Trifluoromethyl pyrrolo isoquinoline derivative and synthesis method thereof

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

Inactive Publication Date: 2016-08-24
SHANGHAI UNIV
View PDF1 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Trifluoromethyl pyrrolo isoquinoline derivative and synthesis method thereof
  • Trifluoromethyl pyrrolo isoquinoline derivative and synthesis method thereof
  • Trifluoromethyl pyrrolo isoquinoline derivative 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 (5 mL) 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 and reacted 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 we...

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, 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.

[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 ]isoquinoline-2-car...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap