CN107382887A - A kind of method of synthesis N alkenyloxy group benzotriazole compounds - Google Patents
A kind of method of synthesis N alkenyloxy group benzotriazole compounds Download PDFInfo
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- CN107382887A CN107382887A CN201710546029.3A CN201710546029A CN107382887A CN 107382887 A CN107382887 A CN 107382887A CN 201710546029 A CN201710546029 A CN 201710546029A CN 107382887 A CN107382887 A CN 107382887A
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- triazole
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- 0 *c(cc1)ccc1C(O[n]1nnc2c1cccc2)=C Chemical compound *c(cc1)ccc1C(O[n]1nnc2c1cccc2)=C 0.000 description 2
- PDDFNYBNTAXNOH-UHFFFAOYSA-N C=C(CO[n]1nnc2c1cccc2)c1ccccc1 Chemical compound C=C(CO[n]1nnc2c1cccc2)c1ccccc1 PDDFNYBNTAXNOH-UHFFFAOYSA-N 0.000 description 1
- FQCDSVCYKHXZBD-UHFFFAOYSA-O [NH2+]=Nc(cccc1)c1NOC(CI)c(cc1)ccc1F Chemical compound [NH2+]=Nc(cccc1)c1NOC(CI)c(cc1)ccc1F FQCDSVCYKHXZBD-UHFFFAOYSA-O 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
Abstract
The invention discloses the synthetic method of the N alkenyloxy group benzotriazole compounds shown in a kind of formula (II)：β iodo N alkoxies BTA, acid binding agent shown in formula (I) is mixed in organic solvent, 4~8h is reacted at 0~40 DEG C, reaction obtains reaction solution completely, and the reaction solution is post-treated to obtain described N alkenyloxy group benzotriazole compounds；Described acid binding agent is potassium tert-butoxide, potassium hydroxide, sodium hydroxide, sodium iodide, pyridine, caustic alcohol, the alkene of 1,8 diazabicylo, 11 carbon 7 or triethylamine；Feed intake the ratio between the amount of material of N alkenyloxy group benzotriazole compounds shown in the formula (1) and described acid binding agent is 1：0.5~2；Inventive substrate adaptability is good, reaction condition is gentle, is not related to the use of metallic catalyst, and safety and environmental protection, operation is simple, is more conducive to its application in medicine synthesizes.
Description
(1) technical field
The present invention relates to a kind of method of synthesis N- alkenyloxy group benzotriazole compounds, with styrene, N- hydroxy benzenes
And triazole etc. is raw material, a variety of N- alkenyloxy groups benzotriazole chemical combination can be realized by two-step reaction in a mild condition
The synthesis of thing.
(2) background technology
Document report about N- alkenyloxy group benzotriazole compounds is less, Kumar seminars in 2013
(M.Kumar, M.Scobie, M.S.Mashuta, G.B.Hammond, B.Xu, Org.Lett.2013,15,724-727) is reported
N- hydroxy benzo triazoles and Terminal Acetylenes reaction generation N- alkenyloxy group benzotriazole compounds in the case where gold is catalyzed.2015
Kong seminars (Lingbing Kong, a Rakesh Ganguly, Yongxin Lib and Rei Kinjo,
Chem.Sci., 2015,6,2893-2902) in the case where gold is catalyzed, generated with N- hydroxy benzo triazoles and end ene compound reaction
N- alkenyloxy group benzotriazole compounds, N-O structures therein and alkenyl ether structure have good reactivity worth, Ke Yijin
One step is converted into other various organic matters,As N-O structures can reset generation carbonyls, the nitrogen of benzo three in a heated condition Azoles can be used as leaving group, so as to introduce other a series of functional groups.And the compound passes through further derivative reaction The product with bioactivity is obtained, such as treats the medicine of angiocardiopathy.But the Au catalyst price needed for-above-mentioned reaction is held high Expensive, ligand structure is complicated, and synthesis is difficult.But the Au catalyst needed for-reaction is expensive, and ligand structure is complicated, and synthesis is difficult.
Based on this, the new method of one synthesis N- alkenyloxy group benzotriazole compound without metal catalytic of design, which seems, very must
Will.
