CN101333220A - Method for synthesizing benzo [4,5]glyoxalino [1,2-alpha]miazine derivates - Google Patents
Method for synthesizing benzo [4,5]glyoxalino [1,2-alpha]miazine derivates Download PDFInfo
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- CN101333220A CN101333220A CNA2008100214931A CN200810021493A CN101333220A CN 101333220 A CN101333220 A CN 101333220A CN A2008100214931 A CNA2008100214931 A CN A2008100214931A CN 200810021493 A CN200810021493 A CN 200810021493A CN 101333220 A CN101333220 A CN 101333220A
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- imidazo
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Abstract
The invention relates to a synthesis method for benzo (4,5) imidazo (1,2-a) pyrimidine derivatives, in particular to a method for synthesizing benzo (4,5) imidazo (1,2-a) pyrimidine derivatives in ionic liquid. The technical proposal of the invention is realized as follows: 1 mmol of 2-amino-benzimidazole, 1 mmol of aldehyde and 1 mmol of beta-dicarbonyl compound are added into 1-2 ml of ionic liquid and reacted for 5-6 hours at 80 DEG C so as to get the corresponding benzo (4,5) imidazo (1,2-a) pyrimidine derivative. The method of the invention has easily available material, simple and secure operation, mild reaction conditions, high yield, simple post-treatment and high atom economy; besides, the ionic liquid can be reused and causes less pollution.
Description
Technical field
The present invention relates to the synthetic method of a kind of benzo [4,5] imidazo [1,2-a] pyridine derivatives, specifically relate to a kind of synthetic method of benzo [4,5] imidazo [1, the 2-a] pyridine derivatives in ionic liquid.
Background technology
Therefore multiple biological activitys such as that benzo [4,5] imidazo [1,2-a] pyridine derivatives has is antitumor, protein kinase inhibition, T cell activation are subjected to chemistry and pharmaceutical science worker's extensive concern.The synthetic method of this compounds has several.Wherein modal method is to be that raw material reacts in organic solvent with the amino benzoglyoxaline of 2-, aldehyde, β-carbonyl ester.But use these methods, the most requirement adopted poisonous or expensive organic solvents, and the reaction times is also longer.2005, have the people in ionic liquid (TMGT), to synthesize this compounds, but their method is only useful to the aromatic aldehyde of para-orientation, the scope of application is narrower.Also there is report to synthesize this compounds recently, but exists reaction process complexity, needs to use special deficiencies such as reaction unit with microwave catalysis.
Summary of the invention
The objective of the invention is to overcome above-mentioned the deficiencies in the prior art part, a kind of gentleness, efficient, environmental friendliness, applied range are provided, productive rate height and ionic liquid can reusable benzo [4,5] imidazo [1,2-a] pyridine derivatives synthetic methods.The present invention is at synthetic benzo [4,5] imidazo [1,2-a] introduce ionic liquid in the process of pyridine derivatives, steam forces down, toxicity is little because ionic liquid has, Heat stability is good, do not burn with do not explode, solubility property uniqueness, reaction product separate advantages such as simple, can be used as the green solvent and the promotor that recycle.
The present invention realizes with following technical scheme: the amino benzoglyoxaline of 2-that adds 1 mmole in 1-2 milliliter ionic liquid, the beta-dicarbonyl compound of the aldehyde of 1 mmole and 1 mmole, reacted 5-6 hour down at 80 ℃, promptly obtain corresponding benzo [4,5] imidazo [1,2-a] pyridine derivatives.
Described ionic liquid is [Bmim] Cl or [Bmim] [BF
4].
Described beta-dicarbonyl compound is methyl aceto acetate, methyl acetoacetate, methyl ethyl diketone, ethyl benzoylacetate.
Described aldehyde is aromatic aldehyde, alkanoic or heterocyclic aldehydes.
Described ionic liquid is by document preparation (M.C.Law, K.Y.Wong, T.H.Chan, GreenChem.2002,4,328).
