CN105541796A - Synthetic method of NH-1,2,3-triazole bipyridine compounds - Google Patents
Synthetic method of NH-1,2,3-triazole bipyridine compounds Download PDFInfo
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- CN105541796A CN105541796A CN201610121084.3A CN201610121084A CN105541796A CN 105541796 A CN105541796 A CN 105541796A CN 201610121084 A CN201610121084 A CN 201610121084A CN 105541796 A CN105541796 A CN 105541796A
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
The invention relates to a novel synthetic method of NH-1,2,3-triazole bipyridine compounds. According to the methods, pyridinecarboxaldehyde, nitroalkane, sodium azide and a catalyst are sequentially added to a reaction solvent in a reaction container, the materials are stirred in the air under a heating condition and react, and the NH-1,2,3-triazole bipyridine compounds are prepared. The method has the benefits as follows: cheap and available AlCl3 is taken as the catalyst, aromatic aldehyde, nitroalkane and sodium azide have a one-pot reaction, the reaction conditions are mild, the yield is high, the raw materials are available, and the NH-1,2,3-triazole bipyridine compounds are synthesized conveniently and effectively.
Description
Technical field
The present invention relates to a kind of NH-1,2, the new synthetic method of 3 triazole dipyridyls.
Technical background
Containing the polymer complex various structures of many nitrogen azoles part, at polymeric material, catalytic material, biomaterial, the fields such as optical material have potential application prospect.In recent years, containing synthesis and the applied research Showed Very Brisk of the polymer complex of many nitrogen azoles part.
Within 2015, Jarowski seminar has synthesized the ligand polymer some pyridine rings having substituent 4-(2-pyridine)-1,2,3 triazole and metal platinum, and have studied its optical property.This seminar finds, substituent sucting electronic effect and can affect ligand-field effect to electronic effect on pyridine ring, has impact to the activated state of Pt-Pt, can affect the luminosity of title complex, thus be expected to synthesize regulatable luminescent material in supramolecule level.Triazole class compounds has certain biological activity, and fungicidal spectrum is wide, also can as pharmaceutical intermediate, in recent years because it to become the study hotspot of region of chemistry and the world of medicine in the widespread use of agricultural chemicals and medicine and other fields.Novel agrochemical containing pyridine ring is of a great variety, and biological activity is also varied.Some more successful agricultural chemicals have: the sterilant boscalid amine etc. of the sterilant fluopicolide researched and developed by Beyer Co., Ltd, BASF AG's research and development, the pesticide imidacloprid of agricultural chemicals company of Japan exploitation, the weedicide fluorine pyridine second sulphur that chemical research institute of Korea S researches and develops is grand.In recent years, emerging click chemistry effectively can synthesize 1,2,3-triazoles, such as by CuAAC (cycloaddition reaction of copper catalysis nitrine and alkynes), corresponding 1,2,3-triazoles can be obtained, but this reaction is not high for the azide reaction activity not having to replace, this determines simultaneously and can not obtain NH-1 by CuAAC, 2,3-triazole.The synthetic method that another method is commonly used is reacted under cupprous katalysis by Terminal Acetylenes and hydrazoic acid, obtains NH-1,2,3-triazole.But in this reaction, hydrazoic acid must have the blocking group of N, therefore finally will carry out deprotection to the blocking group of N and just can obtain NH-1,2,3-triazole.In addition, the synthesis of pyridyl Terminal Acetylenes is comparatively complicated.The people such as such as Prabhath in 2015 synthesize 4-(2-pyridine)-1,2,3 triazole and derivative thereof, are from pyridyl bromo-derivative, successively obtain Terminal Acetylenes by Sonogashira coupling and demethylation silicon.Generally speaking, pyridine synthesis base triazole by this method, whole route contains 4 step reactions.2006, the people such as Gao reported the method by [3+2] cycloaddition pyridine synthesis base triazole.Its detailed process is: the first step is that pyridine-sulfonic acid sodium salt is at RCH
2x, reacts 20min under 60 DEG C (or DMF, 100 DEG C), obtains pyridyl sulfoxide; Second step and aldehyde are at DMF, and 110 DEG C of reaction 20min, obtain alkene; 3rd step is at DMF, with NaN under 120 DEG C of conditions