(3) content of the invention
To solve the problems, such as that prior art is present, object of the present invention is to provide a kind of nitrogen of N- alkenyloxy groups benzo three
The new method of azole compounds synthesis.
To reach above-mentioned purpose, the technical solution adopted by the present invention is as follows：
A kind of synthetic method of N- alkenyloxy group benzotriazole compounds shown in formula (II), described synthetic method
For：
β shown in formula (I)-iodo N- alkoxies BTA, acid binding agent are mixed in organic solvent, 0~40
4~8h is reacted at DEG C, extent of reaction is tracked by TLC, reaction completely obtains reaction solution, and the reaction solution is post-treated to obtain institute
The N- alkenyloxy group benzotriazole compounds stated；Described acid binding agent is potassium tert-butoxide, potassium hydroxide, sodium hydroxide, iodate
Sodium, pyridine, caustic alcohol, the carbon -7- alkene of 1,8- diazabicylos 11 or triethylamine (being preferably potassium tert-butoxide)；Formula (1) institute
Feed intake the ratio between the amount of material of the N- alkenyloxy group benzotriazole compounds shown and described acid binding agent is 1：0.5~2 (is preferably
1:1)；
In formula (I) or formula (II)：
R is C3~12Straight chained alkyl or by halogen, C1~5Alkyl-substituted phenyl.
Synthetic method of the present invention, β-iodo N- alkoxy BTA chemical combination shown in preferably described formula (I)
Thing is selected from one of following：1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole, (the iodo- 1- of 2- are (to toluene by 1-
Base) ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (4- fluorophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,
2,3] triazole, 1- (1- (4- chlorphenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (4- bromophenyls) -
2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (4- aminomethyl phenyls) -2- iodine ethyoxyl) -1H- benzos [d]
[1,2,3] triazole, 1- (1- (4- chloromethyl phenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (2-
Bromophenyl) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (the iodo- 2- octyloxies of 2-) -1H- benzos [d] [1,2,
3] triazole.Most preferably 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole, (the iodo- 1- of 2- are (to toluene by 1-
Base) ethyoxyl) -1H- benzos [d] [1,2,3] triazole or 1- (1- (4- fluorophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,
3] triazole.
Further, described organic solvent is tetrahydrofuran, methanol, ethanol, acetonitrile, ether or dichloromethane；Preferably
Acetonitrile.
Further, the volumetric usage of described organic solvent is with the β shown in formula (I)-nitrogen of iodo N- alkoxies benzo three
The amount of the material of azoles is calculated as 4~12ml/mmol.
The method of reaction solution of the present invention post processing is：After reaction terminates, reaction solution is first concentrated under reduced pressure to give
Grease, gained grease carry out column chromatography for separation again, with volume ratio 20：1 or 9:1 petrol ether/ethyl acetate mixed liquor is
Eluant, eluent, the eluent containing target compound is collected, dried after solvent is evaporated off, produce described N- alkenyloxy group benzotriazoles
Compound.
More specifically, method of the present invention can be carried out as follows：
β shown in formula (1)-iodo N- alkoxies BTA, potassium tert-butoxide are mixed in organic solvent, 0~
4~8h is reacted at 40 DEG C, reaction solution first carries out being concentrated under reduced pressure to give grease, and the grease carries out column chromatography for separation again, with
Volume ratio 20：1 or 9:1 petrol ether/ethyl acetate mixed liquor is eluant, eluent, collects and merges the eluent containing target compound,
Dried after solvent is evaporated off, produce described N- alkenyloxy group benzotriazole compounds；β-iodo N- alkane shown in the formula (1)
The ratio between amount for the material that feeds intake of epoxide BTA and acid binding agent is 1：1；β-iodo N- alkoxy benzenes shown in the formula (I)
And 3-triazole compounds are selected from one of following：1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole, 1- (2-
Iodo- 1- (p-methylphenyl) ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (4- fluorophenyls) -2- iodine ethyoxyl) -1H-
Benzo [d] [1,2,3] triazole, 1- (1- (4- chlorphenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1-
(4- bromophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (4- aminomethyl phenyls) -2- iodine ethyoxyl) -
1H- benzos [d] [1,2,3] triazole, 1- (1- (4- chloromethyl phenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole,
1- (1- (2- bromophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (the iodo- 2- octyloxies of 2-) -1H- benzos
[d] [1,2,3] triazole.Described organic solvent is selected from one of following：Tetrahydrofuran, acetonitrile, methanol, ethanol, ether or dichloro
Methane；The ratio between amount of material of β-iodo N- alkoxy BTAs shown in the volumetric usage and formula (I) of described solvent
For 4~12ml/mmol.
