phenylacetylene with 145.4mg (1.1mmol) 4-anisole acetylene (II-2), other are operated with embodiment 1, obtain title product (I-2) 257.9mg, and yield is 97.2%, white solid.
1HNMR(CDCl
3)：δ＝7.74(d，J＝8.5Hz，2H)，7.59(s，1H)，7.39-7.41(m，3H)，7.32-7.34(m，2H)，6.95(d，J＝8.5Hz，2H)，5.58(s，2H)，3.85(m，3H)
The preparation of embodiment 17:1-benzyl-4-(1-cyclohexenyl)-1,2,3-triazoles
Substitute phenylacetylene with 116.8mg (1.1mmol) 1-cyclohexenyl phenylacetylene (II-3), other are operated with embodiment 1, obtain title product (I-3) 135.5mg, and yield is 56.60%, white solid.
1HNMR(CDCl
3)：δ＝7.36-7.40(m，3H)，7.30(s，1H)，7.30-7.25(m，2H)，6.49-6.51(m，1H)，5.52(s，2H)，2.35-2.38(m，2H)，2.17-2.22(m，2H)，1.73-1.78(m，2H)，1.64-1.69(m，2H).
The preparation of embodiment 18:1-benzyl-4-hexyl-1,2,3-triazoles
Substitute phenylacetylene with 121.2mg (1.1mmol) 1-octyne (II-4), other are operated with embodiment 1, obtain title product (I-4) 222.7mg, and yield is 91.50%.
1HNMR(CDCl
3)：δ＝7.36-7.38(m，3H)，7.25-7.28(m，2H)，7.19(s，1H)，5.50(s，2H)，2.69(t，J＝7.8Hz，2H)，1.63-1.68(m，2H)，1.28-1.35(m，6H)，0.88(t，J＝6.9Hz，3H)
Embodiment 19:1-benzyl-4-is to the preparation of ethoxyl phenenyl-1,2,3-triazoles
Substitute phenylacetylene with 160.8mg (1.1mmol) 4-phenetole acetylene (II-5), other are operated with embodiment 1, obtain title product (I-5) 252.3mg, and yield is 90.33%, white solid.
1HNMR(CDCl
3)：δ＝7.71-7.73(m，2H)，7.58(s，1H)，7.39-7.41(m，3H)，7.32-7.7.33(m，2H)，6.93-6.94(m，2H)，5.58(s，2H)，4.07(q，J＝7.0Hz，2H)，1.44(t，J＝7.0Hz，3H).
The preparation of embodiment 20:1-benzyl-4-pyridyl-1,2,3-triazoles
Substitute phenylacetylene with 153.5mg (1.1mmol) 4-pyridine acetylene hydrochloride (II-6), other are operated with embodiment 1, obtain title product (I-6) 92.1mg, and yield is 38.97%, the yellow-green colour solid.
1HNMR(CDCl
3)：δ＝8.65(d，J＝5.8Hz，2H)，7.80(s，1H)，7.70-7.71(m，2H)，7.41-7.44(m，3H)，7.33-7.35(m，2H)，5.62(s，2H).
The preparation of embodiment 21:1-benzyl-4-phenyl-1,2,3-triazoles
Substitute the benzyl bromine with 126.6mg (1mmol) benzyl chlorine (III-2), other are operated with embodiment 1, obtain title product (I-1) 221.2mg, and yield is 94.00%.
The preparation of embodiment 22:1-ethyl acetate base-4-phenyl-1,2,3-triazoles
Substitute the benzyl bromine with 166.0mg (1mmol) 1-METHYL BROMOACETATE (III-3), other are operated with embodiment 1, obtain title product (I-7) 228.2mg, and yield is 98.80%, white solid.
1HNMR(CDCl
3)：δ＝7.93(s，1H)，7.86-7.87(m，2H)，7.43-7.46(m，2H)，7.35-7.38(m，1H)，5.22(s，2H)，4.31(q，J＝7.2Hz，2H)，1.33(t，J＝7.2Hz，3H).
The preparation of embodiment 23:1-ethyl-4-phenyl-1,2,3-triazoles
Substitute the benzyl bromine with 156.0mg (1mmol) iodoethane (III-4), other are operated with embodiment 1, obtain title product (I-8) 137.9mg, and yield is 79.60%, white solid.
1HNMR(CDCl
3)：7.84-7.86(m，2H)，7.78(s，1H)，7.42-7.46(m，2H)，7.33-7.36(m，1H)，4.48(q，J＝7.4Hz，2H)，1.62(t，J＝7.4Hz，3H).
Embodiment 24:
1-benzyl-4-phthalimide methyl-1,2,3-triazoles
Substitute phenylacetylene with 203.7mg (1.1mmol) phthalic imidine propine (II-7), other are operated with embodiment 1, obtain title product (I-6) 33.1mg, and yield is 10.4%, white solid.
