CN104945341B - A kind of method of the triazole compound of three components one pot process 1,2,3 - Google Patents
A kind of method of the triazole compound of three components one pot process 1,2,3 Download PDFInfo
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- CN104945341B CN104945341B CN201510412769.9A CN201510412769A CN104945341B CN 104945341 B CN104945341 B CN 104945341B CN 201510412769 A CN201510412769 A CN 201510412769A CN 104945341 B CN104945341 B CN 104945341B
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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 kind of method of the triazole compound of three component one pot process 1,2,3, belong to the synthesis technical field of 1,2,3 triazole compounds.Technical scheme main points are：Sodium azide and catalyst are added in solvent dimethyl sulfoxide (DMSO) successively in reaction vessel, then sequentially add halogenated hydrocarbons, DBU and aldehyde compound, 1,2,3 triazole compounds are made in 60 95 DEG C of stirring reactions in reactant mixture.The present invention utilizes three component coupling reaction synthesizing triazazole class compounds, compared with conventional method, shortens reactions steps, simplifies aftertreatment technology, and technique is simple, and easy to operate, reaction is gentle, and the reaction time is short, efficiency high, is adapted to large-scale production.
Description
Technical field
The invention belongs to the synthesis technical field of 1,2,3- triazole compound, and in particular to a kind of three component one kettle ways
The method for synthesizing 1,2,3- triazole compounds.
Background technology
Nitrogen-containing heterocycle compound is the intermediate of many bioactive molecules and natural products, is closed in organic synthesis and medicine
Have the function that in important.In recent years, nitrogen-containing heterocycle compound has been increasingly becoming organic chemist and correlative study person is extensive
Focus of attention.Wherein, 1,2,3- triazole compounds are one of important representatives of Five-membered Heterocyclic Compounds.On 1,
The synthetic method of 2,3- triazoles, mainly have following several：（1）The Azide of the propositions such as Germanization scholar Huisgen in 1963
1, the 3- dipole-diople interactions of thing and alkynes, this kind of reaction has temperature height, time long and the low shortcoming of selectivity；（2）Copper catalysis
Huisgen cycloaddition reactions（Abbreviation CuAAC reaction methods）：2001, famous American chemist's Nobel chemistry Prize winner
K.B.Sharpless proposes the concept of " click chemistry " first, and the CuAAC using azide and terminal alkyne as substrate reacts
Synthesizing triazazole class compound turns into the classics in " click chemistry ", the characteristics of click chemistry：This kind of reaction must be it is effective,
High selectivity, almost 100% Atom economy and require that reaction raw materials are simple and easy to get, reaction condition is gentle, post processing letter
Singly, the advantages of CuAAC reacts：Do not influenceed by the space and electronic effect in nitrine and alkynes activated centre；The choosing of catalyst " copper source "
It is wide to select scope；Reaction medium species is more, such as water, toluene and ionic liquid, but its shortcoming is that the Ni metal remained may draw
Cytotoxicity is played, its application in terms of bioactivity is limited and the reaction is confined to end-group alkyne；（3）Metal Ru catalyzes and synthesizes
Method：Professor Fokin in 2008 has found that under metal Ru catalysis the dibasic 1,2,3- triazole compounds of 1,5- can be synthesized
And RuAAC concept is proposed, this kind of deficiency of the reaction supplemented with CuAAC reactions, 1,5- dibasic 1,2,3- can be synthesized
Triazole compound, it may also be used for the reaction of catalysis non-end alkynes and organic azide；（4）Metal acetylide method：This is anti-
Should the advantages of be without catalyst, but metal acetylide is expensive, source is not easy and its have alkalescence limit its
Synthesis, the application of medicine etc. (Tetrahedron, 2011,67: 289-292)；（5）Organic catalyst method：Fokin etc.