β-iodo-N- alkoxy benzo triazole compounds shown in starting materials of formulae (I) of the present invention can be according to as follows
Prepared by step, but be not limited only to this：
By the N- hydroxy benzo triazoles shown in formula (III), the substituted olefine class compound shown in formula (IV), elemental iodine and
TBHP is mixed in polar solvent 1, and in 2- dichloroethanes, after reacting 4h at 50 DEG C, (thin-layered chromatography monitoring is anti-
Answer terminal) reaction obtain reaction solution completely, reaction solution is concentrated under reduced pressure to give grease through first carrying out, and gained grease carries out post again
Chromatography, with volume ratio 6：1 petrol ether/ethyl acetate mixed liquor is eluant, eluent, collects and merges containing target compound
Eluent, dried after solvent is evaporated off, produce described β-iodo-N- alkoxy benzo triazole compounds；The formula (I)
Shown N- hydroxy benzo triazoles and the substituted olefine class compound shown in formula (II), elemental iodine and TBHP
The ratio between the amount of material of feeding intake is 1.2：1：0.5：2.
In formula (IV), the R be 4- fluorophenyls, 4- chlorobenzyls phenyl, 4- bromophenyls, p-methylphenyl, to chloromethylbenzene
Base, 2- bromophenyls, phenyl or methyl, or hexyl.
Compared with prior art, the beneficial effects of the invention are as follows：
(1) safety and environmental protection, waste gas is not produced, is more conducive to its application in medicine synthesizes；
(2) reaction condition is gentle, and substrate adaptability is good, and a variety of substituents can realize corresponding N- alkenyloxy groups benzo three
Nitrogen azole compounds, yield are improved；
(3) directly using β-iodo N- alkoxy benzo 3-triazole compounds as raw material, whole process does not need catalyst, instead
Should be simple to operate, it is a kind of variation route for synthesizing the N- alkenyloxy group benzotriazole compounds containing various different substituents.
(4) example is embodied
With reference to specific embodiment, the present invention is described in further detail, but protection scope of the present invention and not only
It is limited to this.
Embodiment 1
1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole
By N- hydroxy benzo triazoles (486mg, 3.6mmol), styrene (312mg, 3 mmol), iodine (381mg,
1.5mmol) and TBHP (772mg, 6mmol, 70% aqueous solution) is added in flask, adds solvent 1,2-
Dichloroethanes 20ml, reacted 4 hours at 50 DEG C.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Oil
Ether/ethyl acetate volume ratio 6：1) isolated 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole
833mg。
Embodiment 2
1- (1- (4- fluorophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole will
N- hydroxy benzo triazoles (486mg, 3.6mmol), 4- fluorobenzene ethenes (366mg, 3mmol), iodine (381mg, 1.5mmol)
And TBHP (772mg, 6mmol, 70% aqueous solution) is added in flask, solvent 1,2- dichloroethanes are added
20ml, reacted 4 hours at 50 DEG C.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petroleum ether/acetic acid second
Ester volume ratio 6：1) isolated 1- (1- (4- fluorophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole 758mg.
Embodiment 3
1- (1- (4- chlorphenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole
By N- hydroxy benzo triazoles (486mg, 3.6mmol), 4- chlorostyrenes (416mg, 3mmol), iodine (381mg,
1.5mmol) and TBHP (772mg, 6mmol, 70% aqueous solution) is added in flask, adds solvent 1,2-
Dichloroethanes 20ml, reacted 4 hours at 50 DEG C.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Oil
Ether/ethyl acetate volume ratio 6：1) isolated 1- (1- (4- chlorphenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] three
Azoles 718mg.
