CN107216323A - A kind of 1 phenothiazinyl 3 aryl 3 (2,4,6 pyrimidine trione base) 1 acetone and preparation method thereof - Google Patents
A kind of 1 phenothiazinyl 3 aryl 3 (2,4,6 pyrimidine trione base) 1 acetone and preparation method thereof Download PDFInfo
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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Abstract
The invention provides a kind of aryl 3 (2,4,6 pyrimidine trione base) 1 acetone of 1 phenothiazinyl 3 and preparation method thereof, its structural formula is：
Description
Technical field
The invention belongs to the field of chemical synthesis, more particularly to a kind of 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidines three
Ketone group) -1- acetone and preparation method thereof.
Background technology
N- phenothiazinyls chalcone contains an a, β-unsaturated double-bond due to it, so on N- phenothiazinyl chalcones
Reaction more than around Michael addition reactions or cyclization reaction carry out.It can with hydrazine, nitrile, active methylene compound or
The materials such as amine carry out Michael addition reactions, generate a series of derivatives containing phenothiazinyl, the analog derivative in antibacterial,
There is good application in the field such as antiviral.
Michael addition reactions are the organic reactions of the important formation carbon-carbon key of a class, and most directly application is exactly for it
Increase carbochain, compound of the synthesis containing multiple functional groups, these compounds are respectively provided with the ability further reacted, generated various
The organic compound of type.But traditional Michael reactions are carried out in organic solvent with strong alkali as a catalyst mostly, catalysis
The agent alkalescence too strong or reaction time is longer, has many accessory substances and produces, so that yield is undesirable.
The content of the invention
It is an object of the invention to provide a kind of 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine triones base) -1- acetone
And preparation method thereof, using solid-phase sequencing, a series of new Michael addition compound products for having no document report have been synthesized, should
The method reaction time is short, without solvent, green, environmental protection, economy and simple to operate, reaction condition is gentle, and post processing is simple, production
Rate is high.
To reach above-mentioned purpose, the present invention uses following technical scheme：
A kind of 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine trione base) -1- acetone, its general structure is as follows：
Wherein Ar is phenyl, substituted-phenyl or heterocyclic radical.
The substituted-phenyl is rubigan, p-bromophenyl, p-fluorophenyl, aminomethyl phenyl, methoxyphenyl, p-nitrophenyl
Base, m-nitro base, O-Nitrophenylfluorone, dimethylamino phenyl, hydroxy phenyl, styryl；
The heterocyclic radical is furyl, thienyl or pyridine radicals.
The preparation method of described 1- phenothiazinyl -3- aryl -3- (2,4,6- pyrimidine trione base) -1- acetone, its is specific
Step is as follows：
A mol 1- phenothiazinyls -3- aryl-propenone, B mol catalyst, C mol bars is added into dry mortar
Than appropriate acid, grinding is reacted it, and TLC tracing detections are complete up to reaction, then washing, suction filtration, will be after filtration cakes torrefaction
Obtain 1- phenothiazinyl -3- aryl -3- (2,4,6- pyrimidine trione base) -1- acetone, wherein A:B:C=1:(1~1.5):(1~
1.5)。
The general structure of the 1- phenothiazinyls -3- aryl-propenone is as follows：
Wherein Ar is phenyl, rubigan, p-bromophenyl, p-fluorophenyl, aminomethyl phenyl, methoxyphenyl, p-nitrophenyl
Base, m-nitro base, O-Nitrophenylfluorone, dimethylamino phenyl, hydroxy phenyl, styryl, furyl, thienyl or pyridine
Base.
The catalyst is solid NaOH or anhydrous K2CO3。
The time of the griding reaction is 30~40min.
Represent that raw material reaction is complete when the raw material point of 1- phenothiazinyls -3- aryl-propenone disappears；TLC detections are used
Solvent be that volume ratio is 1:5 ethyl acetate and the mixed solvent of petroleum ether.
During suction filtration, filter cake is repeatedly washed, until the pH of filtrate is in neutrality.