It was found that alkyl quaternary ammonia alkali can effectively be catalyzed azide and Terminal Acetylenes cycloaddition reaction (Org. Lett., 2010,12:
4217-4219)；（6）Activate alkynes and participate in method：Azide and activation alkynes（The activation of alkynes be mainly derived from three keys electron deficient and
Ring strain effect）Carried out under without catalyst and mild condition (ChemBioChem, 2008,9: 1805-1815)；（7）
α-diazonium acetyl class compound and aminated compounds generate triazole chemical combination under Lewis acid catalysis by two step necleophilic reactions
Thing (number of patent application 201110224778.7)；（8）Azide synthesizes 1,2,3- 3-triazole compounds with aldehyde/unsaturated aldehyde
(Angew. Chem. Int. Ed., 2014, 53:10420-10424), however, these synthetic methods all lack in the presence of some
Point, reactions steps are cumbersome low with yield etc..It is contemplated that find a kind of method of more excellent synthesizing triazazole.
At present in multi-component reaction, it is limited to sodium azide, halogenated hydrocarbons mostly using copper catalysis cycloaddition (CuAAC) strategy
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 an end-product is ultimately generated with the method treated different things alike.Multi-component reaction has the following advantages that：Operation
Easy, shortening reactions steps；Change the diversity that initiation material is easily achieved molecule；Starting material has prepared or commercialization, former
Expect simple and easy to get；Single step reaction is easily achieved automated production.For it is current the problem of, it is necessary to research and development are started a kind of new
Sodium azide, three component reactions of halogenated hydrocarbons and aldehyde compound.
The content of the invention
Present invention solves the technical problem that it there is provided three simple and easy to operate component one pot process of a kind of technique
The method of 1,2,3- triazole compounds.
The present invention is to solve above-mentioned technical problem to adopt the following technical scheme that, a kind of three component one pot process 1,2,3- tri-
The method of nitrogen azole compounds, it is characterised in that concretely comprise the following steps：Sodium azide and catalyst are added successively in reaction vessel
Enter into solvent dimethyl sulfoxide (DMSO), then sequentially add halogenated hydrocarbons, the carbon -7- alkene of 1,8- diazabicylos [5.4.0] 11（DBU）
And aldehyde compound, 1,2,3- triazole compounds, wherein catalyst are made in 60-95 DEG C of stirring reaction in reactant mixture
For cuprous oxide, cuprous iodide, stannous chloride, anhydrous cupric sulfate or copper acetate.
Further limit, described halogenated hydrocarbons is iodobenzene, to methyl iodobenzene or adjacent methyl iodobenzene.
Further limit, described aldehyde compound is phenylacetaldehyde.
Further limit, described sodium azide, catalyst, halogenated hydrocarbons, the mol ratio of DBU and aldehyde compound are 2:
0.1:0.1-0.3:1:4。
Further limit, the dosage of described solvent dimethyl sulfoxide (DMSO) corresponds to solvent dimethyl sulfoxide (DMSO) for 1mol sodium azide
1.5mL。
Compared with prior art, the present invention has following beneficial outcomes：（1）Utilize three component coupling reaction synthesizing triazazoles
Class compound, compared with conventional method, shorten reactions steps, simplify aftertreatment technology；（2）Present invention process is simple, operation letter
Just, reaction is gentle, and the reaction time is short, efficiency high, is adapted to large-scale production.
Embodiment
The above of the present invention is described in further details by the following examples, but this should not be interpreted as to this
The scope for inventing above-mentioned theme is only limitted to following embodiment.All technologies realized based on the above of the present invention belong to this hair
Bright scope.
Embodiment 1
2.0mmol sodium azide and 0.1mmol cuprous oxide are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol iodobenzenes and 4.0mmol phenylacetaldehydes are added into reaction bulb, in 60 DEG C of stirring reactions
10h, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then with saturated common salt wash 1 time,
Dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 80.5%.
