CN106866508A - A kind of method that catalysis oxidation heteroaromatic primary alconol prepares heteroaromatic aldehyde - Google Patents
A kind of method that catalysis oxidation heteroaromatic primary alconol prepares heteroaromatic aldehyde Download PDFInfo
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- CN106866508A CN106866508A CN201710037086.9A CN201710037086A CN106866508A CN 106866508 A CN106866508 A CN 106866508A CN 201710037086 A CN201710037086 A CN 201710037086A CN 106866508 A CN106866508 A CN 106866508A
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/48—Aldehydo radicals
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/16—Halogen atoms; Nitro radicals
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
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Abstract
The invention provides a kind of method that catalysis oxidation heteroaromatic primary alconol prepares corresponding heteroaromatic aldehyde.Heteroaromatic primary alconol high selectivity, with air as oxidant, is oxidized to heteroaromatic aldehyde by the method in atmospheric conditions with nitric acid vanadium acyl as catalyst.The method oxidization-hydrogenation ratio is high, and accessory substance is water, green economy environmental protection；Reaction condition is gentle, simple to operate.The catalyst system and catalyzing is oxidant using air, and with base metal as catalyst, reaction condition is gentle, and oxidation efficiency is high, green economy, can be by heteroaromatic primary alconol efficient catalytic selective oxidation into corresponding heteroaromatic aldehyde.With precious metal catalyst system and compared with the catalyst system and catalyzing containing NO free radical, the catalyst system and catalyzing oxidation reaction is with low cost, with application value very high.
Description
Technical field
The present invention relates to a kind of method for preparing heteroaromatic aldehyde.It is specifically related to a kind of to be catalyzed by oxygen source of molecular oxygen
The method that selective oxidation heteroaromatic primary alconol prepares corresponding heteroaromatic aldehyde.
Background technology
Heteroaromatic aldehyde compound is the important organic chemical industry's intermediate of a class, is had in Fine Chemical important
Using.For example 2- pyridine carboxaldehydes can be used as the raw material of synthesis anti-HIV protease inhibitors, and 3- thiophenecarboxaldehydes are used as important medicine
Intermediate is used for synthesizing fungicide, androgen inhibitors, herbicide, herbicide, plant growth regulator etc..Selective oxidation is miscellaneous
The aromatic important method for being to prepare corresponding heteroaromatic aldehyde compound of cyclophane.Tradition uses the side of stoichiometric oxidant
Method, such as such as Sarrett reagents, Jones reagents, activated manganese dioxide, Dess-Martin reagents, although can be in high yield
Realize the heteroaromatic alcohol oxidation corresponding heteroaromatic aldehyde of conversion, but oxidizing process can produce harmful waste residue, pollute environment.Make
When with oxygen being oxidant, the accessory substance of oxidizing process generation is only water, environmental protection (Green Chem., 2012,14,547-
564), exploitation has important application value and prospect using the efficiently catalyzing and oxidizing system that oxygen is oxygen source.But pyridine, piperazine
Piperazine, thiophene contain N, S hetero atom, and its strong complexing easily inactivates metallic catalyst, heterocyclic aromatic compounds selective oxidation
It is very challenging.For example based on noble metal Ru catalyst system and catalyzing can efficiently catalyzing and oxidizing be free of heteroatomic benzylalcohol, fat
Fat alcohol compound, but run into the heterocyclic compound containing N, S and easily inactivate, its practicality is very restricted
(J.Am.Chem.Soc.2001,123,6826-6833)；Using NO free radical as the catalyst system and catalyzing of key component show compared with
Catalysis activity high, wherein with TEMPO as representative.Such as Chinese patent CN1796349A,
CN1789225A reports NaNO respectively2/Br2/ TEMPO, NaNO2This kind of catalyst system and catalyzings of/HCl/TEMPO all use TEMPO, but
TEMPO class compounds are expensive.Exploitation one kind uses air as oxidant, and does not use noble metal, can low temperature,
Efficiently catalyzing and oxidizing heteroaromatic primary alconol prepares the new technology of corresponding heteroaromatic aldehyde under condition of normal pressure, has great importance
And application background.
The content of the invention
It is an object of the invention to provide one kind phase is prepared by oxygen source catalytic selective oxidation heteroaromatic primary alconol of molecular oxygen
The method for answering heteroaromatic aldehyde, the oxidant of the method is air or oxygen, and catalyst is cheap and easy to get, and catalysis activity is high, reaction
Mild condition, accessory substance is few.
A kind of method that catalysis oxidation heteroaromatic primary alconol prepares heteroaromatic aldehyde, step is as follows：
Heteroaromatic primary alconol, catalyst, oxidant are mixed with solvent, at ambient pressure, reaction temperature is 20-120 DEG C, instead
It is 1-30 hours between seasonable, obtains corresponding heteroaromatic aldehyde；
Described heteroaromatic primary alconol is the pyridinemethanol containing substitution base, piperazine methyl alcohol or thenyl alcohol：
R1、R2、R3And R4It is hydrogen, alkyl, phenyl ,-F ,-Cl ,-Br ,-NO2, methoxyl group, ethyoxyl, amino or acetyl ammonia
Base, R1、R2、R3And R4It is identical or different；
In heteroaromatic primary alconol molecule containing substitution base on heterocycle, substituting group position is the one kind in ortho position, meta, contraposition
Or it is two or more, substitution base species is one or more, and the number for replacing base is one or more.
The catalyst is nitric acid vanadium acyl, and the consumption of nitric acid vanadium acyl is the 0.5-20mol%, preferably 1- of heteroaromatic primary alconol
10mol%；When catalyst amount increases, complete transformation time shortens, but cost is improved.
Described oxidant is air or oxygen；
Described solvent is mixed for one or more in acetonitrile, propionitrile, isobutyronitrile, valeronitrile, diethylamine, triethylamine
Close, described solvent load is the 50-300wt% of heteroaromatic primary alconol.
Beneficial effects of the present invention：The catalyst system and catalyzing is oxidant using air, with base metal as catalyst, reaction
Mild condition, oxidation efficiency is high, green economy, can be by heteroaromatic primary alconol efficient catalytic selective oxidation into corresponding heteroaromatic
Aldehyde.With precious metal catalyst system and compared with the catalyst system and catalyzing containing NO free radical, the catalyst system and catalyzing oxidation reaction is with low cost,
With application value very high.
Specific embodiment
Specific embodiment of the invention is further illustrated below in conjunction with technical scheme.
Embodiment 1
1.09g 4- pyridinemethanols, 2mol% nitric acid vanadium acyl (relative to substrate 4- pyridinemethanols) are added to 50mL anti-
Ying Guanzhong, adds 5mL isobutyronitriles, is filled with air balls, closes and finishes reaction tube, and 80 DEG C are warming up under stirring, and keeps 2h, question response
Terminate, be cooled to room temperature.Sampling is analyzed using gas-chromatography, the conversion ratio 96.5% of 4- pyridinemethanols, 4- pyridine carboxaldehydes
Selectivity be more than 99%.
Embodiment 2
10g 4- pyridinemethanols, 1mol% nitric acid vanadium acyl (relative to substrate 4- pyridinemethanols) are added to 250mL reactions
Guan Zhong, adds 20mL isobutyronitriles, is filled with air balls, closes and finishes reaction tube, and 100 DEG C are warming up under stirring, and keeps 30h, question response
Terminate, be cooled to room temperature.Sampling is analyzed using gas-chromatography, the conversion ratio 99.2% of 4- pyridinemethanols, 4- pyridine carboxaldehydes
Selectivity be more than 99%.
Embodiment 3
1.14g 2- thenyl alcohols, 0.5mol% nitric acid vanadium acyl (relative to substrate 2- thenyl alcohols) are added to 50mL
In reaction tube, 5mL acetonitriles are added, be filled with air balls, closed and finish reaction tube, 80 DEG C are warming up under stirring, and keep 30h, question response
Terminate, be cooled to room temperature.Sampling is analyzed using gas-chromatography, the conversion ratio 98.5% of 2- thenyl alcohols, 2 thiophene carboxaldehyde
Selectivity be more than 99%.
Embodiment 4
By the chloro- 2- pyrazines methyl alcohol of 1.44g 3-, 2mol% nitric acid vanadium acyl (2- pyrazines methyl alcohol chloro- relative to substrate 3-), plus
Enter in 50mL reaction tubes, add 5mL acetonitriles, be filled with air balls, close and finish reaction tube, 40 DEG C are warming up under stirring, and keep
10h, question response terminates, and is cooled to room temperature.Sampling is analyzed using gas-chromatography, the conversion ratio of the chloro- 2- pyrazines methyl alcohol of 3-
The selectivity of the chloro- 2- pyrazines formaldehyde of 96.1%, 3- is more than 99%.
