CN106588788A - Method for synthesizing 1,2,3-triazole compound through one-pot two-step method - Google Patents
Method for synthesizing 1,2,3-triazole compound through one-pot two-step method Download PDFInfo
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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
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
Abstract
The invention discloses a method for synthesizing 1,2,3-triazole compound through a one-pot two-step method. An iodo-aryl compound, sodium azide, 1,8-diazabicyclo[5.4.0]-11-carbon-7-alkene and a catalyst cuprous iodide are added into a reaction container containing a solvent dimethyl sulfoxide, the reaction mixture is stirred and react at the temperature of 95 DEG C, and TLC tracking detection is carried out till reacting is complete; after the reaction temperature is reduced to room temperature, a phenylacetaldehyde compound or a terminal-based alkyne compound is added into the reaction container, after the reaction is completed, water and ammonium hydroxide are added into the reaction mixture, the extraction is carried out with dichloromethane three times, washing is carried out with saturated salt water once, drying and suction filtration are carried out, a solvent is spun out, column chromatography purification is carried out, and the target product is obtained. The method is simple in process, convenient to operate, mild in reaction condition, short in reaction time and high in target product yield.
Description
Technical field
The invention belongs to the synthesis technical field of 1,2,3- triazole compound, and in particular to one pot of two-step method synthesis 1,
The method of 2,3- triazole compounds.
Background technology
Heterocyclic compound is too numerous to enumerate, is the emphasis of always chemist research.Wherein 1,2,3- triazoles chemical combination
Thing is exactly the very important Five-membered Heterocyclic Compounds of a class, and with special aromatic structure, stability is strong, in strong acid and by force
Under the conditions of alkali, all without decomposing easily, and easily there are various non-covalent bond effects, such as stronger complexation of metal ions and hydrogen bond
Ability etc..Therefore, 1,2,3- triazoles are various biological living so as to show easily in combination with biological various enzymes, target spot in vivo
Property, such as AntiHIV1 RT activity, antitumor, antibacterial, convulsion and antiviral, often as pharmacophoric group, be incorporated in lead compound or
Previous drugs are carried out with structure of modification to improve its pharmacologically active, is the focus of field of medicaments research.Additionally, triazole is also extensive
It is applied to the fields such as pesticide, biology, macromolecular material and chemical industry.With regard to 1, the synthetic method of 2,3- triazole compounds is main
Have following several：（1）1893, Michael was found that diethyl butyn generates triazole with organic azide
Reaction (Journal für Praktische Chemie, 1893, 48(2):94-95)；（2）Germanization scholar in 1963
Reactions of the Huisgen to nitrine and alkynes has carried out the theoretical research of system, it is proposed that the concept of 1,3- Dipolar Cycloaddition,
And the reaction is generalized in organic chemistry and is extensively applied, later this kind of reaction was referred to as Huisgen reactions by people, traditional
Huisgen reactions often require that substrate has electron withdraw group, and response speed is slow, and the response time is long, it usually needs high-temperature heating,
And react regioselectivity is particularly poor, obtain the triazole mixture that Isosorbide-5-Nitrae-replacement and 1,5- replace；（3）Copper catalysis
Huisgen cycloaddition reactions（Abbreviation CuAAC reaction methods）:Calendar year 2001, famous American chemist's Nobel chemistry Prize winner
K.B.Sharpless proposes first the concept of " click chemistry ", the CuAAC reactions with azide and terminal alkyne as substrate
Synthesizing triazazole class compound becomes the classics in " click chemistry "；（4）Metal Ru catalysis synthesis process：Fokin professors in 2008
It was found that can synthesize the dibasic 1,2,3- 3-triazole compounds of 1,5- under metal Ru catalysis and propose the general of " RuAAC "
Read；（5）Activation alkynes participates in method：Azide and activation alkynes（The activation of alkynes is mainly derived from the electron deficiency of three keys and ring strain effect
Should）Carrying out without the need for catalyst and under mild condition (ChemBioChem, 2008, 9: 1805-1815)；（6）Organic catalysis
Agent method：Fokin etc. find alkyl quaternary ammonia alkali can effectively be catalyzed azide and Terminal Acetylenes cycloaddition reaction (Org. Lett.,
2010, 12: 4217-4219)；（7）Metal acetylide method：The advantage of the reaction is but the metal ethynylation price without the need for catalyst
The alkalescence that lattice are expensive, source is difficult and its have limit its aspects such as synthesis, medicine application (Tetrahedron,
2011, 67: 289-292)；（8）α-diazonium acetyl class compound and aminated compoundss are under Lewis acid catalysiss through two steps parent
Nuclear reaction generates triazole (patent：Application No. CN201110224778.7)；（9）Azide and aldehyde/unsaturated aldehyde synthesis
1,2,3- 3-triazole compounds (Angew. Chem. Int. Ed., 2014, 53: 10420-10424).However, these conjunctions
All there are some shortcomings into method, reactions steps are loaded down with trivial details, yield is low and poor selectivity etc., it is contemplated that find it is a kind of more
The method of excellent synthesis 1,2,3- triazole compounds.
