CN110128357A - A kind of method of intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines - Google Patents
A kind of method of intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines Download PDFInfo
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- CN110128357A CN110128357A CN201910455526.1A CN201910455526A CN110128357A CN 110128357 A CN110128357 A CN 110128357A CN 201910455526 A CN201910455526 A CN 201910455526A CN 110128357 A CN110128357 A CN 110128357A
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Abstract
The invention discloses a kind of methods of intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines, it is characterized in that using cinnamic acid and chiral t-butyl sulfonamide as Material synthesis chiral imines class compound, Pyrazine derivative is synthesized through dimerization reaction again, synthetic route is as follows:The present invention is induced with t-butyl sulfonamide, is carried out the removing of free radical under heating conditions, in reaction process is only needed that Cs is added2CO3Target product can be obtained in weak base, can be avoided intense conditions for the particular/special requirement of reaction unit.This reaction condition is mild, quick, and high income, products therefrom is symmetrical structure, and the synthesis for symmetrical dimeric molecule provides new approaches, this post-reaction treatment process is simple, simultaneously because reaction Efficient Conversion is the single product of product.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of intermolecular [3+3] dimerization synthesis pyrrole of chiral imines
The method of piperazine analog derivative.
Background technique
Pyrazine is the key that many drug molecular structure skeletons part, as orfloxacin, pipemidic acid, pyrazine salt (phosphate,
Sulfate), quinolone, rifampin etc..Pyrazine and its derivative much have important bioactivity, such as antibacterial, anti-inflammatory, drop
Blood glucose isoreactivity.Pyrazine compounds are early in just causing the dense emerging of synthetic organic chemist and Pharmaceutical Chemist 19th century
Interest, modern medicines study expansion, exploitation and application for pyrazine compounds and have put into a large amount of energy.
Synthesis for pyrazine compounds can be roughly divided into following a few classes according to raw material difference:
1. with monoethanolamine (MEA) for Material synthesis.
2. being synthesized from ethylenediamine.
3. using chlorethanol as Material synthesis.
4. using second diene triamine as Material synthesis.
5. using beta-hydroxyethyl ethylenediamine as Material synthesis.
Currently, widely used prior synthesizing method main problem is: it is special that the condition of 1. some consersion units requires,
Such as dehydration, dehydrogenation, deamination reaction, for reaction unit high temperature resistant, high pressure resistant have higher requirement.2. reaction is frequently necessary to make
With metallic catalyst, such as: nickel, copper, chromium, platinum, titanium, cobalt.3. many reaction routes use strong acid and strong base, strong acid and strong base reaction
The introducing of condition will increase the difficulty of post-reaction treatment, while can cause more environmental problems.4. side reaction is more, product is received
Rate difficulty raising etc..Therefore, developing a kind of method that can solve above-mentioned technical problem is very important.
Summary of the invention
The purpose of the present invention is to provide a kind of sides of intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines
Method.It is intended to solve the above problems.
The present invention provides a kind of methods of intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines, are with meat
Cinnamic aldehyde and chiral t-butyl sulfonamide are raw material, under the action of catalyst, synthesis of chiral imine compound, then through in alkalinity
Under the action of substance, dimerization reaction synthesizes Pyrazine derivative 2,5- diformazan ((z)-benzo aldehyde) -2,5- dihydro pyrazine；It is synthesized
Route is as follows:
In above-mentioned reaction, include the following steps:
(1) using α, the cinnamic acid of the unsaturated conjugated aldehyde structure of β-and chiral t-butyl sulfonamide is contained, in lewis acid
Under the action of tetraethyl titanate, by aldehyde radical and amido dehydration contracting and chiral conjugated imines class compound is formed,
(2) it is added under the action of inorganic base cesium carbonate, chiral terf-butylsulfinyl is detached from by the form of free radical,
(3) intermolecular [3+3] dimerization reaction occurs and obtains object Pyrazine derivative 2,5- diformazan ((z)-benzo aldehyde)-
2,5- dihydro pyrazine.