Embodiment 5
By 1.88g 3- bromopyridine -5- methyl alcohol, 5mol% nitric acid vanadium acyl (relative to substrate 3- bromopyridine -5- methyl alcohol), plus
Enter in 50mL reaction tubes, add 5mL triethylamines, be filled with air balls, close and finish reaction tube, 90 DEG C are warming up under stirring, and keep
5h, question response terminates, and is cooled to room temperature.Sampling is analyzed using gas-chromatography, the conversion ratio of 3- bromopyridine -5- methyl alcohol
The selectivity of 99.8%, 3- bromopyridine -5- formaldehyde is more than 99%.
Embodiment 6
By 1.88g 3- bromopyridine -5- methyl alcohol, 5mol% nitric acid vanadium acyl (relative to substrate 3- bromopyridine -5- methyl alcohol), plus
Enter in 50mL reaction tubes, add 5mL acetonitriles, be filled with air balls, close and finish reaction tube, 80 DEG C are warming up under stirring, and keep 8h,
Question response terminates, and is cooled to room temperature.Sampling is analyzed using gas-chromatography, the conversion ratio 99.3% of 3- bromopyridine -5- methyl alcohol,
The selectivity of 3- bromopyridine -5- formaldehyde is more than 99%.
Embodiment 7
1.09g 2- pyridinemethanols, 1mol% nitric acid vanadium acyl (relative to 2- pyridinemethanols) are added to 50mL reaction tubes
In, 5mL acetonitriles are added, air balls are filled with, close and finish reaction tube, 80 DEG C are warming up under stirring, and 6h is kept, question response terminates, cold
But to room temperature.Sampling is analyzed using gas-chromatography, the conversion ratio 98.2% of 2- pyridinemethanols, the selectivity of 2- pyridine carboxaldehydes
More than 99%.
Embodiment 8
1.09g 3- pyridinemethanols, 1mol% nitric acid vanadium acyl (relative to 3- pyridinemethanols) are added to 50mL reaction tubes
In, 10mL isobutyronitriles are added, air balls are filled with, close and finish reaction tube, 100 DEG C are warming up under stirring, and 10h is kept, question response knot
Beam, is cooled to room temperature.Sampling is analyzed using gas-chromatography, the conversion ratio 99.0% of 3- pyridinemethanols, 3- pyridine carboxaldehydes
Selectivity is more than 99%.
Embodiment 9
1.23g5- picoline -2- methyl alcohol, 2mol% nitric acid vanadium acyl (relative to 5- picoline -2- methyl alcohol) are added
To in 50mL reaction tubes, 5mL diethylamine is added, is filled with air balls, closed and finish reaction tube, 50 DEG C are warming up under stirring, and keep 6h,
Question response terminates, and is cooled to room temperature.Sampling is analyzed using gas-chromatography, the conversion ratio of 5- picoline -2- methyl alcohol
The selectivity of 95.2%, 5- picoline -2- formaldehyde is more than 99%.
Embodiment 10
By 1.38g 2- methylamino -3- pyridinemethanols, 5mol% nitric acid vanadium acyl is (relative to 2- methylamino -3- pyridine first
Alcohol), it is added in 50mL reaction tubes, 10mL triethylamines are added, air balls are filled with, close and finish reaction tube, 80 DEG C are warming up under stirring,
And keep 5h, question response to terminate, it is cooled to room temperature.Sampling is analyzed using gas-chromatography, 2- methylamino -3- pyridinemethanols
Conversion ratio 97.2%, the selectivity of 2- methylamino -3- pyridine carboxaldehydes is more than 99%.
Embodiment 11
By 1.82g 3,5- dimethyl -4- nitropyridine -2- methyl alcohol, 5mol% nitric acid vanadium acyl (relative to 3,5- dimethyl -
4- nitropyridine -2- methyl alcohol), it is added in 50mL reaction tubes, 5mL acetonitriles are added, air balls are filled with, close and finish reaction tube, stirring
Under be warming up to 80 DEG C, and keep 6h, question response terminates, and is cooled to room temperature.Sampling is analyzed using gas-chromatography, 3,5- diformazans
The conversion ratio 98.9% of base -4- nitropyridine -2- methyl alcohol, the selectivity of 3,5- dimethyl -4- nitropyridine -2- formaldehyde is more than
99%.