At present in multi-component reaction, using copper catalysis cycloaddition (CuAAC) strategy Hydrazoic acid,sodium salt, halogenated hydrocarbons are limited to mostly
With the reaction of Terminal Acetylenes (Tetrahedron Lett., 2006, 47, 1545).Multi-component reaction refers to 3 or more than 3
Initiation material participates in reaction, and with the method treated different things alike an end-product is ultimately generated.Multi-component reaction has the advantage that：Operation
Easy, shortening reactions steps；Change the multiformity that initiation material is easily achieved molecule；Starting material has been prepared or commercialization, former
Material is simple and easy to get；Single step reaction is easily achieved automated production.For current problem, it is within the contemplation of the invention that starting a kind of new
Hydrazoic acid,sodium salt, halogenated hydrocarbons and aldehyde compound（Or acetylene compound）Three component reactions.
The content of the invention
Present invention solves the technical problem that a kind of process is simple and easy to operate one pot of two-step method synthesis 1 are there is provided,
The method of 2,3- triazole compounds.
The present invention adopts the following technical scheme that one pot of two-step method synthesizes 1,2,3- triazoles to solve above-mentioned technical problem
The method of compound, it is characterised in that concretely comprise the following steps：By iodo aryl class compound, Hydrazoic acid,sodium salt, 1,8- diazabicylos
[5.4.0] 11 carbon -7- alkene（DBU）It is added in the reaction vessel equipped with solvent dimethyl sulfoxide with catalyst Hydro-Giene (Water Science).,
By reactant mixture in 95 DEG C of stirring reactions, to reacting complete, question response is down to room temperature to TLC tracing detections, in reaction vessel
After adding hyacinthin class compound or end group acetylene compound, reaction to terminate, water and ammonia are added in reactant mixture, then
Extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, be dried, sucking filtration, rotation removes solvent, column chromatography purification obtains target product
Thing.
Further preferably, described iodo aryl class compound be iodobenzene, to methyl iodobenzene, to methoxyl group iodobenzene, to bromine
Iodobenzene, to ethyoxyl iodobenzene, adjacent methyl iodobenzene, 3,4- dimethyl iodobenzenes, 2,4,6- trimethyl iodobenzenes, a bromo-iodobenzene, adjacent chlorine iodine
The iodo- 2- Methylnitrobenzenes of benzene, 2- iodine trifluoromethylbenzene or 4-.
Further preferably, described hyacinthin class compound be hyacinthin, p-tolyl acetaldehyde, p-methoxy phenylacetaldehyde or
To ethoxybenzene acetaldehyde.
Further preferably, described end group acetylene compound be phenylacetylene, to methyl phenylacetylene, to Methoxy-phenylacetylene,
To ethoxybenzene acetylene, p-ethyl-phenylacetylene or benzene oxygen propine.
Further preferably, described iodo aryl class compound, Hydrazoic acid,sodium salt, 1,8- diazabicylos [5.4.0] 11
The molar ratio of carbon -7- alkene, catalyst Hydro-Giene (Water Science). and hyacinthin class compound is 1:1.2:0.1-0.3:0.1-0.4:1,
Described iodo aryl class compound, Hydrazoic acid,sodium salt, the carbon -7- alkene of 1,8- diazabicylos [5.4.0] 11, catalyst iodate Asia
Copper is 1 with the molar ratio of end group acetylene compound:1.2:0.1-0.3:0.1-0.4:1.
