CN105801587B - A kind of method that environmental friendly catalysis prepares pyrans simultaneously [2,3 d] pyrimidone derivatives - Google Patents
A kind of method that environmental friendly catalysis prepares pyrans simultaneously [2,3 d] pyrimidone derivatives Download PDFInfo
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Abstract
The invention discloses a kind of method that environmental friendly catalysis prepares pyrans simultaneously [2,3 d] pyrimidone derivatives, belong to ionic liquid-catalyzed technical field.The mol ratio of aromatic aldehyde, barbiturates and malononitrile is 1 in preparation reaction：1：1~1.4, the mole of acidic ionic liquid catalysts is the 3~5% of aromatic aldehyde used, the volume for the ethanol water of reaction dissolvent 60% counted using milliliter as by mM in terms of 7~9 times of aromatic aldehyde mole, reflux time is 10~25min, reaction is cooled to room temperature after terminating, filter, filter residue obtains pyrans simultaneously [2,3 d] pyrimidone derivatives after ethanol is washed, is dried in vacuo.The present invention has the characteristics that catalyst is biodegradable, raw material availability is high, catalytic capability is strong and whole preparation process is simple to operate compared with using the preparation method of other acidic ionic liquid catalysts, is easy to industrialize large-scale application.
Description
Technical field
The invention belongs to ionic liquid-catalyzed technical field, and in particular to a kind of environmental friendly catalysis prepare pyrans simultaneously [2,
3-d] pyrimidone derivatives method.
Background technology
Pyrimidone derivatives are a kind of compounds containing azepine ring structure with significant application value, because of its structure
Changeability causes it to have extensive bioactivity, is had a wide range of applications in medicine and pesticide field, wherein in field of medicaments,
They can be used as antineoplastic, analgesic drug product, bactericide, herbicide, agrochemical, be novel drugs and novel pesticide developmental research
One of focus.In addition, with further investigation of the people to such compound, some heterocyclic fused pyrimidone derivatives are found
Outstanding bioactivity is likewise supplied with, simultaneously [2,3-d] pyrimidone derivatives can be used as blood-pressure drug, antiplatelet drug such as pyrans
Thing, cancer therapy drug, antimicrobial agents, anti-malaria medicaments and the good antagonist of neuropeptide receptor etc..Therefore, pyrans is studied
And the preparation of [2,3-d] pyrimidone derivatives has very important significance.
Pyrans simultaneously [2,3-d] pyrimidone derivatives preparation be typically under inorganic or organic acid catalysis, by aldehyde, have live
Sprinkle the compound (malononitrile or Maxwell acid) of α-hydrogen atom with containing pyrimidone framework compound (barbiturates or 2- amino -4,
6- dihydroxy-pyrimidines) by made from condensation, addition.But often there is the reaction bar that the reaction time is longer, harsh in the above method
The shortcomings of part, relatively low conversion ratio, pollution environment and catalyst can not recycle.Acidic ion liquid is as a kind of functionalization
Ionic liquid due to have the advantages that preferable heat endurance, the acidic site being evenly distributed and easily with product separate and recover and by
Apply in the preparation process of organic compound.Sulfuric acid is hydrogenated succimide salt ion by wherein Farhad Shirini etc.
Liquid [H-Suc] HSO4As a kind of new effective homogeneous catalyst, in the short period of time by aromatic aldehyde, malononitrile and Ba Bi
Appropriate acid catalysis synthesizes a series of pyrans simultaneously [2,3-d] pyrimidone derivatives, and catalyst is not before catalytic activity is reduced
At least 4 times (Succinimidinium hydrogensulfate ([H-Suc] HSO can be recycled by putting4)as an
Efficient ionic liquid catalyst for the synthesis of 5-arylidenepyrimidine-2,
4,6 (1H, 3H, 5H)-trione and pyrano-pyrimidinones derivatives [J], Journal of the
Iranian Chemical Society, 2016,13：457~463).
Result of study about documents and materials shows that the biodegradability of the ionic liquid containing cyclic structure is poor,
Not easily pass through current most popular biological treatment or biological self-purification is degraded.Further, since ionic liquid
Catalyst [H-Suc] HSO4Acidity it is relatively weak, cause usage amount in use larger.Finally, although above-mentioned preparation method
It is catalyzed that yield is higher, but whole process is more complicated, including the second to product pyrans simultaneously [2,3-d] pyrimidone derivatives
Alcohol recrystallizes purification processes and the water removal operation of Cheng Qian was recycled to catalyst.These complicated processes also bring raw material
Recycling rate is relatively low and consumes energy the problems such as larger, environmental pollution is serious, is difficult in industrialized production by large-scale use.
The content of the invention
It is an object of the invention to overcome to prepare pyrans using presence of acidic ionic liquid catalyst in the prior art simultaneously [2,3-d] are phonetic
Have that ionic-liquid catalyst usage amount is larger, not easily biological-degradable during pyridine ketone derivatives, raw material availability is low, product carries
Pure procedure is complicated and the shortcomings of catalyst is using preceding needing to carry out purification processes, and provide a kind of catalyst activity compared with
Good, easily biological-degradable, raw material availability is high, purification of products is easy, reaction condition is gentle and catalysis system can direct circulation make
The method that catalysis prepares pyrans simultaneously [2,3-d] pyrimidone derivatives.
The structural formula of acidic ionic liquid catalysts used in the present invention is：
The method that a kind of environmental friendly catalysis provided by the present invention prepares pyrans simultaneously [2,3-d] pyrimidone derivatives, its
Chemical equation is：
The mol ratio of aromatic aldehyde (I), barbiturates (II) and malononitrile (III) is 1 in wherein reacting：1：1~1.4, acid
The mole of property ionic-liquid catalyst is the 3~5% of aromatic aldehyde used, the ethanol water of reaction dissolvent 60% in terms of milliliter
Volume be by mM in terms of 7~9 times of aromatic aldehyde mole, reaction pressure is an atmospheric pressure, reflux time
For 10~25min, reaction is cooled to room temperature after terminating, pulverizes the solid of precipitation, stands, and filters, filter residue washs through ethanol, vacuum
Pyrans simultaneously [2,3-d] pyrimidone derivatives (IV) are obtained after drying.The acidic ionic liquid catalysts that contain in filtrate and a small amount of
The complete raw material of unreacted, it can be reused without processing.
Aromatic aldehyde used in the present invention is benzaldehyde, 4-chloro-benzaldehyde, p-bromobenzaldehyde, paranitrobenzaldehyde, to methyl
Benzaldehyde, P-methoxybenzal-dehyde, a tolyl aldehyde, o-chlorobenzaldehyde, m chlorobenzaldehyde, m-methoxybenzaldehyde, a nitre
Any of benzaldehyde, o-nitrobenzaldehyde.
The synthetic method of acidic ionic liquid catalysts used in the present invention, with reference to associated materials (A convenient
The under solvent-free conditions of approach for the synthesis of 1,3,5-trioxanes
At room temperature, Monatshefte f ü r Chemie Chemical Monthly, 2014,145 (6)：1017
~1022).
It is of the invention compared with other acidic ion liquids make the preparation method of catalyst, there is advantages below：
1st, acidic ionic liquid catalysts biodegradable is preferable, and environmental pollution is smaller；
2nd, the complete raw material of unreacted can enter next recycling, and utilization rate is high；
3rd, catalyst is without reusable, the time saving and energy saving province's energy consumption of any processing；
4th, reaction temperature is low, mild condition, is easy to practical operation；
5th, the catalytic capability of catalyst is stronger, and usage amount is less；
6th, the purification process of product is easy, is easy to industrialization to mass produce.
Brief description of the drawings
Fig. 1 is the technique that acidic ionic liquid catalysts catalysis of the present invention prepares pyrans simultaneously [2,3-d] pyrimidone derivatives
Flow chart.
Fig. 2 is that acidic ionic liquid catalysts of the present invention prepare 7- amino -5- (4- nitrobenzophenones) -2,4- bis- in catalysis
Oxygen -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6- nitriles reaction in recycle when product yield variation diagram.
Fig. 3 is that acidic ionic liquid catalysts of the present invention prepare 7- amino -5- (4- hydroxy phenyls) -2,4- bis- in catalysis
Oxygen -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6- nitriles reaction in recycle when product yield variation diagram.
Fig. 4 is that acidic ionic liquid catalysts of the present invention prepare 7- amino -5- (2- nitrobenzophenones) -2,4- bis- in catalysis
Oxygen -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6- nitriles reaction in recycle when product yield variation diagram.
Embodiment
The present invention substantive features and remarkable result can be emerged from from following embodiments, but they not to this
Invention imposes any restrictions, and those skilled in the art makes some nonessential modifications and adaptations according to present disclosure,
Belong to protection scope of the present invention.Below by embodiment, the present invention is further illustrated, wherein in embodiment
The test of reaction product characterizes the NMR for the model AVANCE-II 400MHz for using German Bruker companies；
Examination of infrared spectrum characterizes the model Bruker tensor 37FT-IR infrared spectrometers using German Bruker companies
(KBr tablettings)；The fusing point of reaction product is determined using capillary tube method.
Embodiment 1
By 1mmol p-bromobenzaldehydes, 1mmol barbiturates, 1.4mmol malononitrile and 0.05mmol acidic ion liquids point
It is not added in the 50ml single port bottles with stirrer and condenser pipe for filling the ethanol waters of 8ml 60%.Heating reflux reaction
23min, TLC (thin plate chromatography) are detected, and raw material point disappears, and is cooled to room temperature, pulverizes the solid of precipitation, are stood, and are filtered, filter residue warp
Obtain 7- amino -5- (4- bromophenyls) -2,4- dioxies -2,3 after ethanol washing, vacuum drying, 4,5- tetrahydrochysene -1H- pyrans simultaneously [2,
3-d] pyrimidine -6- nitriles, yield 91%, repeated after being directly added into p-bromobenzaldehyde, barbiturates and malononitrile in filtrate
Use.
7- amino -5- (4- bromophenyls) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6- nitriles：
M.p.292~294 DEG C；IR(KBr)：3368,3343,3181,3074,2214,1681,1563cm-1；1H NMR (400MHz,
DMSO-d6)：δ=3.79 (s, 1H), 6.85 (s, 2H), 7.28 (d, J=7.1Hz, 2H), 7.76 (d, J=7.1Hz, 2H),
13.06 (s, 1H), 14.05 (s, 1H)
Embodiment 2
By 1mmol paranitrobenzaldehydes, 1mmol barbiturates, 1.2mmol malononitrile and 0.04mmol acidic ion liquids
In the 50ml single port bottles with stirrer and condenser pipe for being added separately to fill the ethanol waters of 8ml 60%.It is heated to reflux anti-
17min, TLC (thin plate chromatography) detections are answered, raw material point disappears, is cooled to room temperature, pulverizes the solid of precipitation, stand, filters, filter residue
7- amino -5- (4- nitrobenzophenones) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans are obtained after ethanol is washed, is dried in vacuo
And [2,3-d] pyrimidine -6- nitriles, yield 93%, it is laggard that paranitrobenzaldehyde, barbiturates and malononitrile are directly added into filtrate
Row is reused.
7- amino -5- (4- nitrobenzophenones) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6-
Nitrile：M.p.236~238 DEG C；IR(KBr)：3407,3201,3171,2992,2203,1728,1464cm-1；1H NMR
(400MHz, DMSO-d6)：δ=4.98 (s, 1H), 6.74 (s, 2H), 7.49 (d, J=7.1Hz, 2H), 7.97 (d, J=
7.1Hz, 2H), 8.99 (s, 1H), 13.12 (s, 1H)
Embodiment 3
By 1mmol o-methoxybenzaldehydes, 1mmol barbiturates, 1.4mmol malononitrile and 0.05mmol acidic ionic liquids
Body is added separately to fill in the 50ml single port bottles with stirrer and condenser pipe of the ethanol waters of 7ml 60%.It is heated to reflux
25min, TLC (thin plate chromatography) detections are reacted, raw material point disappears, is cooled to room temperature, pulverizes the solid of precipitation, stand, filters, filter
Slag obtains 7- amino -5- (2- methoxyphenyls) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- after ethanol is washed, is dried in vacuo
Pyrans simultaneously [2,3-d] pyrimidine -6- nitriles, yield 87%, m-methoxybenzaldehyde, barbiturates and the third two are directly added into filtrate
Reused after nitrile.
