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Method for synthesizing 5-formonitrile-pyrrole [1,2-a] quinoline derivatives

A 2-a, derivative technology, applied in the direction of organic chemistry, can solve the problems of cumbersome reaction steps, difficult post-processing, strong toxicity, etc.

Active Publication Date: 2014-08-20
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, there are some defects in the above-mentioned various methods. The reaction steps are cumbersome, the conditions are harsh, the yield is low, the post-treatment is difficult, complex ligands are required, and some toxic solvents are used, especially some transition metals. Catalyst, high price, strong toxicity and dependence on highly toxic phosphorus-containing ligands severely restrict its industrial application in many fields

Method used

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  • Method for synthesizing 5-formonitrile-pyrrole [1,2-a] quinoline derivatives
  • Method for synthesizing 5-formonitrile-pyrrole [1,2-a] quinoline derivatives
  • Method for synthesizing 5-formonitrile-pyrrole [1,2-a] quinoline derivatives

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Embodiment 1

[0024] This embodiment is the synthesis of 5-formonitrile-pyrrole [1,2-a] quinoline, using 2-bromophenylacetonitrile, pyrrole-2 formaldehyde, potassium phosphate, and dimethyl sulfoxide as raw materials, and its reaction formula is as follows:

[0025]

[0026] Preparation method: add 0.2mmol pyrrole-2 carboxaldehyde, 0.2mmol 2-bromophenylacetonitrile, 0.3mmol potassium phosphate into a 25ml eggplant-shaped bottle, then add 2ml dimethyl sulfoxide, nitrogen protection, stir at 130°C for 24 hours, TLC plate detection , There is a fluorescent product under ultraviolet light.

[0027] The reaction solution is cooled, extracted, dried, vacuum distilled, washed, recrystallized and filtered to obtain the product.

[0028] The yield is 86.6%. The melting point of this 5-carbonitrile-pyrrole[1,2-a]quinoline is 141-143°C; H NMR spectrum (300Hz, DMSO): δ6.95 (d, J=10.05Hz, 2H) ,7.54(m,1H),7.70(m,1H),7.86(d,J=7.59Hz,1H),8.25(s,1H),8.36(d,J=8.31Hz,1H),8.51(s, 1H); high resolution mas...

Embodiment 2

[0030] This embodiment is the synthesis of 5-formonitrile-pyrrole [1,2-a] quinoline, using 2-bromophenylacetonitrile, pyrrole-2 formaldehyde, potassium phosphate, and dimethyl sulfoxide as raw materials, and its reaction formula is as follows:

[0031]

[0032] Preparation method: add 0.2mmol pyrrole-2 carboxaldehyde, 0.2mmol 2-bromophenylacetonitrile, 0.3mmol potassium phosphate into a 25ml eggplant-shaped bottle, then add 2ml dimethyl sulfoxide, argon protection, stir at 130°C for 24 hours, TLC plate Detection, there is a fluorescent product under ultraviolet light.

[0033] The reaction solution is cooled, extracted, dried, vacuum distilled, washed, recrystallized and filtered to obtain the product.

[0034] The yield is 83.6%. The melting point of this 5-carbonitrile-pyrrole[1,2-a]quinoline is 141-143°C; H NMR spectrum (300Hz, DMSO): δ6.95 (d, J=10.05Hz, 2H) ,7.54(m,1H),7.70(m,1H),7.86(d,J=7.59Hz,1H),8.25(s,1H),8.36(d,J=8.31Hz,1H),8.51(s, 1H); high resolution mass sp...

Embodiment 3

[0036] This embodiment is the synthesis of 5-formonitrile-pyrrole [1,2-a] quinoline, using 2-bromophenylacetonitrile, pyrrole-2 formaldehyde, potassium phosphate, and dimethyl sulfoxide as raw materials, and its reaction formula is as follows:

[0037]

[0038] Preparation method: add 0.2mmol pyrrole-2 carboxaldehyde, 0.3mmol 2-bromophenylacetonitrile, 0.3mmol potassium phosphate into a 25ml eggplant-shaped bottle, then add 2ml dimethyl sulfoxide, nitrogen protection, stir at 130°C for 24 hours, TLC plate detection , There is a fluorescent product under ultraviolet light.

[0039] The reaction solution is cooled, extracted, dried, vacuum distilled, washed, recrystallized and filtered to obtain the product.

[0040] The yield is 80.3%. The melting point of this 5-carbonitrile-pyrrole[1,2-a]quinoline is 141-143°C; H NMR spectrum (300Hz, DMSO): δ6.95 (d, J=10.05Hz, 2H) ,7.54(m,1H),7.70(m,1H),7.86(d,J=7.59Hz,1H),8.25(s,1H),8.36(d,J=8.31Hz,1H),8.51(s, 1H); high resolution mas...

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Abstract

The invention relates to a method for synthesizing 5-formonitrile-pyrrole [1,2-a] quinoline derivatives, belonging to the technical field of chemical preparation. The method comprises the following steps: dissolving a 2-formylimidazole compound with 2-halogenated aryl acetonitrile in an organic solvent according to a weight ratio of (1-1.5) : 1, adding an alkaline medium, stirring under the protection of inert gas at 100-130 DEGC for 18-24 hours for reaction to obtain 5-formonitrile-pyrrole [1,2-a] quinoline derivatives, cooling, extracting, drying, and performing reduced pressure distillation to obtain a pure product. The method has the beneficial effects that (1) the reaction conditions are mild, the catalytic activity is high, the reaction yield is 80% and maximally is 90%, the product selectivity is high, and the substrate expanding range is wide; (2) a catalytic system avoids the participation of transition metal and strong alkali and is low in cost, safe and convenient; a reaction system is low in environmental pollution.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 5-formonitrile-pyrrole [1,2-a] quinoline derivatives. Background technique [0002] 5-carbonitrile-pyrrole [1,2-a] quinoline derivative is an important benzopyrazine heterocyclic compound, which has high thermal stability and electron affinity. Due to its internal The unique molecular conjugated structure is an important skeleton of many important biologically active compounds, and it is also widely used as a fluorescent probe material. The earliest method for synthesizing pyrrole[1,2-a]quinoline derivatives is through three steps: first, 2-oxo-3-quinoline-2-propionic acid ethyl ester is reduced to 1-(2 -quinolyl)-2,3-propanediol, then generate intermediate dibromo derivatives under the effect of hydrobromic acid, and finally generate pyrrole [1,2-a] quinoline product under the effect of strong base, the yield 44% (Edward M. Roberts et al. J. Org. Chem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 韩世清蒋增强张杰童耀何国珍周双利赵丹
Owner NANJING UNIV OF TECH
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