The key reaction equation of building-up process of the present invention is：
。
The present invention has the advantages that compared with prior art：
1st, the present invention is synthesized 1,2,3- triazole compounds using one pot of two-step method, compared with traditional method, does not separate
The aryl azide compound of formation, simplifies aftertreatment technology；
2nd, present invention process is simple, easy to operate, and reaction condition is gentle, and the response time is shorter and target product yield is higher；
3rd, synthetic method of the present invention is applicable not only to halogenated aryl hydrocarbon, Hydrazoic acid,sodium salt and end group acetylene compound one pot process 1,2,
3- triazole compounds, apply also for halogenated aryl hydrocarbon, Hydrazoic acid,sodium salt and hyacinthin class compound one pot process 1,2,3- tri-
Nitrogen azole compounds.
Specific embodiment
The above of the present invention is described in further details by the following examples, but this should not be interpreted as this
The scope for inventing above-mentioned theme is only limitted to below example, and all technologies realized based on the above of the present invention belong to this
Bright scope.
Embodiment 1
Using different cuprous salts as catalyst, by 1.0mmol iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and
0.2mmol catalyst is added sequentially in the reaction bulb equipped with 5.0mL dimethyl sulfoxide, and reactant mixture is anti-in 95 DEG C of stirrings
Should, to reacting complete, question response is down to room temperature for TLC tracking reaction, and 1.0mmol hyacinthin is added in reaction bulb（Or benzene second
Alkynes）, after reaction completely, 50mL water is added in reactant mixture and a few drop ammonia are added, then extracted 3 times with dichloromethane,
Washed 1 time with saturated common salt again, be dried, sucking filtration, rotation removes solvent, column chromatography purification obtains target product, and different catalysts are to anti-
The impact for answering yield is shown in Table 1.
Impact of the different catalysts of table 1 to reaction yield
| Group | Catalyst | Temperature (DEG C) | Response time (h) | Yield (%) |
| 1 | CuI | 95/r.t. | 2.5/0.5 | 92 |
| 2 | CuBr | 95/r.t. | 3.0/0.5 | 80 |
| 3 | CuCl | 95/r.t. | 3.0/0.5 | 80 |
| 4 | Cu2O | 95/r.t. | 2.5/0.5 | 82 |
| 5 | CuSO4·5H2O | 95/r.t | 1.5/0.5 | 79 |
| 6 | Cu(OAc)2·H2O | 95/r.t | 1.5/0.5 | 88 |
| 7 | CuCl2·2H2O | 95/r.t | 2.0/0.5 | 78 |
| 8 | CuBr2 | 95/r.t | 2.0/0.5 | 78 |
| 9 | Cu(acac)2 | 95/r.t | 5.0/0.5 | 45 |
Embodiment 2
1.0mmol iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s are added sequentially to be equipped with
In the reaction bulb of 5.0mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 2.5h, TLC tracking reaction is to having reacted
Entirely, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 0.5h, to reaction mixing
50mL water is added in thing and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, be dried,
Sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 92%.
The data characterization of 1,4- diphenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (400 MHz, CDCl3)δ: 8.20 (s, 1H), 7.95-7.89 (m, 2H), 7.82-7.77 (m, 2H), 7.55 (t, J = 7.7Hz,
2H), 7.50-7.43 (m, 3H), 7.38 (t, J = 7.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ:
148.4, 137.1, 130.3, 129.8, 128.9, 128.4, 125.9, 120.5, 117.6。
Embodiment 3
1.0mmol iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.1mmol DBU and 0.1mmol Hydro-Giene (Water Science) .s are added sequentially to be equipped with
In the reaction bulb of 5.0mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 2.5h, TLC tracking reaction is to having reacted
Entirely, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 0.5h, to reaction mixing
50mL water is added in thing and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, be dried,
Sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 70%.
Embodiment 4
1.0mmol is sequentially added to methyl iodobenzene, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.4mmol Hydro-Giene (Water Science) .s
To in the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 2.5h, TLC tracking reaction is to anti-
Should be complete, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, it is mixed to reaction after reaction 1h
50mL water is added in compound and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, done
Dry, sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 81%.
The data characterization of 1- p-methylphenyl -4- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (400
MHz, CDCl3) δ: 8.16 (s, 1H), 7.91 (d, J = 7.1 Hz, 2H), 7.66 (d, J = 8.4 Hz,
2H), 7.46 (t, J = 7.5 Hz, 2H), 7.35 (dd, J = 16.8, 7.9 Hz, 3H), 2.43 (s, 3H).13C NMR (100 MHz ,CDCl3,) δ: 148.3, 138.9, 134.8, 130.3, 128.92 (s), 128.4,
125.9, 120.4, 117.7, 21.1。
Embodiment 5
1.0mmol is added successively to methoxyl group iodobenzene, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s
Enter in the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 1h, TLC tracking reaction is to anti-
Should be complete, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, it is mixed to reaction after reaction 1h
50mL water is added in compound and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, done
Dry, sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 87%.