Compared with prior art, the invention has the advantages that：
The present invention uses solid-phase sequencing, by barbiturates and 1- phenothiazinyls -3- aryl-propylene reactive ketone, synthesis
A series of new Michael addition compound products for having no document report, i.e. 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine triones
Base) -1- acetone, and its preparation method is explored, while optimizing experiment condition, the reaction time is shortened, is that green syt is done
Contribution is gone out.1- phenothiazinyl -3- aryl -3- (2,4,6- pyrimidine triones base) -1- acetone that the present invention is provided is a series of complete
The new ketones derivant containing phenothiazinyl, with sterilization, it is antibacterial the effects such as, have very in antibacterial, antiviral, medicine and other fields
Good application prospect.
The preparation method of 1- phenothiazinyl -3- aryl -3- (2,4,6- pyrimidine trione base) -1- acetone that the present invention is provided,
1- phenothiazinyls -3- aryl-propenone, catalyst and barbiturates are added to rapid grinding in dry mortar to be reacted,
In process of lapping, raw material is thick as the progress of reaction is begun to change into then to gradually become solid, TLC tracing detections to reaction
Completely, product is through washing, suction filtration, drying to obtain 1- phenothiazinyl -3- aryl -3- (2,4,6- pyrimidine trione base) -1- acetone.
Compared with prior synthesizing method, the present invention uses solid-phase sequencing, and course of reaction is simple, reacting phenomenon substantially, the reaction time is short,
Without solvent, green, environmental protection, economy and simple to operate, reaction condition gently, equipment requirement is low, and the post processing letter of this method
Single, accessory substance is few, and yield is high.Overcome that the prior synthesizing method reaction time is long, accessory substance is more, the shortcomings of low yield, with warp
Ji, advantage conveniently, efficiently, green.
Further, the present invention uses TLC monitoring reaction courses, solvent used is that volume ratio is in preparation process
1:5 ethyl acetate and petroleum ether, monitoring is accurate, beneficial to control extent of reaction and end.Catalyst used in simultaneously of the invention
For solid NaOH or anhydrous K2CO3, cheap and easy to get, catalytic effect is good, makes reaction more rapid and complete, and post processing is simple.
Brief description of the drawings
Fig. 1 is the infared spectrum of product made from embodiment 1；
Fig. 2 is the infared spectrum of product made from embodiment 2；
Fig. 3 is the infared spectrum of product made from embodiment 3；
Fig. 4 is the infared spectrum of product made from embodiment 4；
Fig. 5 is the infared spectrum of product made from embodiment 9；
Fig. 6 is the infared spectrum of product made from embodiment 10；
Fig. 7 is product made from embodiment 41HNMR collection of illustrative plates；
Fig. 8 is product made from embodiment 71HNMR collection of illustrative plates.
Embodiment
The reaction equation of 1- phenothiazinyl -3- aryl -3- (2,4,6- pyrimidine triones base) -1- acetone that the present invention is provided
It is as follows：
Wherein Ar is phenyl, rubigan, p-bromophenyl, p-fluorophenyl, aminomethyl phenyl, methoxyphenyl, p-nitrophenyl
Base, m-nitro base, O-Nitrophenylfluorone, dimethylamino phenyl, hydroxy phenyl, styryl, furyl, thienyl or pyridine
Base.
The present invention is described in further details below in conjunction with preferred embodiments of the present invention.
Embodiment 1
Weigh 0.0015mol barbiturates and 0.0013mol anhydrous Ks2CO3In dry mortar, it is mixed rapidly
It is even, 0.001mol 1- phenothiazinyl -3- phenyl-acryloyl ketone is added, 35min is ground.In process of lapping, mixture can be gradually
Become glutinous, continue to grind until material no longer changes, using TLC tracking and monitoring reaction process, solvent used is volume
Than for 1:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, carry out repeatedly washing to product with pure water and take out
Filter, until the pH of filtrate is in neutrality, then by filter cake natural air drying, obtains grey powder, as 1- phenothiazinyls -3- phenyl -3-
(2,4,6- pyrimidine triones base) -1- acetone.Yield is：86.2%, m.p.104 DEG C~107 DEG C.