3there is [3+2] cycloaddition reaction, obtain 1,2,3-triazoles dipyridyl.The method complex steps, the overall yield of three-step reaction is only 13%.2008, the people such as Sengupta reported a kind of method by unsaturated nitro-compound synthesis triazole dipyridyl.With unsaturated nitro-compound respectively with 3-pyridylaldehyde, 4-pyridylaldehyde and NaN
3make solvent at room temperature, DMSO, 20%L-proline makes reaction 8 ~ 10h under catalyzer, the product yield obtained is respectively 76%, 71%.But the method has some shortcomings: one be pyridine synthesis base unsaturated nitro-compound productive rate low, not easily preserve; Two is that nitroolefin is easily polymerized in the reaction, greatly reduces the yield of reaction; Three is that catalyzer L-proline price is relatively costly, and consumption reaches 20%mol.2010, the people such as Zhang Wensheng were with 3-aryl-2,3-dibromo-propionic acid and NaN
3for raw material, DMF is reaction solvent, Pd
2(dba)
3-Xantphos system is catalyzer, at N
2lower 110 DEG C of reactions 36h " one kettle way " are protected to synthesize a series of 4-aryl-1H-1,2,3-triazole class compounds.In the same year, this seminar has done improvement, with CuI, CsCO to reaction conditions again
3, sodium ascorbate makes catalyzer, DMSO makes solvent, at N
2protect lower 110 DEG C of reaction 4h.Wherein the productive rate of 4-(3-pyridyl)-2H-1,2,3-triazole reaches 95%, but needs N
2protection, used catalyst system complexity, and the substrate that can expand is few.About 2012, the people such as daybreak has reported a series of triazole bipyridyliums derivative with insecticidal activity.Its synthetic method is: first at 0 ~ 5 DEG C by pridylamino diazotization, pyridine synthesis diazonium salt, drip sodium azide synthesis azido-pyridine again, then in the basic conditions, make azido-pyridine respectively in dehydrated alcohol reflux 4 ~ 6h, in distilled water reflux 2 ~ 4h, finally use distilled water diluting, adjust pH to weakly alkaline makes product separate out.The method step is more, and needs control temperature and pH, operates more loaded down with trivial details.
In sum, the method for more than synthesizing NH-1,2,3-triazole Bipyridine compound all has that synthetic route is long, productive rate is low, can fit substrate few or synthesis difficulty, complex operation or the shortcoming such as poor stability, expensive catalyst.
Summary of the invention
Technical problem to be solved by this invention is for above-mentioned prior art, provides a kind of synthetic method of new NH-1,2,3-triazole Bipyridine compound, adopts catalyzer cheap and easy to get, " one kettle way " synthesize target product, simplify operation, add yield.
The solution that problem adopts that the present invention solves above-mentioned proposition is: a kind of NH-1,2, the synthetic method of 3-triazole Bipyridine compound, it is characterized in that: successively pyridylaldehyde, nitroparaffins, sodiumazide, catalyzer are joined in reaction solvent in reaction vessel, in a heated condition, in air, stirring reaction obtains NH-1, and 2,3-triazole Bipyridine compound, its reaction formula is as follows:
Wherein R
1for hydrogen, C
1-C
6alkyl, C
1-C
6alkoxy or halogen, the aldehyde radical on pyridine is that optional position on pyridine ring except N replaces; Wherein R
2for hydrogen, C
1-C
6alkyl, C
1-C
6alkoxyl group or ethyl formate.
By such scheme, described catalyzer is AlCl
3.
By such scheme, described reaction solvent is selected from DMSO, DMF, methyl alcohol, ethanol or acetonitrile.
By such scheme, reaction solvent is DMSO.
By such scheme, described catalyzer mole dosage is 0.05-1.0 times of pyridylaldehyde consumption.
By such scheme, the mol ratio of described pyridylaldehyde, nitroparaffins and sodiumazide is 1:(1.5 ~ 2): 1.2.
By such scheme, react and carry out within the scope of 20 ~ 120 DEG C.
By such scheme, react and carry out at 80 DEG C.
The invention has the beneficial effects as follows: the present invention adopts AlCl cheap and easy to get
3as catalyzer, aromatic aldehyde, nitroparaffins, sodiumazide " one kettle way " react, and reaction conditions is gentle, and productive rate is high, and raw material is easy to get, easily and effectively synthesized NH-1,2,3-triazole Bipyridine compound.Compared with existing method, reaction of the present invention adopts " one kettle way ", shortens synthetic route, and wherein not only sodiumazide can promote that the molecular balance forward generating nitroolefin moves, and AlCl
3good catalytic effect is had to the reaction generating triazole dipyridyl.Therefore reaction conditions of the present invention is gentle, the reaction times is short, security good, easy and simple to handle, substrate spectrum is wide, reaction efficiency is high and catalyzer is cheap, is a kind of method with potential using value.