Embodiment 4
1- (1- (4- bromophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole
By N- hydroxy benzo triazoles (486mg, 3.6mmol), 4- bromstyrols (542mg, 3mmol), iodine
(381mg, 1.5mmol) and TBHP (772mg, 6mmol, 70% aqueous solution) are added in flask, are added molten
Agent 1,2- dichloroethanes 20ml, reacted 4 hours at 50 DEG C.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：
Petrol ether/ethyl acetate volume ratio 6：1) isolated 1- (1- (4- bromophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,
3] triazole 877mg.
Embodiment 5
1- (1- (4- aminomethyl phenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole
By I-hydroxybenzotriazole (486mg, 3.6mmol), 4- methyl styrenes (354mg, 3mmol), iodine
(381mg, 1.5mmol) and TBHP (772mg, 6mmol, 70% aqueous solution) are added in flask, are added molten
Agent 1,2- dichloroethanes 20ml, reacted 4 hours at 50 DEG C.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：
Petrol ether/ethyl acetate volume ratio 6：1) the isolated 705mg of compound 2.
Embodiment 6
1- (1- (4- chloromethyl phenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] three
Azoles
By N- hydroxy benzo triazoles (486mg, 3.6mmol), 4- 1-chloro-4-methyl-benzenes (456 mg, 3mmol), iodine
(381mg, 1.5mmol) and TBHP (772mg, 6mmol, 70% aqueous solution) are added in flask, are added molten
Agent 1,2- dichloroethanes 20ml, reacted 4 hours at 50 DEG C.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：
Petrol ether/ethyl acetate volume ratio 6：1) isolated 1- (1- (4- chloromethyl phenyls) -2- iodine ethyoxyl) -1H- benzos [d]
[1,2,3] triazole 793mg.
Embodiment 7
1- (1- (2- bromophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole
By N- hydroxy benzo triazoles (486mg, 3.6mmol), 2- bromstyrols (546mg, 3mmol), iodine
(381mg, 1.5mmol) and TBHP (772mg, 6mmol, 70% aqueous solution) are added in flask, are added molten
Agent 1,2- dichloroethanes 20ml, reacted 4 hours at 50 DEG C.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：
Petrol ether/ethyl acetate volume ratio 6：1) isolated 1- (1- (2- bromophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,
3] triazole 997mg.
Embodiment 8
1- (2- iodo- 2- (octyloxy) -1H- benzos [d] [1,2,3] triazoles
By N- hydroxy benzo triazoles (486mg, 3.6mmol), 1- octenes (354mg, 3 mmol), iodine (381mg,
1.5mmol) and TBHP (772mg, 6mmol, 70% aqueous solution) is added in flask, adds solvent 1,2-
Dichloroethanes 20ml, reacted 4 hours at 50 DEG C.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Oil
Ether/ethyl acetate volume ratio 6：1) isolated 1- (2- iodo- 2- (octyloxy) -1H- benzos [d] [1,2,3] triazole 839mg.
Embodiment 9
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2ml acetonitrile solvents and is added in flask, and it is small to react 6 at room temperature
When.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
To (1- (1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 103.1mg, yield 87%.
Characterization of The Products：White crystal；Fusing point：74-76℃；1H NMR(500MHz,CDCl3) δ8.10-8.05(d,1H),
7.85–7.75(m,2H),7.60–7.50(m,2H), 7.50–7.40(m,4H),4.94–4.93(d,1H),3.96–3.95(d,
1H).13C NMR(125MHz,CDCl3)δ160.21,142.41,130.47,129.02, 127.67,127.59,126.74,
124.79,123.92,119.45,107.73,87.40.
Embodiment 10
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2ml ether solvents and is added in flask, and it is small to react 6 at room temperature
When.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
To (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 61.6mg, yield 52%.
Characterization of The Products：White crystal；Detected by TLC, rf values 0.26, the rf values of the compound 1 obtained with embodiment 1
It is identical.