Fig. 1 is 1- phenothiazinyl -3- phenyl -3- (2,4,6- pyrimidine triones base) -1- acetone prepared by the embodiment of the present invention 1
Infared spectrum, as shown in Figure 1：3057cm-1Locate the vibration absorption peak for Ar-H, in 3122cm-1Locate the absworption peak for-NH-,
In 2919cm-1, 2848cm-1, 1440cm-1Locate as-CH2Absworption peak, in 1694cm-1, 1651cm-1Locate the feature suction for C=O
Receive peak, 1496cm-1And 1462cm-1The peak at place is the breathing vibration absworption peak of phenyl ring, 742cm-1To be adjacent dibasic on phenyl ring
Absworption peak, 710cm-1, 769cm-1For mono-substituted absworption peak on phenyl ring.In summary, it can be verified that synthesis has obtained 1- fen thiophenes
Piperazine base -3- phenyl -3- (2,4,6- pyrimidine triones base) -1- acetone.
1H NMR:6.78-7.22(m,13H,Ar-H),10.04(s,1H,-CONH),3.94-3.95(d,1H,-
COCHCO-),3.64-3.70(m,1H,-CH),2.63-2.65(d,2H,-COCH2).
Embodiment 2
Weigh 0.0015mol barbiturates and 0.0015mol anhydrous Ks2CO3In dry mortar, it is mixed rapidly
It is even, 0.001mol 1- phenothiazinyls -3- (4- chlorphenyls)-propenone is added, 37min is ground.In process of lapping, mixture
Meeting gradually becomes glutinous, continues to grind up to material no longer changes, uses TLC tracking and monitoring reaction process, solvent used
It is 1 for volume ratio:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, are carried out repeatedly with pure water to product
Suction filtration is washed, until the pH of filtrate is in neutrality, then by filter cake natural air drying, pale yellow powder, as 1- phenothiazinyls -3- is obtained
(4- chlorphenyls) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is：87.4%, m.p.120 DEG C~123 DEG C.
Fig. 2 be the embodiment of the present invention 2 prepare 1- phenothiazinyls -3- (4- chlorphenyls) -3- (2,4,6- pyrimidine triones base) -
The infared spectrum of 1- acetone, as shown in Figure 2：3058cm-1Locate the vibration absorption peak for Ar-H, in 3325cm-1Locate the suction for-NH-
Peak is received, in 2923cm-1, 2846cm-1, 1439cm-1Locate as-CH2Absworption peak, in 1707cm-1, 1674cm-1Locate the spy for C=O
Levy absworption peak, 1594cm-1And 1464cm-1The peak at place is the breathing vibration absworption peak of phenyl ring, 742cm-1Taken for the neighbour two on phenyl ring
The absworption peak in generation, 816cm-1To align substituted absworption peak on phenyl ring.In summary, it can be verified that synthesis has obtained 1- phenthazine
Base -3- (4- chlorphenyls) -3- (2,4,6- pyrimidine triones base) -1- acetone.
1H NMR:6.65-7.16(m,12H,Ar-H),10.24(s,1H,-CONH),3.92-3.94(d,1H,-
COCHCO-),3.74-3.78(m,1H,-CH),2.67-2.68(d,2H,-COCH2).
Embodiment 3
Weigh 0.0012mol barbiturates and 0.0015mol anhydrous Ks2CO3In dry mortar, it is mixed rapidly
It is even, 0.001mol 1- phenothiazinyls -3- (4- bromophenyls)-propenone is added, 33min is ground.In process of lapping, mixture
Meeting gradually becomes glutinous, continues to grind up to material no longer changes, uses TLC tracking and monitoring reaction process, solvent used
It is 1 for volume ratio:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, are carried out repeatedly with pure water to product
Suction filtration is washed, until the pH of filtrate is in neutrality, then by filter cake natural air drying, grey powder, as 1- phenothiazinyls -3- is obtained
(4- bromophenyls) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is 86.9%, m.p.115 DEG C~118 DEG C.
Fig. 3 be the embodiment of the present invention 3 prepare 1- phenothiazinyls -3- (4- bromophenyls) -3- (2,4,6- pyrimidine triones base) -
The infared spectrum of 1- acetone, as shown in Figure 3：3055cm-1Locate the vibration absorption peak for Ar-H, in 3328cm-1Locate the suction for-NH-
Peak is received, in 2922cm-1, 2847cm-1, 1442cm-1Locate as-CH2Absworption peak, in 1710cm-1, 1665cm-1Locate the spy for C=O
Levy absworption peak, 1598cm-1And 1470cm-1The peak at place is the breathing vibration absworption peak of phenyl ring, 738cm-1Taken for the neighbour two on phenyl ring
The absworption peak in generation, 817cm-1To align substituted absworption peak on phenyl ring.In summary, it can be verified that synthesis has obtained 1- phenthazine
Base -3- (4- bromophenyls) -3- (2,4,6- pyrimidine triones base) -1- acetone.