Embodiment 12
By 1.67g 4- methoxyl group -3,5- dimethyl -2- pyridinemethanols, 5mol% nitric acid vanadium acyl (relative to 4- methoxyl groups -
3,5- dimethyl -2- pyridinemethanols), it is added in 50mL reaction tubes, 5mL isobutyronitriles are added, air balls are filled with, close Bi Fanying
Pipe, is warming up to 100 DEG C under stirring, and keeps 6h, and question response terminates, and is cooled to room temperature.Sampling is analyzed using gas-chromatography,
4- methoxyl group -3, the conversion ratio 99.5% of 5- dimethyl -2- pyridinemethanols, 4- methoxyl group -3,5- dimethyl -2- pyridine carboxaldehydes
Selectivity is more than 99%.
Claims (5)
1. a kind of method that catalysis oxidation heteroaromatic primary alconol prepares heteroaromatic aldehyde, it is characterised in that step is as follows：
Heteroaromatic primary alconol, catalyst, oxidant are mixed with solvent, at ambient pressure, reaction temperature is 20-120 DEG C, during reaction
Between be 1-30 hours, obtain corresponding heteroaromatic aldehyde；
Described heteroaromatic primary alconol is the pyridinemethanol containing substitution base, piperazine methyl alcohol or thenyl alcohol：
R1、R2、R3And R4It is hydrogen, alkyl, phenyl ,-F ,-Cl ,-Br ,-NO2, methoxyl group, ethyoxyl, amino or acetylamino, R1、
R2、R3And R4It is identical or different；
The catalyst is nitric acid vanadium acyl, and the consumption of nitric acid vanadium acyl is the 0.5-20mol% of heteroaromatic primary alconol；
Described oxidant is air or oxygen；
Described solvent load is the 50-300wt% of heteroaromatic primary alconol.
2. method according to claim 1, it is characterised in that in the heteroaromatic primary alconol molecule containing substitution base on heterocycle,
Substituting group position is one or more in ortho position, meta, contraposition, and substitution base species is one or more, substitution
The number of base is one or more.
3. method according to claim 1 and 2, it is characterised in that the consumption of the catalyst is heteroaromatic primary alconol
1-10mol%.
4. method according to claim 1 and 2, it is characterised in that described solvent is acetonitrile, propionitrile, isobutyronitrile, penta
One or more mixing in nitrile, diethylamine, triethylamine.
5. method according to claim 3, it is characterised in that described solvent is acetonitrile, propionitrile, isobutyronitrile, valeronitrile, two
One or more mixing in ethamine, triethylamine.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111298793A (en) * | 2020-03-04 | 2020-06-19 | 中国科学院兰州化学物理研究所 | Method for preparing aromatic aldehyde by selectively catalyzing aromatic alcohol with supported nickel catalyst |
| CN115108976A (en) * | 2021-03-18 | 2022-09-27 | 大连理工大学 | Method for preparing pyridine carboxamide through one-step oxidative amidation |
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| CN101148400A (en) * | 2006-09-22 | 2008-03-26 | 中国科学院大连化学物理研究所 | Method for preparing aldehydes and ketones by using oxygen gas to oxidize alcohols |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101148400A (en) * | 2006-09-22 | 2008-03-26 | 中国科学院大连化学物理研究所 | Method for preparing aldehydes and ketones by using oxygen gas to oxidize alcohols |
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| AHMED M. FAYED，ET AL.: "Complexes ofcis-dioxomolybdenum(VI) and oxovanadium(IV) with a tridentate ONS donor ligand: Synthesis, spectroscopic properties,X-ray crystal structure and catalytic activity", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》 * |
| ALI I. ELKURTEHI，ET AL.: "Vanadium Aminophenolate Complexes and Their Catalytic Activity in Aerobic and H2O2-Mediated Oxidation Reactions", 《EUROPEAN JOURNAL OF INORGANIC CHEMISTRY》 * |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111298793A (en) * | 2020-03-04 | 2020-06-19 | 中国科学院兰州化学物理研究所 | Method for preparing aromatic aldehyde by selectively catalyzing aromatic alcohol with supported nickel catalyst |
| CN111298793B (en) * | 2020-03-04 | 2023-01-03 | 中国科学院兰州化学物理研究所 | Method for preparing aromatic aldehyde by selectively catalyzing aromatic alcohol with supported nickel catalyst |
| CN115108976A (en) * | 2021-03-18 | 2022-09-27 | 大连理工大学 | Method for preparing pyridine carboxamide through one-step oxidative amidation |
| CN115108976B (en) * | 2021-03-18 | 2023-10-24 | 大连理工大学 | Method for preparing pyridine carboxamide by one-step oxidation amidation |
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