Embodiment 11
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), sodium hydroxide (20mg, 0.5mmol) is mixed in 2ml ether solvents and is added in flask, and it is small to react 6 at room temperature
When.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
To (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 47.4mg, yield 40%.
Characterization of The Products：White crystal；Detected by TLC, rf values 0.26, the rf values of the compound 1 obtained with embodiment 1
It is identical.
Embodiment 12
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), sodium iodide (75mg, 0.25mmol) is mixed in 2ml acetonitrile solvents and is added in flask, and it is small to react 6 at room temperature
When.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) it is isolated
(1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 42.6mg, yield 36%.
Characterization of The Products：White crystal；Detected by TLC, rf values 0.26, the rf values of the compound 1 obtained with embodiment 1
It is identical.
Embodiment 13
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), pyridine (39.5mg, 0.5mmol) is mixed in 2ml acetonitrile solvents and is added in flask, and it is small to react 6 at room temperature
When.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) it is isolated
(1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 73.9mg, yield 62%.
Characterization of The Products：White crystal；Detected by TLC, rf values 0.26, the rf values of the compound 1 obtained with embodiment 1
It is identical.
Embodiment 14
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium tert-butoxide (28mg, 0.25mmol) is mixed in 2ml acetonitrile solvents and is added in flask, reacts 6 at room temperature
Hour.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
Obtain (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 61.6mg, yield 52%.
Characterization of The Products：White crystal；Detected by TLC, rf values 0.26, the rf values of the compound 1 obtained with embodiment 1
It is identical.
Embodiment 15
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium tert-butoxide (112mg, 1mmol) is mixed in 2ml tetrahydrofuran solvents and is added in flask, reacts 6 at 0 DEG C
Hour.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
Obtain (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 104.3mg, yield 88%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical.
Embodiment 16
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2ml dichloromethane solvents and is added in flask, is reacted at 0 DEG C
6 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
Obtain (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 84.3mg, yield 70%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical.
Embodiment 17
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2ml tetrahydrofuran solvents and is added in flask, anti-at 40 DEG C
Answer 4 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) divide
From obtaining (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 104.3mg, yield
88%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical.
Embodiment 18
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2ml tetrahydrofuran solvents and is added in flask, is reacted at 0 DEG C
8 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
Obtain (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 99.5mg, yield 84%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical.
Embodiment 19
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2ml tetrahydrofuran solvents and is added in flask, at room temperature instead
Answer 6 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) divide
From obtaining (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 67.5mg, yield 57%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical.
Embodiment 20
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium hydroxide (28mg, 0.5mmol) is mixed in 2ml methanol solvates and is added in flask, and it is small to react 6 at room temperature
When.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
To (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 53.3mg, yield 45%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical.
Embodiment 21
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), caustic alcohol (34mg, 0.5mmol) is mixed in 2ml alcohol solvents and is added in flask, and it is small to react 6 at room temperature
When.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) it is isolated
(1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 54.5mg, yield 46%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical.
Embodiment 22
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), the carbon -7- alkene (DBU) (76mg, 0.5mmol) of 1,8- diazabicylos 11 is mixed in 2ml dichloromethane solvents and added
Enter into flask, react 6 hours at room temperature.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petroleum ether/
Ethyl acetate volume ratio 20：It is 1) isolated that (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (is changed
Compound 1) 81.7mg, yield 68%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical.
Embodiment 23
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), triethylamine (50.5mg, 0.5mmol) is mixed in 2ml acetonitrile solvents and is added in flask, and it is small to react 6 at room temperature
When.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
To (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 42.7mg, yield 36%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical
Embodiment 24
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium tert-butoxide (67mg, 0.5mmol) is mixed in 2ml acetonitrile solvents and is added in flask, and it is small to react 6 at room temperature
When.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
To (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 92.4mg, yield 78%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical
Embodiment 25
Compound 1
Example 1 prepare 1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole (182.5mg,
0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2ml tetrahydrofuran solvents and is added in flask, is reacted at 0 DEG C
6 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) separate
Obtain (1- ((1- phenyl vinyls) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 1) 104.3mg, yield 88%.