1H NMR:6.64-7.45(m,12H,Ar-H),10.24(s,1H,-CONH),3.98-4.02(d,1H,-
COCHCO-),3.72-3.76(m,1H,-CH),2.60-2.62(d,2H,-COCH2).
Embodiment 4
Weigh 0.0014mol barbiturates and 0.0014mol NaOH be mixed uniformly in dry mortar, rapidly,
0.001mol 1- phenothiazinyls -3- (4- fluorophenyls)-propenone is added, 34min is ground.In process of lapping, mixture can be by
Gradual change is sticked, and continues to grind until material no longer changes, using TLC tracking and monitoring reaction process, solvent used is body
Product is than being 1:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, are repeatedly washed with pure water to product
Suction filtration, until the pH of filtrate is in neutrality, then by filter cake natural air drying, obtains grey powder, as 1- phenothiazinyls -3- (4- fluorine
Phenyl) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is 87.7%, m.p.115 DEG C~117 DEG C.
Fig. 4 be the embodiment of the present invention 4 prepare 1- phenothiazinyls -3- (4- fluorophenyls) -3- (2,4,6- pyrimidine triones base) -
The infared spectrum of 1- acetone, as shown in Figure 4：3057cm-1Locate the vibration absorption peak for Ar-H, in 3298cm-1Locate the suction for-NH-
Peak is received, in 2927cm-1, 2851cm-1, 1439cm-1Locate as-CH2Absworption peak, in 1711cm-1, 1667cm-1Locate the spy for C=O
Levy absworption peak, 1595cm-1And 1463cm-1The peak at place is the breathing vibration absworption peak of phenyl ring, 742cm-1Taken for the neighbour two on phenyl ring
The absworption peak in generation, 817cm-1To align substituted absworption peak on phenyl ring.In summary, it can be verified that synthesis has obtained 1- phenthazine
Base -3- (4- fluorophenyls) -3- (2,4,6- pyrimidine triones base) -1- acetone.
Fig. 7 be the embodiment of the present invention 4 prepare 1- phenothiazinyls -3- (4- fluorophenyls) -3- (2,4,6- pyrimidine triones base) -
1- acetone1HNMR collection of illustrative plates, as shown in Figure 7：1H NMR:6.64-7.12(m,12H,Ar-H),9.95(s,1H,-CONH),
3.90-3.91(d,1H,-COCHCO-),3.56-3.65(m,1H,-CH),2.70-2.72(d,2H,-COCH2).
Embodiment 5
Weigh 0.0013mol barbiturates and 0.0012mol NaOH be mixed uniformly in dry mortar, rapidly,
0.001mol 1- phenothiazinyls -3- (4- dimethylamino phenyls)-propenone is added, 36min is ground.In process of lapping, mixing
Thing can gradually become glutinous, continue to grind up to material no longer changes, use TLC tracking and monitoring reaction process, expansion used
Agent is that volume ratio is 1:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, are carried out many with pure water to product
Secondary washing suction filtration, until the pH of filtrate is in neutrality, then by filter cake natural air drying, obtains grey powder, as 1- phenothiazinyls -3-
(4- dimethylamino phenyls) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is 86.1%, m.p.105 DEG C~108 DEG C.
IR(KBr)ν(cm-1):3057 (=C-H, Ar-H), 3326 (- NH-), 2972,1380 (- CH3),2922,2850,
1438(-CH2), 1709,1662 (C=O), 1593,1463 (Ar), 743 (neighbour two replaces on phenyl ring), 816 (align on phenyl ring and take
Generation)
1H NMR:6.64-7.12(m,12H,Ar-H),9.86(s,1H,-CONH),3.94-3.95(d,1H,-
COCHCO-),3.67-3.72(m,1H,-CH),2.68-2.70(d,2H,-COCH2),3.11(s,3H,-NCH3).