Embodiment
Below in conjunction with specific embodiment, concrete introduction is done to the present invention.
Embodiment 1:
The synthesis of 4-(2-pyridyl)-2H-1,2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol2-pyridylaldehyde, 0.50mmol Nitromethane 99Min., 0.39mmol sodiumazide, 0.04mmolAlCl
3, 2mLDMSO, at 80 DEG C of lower magnetic force stirring reactions after 12 hours, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:3 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 86%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (600MHz, CDCl
3): δ 7.97 (s, 1H), 7.51 (d, J=1.2Hz, 1H), 6.85 (d, J=3.3Hz, 1H), 6.51 (m, 1H).Nuclear-magnetism carbon spectrogram result is:
13cNMR (150MHz, CDCl
3): δ 145.3,142.8,111.6,107.8.
Embodiment 2:
The synthesis of 4-(3-pyridyl)-2H-1,2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol3-pyridylaldehyde, 0.50mmol Nitromethane 99Min., 0.39mmol sodiumazide, 0.04mmolAlCl
3, 2mLDMSO, at 80 DEG C of lower magnetic force stirring reactions after 12 hours, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:3 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 91%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (500MHz, CDCl
3-DMSO-d6) d=9.06 (s, 1H), 8.57 (s, 1H), 8.15-8.14 (d, J=2.0Hz, 1H), 7.99 (d, J=1.8Hz, 1H), 7.41-7.38 (m, 1H).
Embodiment 3:
The synthesis of 4-(4-pyridyl)-2H-1,2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol4-pyridylaldehyde, 0.50mmol Nitromethane 99Min., 0.39mmol sodiumazide, 0.04mmolAlCl
3, 2mLDMSO, at 80 DEG C of lower magnetic force stirring reactions after 12 hours, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:3 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 80%.
Embodiment 4:
The synthesis of 5-methyl-4-(2-pyridyl)-2H-1,2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol2-pyridylaldehyde, 0.50mmol nitroethane, 0.39mmol sodiumazide, 0.04mmolAlCl
3, 2mLDMSO, at 80 DEG C of lower magnetic force stirring reactions after 12 hours, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:3 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 85%.
Embodiment 5:
The synthesis of 5-methyl-4-(3-pyridyl)-2H-1,2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol3-pyridylaldehyde, 0.50mmol nitroethane, 0.39mmol sodiumazide, 0.04mmolAlCl
3, 2mLDMSO, at 80 DEG C of lower magnetic force stirring reactions after 12 hours, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:3 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 86%.
Embodiment 6:
The synthesis of 5-methyl-4-(4-pyridyl)-2H-1,2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol4-pyridylaldehyde, 0.50mmol nitroethane, 0.39mmol sodiumazide, 0.04mmolAlCl
3, 2mLDMSO, at 80 DEG C of lower magnetic force stirring reactions after 12 hours, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:3 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 80%.
Embodiment 7:
The synthesis of 5-group-4 ethyl formate-4-(2-pyridyl)-2H-1,2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol2-pyridylaldehyde, 0.50mmol ethyl nitroacetate, 0.39mmol sodiumazide, 0.04mmolAlCl
3, 2mLDMSO, at 80 DEG C of lower magnetic force stirring reactions after 12 hours, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:3 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 85%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (400MHz, CDCl
3): δ 8.68 (s, 1H), 8.55 (s, 1H), 7.89 (t, J=7.8Hz, 1H), 7.44-7.36 (m, 1H), 4.51-4.42 (m, 2H), 1.45-1.36 (m, 3H).Nuclear-magnetism carbon spectrogram result is:
13cNMR (125MHz, CDCl
3): δ 161.7,149.1,146.0,142.2,137.6,135.2,125.2,124.6,61.7,14.2.
Embodiment 8:
The synthesis of 5-group-4 ethyl formate-4-(3-pyridyl)-2H-1,2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol3-pyridylaldehyde, 0.50mmol ethyl nitroacetate, 0.39mmol sodiumazide, 0.04mmolAlCl
3, 2mLDMSO, at 80 DEG C of lower magnetic force stirring reactions after 12 hours, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:3 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 85%.