Further, the cinnamic acid, t-butyl sulfonamide, tetraethyl titanate molar ratio be (0.5~1.5):
(0.5~1.5): (0.9~3.0)；Preferably (0.8~1.2): (0.8~1.2): (1.5~2.5).
Further, the molar ratio of chiral conjugated imines class compound and inorganic base cesium carbonate be 0.5~1.5:0.5~
1.5。
Further, the molar ratio of chiral conjugated imines class compound and inorganic base cesium carbonate is preferably 0.8~1.2:
0.8~1.2.
Further, cinnamic acid and chiral t-butyl sulfonamide be under the action of lewis acid tetraethyl titanate, and
Under conditions of organic solvent tetrahydrofuran, reacted under inert gas shielding.
Further, the temperature of the reaction is 40~60 DEG C；The time of the reaction is 3~5h.
Further, the temperature that chiral conjugated imines class compound reacts under the action of inorganic base cesium carbonate be 70~
90 DEG C, the time of reaction is 5~7h.
Advantages of the present invention:
1, it is carried out using chiral t-butyl sulfonamide induced reaction, this is designed as the first task report.
2, the removing of free radical is carried out under heating conditions using chiral terf-butylsulfinyl, this reaction condition temperature
With quick, high income.
3, it only needs that Cs2CO3 weak base is added in reaction process, target product can be obtained, can be avoided intense conditions pair
In the particular/special requirement of reaction unit.
4, reaction product is symmetrical structure, provides new thinking for the synthesis of symmetrical dimeric molecule.
5, this post-reaction treatment process is simple, simultaneously because reaction Efficient Conversion is the single product of product, it is target product
Acquisition provide the condition sent out very much.
Detailed description of the invention
Fig. 1 is the compounds of this invention 31HNMR(300MHz,CDCl3) spectrogram；
Fig. 2 is the compounds of this invention 313CNMR(75MHz,CDCl3) spectrogram；
Fig. 3 is the FTIR spectrogram of the compounds of this invention 3；
Fig. 4 is the compounds of this invention 101HNMR(300MHz,CDCl3) spectrogram；
Fig. 5 is the compounds of this invention 1013CNMR(75MHz,CDCl3) spectrogram；
Fig. 6 is the HRMS spectrogram of the compounds of this invention 10；
Fig. 7 is the synthesis mechanism schematic diagram of the compounds of this invention 10.
Specific embodiment
The present invention will be further described below with reference to the drawings, but the present invention is limited in any way, base
In present invention teach that it is made it is any transform or replace, all belong to the scope of protection of the present invention.
Embodiment 1
A kind of method for present embodiments providing intermolecular [3+3] dimerization synthesis Pyrazine derivative of chiral imines, with meat
Cinnamic aldehyde and chiral t-butyl sulfonamide are raw material, under the action of catalyst, synthesis of chiral imine compound, then through in alkalinity
Under the action of substance, dimerization reaction synthesizes Pyrazine derivative 2,5- diformazan ((z)-benzo aldehyde) -2,5- dihydro pyrazine；It is synthesized
Route is as follows:
The present embodiment provides a kind of methods of intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines, including such as
Lower step:
(1) using α, the cinnamic acid of the unsaturated conjugated aldehyde structure of β-and chiral t-butyl sulfonamide is contained, in lewis acid
Under the action of tetraethyl titanate, by aldehyde radical and amido dehydration contracting and chiral conjugated imines class compound is formed,
(2) it is added under the action of inorganic base cesium carbonate, chiral terf-butylsulfinyl is detached from by the form of free radical,
(3) intermolecular [3+3] dimerization reaction occurs and obtains object Pyrazine derivative 2,5- diformazan ((z)-benzo aldehyde)-
2,5- dihydro pyrazine.