The data characterization of 1- p-methoxyphenyl -4- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (600
MHz, CDCl3) δ: 8.11 (s, 1H), 7.91 (d, J = 7.8 Hz, 2H), 7.69 (d, J = 8.8 Hz,
2H), 7.46 (t, J = 7.1 Hz, 2H), 7.37 (t, J = 7.4 Hz, 1H), 7.04 (d, J = 8.6 Hz,
2H), 3.88 (s, 3H). 13C NMR (150 MHz, CDCl3) δ: 159.9, 148.2, 130.4, 128.9,
128.4, 125.8, 122.2, 117.9, 114.8, 55.7。
Embodiment 6
1.0mmol is added sequentially to bromo-iodobenzene, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s
In reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 1h, TLC tracking reaction is to having reacted
Entirely, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 0.5h, to reaction mixing
50mL water is added in thing and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, be dried,
Sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 82%.
The data characterization of 1- p-bromophenyl -4- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (600 MHz,
DMSO-d 6 ) δ: 9.34 (s, 1H), 7.94 (d, J = 8.7 Hz, 4H), 7.86 (d, J = 8.7 Hz, 2H),
7.51 (t, J = 7.6 Hz, 2H), 7.40 (t, J = 7.4 Hz, 1H). 13C NMR (150 MHz, DMSO-d 6 ) δ: 148.0, 136.3, 133.3, 130.6, 129.5, 128.8, 125.8, 122.4, 121.8, 120.1。
Embodiment 7
1.0mmol is added successively to ethyoxyl iodobenzene, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s
Enter in the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 1h, TLC tracking reaction is to anti-
Should be complete, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 1.5h, to reaction
50mL water is added in mixture and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, done
Dry, sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 83%.
Data characterizations of the 1- to ethoxyl phenenyl -4- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (400
MHz, CDCl3) δ: 8.03 (s, 1H), 7.82 (d, J = 7.1 Hz, 2H), 7.59 (d, J = 9.0 Hz,
2H), 7.37 (t, J = 7.5 Hz, 2H), 7.29 (d, J = 7.4 Hz, 1H), 6.94 (d, J = 9.0 Hz,
2H), 4.01 (q, J = 7.0 Hz, 2H), 1.38 (t, J = 7.0 Hz, 3H). 13C NMR (100 MHz,
CDCl3) δ: 159.2, 148.2, 130.4, 128.9, 128.3, 125.8, 122.2, 117.8, 115.3,
63.9, 14.7。
Embodiment 8
1.0mmol neighbour's methyl iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s are sequentially added
To in the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 5h, TLC tracking reactions are to reaction
Completely, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 1h, to reaction mixing
50mL water is added in thing and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, be dried,
Sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 80%.
The data characterization of 1- o-methyl-phenyl--4- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (400
MHz, CDCl3) δ: 7.97 (s, 1H), 7.94-7.91 (m, 2H), 7.40-7.35 (m, 7H), 2.28 (s,
3H). 13C NMR (100 MHz, CDCl3) δ: 147.6, 136.5, 133.8, 131.6, 130.4, 130.0,
129.0, 128.4, 126.9, 125.9, 121.2, 18.0。
Embodiment 9
By 1.0mmol 3,4- dimethyl iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science). successively
In being added to the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 1.0h, TLC tracking reactions
Complete to reacting, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 0.5h, to
50mL water is added in reactant mixture and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then 1 is washed with saturated common salt
It is secondary, it is dried, sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 88%.
The data characterization of 1- (3,4- 3,5-dimethylphenyls) -4- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR
(400 MHz, CDCl3) δ: 8.07 (s, 1H), 7.83 (d, J = 7.1 Hz, 2H), 7.49 (s, 1H),
7.38 (dd, J = 13.7, 7.8 Hz, 3H), 7.29 (d, J = 7.5 Hz, 1H), 7.19 (d, J = 8.3
Hz, 1H), 2.28 (s, 3H), 2.25 (s, 3H). 13C NMR (100 MHz, CDCl3) δ: 148.2, 138.4,
137.6, 135.0, 130.6, 130.4, 128.89, 128.3, 125.8, 121.7, 117.8, 117.7, 19.9,
19.5。
Embodiment 10
By 1.0mmol 2,4,6- trimethyl iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science). according to
It is secondary to be added in the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 5h, TLC tracking reactions
Complete to reacting, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 1.5h, to
50mL water is added in reactant mixture and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then 1 is washed with saturated common salt
It is secondary, it is dried, sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 85%.