Characterization of The Products：White crystal；Detected by TLC, the contrast of the compound 1 obtained with embodiment 1, rf values are identical
Embodiment 26
Compound 2
1- (1- (4- fluorophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole prepared by Example 2
(191.5mg, 0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2m acetonitrile solvents and is added in flask, at 0 DEG C
Reaction 6 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1)
Isolated (1- ((1- (4- fluorophenyls) vinyl) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 2) 65.1mg,
Yield 51%.
Characterization of The Products：White solid, fusing point：101-102℃；1H NMR(400MHz,CDCl3) δ8.15-8.05(d,
1H),7.85–7.75(m,2H),7.60–7.55(m,2H), 7.50–7.40(m,1H),7.20–7.15(m,2H),4.92–
4.91(d,1H), 4.00–3.99(d,1H).13C NMR(100MHz,CDCl3)δ165.00,162.51, 160.38,
143.45,128.72,127.98,127.89,127.77,127.74,127.70, 125.02,120.59,115.96,
115.74,108.69,88.37.
Embodiment 27
Compound 3
1- (1- (4- chlorphenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole prepared by Example 3
(199.5mg, 0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2m acetonitrile solvents and is added in flask, at 0 DEG C
Reaction 6 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20： 1)
Isolated (1- ((1- (4- chlorphenyls) vinyl) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 3) 121.9mg,
Yield 90%.
Characterization of The Products：White solid, fusing point：90-91℃；1H NMR(400MHz,CDCl3)δ 8.13-8.11(d,1H),
7.77-7.75(m,2H),7.60-7.58(m,2H), 7.49-7.47(m,3H),4.98-4.97(d,1H),4.04-4.03(d,
1H). 13C NMR(100MHz,CDCl3)δ160.21,143.45,136.10,129.95, 129.01,128.76,127.74,
127.14,125.05,120.61,108.67,88.96.
Embodiment 28
Compound 4
1- (1- (4- bromophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole prepared by Example 4
(261mg, 0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) are mixed in 2m acetonitrile solvents and are added in flask, anti-at 0 DEG C
Answer 6 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) divide
From obtain (1- ((1- (4- chlorphenyls) vinyl) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 4) 84.7mg, receive
Rate 43%.
Characterization of The Products：White solid, fusing point：101-103℃；1H NMR(400MHz,CDCl3) δ8.13-8.11(d,
1H), 7.70-7.68 (m, 2H), 7.64-7.52 (m, 2H), 7.59-7.57 (m, 2H), 7.5,0-7.46 (m, 1H), 5.00-
4.98(d,1H),4.05- 4.04(d,1H).
13C NMR(101MHz,CDCl3)δ160.27,143.45,131.97,130.41, 128.76,127.74,
127.35,125.05,124.38,120.62,108.66,89.03.
Embodiment 29
Compound 5
1- (1- (4- aminomethyl phenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole prepared by Example 5
(189.5mg, 0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2m acetonitrile solvents and is added in flask, at 0 DEG C
Reaction 6 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20： 1)
Isolated (1- ((1- (4- aminomethyl phenyls) vinyl) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 5)
120.6mg yield 67%.
Characterization of The Products：White solid；Fusing point：94-96℃；1H NMR(400MHz,CDCl3)δ8.10- 8.08(d,1H),
7.70-7.68 (m, 2H), 7.56-7.54 (m, 2H), 7.46-7.42 (m, 1H), 7.28-7.26 (m, 2H), 4.91-4.90 (d,
1H),3.93-3.92(d, 1H),2.42(s,3H).13C NMR(100MHz,CDCl3)δ161.38,143.44, 140.26,
129.40,128.69,128.62,127.79,125.75,124.97,120.44, 108.83,87.61,21.41.
Embodiment 30
Compound 6
1- (1- (4- chloromethyl phenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole prepared by Example 6
(206.5mg, 0.5mmol), potassium tert-butoxide (56mg, 0.5 mmol) is mixed in 2m acetonitrile solvents and is added in flask, at 0 DEG C
Reaction 6 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1)
Isolated (1- ((1- (4- chloromethyl phenyls) vinyl) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 6)
79.8mg, yield 56%.