1H?NMR(CDCl
3)：δ＝7.84(s，1H)，7.72-7.81(m，4H)，7.14-7.27(m，5H)，5.81(s，2H)，4.81(s，2H).
Embodiment 25:
1-benzyl-4-rubigan-1,2,3-triazoles
With 150.2mg (1.1mmol) chlorobenzene acetylene (II-8) is substituted phenylacetylene, other are operated with embodiment 1, obtain title product (I-10) 243.6mg, and yield is 90.3%, white solid.
1H?NMR(CDCl
3)：δ＝7.74-7.76(m，2H)，7.66(s，1H)，7.33-7.42(m，7H)，5.60(s，2H).
Embodiment 26:
Fluorophenyl-1,2,3-triazoles between 1-benzyl-4-
Substitute phenylacetylene with fluorobenzene acetylene (II-9) between 132.1mg (1.1mmol), other are operated with embodiment 1, obtain title product (I-11) 221.9mg, and yield is 87.6%, white solid.
1H?NMR(CDCl
3)：δ＝7.68(s，1H)，7.53-7.58(m，2H)，7.32-7.44(m，6H)，7.00-7.04(m，1H)，5.60(s，2H).
Embodiment 27:
Substitute the benzyl bromine with 137.0mg (1mmol) 1-bromination of n-butane (III-5), other are operated with embodiment 1, obtain title product (I-12) 58.2mg, and yield is 28.91%, white solid.
1H?NMR(CDCl
3)：δ＝7.85-7.87(m，2H)，7.77(s，1H)，7.43-7.46(m，2H)，7.33-7.37(m，1H)，4.43(t，J＝7.2Hz，2H)，1.93-1.99(m，2H)，1.38-1.46(m，2H)，1.00(t，J＝7.5Hz，3H)。
Claims (10)
1. the 1H-1 shown in the formula (I), 2, the preparation method of 3-triazole class compounds; Described preparation method is: the halides shown in the formula (III) is mixed with end-group alkyne compounds and the sodiumazide shown in the formula (II); In reaction solvent under the katalysis of porous copper in 25～80 ℃ of reaction 5～85h, after reaction finished, the reaction solution aftertreatment made the 1H-1 shown in the formula (I); 2, the 3-triazole class compounds; Described solvent is deionized water, acetonitrile, absolute ethyl alcohol, toluene, acetone, N, dinethylformamide, THF or dioxane;
In formula (I), formula (II) or the formula (III), X is halogen, OAc, OMs or OTf; R
1Be C1 to C13 alkyl, benzyl, substituted benzyl or ethyl acetate base, the substituting group on the said substituted benzyl phenyl ring is single halogen or the single C1 to C5 of replacement alkyl of replacing; R
2Be C6 to C13 alkyl, 5 yuan to 9 yuan cycloalkenyl groups, phenyl, substituted-phenyl or pyridyl, the substituting group of said substituted-phenyl is single C1 to C5 alkoxyl group or single halogen that replaces of replacing.
2. 1H-1 as claimed in claim 1,2, the preparation method of 3-triazole class compounds is characterized in that: X is Br, Cl or I; R
1Be benzyl, C1 to C4 alkyl or ethyl acetate base; R
2For phenyl, p-methoxyphenyl, to ethoxyl phenenyl, rubigan, a fluorophenyl, 4-pyridyl, 1-cyclohexenyl, phthalimide methyl or C6 to C10 alkyl.
3. 1H-1 as claimed in claim 1,2, the preparation method of 3-triazole class compounds is characterized in that: described reaction solvent is a deionized water.
4. like the described 1H-1 of one of claim 1～3,2, the preparation method of 3-triazole class compounds is characterized in that: the aperture of described porous copper is 5～150 μ m.
5. 1H-1 as claimed in claim 4,2, the preparation method of 3-triazole class compounds is characterized in that: the aperture of described porous copper is 5～20 μ m.
6. 1H-1 as claimed in claim 5,2, the preparation method of 3-triazole class compounds is characterized in that: the aperture of described porous copper is 5 μ m.
7. like the described 1H-1 of one of claim 1～3; 2; The preparation method of 3-triazole class compounds is characterized in that: described halides is 1: 1.0～1.2: 1.2～2: 0.05～0.15 with the ratio of the amount of substance of end-group alkyne compounds, sodiumazide, porous copper.
8. 1H-1 as claimed in claim 6; 2; The preparation method of 3-triazole class compounds; It is characterized in that: described halides is 1: 1.1: 2 with the ratio of the amount of substance of end-group alkyne compounds, sodiumazide, porous copper: 0.05, and the volumetric usage of said reaction solvent is counted 4ml/mmol with the mole number of halides.
9. like the described 1H-1 of one of claim 1～3,2, the preparation method of 3-triazole class compounds is characterized in that: temperature of reaction is 55～60 ℃, the reaction times is 8～50h.
10. 1H-1 as claimed in claim 8,2, the preparation method of 3-triazole class compounds is characterized in that: temperature of reaction is 55～60 ℃, the reaction times is 8～50h.
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