The data characterization of 1- trimethylphenyl -4- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (400
MHz, CDCl3) δ: 7.95-7.91 (m, 2H), 7.84 (s, 1H), 7.46 (t, J = 7.6 Hz, 2H),
7.40-7.33 (m, 1H), 7.01 (s, 2H), 2.37 (s, 3H), 2.02 (s, 6H ). 13C NMR (100
MHz, CDCl3) δ: 147.6, 140.1, 135.1, 133.5, 130.5, 129.0, 128.3, 125.8, 121.5,
21.2, 17.4。
Embodiment 11
Bromo-iodobenzene, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s between 1.0mmol are added sequentially to
In reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 0.5h, TLC tracking reactions are to reaction
Completely, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 1h, to reaction mixing
50mL water is added in thing and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, be dried,
Sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 94%.
The data characterization of 1- m-bromophenyl -4- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (400 MHz,
CDCl3) δ: 8.11 (s, 1H), 7.91 (s, 1H), 7.83 (d, J = 7.1 Hz, 2H), 7.68 (d, J =
10.1 Hz, 1H), 7.51 (d, J = 8.8 Hz, 1H), 7.39 (t, J = 7.5 Hz, 2H), 7.36-7.29
(m, 2H). 13C NMR (100 MHz, CDCl3) δ: 148.7, 131.8, 131.1, 129.9, 129.0, 128.6,
126.7, 125.9, 123.5, 123.3, 119.0, 117.4。
Embodiment 12
1.0mmol neighbour's chloroiodobenzones, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s are added sequentially to
In reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 1.5h, TLC tracking reactions are to reaction
Completely, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 2h, to reaction mixing
Dichloromethane extraction is added in thing（50mL×3）50mL water is added in reactant mixture and a few drop ammonia are added, then with two
Chloromethanes are extracted 3 times, then are washed 1 time with saturated common salt, are dried, sucking filtration, and rotation removes solvent, and column chromatography purification obtains target product,
Yield 82%.
The data characterization of 1- Chloro-O-Phenyl -4- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (400 MHz,
CDCl3) δ: 8.21 (s, 1H), 7.95-7.90 (m, 2H), 7.68 (dd, J = 6.1, 3.4 Hz, 1H),
7.62-7.57 (m, 1H), 7.50-7.43 (m, 4H), 7.37 (t, J = 7.4 Hz, 1H); 13C NMR (100
MHz, CDCl3) δ: 147.6, 134.9, 130.8, 130.2, 129.0, 128.5, 128.0, 127.8, 125.9,
121.6。
Embodiment 13
By 1.0mmol o-trifluoromethyl iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science). successively
In being added to the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 2h, TLC tracking reaction is extremely
Reaction is complete, and question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 1.5h, to anti-
Answer and add in mixture 50mL water and add a few drop ammonia, then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt,
It is dried, sucking filtration, rotation removes solvent, column chromatography purification obtains target product, yield 70%.
The data characterization of 4- phenyl -1- (2- (trifluoromethyl) phenyl) -1,2,3- triazoles：Off-white color crystal；1H NMR
(400 MHz, CDCl3) δ: 8.06 (s, 1H), 7.90 (dd, J = 11.3, 8.3 Hz, 3H), 7.73 (dt,J = 27.0, 7.5 Hz, 2H), 7.62 (d, J = 7.6 Hz, 1H), 7.47 (t, J = 7.5 Hz, 2H),
7.38 (t, J = 7.4 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ: 147.8, 134.9, 133.1,
130.5, 130.0, 129.0 (d, J = 5.2 Hz), 128.5, 127.4 (q, J = 5.0 Hz), 126.4,
125.9, 124.0, 122.2, 121.3。
Embodiment 14
By 1.0mmol nitro iodobenzene, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science). between methyl according to
Secondary to be added in the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 3.5h, TLC tracking is anti-
Should be to reacting complete, question response is down to room temperature, and 1.0mmol hyacinthin is added in reaction bulb（Or phenylacetylene）, after reaction 2h, to
50mL water is added in reactant mixture and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then 1 is washed with saturated common salt
It is secondary, it is dried, sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 75%.