Characterization of The Products：White solid；Fusing point：98-99℃；1H NMR(400MHz,CDCl3)δ8.12- 8.10(d,1H),
7.81-7.80 (d, 2H), 7.57-7.56 (m, 2H), 7.52-7.50 (m, 2H), 7.48-7.45 (m, 1H), 5.00-4.99 (d,
1H), 4.65 (s, 2H) 4.03- 4.20 (d, 1H), 2.42 (s, 3H)13C NMR(125MHz,CDCl3)δ160.68,
143.47,139.34,131.56,128.93,128.70,127.79,126.14,125.01, 120.58,108.72,89.00,
45.43.
Embodiment 31
Compound 7
1- (1- (2- bromophenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole prepared by Example 7
(221.5mg, 0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2m acetonitrile solvents and is added in flask, at 0 DEG C
Reaction 6 hours.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20： 1)
It is isolated that (1- ((1- (2- bromophenyls) vinyl) epoxide) -1H- benzos [d] [1,2,3] triazole (compound 797.6mg, is received
Rate 62%.
Characterization of The Products：Weak yellow liquid；1H NMR(400MHz,CDCl3)δ8.09-8.07(d, 1H),7.80-7.78
(m,1H),7.71-7.69(m,1H),7.66-7.64(m,1H), 7.59-7.56(m,1H),7.46-7.39(m,2H),7.35-
7.32(m,1H),4.75- 4.74(d,1H),4.31-4.30(d,1H).13C NMR(125MHz,CDCl3)δ 160.44,
143.38,133.33,132.12,131.48,128.57,127.81,127.50, 124.89,123.07,120.37,
109.33,93.60.
Embodiment 32
Compound 8
Example 8 prepare 1- (2- iodo- 2- (octyloxy) -1H- benzos [d] [1,2,3] triazole (186.5mg,
0.5mmol), potassium tert-butoxide (56mg, 0.5mmol) is mixed in 2m acetonitrile solvents and is added in flask, and it is small that 6 are reacted at 0 DEG C
When.After TLC detection reactions terminate, with column chromatography chromatogram method (eluent：Petrol ether/ethyl acetate volume ratio 20：1) it is isolated
1- (2- octenyls epoxide) -1H- benzos [d] [1,2,3] triazole (compound 8) 63.7mg, yield 52%.
Characterization of The Products：Weak yellow liquid；1H NMR(400MHz,CDCl3)δ8.03-8.01(d, 1H),7.52-7.45
(m,2H),7.39-7.36(t,1H),4.21-4.20(d,1H), 3.59-3.58(d,1H),2.43-2.40(t,2H),1.74-
1.68(m,2H),1.45-1.42 (m,2H),1.33-1.32(m,4H),0.90-0.88(t,3H).13C NMR(125MHz,
CDCl3)δ164.15,143.19,128.25,127.56,124.62,120.17, 108.62,86.73,31.35,31.19,
28.49,26.80,22.39,13.89。
Claims (9)
1. the synthetic method of the N- alkenyloxy group benzotriazole compounds shown in a kind of formula (II), it is characterised in that described
Synthetic method is：
β shown in formula (I)-iodo N- alkoxies BTA, acid binding agent are mixed in organic solvent, at 0~40 DEG C
4~8h is reacted, reaction completely obtains reaction solution, and the reaction solution is post-treated to obtain described N- alkenyloxy group benzotriazoles
Compound；Described acid binding agent is potassium tert-butoxide, potassium hydroxide, sodium hydroxide, sodium iodide, pyridine, caustic alcohol, 1,8- diazas
Carbon -7- the alkene of two ring 11 or triethylamine；N- alkenyloxy group benzotriazole compounds shown in the formula (1) tie up acid with described
Feed intake the ratio between the amount of material of agent is 1：0.5~2；
In formula (I) or formula (II)：
R is C3~12Straight chained alkyl or by halogen, C1~5Alkyl-substituted phenyl.