Embodiment 6
Weigh 0.0015mol barbiturates and 0.0011mol anhydrous Ks2CO3In dry mortar, it is mixed rapidly
It is even, 0.001mol 1- phenothiazinyls -3- (4- methoxyphenyls)-propenone is added, 32min is ground.In process of lapping, mix
Compound can gradually become glutinous, continue to grind up to material no longer changes, use TLC tracking and monitoring reaction process, exhibition used
It is that volume ratio is 1 to open agent:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, are carried out with pure water to product
Repeatedly washing suction filtration, until the pH of filtrate is in neutrality, then by filter cake natural air drying, obtains purple powder, as 1- phenothiazinyls-
3- (4- methoxyphenyls) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is 86.35, m.p.114 DEG C~118 DEG C.
IR(KBr)ν(cm-1):3054 (=C-H, Ar-H), 3315 (- NH-), 2976,1385 (- CH3),2920,2847,
1442(-CH2), 1712,1668 (C=O), 1593,1462 (Ar), 741 (neighbour two replaces on phenyl ring), 817 (align on phenyl ring and take
Generation)
1H NMR:6.63-7.12(m,12H,Ar-H),9.92(s,1H,-CONH),3.92-3.93(d,1H,-
COCHCO-),3.65-3.68(m,1H,-CH),2.58-2.60(d,2H,-COCH2),4.15(s,3H,-OCH3).
Embodiment 7
Weigh 0.0014mol barbiturates and 0.0015mol anhydrous Ks2CO3In dry mortar, it is mixed rapidly
It is even, 0.001mol 1- phenothiazinyls -3- (4- aminomethyl phenyls)-propenone is added, 38min is ground.In process of lapping, mixing
Thing can gradually become glutinous, continue to grind up to material no longer changes, use TLC tracking and monitoring reaction process, expansion used
Agent is that volume ratio is 1:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, are carried out many with pure water to product
Secondary washing suction filtration, until the pH of filtrate is in neutrality, then by filter cake natural air drying, obtains purple powder, as 1- phenothiazinyls -3-
(4- aminomethyl phenyls) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is 86.0%, m.p.118 DEG C~120 DEG C.
IR(KBr)ν(cm-1):3058 (=C-H, Ar-H), 3324 (- NH-), 2971,1378 (- CH3),2851,1440(-
CH2), 1708,1668 (C=O), 1594,1462 (Ar), 743 (neighbour two replaces on phenyl ring), 816 (substitution is aligned on phenyl ring)
Fig. 8 is 1- phenothiazinyls -3- (4- aminomethyl phenyls) -3- (2,4,6- pyrimidine triones prepared by the embodiment of the present invention 7
Base) -1- acetone1HNMR collection of illustrative plates, as shown in Figure 7：1H NMR:6.58-7.01(m,12H,Ar-H),10.42(s,1H,-
CONH),3.87-3.90(d,1H,-COCHCO-),3.59-3.67(m,1H,-CH),2.75-2.77(d,2H,-COCH2),
2.45(s,3H,-CH3).
Embodiment 8
Weigh 0.0011mol barbiturates and 0.0013mol NaOH be mixed uniformly in dry mortar, rapidly,
0.001mol 1- phenothiazinyls -3- (4- nitrobenzophenones)-propenone is added, 31min is ground.In process of lapping, mixture meeting
Gradually become glutinous, continue to grind until material no longer changes, using TLC tracking and monitoring reaction process, solvent used is
Volume ratio is 1:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, multiple water is carried out with pure water to product
Suction filtration is washed, until the pH of filtrate is in neutrality, then by filter cake natural air drying, purple powder, as 1- phenothiazinyls -3- (4- is obtained
Nitrobenzophenone) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is 88.2%, m.p.117 DEG C~120 DEG C.
IR(KBr)ν(cm-1):3057 (=C-H, Ar-H), 3325 (- NH-), 2922,2847,1439 (- CH2),1707,
1656 (C=O), 1593,1463 (Ar), 743 (neighbour two replaces on phenyl ring), 817 (substitution is aligned on phenyl ring), 1494,1357 (-
NO2).
1H NMR:6.79-8.00(m,12H,Ar-H),10.12(s,1H,-CONH),3.94-3.96(d,1H,-
COCHCO-),3.70-3.76(m,1H,-CH),2.65-2.67(d,2H,-COCH2).