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, 2H), 7.50-7.43 (m, 3H), 7.38 (t, 1H)。
Embodiment 2
2.0mmol sodium azide and 0.1mmol cuprous iodides are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol iodobenzenes and 4.0mmol phenylacetaldehydes are added into reaction bulb, in 60 DEG C of stirring reactions
10h, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then with saturated common salt wash 1 time,
Dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 79.0%.
Embodiment 3
2.0mmol sodium azide and 0.1mmol cuprous oxide are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol iodobenzenes and 4.0mmol phenylacetaldehydes are added into reaction bulb, in 80 DEG C of stirring reactions
10h, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then with saturated common salt wash 1 time,
Dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 84.1%.
Embodiment 4
2.0mmol sodium azide and 0.1mmol cuprous iodides are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol iodobenzenes and 4.0mmol phenylacetaldehydes are added into reaction bulb, in 80 DEG C of stirring reactions
10h, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then with saturated common salt wash 1 time,
Dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 86.7%.
Embodiment 5
2.0mmol sodium azide and 0.1mmol cuprous oxide are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol iodobenzenes and 4.0mmol phenylacetaldehydes are added into reaction bulb, in 95 DEG C of stirring reactions
10h, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then with saturated common salt wash 1 time,
Dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 90.0%.
Embodiment 6
2.0mmol sodium azide and 0.1mmol cuprous iodides are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol iodobenzenes and 4.0mmol phenylacetaldehydes are added into reaction bulb, in 95 DEG C of stirring reactions
10h, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then with saturated common salt wash 1 time,
Dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 89.3%.
Embodiment 7
2.0mmol sodium azide and 0.1mmol cuprous oxide are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol are added to methyl iodobenzene and 4.0mmol phenylacetaldehydes into reaction bulb, stirred in 60 DEG C
Reaction 10h is mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 81.0%.
The data characterization of 1- p-methylphenyl -4- phenyl -1,2,3- triazoles：
Off-white color crystal；
1H NMR（400MHz, CDCl3）δ = 8.16 (s, 1H), 7.91 (d, 2H), 7.66 (d, 2H), 7.46
(t, 2H), 7.35 (dd, 3H), 2.43 (s, 3H)。
Embodiment 8
2.0mmol sodium azide and 0.1mmol cuprous iodides are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol are added to methyl iodobenzene and 4.0mmol phenylacetaldehydes into reaction bulb, stirred in 60 DEG C
Reaction 10h is mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 80.9%.
Embodiment 9
2.0mmol sodium azide and 0.1mmol cuprous oxide are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol are added to methyl iodobenzene and 4.0mmol phenylacetaldehydes into reaction bulb, stirred in 80 DEG C
Reaction 10h is mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 87.0%.
Embodiment 10
2.0mmol sodium azide and 0.1mmol cuprous iodides are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol are added to methyl iodobenzene and 4.0mmol phenylacetaldehydes into reaction bulb, stirred in 60 DEG C
Reaction 10h is mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 85.4%.
Embodiment 11
2.0mmol sodium azide and 0.1mmol cuprous oxide are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol are added to methyl iodobenzene and 4.0mmol phenylacetaldehydes into reaction bulb, stirred in 95 DEG C
Reaction 10h is mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100 mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, the % of yield 90.1.
Embodiment 12
2.0mmol sodium azide and 0.1mmol cuprous iodides are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol are added to methyl iodobenzene and 4.0mmol phenylacetaldehydes into reaction bulb, stirred in 60 DEG C
10 h of reaction are mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 87.0%.
Embodiment 13
2.0mmol sodium azide and 0.1mmol cuprous oxide are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.1mmol DBU, 1.0mmol neighbour's methyl iodobenzene and 4.0mmol phenylacetaldehydes are added into reaction bulb, stirred in 60 DEG C
Reaction 10h is mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 80.7%.