Embodiment 9:
The synthesis of 5-group-4 ethyl formate-4-(4-pyridyl)-2H-1,2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol4-pyridylaldehyde, 0.50mmol ethyl nitroacetate, 0.39mmol sodiumazide, 0.04mmolAlCl
3, 2mLDMSO, at 80 DEG C of lower magnetic force stirring reactions after 12 hours, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:3 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 80%.
The present invention adopts AlCl cheap and easy to get
3as catalyzer, pyridylaldehyde, nitroparaffins, sodiumazide one pot reaction, easily and effectively synthesize NH-1,2,3-triazole Bipyridine compound, compared with existing method, reaction conditions of the present invention is gentle, the reaction times is short, security good, low in raw material price, raw material are easy to get, simple operation, reaction efficiency is high and catalyzer is cheap, is a kind of method with potential using value.
Above-mentioned example of executing does not limit the present invention in any form, all employings be equal to replace or etc. the technical scheme that obtains of the mode of little conversion, all drop in protection scope of the present invention.
Claims (8)
1. a NH-1,2, the synthetic method of 3-triazole Bipyridine compound, it is characterized in that: successively pyridylaldehyde, nitroparaffins, sodiumazide, catalyzer are joined in reaction solvent in reaction vessel, in a heated condition, in air, stirring reaction obtains NH-1, and 2,3-triazole Bipyridine compound, its reaction formula is as follows:
Wherein R
1for hydrogen, C
1-C
6alkyl, C
1-C
6alkoxy or halogen, the aldehyde radical on pyridine is that optional position on pyridine ring except N replaces; Wherein R
2for hydrogen, C
1-C
6alkyl, C
1-C
6alkoxyl group or group-4 ethyl formate.
2. synthetic method according to claim 1, is characterized in that: described catalyzer is AlCl
3.
3. synthetic method according to claim 1 and 2, is characterized in that: described reaction solvent is selected from DMSO, DMF, methyl alcohol, ethanol or acetonitrile.
4. synthetic method according to claim 3, is characterized in that: reaction solvent is DMSO.
5. synthetic method according to claim 1, is characterized in that: described catalyzer mole dosage is 0.05-1.0 times of pyridylaldehyde consumption.
6. synthetic method according to claim 1, is characterized in that: the mol ratio of described pyridylaldehyde, nitroparaffins and sodiumazide is 1:(1.5 ~ 2): 1.2.
7. synthetic method according to claim 1, is characterized in that: react and carry out within the scope of 20 ~ 120 DEG C.
8. synthetic method according to claim 7, is characterized in that: react and carry out at 80 DEG C.
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| WO2019133770A3 (en) * | 2017-12-29 | 2019-08-15 | Biomarin Pharmaceutical Inc. | Glycolate oxidase inhibitors for the treatment of disease |
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| CN116284772A (en) * | 2023-02-09 | 2023-06-23 | 四川大学 | Bipyridine triazole covalent organic polymer and preparation method and application thereof |
| RU2805308C2 (en) * | 2017-12-29 | 2023-10-13 | Байомарин Фармасьютикал Инк. | Glycolatoxidase inhibitors for the treatment of diseases |
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| WO2019133770A3 (en) * | 2017-12-29 | 2019-08-15 | Biomarin Pharmaceutical Inc. | Glycolate oxidase inhibitors for the treatment of disease |
| CN111788187A (en) * | 2017-12-29 | 2020-10-16 | 生物马林药物股份有限公司 | Glycolate oxidase inhibitors for disease treatment |
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| RU2805308C2 (en) * | 2017-12-29 | 2023-10-13 | Байомарин Фармасьютикал Инк. | Glycolatoxidase inhibitors for the treatment of diseases |
| CN110590760A (en) * | 2019-09-06 | 2019-12-20 | 武汉工程大学 | 2, 1-benzisoxazole derivative and synthetic method and application thereof |
| CN110590760B (en) * | 2019-09-06 | 2023-06-06 | 武汉工程大学 | 2, 1-benzisoxazole derivative and synthetic method and application thereof |
| CN116284772A (en) * | 2023-02-09 | 2023-06-23 | 四川大学 | Bipyridine triazole covalent organic polymer and preparation method and application thereof |
| CN116284772B (en) * | 2023-02-09 | 2024-02-27 | 四川大学 | Bipyridine triazole covalent organic polymer and preparation method and application thereof |
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