The data characterization of 1- (4- methyl-3-nitro phenyl) -4- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR
(400 MHz, CDCl3) δ: 8.41 (s, 1H), 8.26 (s, 1H), 8.05 (d, J = 10.5 Hz, 1H),
7.92 (d, J = 8.4 Hz, 2H), 7.56 (d, J = 8.3 Hz, 1H), 7.48 (t, J = 7.5 Hz, 2H),
7.40 (t, J = 7.4 Hz, 1H), 2.70 (s, 3H). 13C NMR (100 MHz, CDCl3) δ: 134.4,
134.0, 129.0, 128.8, 125.9, 124.4, 117.2, 116.2, 20.3。
Embodiment 15
1.0mmol iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s are added sequentially to be equipped with
In the reaction bulb of 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 2h, TLC tracking reaction is treated to reacting complete
Room temperature is down in reaction, and 1.0mmol p-tolyl acetaldehyde is added in reaction bulb（Or to methyl phenylacetylene）, after reaction 0.5h, to
50mL water is added in reactant mixture and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then 1 is washed with saturated common salt
It is secondary, it is dried, sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 87%.
The data characterization of 1- phenyl -4- (p-methylphenyl) -1,2,3- triazoles：Off-white color crystal；1H NMR (400
MHz, CDCl3) δ: 8.16 (s, 1H), 7.80 (dd, J = 6.0 Hz, 7.6 Hz, 4H), 7.57-7.26 (m,
5H), 2.40 (s, 3H). 13C NMR (100 MHz, CDCl3) δ: 148.5, 138.3, 137.1, 129.8,
129.6, 128.7, 127.4, 125.8, 120.5, 117.3, 21.3。
Embodiment 16
1.0mmol iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s are added sequentially to be equipped with
In the reaction bulb of 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 2h, TLC tracking reaction is treated to reacting complete
Room temperature is down in reaction, and 1.0mmol p-methoxy phenylacetaldehydes are added in reaction bulb（Or to Methoxy-phenylacetylene）, after reaction 1h,
50mL water is added in reactant mixture and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed with saturated common salt
1 time, it is dried, sucking filtration, rotation removes solvent, column chromatography purification obtains target product, yield 80%.
The data characterization of 4- (4- methoxyphenyls) -1- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (400
MHz, CDCl3) δ: 8.11 (s, 1H), 7.82 (d, J = 8.7 Hz, 2H), 7.77 (d, J = 7.7 Hz,
2H), 7.52 (t, J = 7.8 Hz, 2H), 7.42 (t, J = 7.4 Hz, 1H), 6.97 (d, J = 8.7 Hz,
2H), 3.83 (s, 3H). 13C NMR (100 MHz, CDCl3) δ: 159.8, 148.3, 137.1, 129.8,
128.7, 127.2, 122.9, 120.4, 116.8, 114.3, 55.3。
Embodiment 17
1.0mmol iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s are added sequentially to be equipped with
In the reaction bulb of 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 2h, TLC tracking reaction is treated to reacting complete
Room temperature is down in reaction, and 1.0mmol is added in reaction bulb to ethoxybenzene acetaldehyde（Or to ethoxybenzene acetylene）, after reaction 1h,
50mL water is added in reactant mixture and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed with saturated common salt
1 time, it is dried, sucking filtration, rotation removes solvent, column chromatography purification obtains target product, yield 78%.
The data characterization of 4- (4- ethoxyl phenenyls) -1- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (400
MHz, CDCl3) δ: 8.12 (s, 1H), 7.81 (dd, J = 8.4 Hz, J = 8 Hz, 4H), 7.55 (t, J
= 7.6 Hz, 2H), 7.45 (t, J = 7.6 Hz, 1H), 6.98 (d, J = 8.4 Hz, 2H), 4.09 (q, J
= 7.6 Hz, 2H), 1.45 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ: 159.2,
148.3, 137.1, 129.8, 128.7, 127.2, 122.8, 120.5, 116.7, 114.9, 63.5, 14.8。
Embodiment 18
1.0mmol iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s are added sequentially to be equipped with
In the reaction bulb of 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 2h, TLC tracking reaction is treated to reacting complete
Room temperature is down in reaction, and 1.0mmol p-ethyl-phenylacetylenes are added in reaction bulb, after reaction 1h, is added in reactant mixture
50mL water simultaneously adds a few drop ammonia, is then extracted 3 times with dichloromethane, then is washed 1 time with saturated common salt, is dried, and sucking filtration, rotation is removed
Solvent, column chromatography purification obtains target product, yield 85%.
