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Trifluoromethylpyrroloisoquinoline derivatives and synthesis method thereof

A kind of technology of trifluoromethylpyrrole and isoquinoline, applied in the direction of organic chemistry etc.

Inactive Publication Date: 2017-11-10
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Summarizing the synthesis methods so far, it is not difficult to see that there are almost no trifluoromethyl-containing products in the currently synthesized pyrroloisoquinoline derivatives

Method used

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  • Trifluoromethylpyrroloisoquinoline derivatives and synthesis method thereof
  • Trifluoromethylpyrroloisoquinoline derivatives and synthesis method thereof
  • Trifluoromethylpyrroloisoquinoline derivatives and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add isoquinoline (65~84.5 mg, 0.5~0.65 mmol), phenylacetylene (51 mg, 0.5 mmol), methyl trifluoromethylpropiolate (114 mg, 0.75 mmol) into a round bottom flask, bromide Cuprous (7.2 mg, 10 mol%), toluene (5mL) as solvent, nitrogen protection, reaction at room temperature for 16 to 24 hours; then add copper bromide (11.2 mg, 10 mol%) as a catalyst, base pyridine (40 mg, 0.5 mmol), heated to 100~120°C for 18~24 hours, cooled to room temperature, diluted with saturated brine, extracted three times with ethyl acetate, and the combined organic layer was washed with anhydrous Na 2 SO 4 After drying, the pure product was separated by column chromatography. Pale yellow solid.

[0025] Structural formula:

[0026]

[0027] Chinese name:

[0028] 1-benzoyl-3-(trifluoromethyl)pyrrolo[2,1- a ]Methyl isoquinoline-2-carboxylate

[0029] English name:

[0030] Methyl 1-benzoyl-3-(trifluoromethyl)pyrrolo[2,1- a ]isoquinoline-2-carboxylate

[0031] Molecular weight: 397.0926...

Embodiment 2

[0037] Add isoquinoline (65~84.5 mg, 0.5~0.65 mmol), p-methylphenylacetylene (58 mg, 0.5 mmol), methyl trifluoromethylpropiolate (114 mg, 0.75 mmol) into a round bottom flask , cuprous bromide (7.2 mg, 10 mol%), toluene (5 mL) as a solvent, nitrogen protection, reaction at room temperature for 16 to 24 hours; then add copper bromide (11.2 mg, 10 mol%) as a catalyst, Base pyridine (40 mg, 0.5 mmol), heated to 100~120°C and reacted for 18~24 hours, cooled to room temperature, diluted with saturated saline, extracted three times with ethyl acetate, and the combined organic layer was washed with anhydrous Na 2 SO 4 After drying, the pure product was separated by column chromatography. Pale yellow solid.

[0038] Structural formula:

[0039]

[0040] Chinese name:

[0041] 1-(4-methylbenzoyl)-3-(trifluoromethyl)pyrrolo[2,1- a ]Methyl isoquinoline-2-carboxylate

[0042] English name:

[0043] Methyl 1-(4-methylbenzoyl)-3-(trifluoromethyl)pyrrolo[2,1- a ]isoquinoline-2-car...

Embodiment 3

[0050] Add isoquinoline (65~84.5 mg, 0.5~0.65 mmol), m-methylphenylacetylene (58 mg, 0.5 mmol), methyl trifluoromethylpropiolate (114 mg, 0.75 mmol) into a round bottom flask , cuprous bromide (7.2 mg, 10 mol%), toluene (5 mL) as a solvent, nitrogen protection, and reacted at room temperature for 16 to 24 hours; then copper bromide (11.2 mg, 10 mol%) was added as a catalyst, Base pyridine (40 mg, 0.5 mmol), heated to 100~120°C and reacted for 18~24 hours, cooled to room temperature, diluted with saturated saline, extracted three times with ethyl acetate, and the combined organic layer was washed with anhydrous Na 2 SO 4 After drying, the pure product was separated by column chromatography. Pale yellow solid.

[0051] Structural formula:

[0052]

[0053] Chinese name:

[0054] 1-(3-methylbenzoyl)-3-(trifluoromethyl)pyrrolo[2,1- a ]Methyl isoquinoline-2-carboxylate

[0055] English name:

[0056] Methyl 1-(3-methylbenzoyl)-3-(trifluoromethyl)pyrrolo[2,1- a ]isoquinol...

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Abstract

The invention relates to a trifluoromethyl pyrrolo isoquinoline derivative and a synthesis method thereof. The structure of the compound is as shown in the description, wherein R1 is H or methyl or methoxyl or nitryl, and R2 is aryl or heterocyclic aryl. According to the method, polysubstituted isoquinoline, aromatic terminal alkyne and trifluoromethyl methyl propiolate prepared with a mature synthesis technique are adopted as raw materials, and the polysubstituted pyrrolo isoquinoline derivative containing trifluoromethyl is synthesized with a three-component step-by-step one-pot method. In the reactive oxidation process, a traditional oxidizing agent is omitted in the method, and oxygen in the air is adopted as an oxidizing agent, which embodies the concept of environment-friendly and sustainable chemistry. Regioselectivity is high, and the yield is high. Thus, the method is a new effective method for synthesizing polysubstituted pyrrolo isoquinoline derivative containing trifluoromethyl.

Description

technical field [0001] The invention relates to a trifluoromethylpyrroloisoquinoline derivative and a synthesis method thereof. Background technique [0002] Pyrroloisoquinoline compounds are an important class of derivatives in heterocyclic compounds, which have a wide range of biological activities, such as antiviral, antitumor and antibacterial. Pyrroloisoquinolines as a class N - Bridgehead bicyclic systems, known for their potential biological activity and presence in many natural alkaloids. [0003] There are few reports and studies on pyrroloisoquinoline derivatives containing trifluoromethyl. Due to the special pharmaceutical activity of pyrroloisoquinoline derivatives and the particularity of fluorine atoms, pyrroloisoquinoline heterocyclic derivatives containing trifluoromethyl may have new utility in pharmaceutical and pesticide intermediates. In this method, for the first time, a trifluoromethyl group is introduced into pyrroloisoquinoline derivatives, and a s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 陶莉莉徐志亮陈杰韩靖张慧曹卫国
Owner SHANGHAI UNIV
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