Embodiment 9
Weigh 0.0015mol barbiturates and 0.0015mol anhydrous Ks2CO3In dry mortar, it is mixed rapidly
It is even, 0.001mol 1- phenothiazinyls -3- (2- thienyls)-propenone is added, 39min is ground.In process of lapping, mixture
Meeting gradually becomes glutinous, continues to grind up to material no longer changes, uses TLC tracking and monitoring reaction process, solvent used
It is 1 for volume ratio:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, are carried out repeatedly with pure water to product
Suction filtration is washed, until the pH of filtrate is in neutrality, then by filter cake natural air drying, purple powder, as 1- phenothiazinyls -3- is obtained
(2- thienyls) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is 85.8%, m.p.113 DEG C~116 DEG C.
Fig. 5 be the embodiment of the present invention 9 prepare 1- phenothiazinyls -3- (2- thienyls) -3- (2,4,6- pyrimidine triones base) -
The infared spectrum of 1- acetone, as shown in Figure 5：3058cm-1Locate the vibration absorption peak for Ar-H, in 3322cm-1Locate the suction for-NH-
Peak is received, in 2922cm-1, 2848cm-1, 1438cm-1Locate as-CH2Absworption peak, in 1708cm-1, 1668cm-1Locate the spy for C=O
Levy absworption peak, 1573cm-1And 1464cm-1The peak at place is the breathing vibration absworption peak of phenyl ring, 743cm-1Taken for the neighbour two on phenyl ring
The absworption peak in generation.In summary, it can be verified that synthesis has obtained 1- phenothiazinyls -3- (2- thienyls) -3- (2,4,6- pyrimidines three
Ketone group) -1- acetone.
1H NMR:6.78-6.99(m,8H,Ar-H),10.53(s,1H,-CONH),3.93-3.95(d,1H,-
COCHCO-),3.67-3.72(m,1H,-CH),2.60-2.62(d,2H,-COCH2),6.49-6.65(d,1H,Thy-H),
6.86-6.88(m,1H,Thy-H),7.01-7.03(d,1H,Thy-H).
Embodiment 10
Weigh 0.0015mol barbiturates and 0.0013mol NaOH be mixed uniformly in dry mortar, rapidly,
0.001mol 1- phenothiazinyls -3- (2- pyridine radicals)-propenone is added, 30min is ground.In process of lapping, mixture can be by
Gradual change is sticked, and continues to grind until material no longer changes, using TLC tracking and monitoring reaction process, solvent used is body
Product is than being 1:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, are repeatedly washed with pure water to product
Suction filtration, until the pH of filtrate is in neutrality, then by filter cake natural air drying, obtains grey powder, as 1- phenothiazinyls -3- (2- pyrroles
Piperidinyl) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is 87.6%, m.p.112 DEG C~115 DEG C.
Fig. 6 is 1- phenothiazinyls -3- (2- pyridine radicals) -3- (2,4,6- pyrimidine triones prepared by the embodiment of the present invention 10
Base) -1- acetone infared spectrum, as shown in Figure 6：3058cm-1Locate the vibration absorption peak for Ar-H, in 3321cm-1Locate as-NH-
Absworption peak, in 2929cm-1, 2854cm-1, 1440cm-1Locate as-CH2Absworption peak, in 1706cm-1, 1656cm-1Locate as C=O
Characteristic absorption peak, 1581cm-1And 1464cm-1The peak at place is the breathing vibration absworption peak of phenyl ring, 744cm-1For the neighbour on phenyl ring
Dibasic absworption peak.In summary, it can be verified that synthesis has obtained 1- phenothiazinyls -3- (2- pyridine radicals) -3-, and (2,4,6- is phonetic
The ketone group of pyridine three) -1- acetone.
1H NMR:6.63-7.11(m,8H,Ar-H),10.29(s,1H,-CONH),3.96-3.98(d,1H,-
COCHCO-),3.70-3.74(m,1H,-CH),2.51-2.58(d,2H,-COCH2),7.23-7.25(d,1H,Py-H),
7.93-8.00(m,1H,Py-H),8.77-8.79(d,1H,Py-H).
