CN109705013A - A kind of 1-(4- methylbenzyl) -3- amino -4- first seleno maleimide compound and preparation method - Google Patents
A kind of 1-(4- methylbenzyl) -3- amino -4- first seleno maleimide compound and preparation method Download PDFInfo
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Abstract
The present invention relates to a kind of 1- (4- methylbenzyl) -3- amino -4- first seleno maleimide compound and preparation methods, in organic solvent, under Oxygen Condition, using dimethyl diselenide ether, N- (4- methylbenzyl) maleimide and morpholine as reaction raw materials, the carbon-carbon double bond of maleimide by the tandem reaction that transition metal copper is catalyzed while oxidative coupling reaction occur to obtain 1- (4- methylbenzyl) -3- morpholine base -4- first seleno maleimide compound.The method reaction condition is simple, the yield of product and purity is high, new synthetic route and method has been opened up for the preparation of 3- amino -4- first seleno maleimide compound, with good application potential and researching value.
Description
Technical field
The invention belongs to organic compound synthesis technical fields, more particularly, to a kind of 1- (4- methylbenzyl) -3- amino -
4- first seleno maleimide compound and preparation method.
Background technique
Maleimide is widely present in natural products, bioactive molecule as a kind of important amides compound
And in clinical medicine molecule, and precursor structure can also be prepared by various conversion reactions succinimide, pyrrolidines,
Therefore how the derivatives such as lactim based on the application of maleimide compound different field, synthesize to efficient green
Derivative with maleimide skeleton is always the target that organic chemist pursues.Such as: the Jiang Xianxing religion of Zhongshan University
It awards using organic alkali catalyst, with the pure and mild maleimide of-two sulphur -2,5- of Isosorbide-5-Nitrae bis- for substrate, is connected by diastereomeric selection
The preparation of Michael-Aldol [3+2] cyclization has the chiral and heterocycle compound of thiophane skeleton structure
(Diastereoselective Synthesis of Biheterocyclic Tetrahydrothiophene
Derivatives via Base-Catalyzed Cascade Michael-Aldol [3+2] Annulation of Isosorbide-5-Nitrae-
Dithiane-2,5-diol with Maleimides, J.Org.Chem., 2015,80,6870-6874), it is living to pass through pharmacology
Journal of Sex Research finds that such compound has good biological and pharmacoligical activities simultaneously；2008, A.Yu.Simonov et al. report
(Synthesis of 4_substituted 3- [3- (dialkylaminomethyl) indol-1-yl] maleimides
And study of their ability to inhibit protein kinase C α, prevent development
Of multiple drug resistance of tumor cells and cytotoxicity,
Russ.Chem.Bull.2008,57,2011-2020；), albumen can be inhibited using 3- amino -4- aromatic thiohydroxy maleimide
Kinases prevents multiple development drug resistance of tumor cell and cytotoxicity.
So important just because of the compound containing maleimide structure, people synthesize it to have carried out and largely grind
Study carefully, however only has the relevant report of an example for the synthesis of seleno maleimide, 2017, the Institute of Technology, India
Mahiuddin Baidya et al. reports (Ru (II)-Catalyzed C-H Functionalization on
Maleimides with Electrophiles:A Demonstration of Umpolung Strategy, Org.Lett.,
2017,19,1902-1905；), 3- arylseleno is synthesized with diaryldiselenides using expensive ruthenium catalysis maleimide
Maleimide, reaction equation are as follows:
Although the prior art can solve the selenium glycosylation reaction of maleimide, for the alkane seleno of maleimide
The bifunctional dough reaction for changing carbon-carbon double bond in the maleimide structure of reaction and diselenide participation is not reported so far.
Therefore, for it is easy, be easily handled, raw material that substrate is cheap and easy to get prepares 3- amino -4- alkane seleno maleimide chemical combination
Object is particularly important, especially with three groups of dimethyl diselenide ether, N- (4- methylbenzyl) maleimide and morpholine
Tandem reaction is divided to synthesize 1- (4- methylbenzyl) -3- morpholine base -4- first seleno maleimide compound, there are still continuation
The necessity studied and explored, this is also the basis that the present invention is accomplished and power place.
Summary of the invention
The technical problem to be solved by the present invention is to 1- (4- methylbenzyl) -3- morpholine base -4- first seleno maleimides
The synthetic route problem of the preparation method of amine compounds.