7- amino -5- (2- methoxyphenyls) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6-
Nitrile：m.p.>300℃；IR(KBr)：3421,3205,3142,3013,2278,1761,1612cm-1；1H NMR (400MHz,
DMSO-d6)：δ=3.77 (s, 1H), 4.18 (s, 1H), 7.12~7.42 (m, 4H), 7.47 (d, J=4.5Hz, 1H), 10.75
(s, 1H), 10.97 (s, 1H)
Embodiment 4
By 1mmol parahydroxyben-zaldehydes, 1mmol barbiturates, 1.1mmol malononitrile and 0.03mmol acidic ion liquids
In the 50ml single port bottles with stirrer and condenser pipe for being added separately to fill the ethanol waters of 9ml 60%.It is heated to reflux anti-
19min, TLC (thin plate chromatography) detections are answered, raw material point disappears, is cooled to room temperature, pulverizes the solid of precipitation, stand, filters, filter residue
7- amino -5- (4- hydroxy phenyls) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans are obtained after ethanol is washed, is dried in vacuo
And [2,3-d] pyrimidine -6- nitriles, yield 90%, it is laggard that parahydroxyben-zaldehyde, barbiturates and malononitrile are directly added into filtrate
Row is reused.
7- amino -5- (4- hydroxy phenyls) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6-
Nitrile：M.p.163~165 DEG C；IR(KBr)：3461,3254,3128,3090,2297,2239,1731,1682,1554cm-1；1H
NMR (400MHz, DMSO-d6)：δ=4.35 (s, 1H), 6.08 (s, 1H), 6.57 (d, J=7.6Hz, 2H), 6.86 (s, 2H),
7.04 (d, J=7.5Hz, 2H), 10.83 (s, 1H), 10.92 (s, 1H)
Embodiment 5
1mmol benzaldehydes, 1mmol barbiturates, 1mmol malononitrile and 0.03mmol acidic ion liquids are separately added into
Into the 50ml single port bottles with stirrer and condenser pipe for filling the ethanol waters of 7ml 60%.Heating reflux reaction 15min,
TLC (thin plate chromatography) is detected, and raw material point disappears, and is cooled to room temperature, pulverizes the solid of precipitation, is stood, and is filtered, and filter residue is washed through ethanol
Wash, be dried in vacuo after obtain 7- amino -5- (4- phenyl) -2,4- dioxies -2,3, simultaneously [2,3-d] are phonetic for 4,5- tetrahydrochysene -1H- pyrans
Pyridine -6- nitriles, yield 92%, reused after being directly added into benzaldehyde, barbiturates and malononitrile in filtrate.
7- amino -5- (4- phenyl) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6- nitriles：
M.p.236~238 DEG C；IR(KBr)：3377,3304,3218,3119,2136,1690,1568cm-1；1H NMR (400MHz,
DMSO-d6)：δ=4.26 (s, 1H), 6.79 (s, 2H), 7.08~7.18 (m, 3H), 7.34 (t, J=7.4Hz, 2H), 10.86
(s, 1H), 10.91 (s, 1H)
Embodiment 6
By 1mmol m-nitrobenzaldehydes, 1mmol barbiturates, 1.2mmol malononitrile and 0.04mmol acidic ion liquids
In the 50ml single port bottles with stirrer and condenser pipe for being added separately to fill the ethanol waters of 8ml 60%.It is heated to reflux anti-
21min, TLC (thin plate chromatography) detections are answered, raw material point disappears, is cooled to room temperature, pulverizes the solid of precipitation, stand, filters, filter residue
7- amino -5- (3- nitrobenzophenones) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans are obtained after ethanol is washed, is dried in vacuo
And [2,3-d] pyrimidine -6- nitriles, yield 88%, it is laggard that m-nitrobenzaldehyde, barbiturates and malononitrile are directly added into filtrate
Row is reused.
7- amino -5- (3- nitrobenzophenones) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6-
Nitrile：M.p.238~240 DEG C；IR(KBr)：3308,3297,3244,2939,2205,1601,1471cm-1；1H NMR
(400MHz, DMSO-d6)：δ=3.90 (s, 1H), 6.79 (s, 2H), 8.15 (d, J=6.5Hz, 2H), 8.34 (s, 1H),
10.17 (s, 1H), 12.04 (s, 1H)
Embodiment 7
By 1mmol o-nitrobenzaldehydes, 1mmol barbiturates, 1.4mmol malononitrile and 0.05mmol acidic ion liquids
In the 50ml single port bottles with stirrer and condenser pipe for being added separately to fill the ethanol waters of 7ml 60%.It is heated to reflux anti-
25min, TLC (thin plate chromatography) detections are answered, raw material point disappears, is cooled to room temperature, pulverizes the solid of precipitation, stand, filters, filter residue
7- amino -5- (2- nitrobenzophenones) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans are obtained after ethanol is washed, is dried in vacuo
And [2,3-d] pyrimidine -6- nitriles, yield 86%, it is laggard that o-nitrobenzaldehyde, barbiturates and malononitrile are directly added into filtrate
Row is reused.