Embodiment 11
Weigh 0.0014mol barbiturates and 0.0014mol NaOH be mixed uniformly in dry mortar, rapidly,
0.001mol 1- phenothiazinyls -3- (2- furyls)-propenone is added, 40min is ground.In process of lapping, mixture can be by
Gradual change is sticked, and continues to grind until material no longer changes, using TLC tracking and monitoring reaction process, solvent used is body
Product is than being 1:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, are repeatedly washed with pure water to product
Suction filtration, until the pH of filtrate is in neutrality, then by filter cake natural air drying, obtains grey powder, as 1- phenothiazinyls -3- (2- furans
Mutter base) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is 85.7%, m.p.110 DEG C~114 DEG C.
IR(KBr)ν(cm-1):3058 (=C-H, Ar-H), 3318 (- NH-), 2922,2849,1438 (- CH2),1716,
1664 (C=O), 1592,1463 (Ar), 743 (neighbour two replaces on phenyl ring), 1040,1126 (C-O-C)
1H NMR:6.65-7.03(m,8H,Ar-H),10.08(s,1H,-CONH),3.91-3.93(d,1H,-
COCHCO-),3.64-3.69(m,1H,-CH),2.55-2.57(d,2H,-COCH2),6.03-6.06(d,1H,Fu-H),
6.29-6.36(m,1H,Fu-H),7.23-7.25(d,1H,Fu-H).
Embodiment 12
Weigh 0.001mol barbiturates and 0.001mol NaOH are mixed uniformly in dry mortar, rapidly, then
0.001mol 1- phenothiazinyls -3- (3- nitrobenzophenones)-propenone is added, 35min is ground.In process of lapping, mixture can be by
Gradual change is sticked, and continues to grind until material no longer changes, using TLC tracking and monitoring reaction process, solvent used is body
Product is than being 1:5 ethyl acetate and the mixed solvent of petroleum ether, after question response terminates, are repeatedly washed with pure water to product
Suction filtration, until the pH of filtrate is in neutrality, then by filter cake natural air drying, obtains purple powder, as 1- phenothiazinyls -3- (3- nitre
Base phenyl) -3- (2,4,6- pyrimidine triones base) -1- acetone.Yield is 89.0%, m.p.106 DEG C~108 DEG C.
IR(KBr)ν(cm-1):3054 (=C-H, Ar-H), 3331 (- NH-), 2921,2850,1440 (- CH2),1712,
1667 (C=O), 1594,1462 (Ar), 744 (neighbour two replaces on phenyl ring), 1515,1357 (- NO2).
1H NMR:6.64-8.02(m,12H,Ar-H),10.02(s,1H,-CONH),3.88-3.90(d,1H,-
COCHCO-),3.70-3.78(m,1H,-CH),2.69-2.71(d,2H,-COCH2).
In addition to the implementation, raw material 1- phenothiazinyls -3- aryl-propenone can also use following material, and wherein Ar is
O-Nitrophenylfluorone, hydroxy phenyl, styryl etc.；It is numerous to list herein.
In addition, 1- phenothiazinyls -3- aryl-propenone in the present invention can be prepared using following methods：
10- acetyl phenothiazines (1.21g, 0.005mol), NaOH particles are added in the three-necked flask dried to 250mL
(0.24g, 0.006mol) and absolute methanol 15mL, stirs 10min at room temperature, and the absolute methanol of aromatic aldehyde (0.006mol) is added dropwise
Solution 10mL, back flow reaction 30min (TLC monitors the reaction process).Reaction is cooled to room temperature after terminating, by gained reaction solution
All solids are separated out in 40mL frozen water, suction filtration, filter cake is washed with frozen water, natural air drying, then it is carried out again with absolute methanol
Crystallization, that is, obtain obtaining 1- phenothiazinyls -3- aryl-propenone.Its reaction equation is as follows：
Wherein Ar is phenyl, rubigan, p-bromophenyl, p-fluorophenyl, aminomethyl phenyl, methoxyphenyl, p-nitrophenyl
Base, m-nitro base, O-Nitrophenylfluorone, dimethylamino phenyl, hydroxy phenyl, styryl, furyl, thienyl or pyridine
Base.
The present invention uses solid-phase sequencing, by barbiturates and 1- phenothiazinyls -3- aryl-propylene reactive ketone, synthesis
A series of new Michael addition compound products for having no document report, i.e. 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine triones
Base) -1- acetone, and its preparation method is explored, while optimizing experiment condition, the reaction time is shortened, is that green syt is done
Contribution is gone out.1- phenothiazinyl -3- aryl -3- (2,4,6- pyrimidine triones base) -1- acetone that the present invention is provided is a series of complete
The new ketones derivant containing phenothiazinyl, with sterilization, it is antibacterial the effects such as, have well in the field such as antibacterial, antiviral
Application prospect.
It is described above, only it is presently preferred embodiments of the present invention, not the present invention is imposed any restrictions, it is every according to the present invention
Any simple modification, change and equivalent structure transformation that technical spirit is made to above example, still fall within skill of the present invention
In the protection domain of art scheme.
Claims (8)
1. a kind of 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine trione base) -1- acetone, it is characterised in that its general structure
It is as follows：
Wherein Ar is phenyl, substituted-phenyl or heterocyclic radical.
2. 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine trione base) -1- acetone, its feature according to claim 1
It is：The substituted-phenyl be rubigan, p-bromophenyl, p-fluorophenyl, aminomethyl phenyl, methoxyphenyl, p-nitrophenyl,
M-nitro base, O-Nitrophenylfluorone, dimethylamino phenyl, hydroxy phenyl, styryl；
The heterocyclic radical is furyl, thienyl or pyridine radicals.
3. the preparation side of 1- phenothiazinyl -3- aryl -3- (2,4,6- pyrimidine triones base) -1- acetone described in claim 1 or 2
Method, it is characterised in that it is comprised the following steps that：
A mol 1- phenothiazinyls -3- aryl-propenone, B mol catalyst, C mol barbitals is added into dry mortar
Acid, grinding is reacted it, and TLC tracing detections are until reaction is complete, and then washing, suction filtration, will be obtained after filtration cakes torrefaction
1- phenothiazinyl -3- aryl -3- (2,4,6- pyrimidine trione base) -1- acetone, wherein A:B:C=1:(1~1.5):(1~1.5).
4. the preparation of 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine triones base) -1- acetone according to claim 3
Method, it is characterised in that：The general structure of the 1- phenothiazinyls -3- aryl-propenone is as follows：
Wherein Ar be phenyl, rubigan, p-bromophenyl, p-fluorophenyl, aminomethyl phenyl, methoxyphenyl, p-nitrophenyl,
Nitrobenzophenone, O-Nitrophenylfluorone, dimethylamino phenyl, hydroxy phenyl, styryl, furyl, thienyl or pyridine radicals.
5. the preparation of 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine triones base) -1- acetone according to claim 3
Method, it is characterised in that：The catalyst is solid NaOH or anhydrous K2CO3。
6. the preparation of 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine triones base) -1- acetone according to claim 3
Method, it is characterised in that：The time of the griding reaction is 30~40min.
7. the preparation of 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine triones base) -1- acetone according to claim 3
Method, it is characterised in that：Represent that raw material reaction is complete when the raw material point of 1- phenothiazinyls -3- aryl-propenone disappears；TLC
Detection solvent used is that volume ratio is 1:5 ethyl acetate and the mixed solvent of petroleum ether.
8. the preparation of 1- phenothiazinyls -3- aryl -3- (2,4,6- pyrimidine triones base) -1- acetone according to claim 3
Method, it is characterised in that：During suction filtration, filter cake is repeatedly washed, until the pH of filtrate is in neutrality.
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| CN110250214A (en) * | 2019-06-01 | 2019-09-20 | 山东省农业科学院植物保护研究所 | A kind of peanut root-knot nematode attractant and preparation method thereof |
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| US4833138A (en) * | 1987-10-23 | 1989-05-23 | Washington University | Phenothiazinealkaneamines for treatment of neurotoxic injury |
| CN104592311A (en) * | 2014-12-27 | 2015-05-06 | 陕西科技大学 | 1-ferrocenyl-3-aryl-3-(2,4,6-pyrimidinetriketo)-acetone and preparation method thereof |
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| CN110250214A (en) * | 2019-06-01 | 2019-09-20 | 山东省农业科学院植物保护研究所 | A kind of peanut root-knot nematode attractant and preparation method thereof |
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