The data characterization of 1- o-methyl-phenyl -4- phenyl -1,2,3- triazoles：
Off-white color crystal；
1H NMR (400MHz, CDCl3) δ = 7.97 (s, 1H), 7.94-7.91 (m, 2H), 7.49-7.35
(m, 7H), 2.28 (s, 3H)。
Embodiment 14
2.0mmol sodium azide and 0.1mmol cuprous iodides are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol are added to methyl iodobenzene and 4.0mmol phenylacetaldehydes into reaction bulb, stirred in 60 DEG C
Reaction 10h is mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 78.0%.
Embodiment 15
2.0mmol sodium azide and 0.1mmol cuprous oxide are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.1mmol DBU, 1.0mmol neighbour's methyl iodobenzene and 4.0mmol phenylacetaldehydes are added into reaction bulb, stirred in 80 DEG C
Reaction 10h is mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 88.7%.
Embodiment 16
2.0mmol sodium azide and 0.1mmol cuprous iodides are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.3mmol DBU, 1.0mmol are added to methyl iodobenzene and 4.0mmol phenylacetaldehydes into reaction bulb, stirred in 80 DEG C
10 h of reaction are mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 86.9%.
Embodiment 17
2.0mmol sodium azide and 0.1mmol cuprous oxide are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.1mmol DBU, 1.0mmol neighbour's methyl iodobenzene and 4.0mmol phenylacetaldehydes are added into reaction bulb, stirred in 95 DEG C
Reaction 10h is mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 89.0%.
Embodiment 18
2.0mmol sodium azide and 0.1mmol cuprous iodides are added sequentially to anti-equipped with 3mL solvent dimethyl sulfoxide (DMSO)s
Answer in bottle, then 0.1mmol DBU, 1.0mmol neighbour's methyl iodobenzene and 4.0mmol phenylacetaldehydes are added into reaction bulb, stirred in 95 DEG C
Reaction 10h is mixed, after reaction terminates, ethyl acetate extraction is added into reactant mixture（100mL×3）, then use saturated aqueous common salt
Wash 1 time, dry, filter, rotation removes solvent, and column chromatography purifies to obtain target product, yield 89.2%.
Embodiment above describes the general principle of the present invention, main features and advantages, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, the original for simply illustrating the present invention described in above-described embodiment and specification
Reason, under the scope for not departing from the principle of the invention, various changes and modifications of the present invention are possible, and these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (3)
- A kind of 1. method of the triazole compound of three component one pot process 1,2,3-, it is characterised in that concretely comprise the following steps： Sodium azide and catalyst are added in solvent dimethyl sulfoxide (DMSO) successively in reaction vessel, then sequentially add halogenated hydrocarbons, 1, Carbon -7- the alkene of 8- diazabicylos [5.4.0] 11 and aldehyde compound, reactant mixture is made in 60-95 DEG C of stirring reaction 1,2,3- triazole compound, wherein catalyst are cuprous oxide, cuprous iodide, stannous chloride, anhydrous cupric sulfate or acetic acid Copper, halogenated hydrocarbons are iodobenzene, are phenylacetaldehyde to methyl iodobenzene or adjacent methyl iodobenzene, aldehyde compound.
- 2. the method for the triazole compound of three components one pot process 1,2,3- according to claim 1, its feature exist In：Described sodium azide, catalyst, halogenated hydrocarbons, the carbon -7- alkene of 1,8- diazabicylos [5.4.0] 11 and aldehyde compound Mol ratio be 2:0.1:0.1-0.3:1:4.
- 3. the method for the triazole compound of three components one pot process 1,2,3- according to claim 1, its feature exist In：The dosage of described solvent dimethyl sulfoxide (DMSO) is that 1mol sodium azide corresponds to solvent dimethyl sulfoxide (DMSO) 1.5mL.
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| CN106588693B (en) * | 2016-11-11 | 2019-01-18 | 河南师范大学 | A kind of synthetic method of aryl azide compound |
| CN106588788B (en) * | 2016-11-11 | 2019-07-16 | 河南师范大学 | The method of one pot of two-step method synthesis 1,2,3- triazole compound |
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