The cinnamic acid, t-butyl sulfonamide, tetraethyl titanate molar ratio be (0.5~1.5): (0.5~
1.5): (0.9~3.0)；
In above-mentioned reaction, the molar ratio of chiral conjugated imines class compound and inorganic base cesium carbonate is 0.5~1.5:0.5
~1.5.
In above-mentioned reaction, cinnamic acid and chiral t-butyl sulfonamide under the action of lewis acid tetraethyl titanate,
And under conditions of organic solvent tetrahydrofuran, reacted under inert gas shielding.
In above-mentioned reaction, the temperature of the reaction is 40~60 DEG C, and the time of the reaction is 3~5h.
In above-mentioned reaction, under the action of inorganic base cesium carbonate, the temperature of reaction is chiral conjugated imines class compound
70~90 DEG C, the time of reaction is 5~7h.
Embodiment 2
A kind of method for present embodiments providing intermolecular [3+3] dimerization synthesis Pyrazine derivative of chiral imines, with meat
Cinnamic aldehyde and chiral t-butyl sulfonamide are raw material, under the action of catalyst, synthesis of chiral imine compound, then through in alkalinity
Under the action of substance, dimerization reaction synthesizes Pyrazine derivative 2,5- diformazan ((z)-benzo aldehyde) -2,5- dihydro pyrazine；It is synthesized
Route is as follows:
A kind of method for present embodiments providing intermolecular [3+3] dimerization synthesis Pyrazine derivative of chiral imines, including
Following steps:
(1) using α, the cinnamic acid of the unsaturated conjugated aldehyde structure of β-and chiral t-butyl sulfonamide is contained, in lewis acid
Under the action of tetraethyl titanate, by aldehyde radical and amido dehydration contracting and chiral conjugated imines class compound is formed,
(2) it is added under the action of inorganic base cesium carbonate, chiral terf-butylsulfinyl is detached from by the form of free radical,
(3) intermolecular [3+3] dimerization reaction occurs and obtains object Pyrazine derivative 2,5- diformazan ((z)-benzo aldehyde)-
2,5- dihydro pyrazine.
In above-mentioned reaction, the molar ratio preferably (0.8 of the cinnamic acid, t-butyl sulfonamide, tetraethyl titanate
~1.2): (0.8~1.2): (1.5~2.5).
In above-mentioned reaction, the molar ratio of chiral conjugated imines class compound and inorganic base cesium carbonate is preferably 0.8~
1.2:0.8~1.2.
In above-mentioned reaction, cinnamic acid and chiral t-butyl sulfonamide under the action of lewis acid tetraethyl titanate,
And under conditions of organic solvent tetrahydrofuran, reacted under inert gas shielding.
In above-mentioned reaction, the temperature of the reaction is 40~60 DEG C, and the time of the reaction is 3~5h.
In above-mentioned reaction, under the action of inorganic base cesium carbonate, the temperature of reaction is chiral conjugated imines class compound
70~90 DEG C, the time of reaction is 5~7h.
Embodiment 3
A kind of method for present embodiments providing intermolecular [3+3] dimerization synthesis Pyrazine derivative of chiral imines: with meat
Cinnamic aldehyde (1.74g, 13.20mmol), (R)-t-butyl sulfonamide (1.45g, 12.00mmol), tetraethyl titanate (Ti
(EtO)4, 5mL, 24.00mmol), be added in the round-bottomed flask for having been loaded with dry tetrahydrofuran (20mL) and magnetic stir bar,
50 DEG C are heated under inert gas shielding, and the reaction time 4 hours, reaction process is monitored by thin layer plate layer chromatography (TLC) during reaction.