In order to solve the above technical problems, the present invention provides following technical proposals:
In organic solvent, under Oxygen Condition, with dimethyl diselenide ether, N- (4- methylbenzyl) maleimide and morphine
Quinoline is reaction raw materials, makes the carbon-carbon double bond of maleimide by the tandem reaction that transition metal copper is catalyzed while oxygen occurs
Change coupling reaction and obtains 1- (4- methylbenzyl) -3- morpholine base -4- first seleno maleimide compound.
Above-mentioned reaction process can be indicated with following reaction equations:
N- (4- methylbenzyl) maleimide of structure shown in the dimethyl diselenide ether of structure shown in (I), formula (II)
The molar ratio of the morpholine of structure shown in amine and formula (III) is 4: 2: 3.
(1) transition-metal catalyst copper
Transition-metal catalyst copper in the present invention is copper acetate, copper chloride, copper bromide or cuprous iodide, preferably acetic acid
Copper, with molar amount, the dosage of the copper acetate and the formula (II) amount ratio are 0.1: 1-0.3: 1, preferably 0.1.
(2) organic solvent
Reaction dissolvent in the present invention is organic solvent, and the organic solvent is dimethyl sulfoxide, N, N- dimethyl formyl
Amine, n,N-dimethylacetamide, N-Methyl pyrrolidone, methylene chloride, ethyl acetate, pyridine, six alkane of Isosorbide-5-Nitrae-dioxy, 1,2-
At least one of dichloroethanes, acetonitrile, toluene, tetrahydrofuran, ethyl alcohol, carbon tetrachloride, chloroform, n-butanol, preferably N- methyl
Pyrrolidones.
(3) alkali
Alkali in the present invention is inorganic base, and the alkali is lithium carbonate, cesium carbonate, potassium carbonate, sodium carbonate, sodium acetate, acetic acid
Lithium, potassium phosphate, sodium tert-butoxide, tert-butyl alcohol lithium or potassium tert-butoxide, preferably sodium carbonate.
(4) reaction temperature
In preparation method of the invention, reaction temperature is 100-120 DEG C, may be, for example, 100 DEG C, 110 DEG C in non-limiting manner
With 120 DEG C, preferably 120 DEG C of reaction temperature.
(5) reaction time
In the preparation process in accordance with the present invention, the reaction time, there is no particular limitation, such as can be detected by liquid chromatograph
The residual percentage of target product or raw material and determine suitable reaction time, it typically is 10-12 hours, non-limiting example
For example 10 hours, 11 hours or 12 hours, the reaction time preferably 12 hours.
(6) it isolates and purifies
Mixture resulting after reaction can be isolated and purified further, purer final products have been obtained.This
The field method well-known to the ordinarily skilled artisan isolated and purified, such as can chromatograph, distill, filter, be centrifuged, wash using extraction, column
It washs, be fractionated and adsorb or the methods of at least two combination is isolated and purified, such as extraction, column chromatography.
Certainly it directly reacts if necessary to which the reaction mixture of acquisition can also be introduced directly into other processes to produce
Other products.Optionally, before being introduced into other processes, reaction mixture can be pre-processed, for example, concentration, extraction
It one of takes and is evaporated under reduced pressure or kinds of experiments operation, to obtain crude product or pure product, be then introduced into other works
Sequence.
In a preferred embodiment, post-processing step after reaction can be following method: after reaction,
Ethyl acetate dilution will be added after reaction solution cooling, the solution after dilution is transferred in separatory funnel, is extracted with saturated salt solution
It takes, isolates water phase and organic phase, then be extracted with ethyl acetate water phase 3 times, merge organic phase, 5g anhydrous sodium sulfate is added, it is quiet
Only 30min is washed filter cake 3 times with 5mL ethyl acetate every time, then spin off solvent, concentrate is passed through pillar layer separation totally
(wherein silica gel is 300-400 mesh silica gel), using petroleum ether and ethyl acetate mixtures as eluant, eluent, collects eluent, after concentration
Obtain target product.