2. synthetic method as claimed in claim 1, it is characterised in that β-iodo N- alkoxy benzos shown in the formula (I)
3-triazole compounds are selected from one of following：1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole, (2- is iodo- by 1-
1- (p-methylphenyl) ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (4- fluorophenyls) -2- iodine ethyoxyl) -1H- benzos
[d] [1,2,3] triazole, 1- (1- (4- chlorphenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (4- bromobenzenes
Base) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (4- aminomethyl phenyls) -2- iodine ethyoxyl) -1H- benzos
[d] [1,2,3] triazole, 1- (1- (4- chloromethyl phenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (2-
Bromophenyl) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (the iodo- 2- octyloxies of 2-) -1H- benzos [d] [1,2,3]
Triazole.
3. synthetic method as claimed in claim 2, it is characterised in that β-iodo N- alkoxy benzos shown in the formula (I)
3-triazole compounds are selected from one of following：1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole, (2- is iodo- by 1-
1- (p-methylphenyl) ethyoxyl) -1H- benzos [d] [1,2,3] triazole or 1- (1- (4- fluorophenyls) -2- iodine ethyoxyl) -1H- benzene
And [d] [1,2,3] triazole.
4. synthetic method as claimed in claim 1, it is characterised in that described organic solvent is tetrahydrofuran, methanol, second
Alcohol, acetonitrile, ether or dichloromethane.
5. synthetic method as claimed in claim 1, it is characterised in that the volumetric usage of described organic solvent is with formula (I) institute
The amount of the material of the β shown-iodo N- alkoxy BTAs is calculated as 4~12ml/mmol.
6. synthetic method as claimed in claim 1, it is characterised in that described acid binding agent is potassium tert-butoxide.
7. synthetic method as claimed in claim 1, it is characterised in that β-iodo N- alkoxy benzos shown in the formula (1)
The ratio between amount for the material that feeds intake of triazole and acid binding agent is 1：1.
8. the synthetic method as described in one of claim 1~7, it is characterised in that the method for reaction solution post processing is：Instead
After should terminating, described reaction solution first being carried out to be concentrated under reduced pressure to give grease, the grease carries out column chromatography for separation again, with
Volume ratio 20：1 or 9:1 petrol ether/ethyl acetate mixed liquor is eluant, eluent, collects and merges the eluent containing target compound,
Dried after solvent is evaporated off, produce described N- alkenyloxy group benzotriazole compounds.
9. synthetic method as claimed in claim 1, it is characterised in that described method is carried out as follows：
β shown in formula (1)-iodo N- alkoxies BTA, potassium tert-butoxide are mixed in organic solvent, at 0~40 DEG C
4~8h of lower reaction, reaction solution first carry out being concentrated under reduced pressure to give grease, and the grease carries out column chromatography for separation again, with volume
Than 20：1 or 9:1 petrol ether/ethyl acetate mixed liquor is eluant, eluent, collects and merges the eluent containing target compound, is evaporated off
Dried after solvent, produce described N- alkenyloxy group benzotriazole compounds；β-iodo N- alkoxies shown in the formula (1)
The ratio between amount for the material that feeds intake of BTA and acid binding agent is 1：1；β-iodo N- alkoxies benzo three shown in the formula (I)
Nitrogen azole compounds are selected from one of following：1- (the iodo- 1- phenyl ethoxies of 2-) -1H- benzos [d] [1,2,3] triazole, 1- (the iodo- 1- of 2-
(p-methylphenyl) ethyoxyl) -1H- benzos [d] [1,2,3] triazole, 1- (1- (4- fluorophenyls) -2- iodine ethyoxyl) -1H- benzos
[d] [1,2,3] triazole, 1- (1- (4- chlorphenyls) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazoles or 1- (1- (4- bromines
Phenyl) -2- iodine ethyoxyl) -1H- benzos [d] [1,2,3] triazole；Described organic solvent is selected from one of following：Tetrahydrofuran,
Acetonitrile, ether or dichloromethane；The volumetric usage of described solvent and β-iodo N- alkoxy BTAs shown in formula (I)
The ratio between the amount of material be 4~12ml/mmol.
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