Post-reaction treatment:
Reaction raw materials cinnamic acid is monitored by TLC to completely disappear, and is stopped heating, is quickly vigorously stirred down after being cooled to room temperature
Saturated sodium bicarbonate solution is added to there are white depositions, filter cake is washed with ethyl acetate after filtering, and filtrate is through being saturated chlorination
After sodium solution washing, ethyl acetate extraction, organic solvent phase is collected, after, filtering dry through anhydrous magnesium sulfate, concentration, is used
300-400 mesh silica gel carries out column chromatographic isolation and purification, eluant, eluent ratio are as follows: petrol ether/ethyl acetate (EtOAc/
Petroleumether)=1/5 (it is 60~90 DEG C that column, which chromatographs the boiling range of used petroleum ether), isolated chirality conjugated imines
Compound 3 (3.03g, yield 95%).
3 Structural Identification of compound:
Under the monitoring of Thin-Layer Chromatography thin-layered chromatography:
(EtOAc/hexane=1/5): Rf=0.25 (UV)
If Fig. 1-2 shows, characterized as nuclear magnetic resonance spectrometer intermediate compound 3 to made from:
1HNMR(300MHz,CDCl3) δ ppm:8.39-8.36 (d, J=6.9,2H), 7.55-7.53 (d, J=5.7,2H),
7.40-7.39 (m, J=4.8,3H), 7.11-7.09 (d, J=6.9,1H), 7.07-7.05 (m, J=6.9,1H), 1.23 (s,
9H).
13CNMR(75MHz,CDCl3)δppm:163.9,146.5,135.0,130.3,129.0,129.0,128.0,
126.0,57.6,22.5.
Infrared spectrum analyzer is converted by fourier to be analyzed:
FTIR(KBr):νmax(cm–1):3454,3052,3004,2970,2960,2930,2866,1664,1600,1580,
1450,1360,1320,1300,1250,1150,1060,990,950,850,796,758,720,690.
2. the preparation process of Pyrazine derivative 10 is as follows:
The chemical synthesis route of Pyrazine derivative 10
Reaction process:
Compound 3 (100mg, 0.43mmol), cesium carbonate (Cs2CO3, 138mg, 0.43mmol) and it is added to equipped with dry second
In nitrile (MeCN, 20mL) and the round-bottomed flask of magnetic stir bar, 80 DEG C are heated to, the reaction time is 6 hours, is passed through during reaction
The process of TLC monitoring reaction.
As shown in fig. 7, the synthesizer of intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines in the present embodiment
It manages as follows:
1, the terf-butylsulfinyl in compound 3 carries out free radical dissociation in the presence of alkali, obtains containing imines certainly
By the compound 5 of base；
2, α free radical compounds 6 of imines and imines are formed by way of 1,3- hydrogen migration；
3, compound intermediate 6 obtains compound α amidos of 7 alkene by the free radical homolysis of intramolecular imine double bond
Free radical monomer；
4,7 liang of molecules of compound join alkene α amido free radical monomer, obtain dimer compound 8 by two molecule dimerization；
5, compound 8 obtains amido free radical compounds 9 by 1,2- hydrogen migration；
6, process obtains target compound 10 to compound 9 after post treatment.
Post-reaction treatment:
Reaction raw materials compound 3 is monitored by TLC to completely disappear, and is stopped heating, is cooled to room temperature, reaction solution is through water washing
It is extracted afterwards with ethyl acetate, the organic solvent being obtained by extraction mutually after drying, filtering, concentration, uses 300-400 mesh silica gel
Carry out column chromatographic isolation and purification, eluant, eluent ratio are as follows: ethyl acetate/petroleum ether (EtOAc/Petroleumether)=1:10
(wherein the boiling range of petroleum ether is 60~90 DEG C), isolated pyrazine compounds 10 (54mg, yield 96%).
10 Structural Identification of compound:
TLC (EtOAc/hexane=1/10): Rf=0.25 (UV)
As in Figure 3-5, pass through high resolution mass spectrometer and nuclear magnetic resonance spectrometer the product qualitative characterization to made from:
1HNMR(300MHz,CDCl3) δ ppm:7.44-7.42 (m, J=3.6,12H), 7.37 (s, 1H), 5.91 (s, 1H),
5.85(s,1H).