The data characterization of 4- (4- ethylphenyls) -1- phenyl -1,2,3- triazoles：Off-white color crystal；1H NMR (400
MHz, CDCl3) δ: 8.16 (s, 1H), 7.81 (dd, J = 8.4 Hz, J = 8.0 Hz, 4H), 7.54 (t,J = 7.2 Hz, 2H), 7.44 (t, J = 7.6 Hz, 1H), 7.29 (d, J = 8.0 Hz, 2H), 2.69 (q,J = 7.6 Hz, 2H), 1.27 (t, J = 7.6 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ: 148.5,
144.7, 137.1, 129.7, 128.7, 128.4, 127.6, 125.8, 120.5, 117.2, 28.7, 15.5。
Embodiment 19
1.0mmol iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s are added sequentially to be equipped with
In the reaction bulb of 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 2h, TLC tracking reaction is treated to reacting complete
Room temperature is down in reaction, and 1.0mmol benzene oxygen propine is added in reaction bulb, after reaction 0.5h, in reactant mixture 50mL is added
Water simultaneously adds a few drop ammonia, is then extracted 3 times with dichloromethane, then is washed 1 time with saturated common salt, is dried, sucking filtration, and rotation is except molten
Agent, column chromatography purification obtains target product, yield 92%.
The data characterization of 4- (phenoxymethyl) -1- phenyl -1H-1,2,3- triazoles：Off-white color crystal；1H NMR
(400 MHz, CDCl3) δ: 8.06 (s, 1H), 7.74 (d, J = 7.6 Hz, 2H), 7.54-7.43 (m,
3H), 7.32 (t, J = 8.0 Hz, 2H), 7.04-6.98 (m, 3H), 5.31 (s, 2H). 13C NMR (100
MHz, CDCl3) δ: 158.2, 145.1, 137.0, 129.8, 129.6, 128.9, 121.4, 120.9, 120.6,
114.8, 62.0。
Embodiment 20
1.0mmol neighbour's methyl iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s are sequentially added
To in the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 5h, TLC tracking reactions are to reaction
Completely, question response is down to room temperature, and 1.0mmol benzene oxygen propine is added in reaction bulb, after reaction 1h, adds in reactant mixture
50mL water simultaneously adds a few drop ammonia, is then extracted 3 times with dichloromethane, then is washed 1 time with saturated common salt, is dried, and sucking filtration, rotation is removed
Solvent, column chromatography purification obtains target product, yield 80%.
The data characterization of 4- (phenoxymethyl) -1- (o-tolyl) -1H-1,2,3- triazoles：Off-white color crystal；1H
NMR (400 MHz, CDCl3) δ: 7.81 (s, 1H), 7.44-7.30 (m, 6H), 7.04-6.97 (m, 3H),
5.32 (s, 2H), 2.22 (s, 3H). 13C NMR (100 MHz, CDCl3) δ: 158.2, 144.1, 136.4,
133.7, 131.5, 130.0, 129.6, 126.9, 126.0, 124.3, 121.4, 114.8, 62.1, 17.9。
Embodiment 21
1.0mmol is added successively to methoxyl group iodobenzene, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science) .s
Enter in the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 1h, TLC tracking reaction is to anti-
Should be complete, question response is down to room temperature, and 1.0mmol benzene oxygen propine is added in reaction bulb, after reaction 1h, adds in reactant mixture
Enter 50mL water and add a few drop ammonia, then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, be dried, sucking filtration, rotation
Except solvent, column chromatography purification obtains target product, yield 89%.
The data characterization of 1- (4- methoxyphenyls) -4- (phenoxymethyl) -1H-1,2,3- triazoles：Off-white color crystal
；1H NMR (400 MHz, CDCl3) δ: 7.97 (s, 1H), 7.64-7.60 (m, 2H), 7.33-7.29 (m,
2H), 7.03-6.99 (m, 5H), 5.28 (s, 2H), 3.85 (s, 3H). 13C NMR (100 MHz, CDCl3)δ: 159.9, 158.2, 144.8, 130.4, 129.6, 122.3, 121.3, 121.1, 114.8, 114.8,
62.0, 55.6。
Embodiment 22
By 1.0mmol 2,4,6- trimethyl iodobenzenes, 1.2mmol Hydrazoic acid,sodium salt, 0.3mmol DBU and 0.2mmol Hydro-Giene (Water Science). according to
It is secondary to be added in the reaction bulb equipped with 5mL dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions 5h, TLC tracking reactions
Complete to reacting, question response is down to room temperature, and 1.0 mmol benzene oxygen propine are added in reaction bulb, mixed to reaction after reaction 1.5h
50mL water is added in compound and a few drop ammonia are added, is then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, done
Dry, sucking filtration, rotation removes solvent, and column chromatography purification obtains target product, yield 82%.
