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Preparation method of polysubstituted pyrroloquinoline derivate

A technology of pyrrole derivatives and multi-substitution, applied in the direction of organic chemistry, etc., can solve the problems of long synthesis route, harsh reaction conditions, and increased synthesis cost.

Inactive Publication Date: 2017-05-31
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction conditions of this method are harsh, and protection / deprotection steps are required, the synthesis route is long, and the synthesis cost is increased (Acta Pharmaceutica Sinica, 51, 2016, 762-769)

Method used

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  • Preparation method of polysubstituted pyrroloquinoline derivate
  • Preparation method of polysubstituted pyrroloquinoline derivate

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0024] Example 1 Preparation of tert-butyl 3,4-diphenyl-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1-carboxylate.

[0025] .

[0026] Weigh E-3-(2-aminophenyl)-1-phenyl-2-propen-1-one (1.0mmol), benzaldehyde (1.0mmol), magnesium sulfate (1.176g), add to the round bottom flask , add 2 mL of organic solvent, and stir overnight at room temperature. After filtration, concentrate the filtrate, add N-dibenzylidene-glycine tert-butyl ester (1.0 mmol), triethylamine (1.0 mmol), add organic solvent 10 mL, and stir at room temperature for 24 hours. Then concentrate the filtrate, add an organic solvent to dissolve the reactant, adjust the pH to neutrality, add 10% citric acid aqueous solution, stir and react at room temperature for 24 hours, and remove the solvent by rotary evaporation, then pass through column chromatography (eluent: sherwood oil: acetic acid ethyl ester = 10:1) to obtain quinolinopyrrole derivative A with a yield of 82% and dr > 20:1. 1 H NMR (600 MHz, CDCl ...

example 2

[0027] Example 2 Preparation of tert-butyl 4-p-fluorophenyl-3-phenyl-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1-carboxylate.

[0028] .

[0029] Weigh E-3-(2-aminophenyl)-1-phenyl-2-propen-1-one (1.0mmol), p-fluorobenzaldehyde (1.0mmol), magnesium sulfate (1.176g), add to the round bottom Add 2 mL of organic solvent to the flask, and stir overnight at room temperature. Next, after filtration, the filtrate was concentrated, N-dibenzylidene-glycine tert-butyl ester (1.0 mmol), triethylamine (1.0 mmol) were added, and 10 mL of organic solvent was added, and stirred at room temperature for 24 hours. Then concentrate the filtrate, add an organic solvent to dissolve the reactant, adjust the pH to neutrality, add 10% citric acid aqueous solution, stir and react at room temperature for 24 hours, and remove the solvent by rotary evaporation, then pass through column chromatography (eluent: sherwood oil: acetic acid Ethyl ester = 10:1) to obtain quinolinopyrrole derivative B ...

example 3

[0030] Example 3 Preparation of tert-butyl 4-m-methoxyphenyl-3-phenyl-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1-carboxylate .

[0031] .

[0032] Weigh E-3-(2-aminophenyl)-1-phenyl-2-propen-1-one (1.0mmol), m-methoxybenzaldehyde (1.0mmol), magnesium sulfate (1.176g), add In a round bottom flask, add 2 mL of organic solvent, and stir overnight at room temperature. Next, after filtration, the filtrate was concentrated, N-dibenzylidene-glycine tert-butyl ester (1.0 mmol), triethylamine (1.0 mmol) were added, and 10 mL of organic solvent was added, and stirred at room temperature for 24 hours. Then concentrate the filtrate, add an organic solvent to dissolve the reactant, adjust the pH to neutrality, add 10% citric acid aqueous solution, stir and react at room temperature for 24 hours, and remove the solvent by rotary evaporation, then pass through column chromatography (eluent: sherwood oil: acetic acid Ethyl ester = 10:1) to obtain quinolinopyrrole derivative C with...

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Abstract

The invention discloses a preparation method of a polysubstituted pyrroloquinoline derivate. The preparation method is characterized in that aminochalcone and aldehyde are condensed to obtain chalcone imine; the chalcone imine and glycinate imine are subjected to series cyclizing through Michael / Mannich and then are subjected to acidizing, and thus the polysubstituted pyrroloquinoline derivate containing four chiral centers, as shown in formula (I), can be generated based on high diastereoselectivity. The preparation method is on the basis of series reaction, and has the advantages that the environmental protection is achieved; the synthesizing steps are simple and convenient; the atom economy is ensured; the diastereoselectivity is high; in addition, the reaction conditions are mild; the substance is wide in applicable scope; the operation is simple and safe; the preparation method is applicable to industrial production.

Description

technical field [0001] The invention relates to a preparation method of multi-substituted quinolinopyrrole derivatives, belonging to the technical field of organic synthesis chemistry. Background technique [0002] Quinolinopyrrole derivatives are a very important class of structural units that widely exist in biologically active compounds and natural products. For example, Aplidiopsamine A is extracted from ascidian animals and can be used in the treatment of malaria (J. Org. Chem. 2010, 75, 8291-8294). 5-HTRs Ligands-1 (J. Med. Chem. 2012, 55,9446-9466) and 5-HTRs Ligands-2 (US 2006 / 0014778 A1) can be used as modulators of serotonin receptors for various Treatment of diseases such as: metabolic diseases including but not limited to obesity, diabetes, diabetic complications, atherosclerosis, burden of glucose tolerance and dyslipidemia; central nervous system diseases including but not limited to anxiety, depression, obsessive-compulsive headaches, panic attacks, psychosi...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 刘章琴刘盛蜀马学兵李元庆管晓渝
Owner SOUTHWEST UNIVERSITY
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