Compare with existing method, the present invention has following beneficial effect:
General synthetic method needs at high temperature or in the organic solvent of toxic and volatile to carry out.The present invention is at synthetic benzo [4,5] imidazo [1,2-a] introduce ionic liquid in the process of pyridine derivatives, steam forces down, toxicity is little because ionic liquid has, Heat stability is good, do not burn with do not explode, solubility property uniqueness, reaction product separate advantages such as simple, productive rate height and ionic liquid can be reused, and can be used as the green solvent and the promotor that recycle.
Embodiment
The present invention is described further below in conjunction with specific embodiment.
Embodiment 1-24.
Reaction raw materials, reaction conditions and productive rate are as shown in table 1:
Table 1
*
*The ionic liquid consumption is 1.5 milliliters, and temperature of reaction is 80 ℃, and used ionic liquid is [Bmim] Cl.
In the table 1, the beta-dicarbonyl compound of embodiment 1-9 reaction is a methyl aceto acetate, and the beta-dicarbonyl compound of embodiment 10-18 reaction is a methyl ethyl diketone, and the beta-dicarbonyl compound of embodiment 19-24 reaction is a methyl acetoacetate.
Table 2 is the result that embodiment 1 intermediate ion liquid circulation is used.
Table 2
By table 1 and table 2 as can be known, method raw material of the present invention is easy to get, safety simple to operate, reaction conditions gentleness, yield height, aftertreatment is simple, Atom economy is high, and ionic liquid can reuse, and environmental pollution is little, thereby has bigger implementary value and potential economic results in society.
Claims (4)
1. benzo [4,5] imidazo [1,2-a] synthetic method of pyridine derivatives, it is characterized in that: the amino benzoglyoxaline of 2-that in 1-2 milliliter ionic liquid, adds 1 mmole, the beta-dicarbonyl compound of the aldehyde of 1 mmole and 1 mmole reacted 5-6 hour down at 80 ℃, promptly obtained corresponding benzo [4,5] imidazo [1,2-a] pyridine derivatives.
2. the synthetic method of benzo according to claim 1 [4,5] imidazo [1,2-a] pyridine derivatives, it is characterized in that: described ionic liquid is [Bmim] Cl or [Bmim] [BF
4].
3. the synthetic method of benzo according to claim 1 and 2 [4,5] imidazo [1,2-a] pyridine derivatives, it is characterized in that: described beta-dicarbonyl compound is methyl aceto acetate, methyl acetoacetate, methyl ethyl diketone, ethyl benzoylacetate.
4. the synthetic method of benzo according to claim 1 and 2 [4,5] imidazo [1,2-a] pyridine derivatives, it is characterized in that: described aldehyde is aromatic aldehyde, alkanoic or heterocyclic aldehydes.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100214931A CN101333220A (en) | 2008-08-05 | 2008-08-05 | Method for synthesizing benzo [4,5]glyoxalino [1,2-alpha]miazine derivates |
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| CNA2008100214931A CN101333220A (en) | 2008-08-05 | 2008-08-05 | Method for synthesizing benzo [4,5]glyoxalino [1,2-alpha]miazine derivates |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103435618A (en) * | 2013-08-22 | 2013-12-11 | 中国药科大学 | Method for synthesizing fused-heterocycle compound |
| CN110172061A (en) * | 2019-06-21 | 2019-08-27 | 江苏师范大学 | A kind of synthetic method of pyrrolo- [3,4-b] quinoline -1,8- derovatives |
-
2008
- 2008-08-05 CN CNA2008100214931A patent/CN101333220A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103435618A (en) * | 2013-08-22 | 2013-12-11 | 中国药科大学 | Method for synthesizing fused-heterocycle compound |
| CN103435618B (en) * | 2013-08-22 | 2016-03-23 | 中国药科大学 | A kind of method of synthesizing fused heterocyclic compound |
| CN110172061A (en) * | 2019-06-21 | 2019-08-27 | 江苏师范大学 | A kind of synthetic method of pyrrolo- [3,4-b] quinoline -1,8- derovatives |
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