Perfluoroalkyl indolizine derivative and synthesis method thereof

A technology of perfluoroalkyl indolizine and perfluoroalkyl, which is applied in the field of perfluoroalkyl indolizine derivatives and synthesis thereof, can solve the problems of cumbersome reaction steps, complicated operation, difficult to obtain raw materials and the like, and achieves novel structure. , the effect of high regional selectivity

Inactive Publication Date: 2016-10-26
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Summarizing the synthesis methods so far, it is not difficult to see that in the previous synthesis methods, catalysts or even metal catalysts were often needed; or the raw materials were difficult to obtain, and the raw materials had to be synthesized first, and then the next reaction was carried out, which made the reaction steps cumbersome. The operation is complicated, whether adding catalysts or stepwise reactions have their shortcomings

Method used

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  • Perfluoroalkyl indolizine derivative and synthesis method thereof
  • Perfluoroalkyl indolizine derivative and synthesis method thereof
  • Perfluoroalkyl indolizine derivative and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Example 1: Pyridine (158 mg, 2 mmol), ω bromoacetophenone (438 mg, 2.2 mmol), and acetonitrile (5 mL) were added to a round-bottomed flask, and reacted at 40 ° C for 4 hours to form a salt , then added methyl trifluoromethylpropiolate (152 mg, 1 mmol), N, N-diisopropylethylamine (258 mg, 1 mmol) and reacted for 7 hours, cooled to room temperature, spin-dried the solvent, and The pure product was isolated by chromatography. white solid. Yield 90%. Structural formula:

[0024]

[0025] Chinese name: methyl 3-benzoyl-2-(trifluoromethyl)indolizine-1-carboxylate

[0026] English name: Methyl 3-benzoyl-2-(trifluoromethyl)indolizine-1-carboxylate

[0027] Molecular weight: 347.08

[0028] Appearance: white solid

[0029] Melting point: 78.0-79.2 °C

[0030] H NMR spectrum (500MHz, CDCl 3, Internal standard: TMS): δ: 3.98 (s, 3H), 6.89-6.92 (m, 1H), 7.28-7.31 (m, 1H), 7.49-7.52 (m, 2H), 7.63-7.66 (m, 1H) , 7.85-7.87 (m, 2H),8.37-8.40 (m, 2H) ppm;

[0031] C NMR sp...

Embodiment 2

[0034] Add pyridine (158 mg, 2 mmol), 2-bromo-4'-methoxyacetophenone (502 mg, 2.2 mmol) and acetonitrile (5 mL) as solvent in a round-bottomed flask, and react 4 at 40° C. Salt was formed after 1 hour, then added methyl trifluoromethylpropiolate (152 mg, 1 mmol), N, N-diisopropylethylamine (258 mg, 1 mmol) and reacted for 7 hours, then cooled to room temperature, and the solvent was vortexed Drying, the pure product was separated by column chromatography. white solid. Yield 91%. Structural formula:

[0035]

[0036] Chinese name: methyl 3-benzoyl-(4-methoxy)-2-(trifluoromethyl)indolizine-1-carboxylate

[0037] English name: Methyl 3-(4-methoxybenzoyl)-2-(trifluoromethyl)indolizine-1-carboxylate

[0038] Molecular weight: 377.09

[0039] Appearance: white solid

[0040] Melting point: 129.4-130.7°C

[0041] H NMR spectrum (500MHz, CDCl 3, Internal standard: TMS): δ: 3.87 (s, 3H), 3.95 (s, 3H), 6.82-6.85 (m, 1H), 6.93-6.96 (m, 2H), 7.22-7.25 (m, 1H) , 7.81 -7.84 (m,...

Embodiment 3

[0045] Pyridine (158 mg, 2 mmol), 2-bromo-4'-nitroacetophenone (537 mg, 2.2 mmol) and acetonitrile (5 mL) were added to a round bottom flask, and reacted at 40 °C for 4 hours After forming a salt, add methyl trifluoromethylpropiolate (152 mg, 1 mmol), N, N-diisopropylethylamine (258 mg, 1 mmol) and react for 7 hours, cool to room temperature, and spin the solvent Drying, the pure product was separated by column chromatography. white solid. Yield 93%. Structural formula:

[0046]

[0047] Chinese name: methyl 3-benzoyl-(4-nitro)-2-(trifluoromethyl)indolizine-1-carboxylate

[0048] English name: methyl 3-(4-nitrobenzoyl)-2-(trifluoromethyl)indolizine-1-carboxylate

[0049] Molecular weight: 392.06

[0050] Appearance: white solid

[0051] Melting point: 176.0-177.9°C

[0052] H NMR spectrum (500MHz, CDCl 3, Internal standard: TMS): δ: δ 3.97 (s, 3H), 7.01-7.04 (m,1H), 7.37-7.41 (m, 1H), 7.97-8.00 (m, 2H), 8.32-8.34 (m, 1H), 8.40-8.41 (d,1H ), 8.73-8.75 (d, 1H) ppm...

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Abstract

The invention relates to a perfluoroalkyl indolizine derivative and a synthesis method thereof. A structural formula of the perfluoroalkyl indolizine derivative is as shown in the specification, wherein R1 refers to H, CH3 and CO2Me; R2 refers to hydrogen, chlorine, methoxyl, nitryl or methyl; RF refers to C1-C3 perfluoroalkyl. Easily acquirable pyridine derivatives, w-bromoacetophenone derivatives and perfluoroalkyl methyl propiolate mature in synthesis technique are adopted as raw materials for one-pot synthesis of the perfluoroalkyl indolizine derivative step by step. The perfluoroalkyl methyl propiolate used as the raw materials is subjected to Michael addition under certain conditions to obtain the perfluoroalkyl indolizine derivative, operations are greatly simplified, and high atom economy and environment friendliness are realized; due to adoption of acetonitrile as a solvent, low environment pollution is realized; high regioselectivity and high yield are achieved. Therefore, the synthesis method is a novel effective method for synthesis of the perfluoroalkyl indolizine derivative.

Description

technical field [0001] The invention relates to a perfluoroalkyl indazine derivative and a synthesis method thereof. Background technique [0002] Indolizine derivatives substituted with multifunctional groups are a very important class of compounds, which have received widespread attention due to their wide range of biological and pharmacological activities, such as antitumor, antibacterial, antihypertensive, anti-inflammatory and antiarrhythmic, etc. . Indazine derivatives are also a series of basic structural units of natural products, so it is of scientific significance to design simple and effective methods to synthesize indazine derivatives. [0003] However, how to synthesize rings economically and efficiently is still a hotspot in synthesis. Judging from the many published research results so far, although many different multifunctional indolizines with novel structures have been synthesized, many synthetic methods have shown low regioselectivity, and the research ...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 何东顼玉红韩靖陈杰张慧曹卫国
Owner SHANGHAI UNIV
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