13CNMR(75MHz,CDCl3)δppm:150.6,133.5,131.2,129.1,127.4,118.2,96.3.
HRMS(ESI):calculatedforC18H14N2[M+4H]4+:258.1157,found262.1441.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Anyone skilled in the art within the technical scope of the present disclosure, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.
Claims (8)
1. a kind of method of intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines, it is characterised in that: with cinnamic acid and
Chiral t-butyl sulfonamide is raw material, under the action of catalyst, synthesis of chiral imine compound, then through in alkaline matter
Under effect, dimerization reaction synthesizes 2,5- diformazan ((z)-benzo aldehyde) -2,5- dihydro pyrazine；Its synthetic route is as follows:
2. the method for intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines according to claim 1, feature
It is:
(1) using α, the cinnamic acid of the unsaturated conjugated aldehyde structure of β-and chiral t-butyl sulfonamide is contained, in lewis acid metatitanic acid
Under the action of tetra-ethyl ester, by aldehyde radical and amido dehydration contracting and chiral conjugated imines class compound is formed,
(2) it is added under the action of inorganic base cesium carbonate, chiral terf-butylsulfinyl is detached from by the form of free radical,
(3) intermolecular [3+3] dimerization reaction occurs and obtains object Pyrazine derivative 2,5- diformazan ((z)-benzo aldehyde) -2,5-
Dihydro pyrazine.
3. the method for intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines according to claim 2, feature
Be: the cinnamic acid, t-butyl sulfonamide, tetraethyl titanate molar ratio be (0.5~1.5): (0.5~1.5):
(0.9~3.0)；Preferably (0.8~1.2): (0.8~1.2): (1.5~2.5).
4. the method for intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines according to claim 2, feature
Be: the molar ratio of chiral conjugated imines class compound and inorganic base cesium carbonate is 0.5~1.5:0.5~1.5.
5. the method for intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines according to claim 2 or 4,
Be characterized in that: the molar ratio of chiral conjugated imines class compound and inorganic base cesium carbonate is preferably 0.8~1.2:0.8~1.2.
6. the method for intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines according to claim 2, feature
Be: cinnamic acid and chiral t-butyl sulfonamide are under the action of lewis acid tetraethyl titanate, and in organic solvent tetrahydro
Under conditions of furans, reacted under inert gas shielding.
7. the method for intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines according to claim 6, feature
Be: the temperature of the reaction is 40~60 DEG C, and the time of the reaction is 3~5h.
8. the method for intermolecular [3+3] the dimerization synthesis Pyrazine derivative of chiral imines according to claim 2, feature
Be: for chiral conjugated imines class compound under the action of inorganic base cesium carbonate, the temperature of reaction is 70~90 DEG C, reaction when
Between be 5~7h.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112080755A (en) * | 2020-09-02 | 2020-12-15 | 昆明海关技术中心 | Method for electrocatalytic hydrolysis of chiral imine |
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2019
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Non-Patent Citations (4)
| Title |
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| GUANGCHENG LIU等: "Catalytic Asymmetric Synthesis of tert-Butanesulfinamide. Application to the Asymmetric Synthesis of Amines", 《J. AM. CHEM. SOC.》 * |
| MARYANN T. ROBAK等: "Synthesis and Applications of tert-Butanesulfinamide", 《CHEM. REV.》 * |
| WEN CHEN等: "Iodine mediated deprotection of N-tert-butanesulfinyl amines: a functional group compatible method", 《CHEM. COMMUN.》 * |
| 方起程: "《天然药物化学研究》", 30 September 2006 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112080755A (en) * | 2020-09-02 | 2020-12-15 | 昆明海关技术中心 | Method for electrocatalytic hydrolysis of chiral imine |
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