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A kind of pyrido[2',1':2,3]piperido[1,6-a]pyrrole salt and its synthesis method

A 6-a, pyrrole salt technology, applied in the field of medicine, can solve the problems of low yield and complicated steps, and achieve the effect of simple steps, narrow melting point range and high yield

Inactive Publication Date: 2018-09-28
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But above-mentioned patent steps are complicated, and productive rate is low

Method used

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  • A kind of pyrido[2',1':2,3]piperido[1,6-a]pyrrole salt and its synthesis method
  • A kind of pyrido[2',1':2,3]piperido[1,6-a]pyrrole salt and its synthesis method
  • A kind of pyrido[2',1':2,3]piperido[1,6-a]pyrrole salt and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of pyrido[2',1':2,3]piperidin[1,6-a]pyrrole salt, its general chemical structure formula is:

[0026]

[0027] The synthetic method of above-mentioned pyrido[2',1':2,3]piperidin[1,6-a]pyrrole salt, comprises the following steps:

[0028] (1) Under nitrogen protection, 0.20 mmol of 2-(1H-pyrrol-1-yl)pyridine, 0.22 mmol of toluene, and cobalt catalyst CoCp (CO)I were sequentially added to the schlenk tube. 2 2.0mol%, silver acetate AgOAc 4.0mol%, copper acetate monohydrate Cu(OAc) 2 ·H 2 O 0.20 mmol, silver tetrafluoroborate, AgBF 4 0.20mmol and 1,2-dichloroethane 2mL;

[0029] (2) Place the reaction tube in step (1) under the condition of an oil bath at 135° C. and stir for 24 hours;

[0030] (3) After the reaction is completed, the reaction tube is cooled to room temperature, the reaction mixture is desalted, washed with dichloromethane, concentrated, and purified by column chromatography. The column chromatography conditions are: 200-300 mesh silica gel...

Embodiment 2

[0032] A kind of pyrido[2',1':2,3]piperidin[1,6-a]pyrrole salt, its general chemical structure formula is:

[0033]

[0034] The synthetic method of above-mentioned pyrido[2',1':2,3]piperidin[1,6-a]pyrrole salt, comprises the following steps:

[0035] (1) Under nitrogen protection, 0.20 mmol of 2-(1H-pyrrol-1-yl)pyridine, 0.22 mmol of 1,2-bis(thiophen-2-yl)acetylene, cobalt catalyst CoCp (CO ) I 2 2.0mol%, silver acetate AgOAc 4.0mol%, copper acetate monohydrate Cu(OAc) 2 ·H 2 O 0.20mmol, silver tetrafluoroborate, AgBF 4 0.20mmol and 1,2-dichloroethane 2mL;

[0036] (2) Place the reaction tube in step (1) under the condition of an oil bath at 135° C. and stir for 24 hours;

[0037] (3) After the reaction is completed, the reaction tube is cooled to room temperature, the reaction mixture is desalted, washed with dichloromethane, concentrated, and purified by column chromatography. The column chromatography conditions are: 200-300 mesh silica gel, and the eluent is dic...

Embodiment 3

[0039] A kind of pyrido[2',1':2,3]piperidin[1,6-a]pyrrole salt, its general chemical structure formula is:

[0040]

[0041] The synthetic method of above-mentioned pyrido[2',1':2,3]piperidin[1,6-a]pyrrole salt, comprises the following steps:

[0042] (1) Under nitrogen protection, 0.20 mmol of 2-(1H-pyrrol-1-yl)pyridine, 0.22 mmol of toluene, and cobalt catalyst CoCp (CO)I were sequentially added to the schlenk tube. 2 2.2mol%, silver acetate AgOAc 4.3mol%, copper acetate monohydrate Cu(OAc) 2 ·H 2 O 0.22 mmol, silver tetrafluoroborate, AgBF 4 0.22mmol and 3mL of 1,2-dichloroethane;

[0043] (2) Place the reaction tube in step (1) under the condition of an oil bath at 140° C. and stir for 16 hours;

[0044] (3) After the reaction is completed, the reaction tube is cooled to room temperature, the reaction mixture is desalted, washed with methanol, concentrated, and purified by column chromatography. The column chromatography conditions are: 200-300 mesh silica gel, and ...

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Abstract

The invention belongs to the technical field of medicine, and particularly relates to a pyridino-[2',1':2,3]piperidine[1,6-a] pyrrole salt and a synthesis method thereof. Under the insert gas protection, 2-(1H-pyrrole-1-yl) naphthyridine, aromatic alkyne, cobalt catalysts, silver acetate AgOAc, cupric acetate monohydrate Cu(OAc)2.H2O, silver tetrafluoroborate AgBF4 and organic solvents are sequentially added into a reaction pipe; stirring reaction is performed for 16 to 30h under the condition of 130 to 140 DEG C; after the reaction is completed, the reaction pipe is cooled to the room temperature; a reaction mixture is subjected to desalting, washing, concentration and purification to obtain a target product. The pyridino-[2',1':2,3]piperidine[1,6-a] pyrrole salt provided by the invention belongs to important alkaloid, has the advantages that high biological activity or even high medical values are realized; the steps of the synthesis method are simple; the yield can reach 84 percent; the yield is high.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a pyrido[2',1':2,3]piperidin[1,6-a]pyrrole salt and a synthesis method thereof. Background technique [0002] As an important alkaloid, pyrido[2',1':2,3]piperidin[1,6-a]pyrrole salt has important biological activity and certain medicinal value, pyrido[2',1 ':2,3]piperidine[1,6-a]pyrrole salt is a new alkaloid, which has not been reported in the prior art and its synthesis method. [0003] Chinese patent CN102741251B discloses a pyridocyclic derivative, its pharmaceutically acceptable salt, its stereoisomer or its solvate: wherein R1, R2, R3, Q, X and Y are as defined in the specification; The invention also relates to the preparation method of these compounds, the pharmaceutical composition containing these compounds, and the application of these compounds in the preparation of medicines for treating and / or preventing non-insulin-dependent diabetes, hyperglycemia, h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14A61P39/06
CPCC07D471/14
Inventor 李亭杨昱涵李波柳文敏桑志培于林涛马勤阁
Owner NANYANG NORMAL UNIV
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