7- amino -5- (2- nitrobenzophenones) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6-
Nitrile：M.p.232~235 DEG C；IR(KBr)：3301,3229,3139,2934,2168,1641,1530cm-1；1H NMR
(400MHz, DMSO-d6)：δ=3.89 (s, 1H), 6.84 (s, 2H), 7.58~7.66 (m, 3H), 10.16 (s, 1H), 10.81
(s, 1H)
Embodiment 8
It is probe reaction with embodiment 2, makees the active replica test of catalysts acidic ion liquid, ionic liquid
Reuse 7 times, product 7- amino -5- (4- nitrobenzophenones) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans are simultaneously [2,3-d]
Fig. 2 is shown in the yield change of pyrimidine -6- nitriles.
Embodiment 9
It is probe reaction with embodiment 4, makees the active replica test of catalysts acidic ion liquid, ionic liquid
Reuse 7 times, product 7- amino -5- (4- hydroxy phenyls) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans are simultaneously [2,3-d]
Fig. 3 is shown in the yield change of pyrimidine -6- nitriles.
Embodiment 10
It is probe reaction with embodiment 7, makees the active replica test of catalysts acidic ion liquid, ionic liquid
Reuse 7 times, product 7- amino -5- (2- nitrobenzophenones) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans are simultaneously [2,3-d]
Fig. 4 is shown in the yield change of pyrimidine -6- nitriles.
It can be seen that by Fig. 2,3 and 4：Acidity of catalyst ionic liquid is recycling catalysis preparation 7- amino -5- (4- nitre
Base phenyl) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6- nitriles, 7- amino -5- (4- hydroxy benzenes
Base) -2,4- dioxies -2,3,4,5- tetrahydrochysene -1H- pyrans simultaneously [2,3-d] pyrimidine -6- nitriles and 7- amino -5- (2- nitrobenzophenones) -2,
4- dioxies -2,3, yield of 4, the 5- tetrahydrochysene -1H- pyrans simultaneously during [2,3-d] pyrimidine -6- nitriles is in a slight decrease, but reduces width
Degree is smaller.In catalysis prepare pyrans it could therefore be concluded that going out the acidity of catalyst ionic liquid simultaneously [2,3-d] pyrimidone spreads out
It can be recycled in the process of biology, its catalytic activity is not obviously lowered.
Claims (2)
1. a kind of method that environmental friendly catalysis prepares pyrans simultaneously [2,3-d] pyrimidone derivatives, it is characterised in that the preparation
The mol ratio of aromatic aldehyde, barbiturates and malononitrile is 1 in reaction：1：1~1.4, the mole of acidic ionic liquid catalysts
The 3~5% of aromatic aldehyde used, the volume of the ethanol water of reaction dissolvent 60% counted using milliliter as by mM in terms of virtue
7~9 times of fragrant aldehyde mole, reaction pressure are an atmospheric pressure, and reflux time is 10~25min, and reaction terminates rear cold
But to room temperature, the solid of precipitation is pulverized, is stood, is filtered, filter residue obtains pyrans simultaneously [2,3-d] after ethanol is washed, is dried in vacuo
Pyrimidone derivatives；
The aromatic aldehyde be benzaldehyde, 4-chloro-benzaldehyde, p-bromobenzaldehyde, paranitrobenzaldehyde, p-tolyl aldehyde, to methoxy
Benzaldehyde, a tolyl aldehyde, o-chlorobenzaldehyde, m chlorobenzaldehyde, m-methoxybenzaldehyde, m-nitrobenzaldehyde, adjacent nitre
Any of benzaldehyde；
The structural formula of the acidic ionic liquid catalysts is：
2. the method that a kind of environmental friendly catalysis as claimed in claim 1 prepares pyrans simultaneously [2,3-d] pyrimidone derivatives, its
It is characterised by, the acidic ionic liquid catalysts contained in the filtered filtrate, at least 7 can be reused without processing
It is secondary.
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| CN111484499B (en) * | 2020-06-12 | 2021-06-29 | 南京欣久医药科技有限公司 | Method for preparing drug intermediate chromene pyrimido indazolone derivative through catalysis |
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