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Trifluoromethyl pyrroloquinoline derivative and synthetic method thereof

A technology of trifluoromethylpyrrole and synthesis method, applied in the direction of organic chemistry, etc., can solve problems such as inability to reflect diversity, and achieve the effect of good yield and high regioselectivity

Inactive Publication Date: 2016-06-15
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Summarizing the synthesis methods so far, it is not difficult to see that in the past synthesis methods, strong bases, higher temperatures or noble metal catalysts are often required; and there are certain limitations in substrates, which cannot reflect diversity
Furthermore, there are almost no perfluoroalkyl-containing products in the currently synthesized pyrrolo[1,2-a]quinoline derivatives

Method used

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  • Trifluoromethyl pyrroloquinoline derivative and synthetic method thereof
  • Trifluoromethyl pyrroloquinoline derivative and synthetic method thereof
  • Trifluoromethyl pyrroloquinoline derivative and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add quinoline (65~84.5mg, 0.5~0.65mmol), phenylacetylene (51mg, 0.5mmol), methyl trifluoromethylynoate (114mg, 0.75mmol), cuprous iodide (9.5 mg, 10%mol), dichloromethane (5mL) as solvent, react at room temperature for 24~30 hours; then spin dry and use dimethyl sulfoxide as solvent, add copper bromide (11.2mg, 10%mol), 4-Dimethylaminopyridine (12.2 mg, 20% mol) was heated to 100-120 ° C for 18-24 hours, cooled to room temperature and extracted three times with saturated saline and ethyl acetate, the organic layers were combined and spin-dried, and the column The pure product was isolated by chromatography. Pale yellow solid. Yield 84%.

[0028] Structural formula:

[0029]

[0030] Chinese name: methyl 3-benzoyl-1-(trifluoromethyl)pyrrolo[1,2-a]quinoline-2-carboxylate

[0031] English name:

[0032] methyl3-benzoyl-1-(trifluoromethyl)pyrrolo[1,2-a]quinoline-2-carboxylate

[0033] Molecular weight: 397.09

[0034] Appearance: light yellow solid

[0035] Proto...

Embodiment 2

[0039] Add quinoline (65~84.5mg, 0.5~0.65mmol), p-methylphenylacetylene (58mg, 0.5mmol), methyl trifluoromethylynoate (114mg, 0.75mmol) and iodide in a round bottom flask Copper (9.5mg, 10%mol), dichloromethane (5mL) as solvent, react at room temperature for 24~30 hours; then spin dry and use dimethyl sulfoxide as solvent, add copper bromide (11.2mg, 10% mo), 4-dimethylaminopyridine (12.2 mg, 20% mmol) was heated to 100-120 ° C for 18-24 hours, cooled to room temperature and extracted three times with saturated saline and ethyl acetate, and the organic layers were combined and spun Drying, the pure product was separated by column chromatography. Pale yellow solid. Yield 90%.

[0040] Structural formula:

[0041]

[0042] Chinese name: Methyl 3-(4-methylbenzoyl)-1-(trifluoromethyl)pyrrolo[1,2-a]quinoline-2-carboxylate

[0043] English name:

[0044] methyl3-(4-methylbenzoyl)-1-(trifluoromethyl)pyrrolo[1,2-a]quinoline-2-carboxylate

[0045] Molecular weight: 411.11

[...

Embodiment 3

[0051] Add quinoline (65~84.5mg, 0.5~0.65mmol), p-methoxyphenylacetylene (66mg, 0.5mmol), methyl trifluoromethyl alkynoate (114mg, 0.75mmol), iodide Cuprous (9.5 mg, 10% mol), dichloromethane (5 mL) as solvent, react at room temperature for 24 to 30 hours; then spin dry and use dimethyl sulfoxide as solvent, add copper bromide (11.2 mg, 10 %mol), 4-dimethylaminopyridine (12.2mg, 20%mol) was heated to 100~120°C for 18~24 hours, cooled to room temperature and extracted three times with saturated saline and ethyl acetate, and the organic layers were combined Spin-dry and separate by column chromatography to obtain a pure product. Pale yellow solid. Yield 91%.

[0052] Structural formula:

[0053]

[0054] Chinese name: Methyl 3-(4-methylbenzoyl)-1-(trifluoromethyl)pyrrolo[1,2-a]quinoline-2-carboxylate

[0055] English name:

[0056] Methyl

[0057] 3-(4-methoxybenzoyl)-1-(trifluoromethyl)pyrrolo[1,2-a]quinoline-2-carboxylate

[0058] Molecular weight: 427.10

[0059] A...

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Abstract

The invention relates to a trifluoromethyl pyrroloquinoline derivative and a synthetic method thereof. The structure of the derivative is shown in the specification. According to the synthetic method, polysubstituted quinoline, aromatic terminal alkyne and trifluoromethyl acetylenic acid ester synthesized by virtue of a mature synthesis measure are taken as raw materials to synthesize the trifluoromethyl pyrroloquinoline derivative by virtue of a substep one-pot method; conventional oxidants are abandoned, and oxygen in air is utilized as an oxidant, so that the environment-friendly and sustainable chemical idea is embodied; and the regioselectivity is high, and the yield is good. Therefore, the synthetic method is an effective novel method for synthesizing the trifluoromethyl-containing polysubstituted pyrroloquinoline derivative.

Description

technical field [0001] The invention relates to a trifluoromethylpyrroloquinoline derivative and a synthesis method thereof. Background technique [0002] Most heterocyclic compounds have certain biological activity, and quinoline and pyrrole heterocyclic compounds are common types of heterocyclic compounds with biological and pharmacological activities. Pyrrolo[1,2-a]quinolines as a class of [0003] The N-bridgehead bicyclic system is known for its potential biological activity and its presence in many natural alkaloids. [0004] There are few reports and studies on pyrrolo[1,2-a]quinoline derivatives containing perfluoroalkyl groups. Due to the special pharmaceutical activity of pyrroloquinoline derivatives and the particularity of fluorine atoms, pyrroloquinoline heterocyclic derivatives containing perfluoroalkyl may have new utility in pharmaceutical and pesticide intermediates. In this method, trifluoromethyl is introduced into pyrroloquinoline derivatives for the f...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 徐志亮陈杰韩靖张慧曹卫国
Owner SHANGHAI UNIV
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