The preparation method of 1- (4- methylbenzyl) -3- morpholine base -4- first seleno maleimide provided by the invention has
It has the advantages that:
A) high efficiency, high yield, post-processing simplicity are reacted；
B) tandem reaction of three components is participated in using dimethyl diselenide ether as first seleno reagent；
C) using mantoquita and oxygen cheap and easy to get as catalyst system；
The present invention is to have N- (the 4- methyl benzyl of structure shown in the dimethyl diselenide ether of the structure as shown in formula (I), formula (II)
Base) the N- methylmaleimido of structure shown in maleimide and formula (III) is reaction raw materials, in transition metal copper/oxygen
Under catalytic action, obtained shown in formula (IV) by the oxidative coupling reaction of the carbon-carbon double bond in N- methylmaleimido structure
1- (4- methylbenzyl) -3- morpholine base -4- first seleno maleimide compound of structure.The synthetic method will be conduct
The important development and supplement of easy to operate, low-cost 3- amino -4- alkane seleno maleimide synthetic method are Malaysia
The MOLECULE DESIGN of imide derivative and synthesis provide new strategy, have important social effect and economic significance.
Specific embodiment
Below by specific embodiment, the present invention is described in detail, but the purposes of these exemplary embodiments and
Purpose is only used to enumerate the present invention, not constitutes any type of any restriction to real protection scope of the invention, more non-to incite somebody to action
Protection scope of the present invention is confined to this.
The data and purity of noval chemical compound given by following embodiment are identified by nuclear magnetic resonance.
Embodiment 1
The synthesis of 1- (4- methylbenzyl) -3- morpholine base -4- first seleno maleimide compound
At room temperature, by N- (4- methylbenzyl) maleimide (0.2mmol, 1equiv), morpholine (0.3mmol,
1.5equiv), sodium carbonate (0.8mmol, 4equiv), copper acetate (0.02mmol, 0.1equiv) and 1mL N- crassitude
Ketone is added in reaction tube, is then charged with oxygen, and replace three times, with syringe injection dimethyl diselenide ether (0.4mmo,
2equiv), 12h is stirred under 120 DEG C of reaction temperatures.Reaction mixture is cooling, ethyl acetate is then added and is diluted,
Solution after dilution is transferred in separatory funnel, is extracted with saturated salt solution, isolates water phase and organic phase, then use acetic acid
Ethyl ester aqueous phase extracted 3 times, merge organic phase, 5g anhydrous sodium sulfate is added, static 30min is washed with 5mL ethyl acetate every time
Filter cake totally 3 times, solvent is then spun off, obtaining product through column chromatography for separation, (eluant, eluent: petroleum ether: ether=8: 1), product is
Yellow liquid, yield 80%, products weight 61mg.
The data of the nuclear magnetic resonance spectroscopy of products therefrom are as follows:
1H NMR (500MHz, CDCl3): δ 7.26 (d, J=7.8Hz, 2H), 7.11 (d, J=7.8Hz, 2H), 4.60 (s,
2H), 4.11 (t, J=4.70Hz, 4H), 3.77 (t, J=4.70Hz, 4H), 2.31 (s, 3H), 2.18 (s, 3H)；
The data of the carbon-13 nmr spectra of products therefrom are as follows:
13C NMR (125MHz, CDCl3): δ 169.9,166.4,148.7,137.4,133.7,129.2,128.7,89.7,
67.0,48.5,41.6,21.1,9.6；
HRMS (ESI): calcd for C17H20N2O3Se[M+H]+381.0718 found 381.0722.
It can be seen that by above-described embodiment 1, when using the method described in the present invention, can be obtained with high yield, high-purity
1- (4- methylbenzyl) -3- morpholine base -4- first seleno maleimide compound.
Embodiment 2-4
It is same as Example 1 in addition to transition-metal catalyst copper acetate therein is replaced with following mantoquita respectively
Mode and implement embodiment 2-4 respectively, the yield of used compound nantokite and corresponding product is as shown in table 1 below.
Table 1
It can be seen that by upper table 1, when using other mantoquitas, cuprous iodide can smoothly react but the decline of the yield of product
It is bigger, and copper chloride and copper bromide can not be catalyzed the reaction thus demonstrate copper acetate be the reaction successfully it is crucial because
Element, and it is maximally efficient to the reaction system.
Embodiment 5-19
In addition to organic solvent N-Methyl pyrrolidone therein is replaced with following organic solvent respectively, with embodiment
1 identical mode and implement implement 5-19 respectively, the yield of used organic solvent and corresponding product is as shown in table 2 below.
Table 2
| Number | Solvent | Reaction yield (%) |
| Embodiment 5 | Dimethyl sulfoxide | 19 |
| Embodiment 6 | N,N-Dimethylformamide | 10 |
| Embodiment 7 | N,N-dimethylacetamide | 11 |
| Embodiment 8 | Methylene chloride | It does not react |
| Embodiment 9 | Ethyl acetate | It does not react |
| Embodiment 10 | Pyridine | It does not react |
| Embodiment 11 | Six alkane of Isosorbide-5-Nitrae-dioxy | It does not react |
| Embodiment 12 | 1,2- dichloroethanes | It does not react |
| Embodiment 13 | Acetonitrile | It does not react |
| Embodiment 14 | Toluene | It does not react |
| Embodiment 15 | Tetrahydrofuran | It does not react |
| Embodiment 16 | Ethyl alcohol | It does not react |
| Embodiment 17 | Carbon tetrachloride | It does not react |
| Embodiment 18 | Chloroform | It does not react |
| Embodiment 19 | N-butanol | It does not react |
It can be seen that by upper table 2, when using other organic solvents, in addition in intensive polar solvent such as dimethyl sulfoxide and N, N- bis-
Methylacetamide can react, but yield still decreases；And it is not any under the conditions of nonpolarity or even weak ligand solvent
Product.This demonstrate that can the suitable selection of organic solvent carry out significant, even conclusive influence to reaction.
Embodiment 20-28
In addition to alkali sodium carbonate therein is replaced with following inorganic base respectively, divide in the same manner as example 1
Do not implement embodiment 20-28, the yield of used alkali cpd and corresponding product is as shown in table 3 below.
Table 3
| Number | Alkali | Reaction yield (%) |
| Embodiment 20 | Cesium carbonate | It does not react |
| Embodiment 21 | Lithium carbonate | It does not react |
| Embodiment 22 | Potassium carbonate | It does not react |
| Embodiment 23 | Potassium phosphate | It does not react |
| Embodiment 24 | Sodium acetate | It does not react |
| Embodiment 25 | Lithium acetate | It does not react |
| Embodiment 26 | Tert-butyl alcohol lithium | It does not react |
| Embodiment 27 | Sodium tert-butoxide | It does not react |
| Embodiment 28 | Potassium tert-butoxide | It does not react |
It can be seen that by upper table 3, when using other alkali, almost do not react, thus demonstrating sodium carbonate is the reaction
Successful key factor, and it is maximally efficient to the reaction system.
In conclusion can clearly be found out by above-mentioned all embodiments, urged when using method of the invention using transition metal
Agent (especially copper acetate), inorganic base (especially sodium carbonate) and suitable organic solvent (especially N- crassitude
Ketone) composed by recombination reaction system when, dimethyl diselenide ether, N- (4- methylbenzyl) maleimide and morphine can be made
Quinoline synthesizes to obtain 1- (4- methylbenzyl) -3- with high yield and high-purity by the tandem reaction of three components under Oxygen Condition
Morpholine base -4- first seleno maleimide compound provides completely new synthesis road for the efficient quick synthesis of the compound
Line.
Finally, it should be noted that the above embodiments are only used to illustrate the technical solution of the present invention., rather than its limitations；To the greatest extent
Pipe present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that: its according to
Right scientific research modifies the technical solutions described in the foregoing embodiments, or to some or all of the technical features
It is equivalently replaced；And these are modified or replaceed, various embodiments of the present invention skill that it does not separate the essence of the corresponding technical solution
The range of art scheme.
Claims (8)
1. a kind of preparation method of 1- (4- methylbenzyl) -3- amino -4- first seleno maleimide compound, feature exist
In in organic solvent, under Oxygen Condition, to have structure shown in the dimethyl diselenide ether of the structure as shown in formula (I), formula (II)
N- (4- methylbenzyl) maleimide and formula (III) shown in structure N- methylmaleimido be reaction raw materials, in mistake
It crosses under metallic copper catalytic action, passes through the oxidative coupling reaction of the carbon-carbon double bond in N- (4- methylbenzyl) maleimide structure
Obtain 1- (4- methylbenzyl) -3- morpholine base -4- first seleno maleimide compound of structure shown in formula (IV).
2. preparation method as described in claim 1, which is characterized in that the transition-metal catalyst copper is copper acetate, chlorination
Copper, copper bromide or cuprous iodide, preferably copper acetate.
3. preparation method according to claim 1, which is characterized in that the reaction dissolvent is organic solvent, described organic
Solvent is dimethyl sulfoxide, n,N-Dimethylformamide, n,N-dimethylacetamide, N-Methyl pyrrolidone, methylene chloride, second
Acetoacetic ester, pyridine, six alkane of Isosorbide-5-Nitrae-dioxy, 1,2- dichloroethanes, acetonitrile, toluene, tetrahydrofuran, ethyl alcohol, carbon tetrachloride, chloroform,
At least one of n-butanol, preferably N-Methyl pyrrolidone.
4. preparation method as described in claim 1, which is characterized in that the alkali is lithium carbonate, cesium carbonate, potassium carbonate, carbonic acid
Sodium, sodium acetate, lithium acetate, potassium phosphate, sodium tert-butoxide, tert-butyl alcohol lithium or potassium tert-butoxide, preferably sodium carbonate.
5. preparation method according to claim 1, it is characterised in that: the dimethyl diselenide ether of structure shown in (I), formula
(II) molar ratio of the morpholine of structure shown in N- (4- methylbenzyl) maleimide and formula (III) of structure shown in is 4: 2:
3。
6. preparation method according to claim 1, which is characterized in that the temperature of the range is 100-120 DEG C.
7. preparation method according to claim 1, which is characterized in that the time of the reaction is 10-12h.
8. the preparation side of 1- (4- methylbenzyl) -3- amino -4- first seleno maleimide compound as described in claim 1
Method, it is characterised in that: after reaction, extractant extraction will be added after reaction solution cooling, isolate water phase and organic phase, take and contain
The organic phase of extractant and target product is simultaneously dry with anhydrous sodium sulfate, is concentrated under reduced pressure, and concentrate is passed through pillar layer separation (its
Middle silica gel is 300-400 mesh silica gel), it is 95: 5 mixed liquors as eluant, eluent using petroleum ether and ether volume ratio, collects eluent, rotation
The 1- as shown in formula (IV) (4- methylbenzyl) -3- amino -4- first seleno maleimide compound is obtained after steaming solvent.
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Cited By (5)
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| CN111333564A (en) * | 2019-12-30 | 2020-06-26 | 温州医科大学 | Synthetic method of 3-alkylmercapto-1-methyl-4-morpholinyl maleimide compound |
| CN111393350A (en) * | 2019-12-30 | 2020-07-10 | 温州医科大学 | Synthesis method of N-methyl-3-substituted benzylmercapto-4-morpholinyl maleimide compound |
| CN111606843A (en) * | 2020-06-17 | 2020-09-01 | 温州医科大学 | Synthetic method of 2-phenylseleno-3-amino-1, 4-naphthoquinone |
| CN111620840A (en) * | 2020-06-17 | 2020-09-04 | 温州医科大学 | Synthetic method of 2-morpholinyl-3-arylseleno naphthoquinone |
| CN111978235A (en) * | 2020-08-12 | 2020-11-24 | 温州医科大学 | Preparation method of 3-amino-4-methylmercaptomaleimide compound |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111333564A (en) * | 2019-12-30 | 2020-06-26 | 温州医科大学 | Synthetic method of 3-alkylmercapto-1-methyl-4-morpholinyl maleimide compound |
| CN111393350A (en) * | 2019-12-30 | 2020-07-10 | 温州医科大学 | Synthesis method of N-methyl-3-substituted benzylmercapto-4-morpholinyl maleimide compound |
| CN111333564B (en) * | 2019-12-30 | 2023-08-18 | 温州医科大学 | Synthesis method of 3-alkylthio-1-methyl-4-morpholinylmaleimide compound |
| CN111393350B (en) * | 2019-12-30 | 2024-01-05 | 温州医科大学 | Synthesis method of N-methyl-3-substituted benzyl mercapto-4-morpholinyl maleimide compound |
| CN111606843A (en) * | 2020-06-17 | 2020-09-01 | 温州医科大学 | Synthetic method of 2-phenylseleno-3-amino-1, 4-naphthoquinone |
| CN111620840A (en) * | 2020-06-17 | 2020-09-04 | 温州医科大学 | Synthetic method of 2-morpholinyl-3-arylseleno naphthoquinone |
| CN111620840B (en) * | 2020-06-17 | 2023-06-30 | 温州医科大学 | Synthesis method of 2-morpholino-3-arylseleno naphthoquinone |
| CN111978235A (en) * | 2020-08-12 | 2020-11-24 | 温州医科大学 | Preparation method of 3-amino-4-methylmercaptomaleimide compound |
| CN111978235B (en) * | 2020-08-12 | 2023-08-18 | 温州医科大学 | Preparation method of 3-amino-4-methylmercapto maleimide compound |
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