The data characterization of 1- benzyl -4- (phenoxymethyl) -1H-1,2,3- triazoles：Off-white color crystal；1H NMR
(400 MHz, CDCl3) δ: 7.65 (s, 1H), 7.63 (t, J = 7.6 Hz, 2H), 7.03-6.97 (m,
5H), 5.34 (s, 2H), 2.35 (s, 3H), 1.95 (s, 6H). 13C NMR (100 MHz, CDCl3) δ:
158.2, 144.2, 140.1, 135.1, 133.4, 129.5, 129.1, 124.6, 121.4, 115.0, 62.3,
21.1, 17.3。
Ultimate principle, principal character and the advantage of the present invention is embodiment above describes, the technical staff of the industry should
Understand, the present invention is not restricted to the described embodiments, the original for simply illustrating the present invention described in above-described embodiment and description
Reason, under the scope without departing from the principle of the invention, the present invention also has various changes and modifications, and these changes and improvements each fall within
In the scope of protection of the invention.
Claims (5)
1. the method that one pot of two-step method synthesizes 1,2,3- triazole compounds, it is characterised in that concretely comprise the following steps：By iodo virtue
Base class compound, Hydrazoic acid,sodium salt, the carbon -7- alkene of 1,8- diazabicylos [5.4.0] 11 and catalyst Hydro-Giene (Water Science). are added to dress
In having the reaction vessel of solvent dimethyl sulfoxide, by reactant mixture in 95 DEG C of stirring reactions, TLC tracing detections are to having reacted
Entirely, question response is down to room temperature, after adding hyacinthin class compound or end group acetylene compound, reaction to terminate in reaction vessel,
Water and ammonia are added in reactant mixture, is then extracted 3 times with dichloromethane, then washed 1 time with saturated common salt, be dried, taken out
Filter, rotation removes solvent, and column chromatography purification obtains target product.
2. the method that one pot of two-step method according to claim 1 synthesizes 1,2,3- triazole compounds, it is characterised in that：
Described iodo aryl class compound be iodobenzene, to methyl iodobenzene, to methoxyl group iodobenzene, to bromo-iodobenzene, to ethyoxyl iodobenzene, neighbour
Methyl iodobenzene, 3,4- dimethyl iodobenzenes, 2,4,6- trimethyl iodobenzenes, a bromo-iodobenzene, adjacent chloroiodobenzone, 2- iodine trifluoromethylbenzene or 4-
Iodo- 2- Methylnitrobenzenes.
3. the method that one pot of two-step method according to claim 1 synthesizes 1,2,3- triazole compounds, it is characterised in that：
Described hyacinthin class compound is hyacinthin, p-tolyl acetaldehyde, p-methoxy phenylacetaldehyde or to ethoxybenzene acetaldehyde.
4. the method that one pot of two-step method according to claim 1 synthesizes 1,2,3- triazole compounds, it is characterised in that：
Described end group acetylene compound be phenylacetylene, to methyl phenylacetylene, to Methoxy-phenylacetylene, to ethoxybenzene acetylene, to second
Base phenylacetylene or benzene oxygen propine.
5. the method that one pot of two-step method according to claim 1 synthesizes 1,2,3- triazole compounds, it is characterised in that：
Described iodo aryl class compound, Hydrazoic acid,sodium salt, the carbon -7- alkene of 1,8- diazabicylos [5.4.0] 11, catalyst iodate Asia
Copper is 1 with the molar ratio of hyacinthin class compound:1.2:0.1-0.3:0.1-0.4:1, described iodo aryl class chemical combination
Thing, Hydrazoic acid,sodium salt, the carbon -7- alkene of 1,8- diazabicylos [5.4.0] 11, catalyst Hydro-Giene (Water Science). and end group acetylene compound
Molar ratio is 1:1.2:0.1-0.3:0.1-0.4:1.
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