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Spiro[3,5'-pyrrole[2,1-a]isoquinoline-oxindole] compound and preparation method thereof

A technology of indole and isoquinoline, which is applied in the direction of organic chemistry, can solve the problems of insufficient structure types, and achieve the effects of wide application range, simple operation and easy purification

Inactive Publication Date: 2017-06-20
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, there are still some limitations in the existing artificial synthesis technology, such as the synthesized indazine derivatives, except for the basic skeleton of indazine, mainly have some branched chain or ring structures, and their structural types are not wide enough.
It is still a challenging work to synthesize inzine derivatives with more complex spatial structures, especially those containing spiro ring structures.

Method used

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  • Spiro[3,5'-pyrrole[2,1-a]isoquinoline-oxindole] compound and preparation method thereof
  • Spiro[3,5'-pyrrole[2,1-a]isoquinoline-oxindole] compound and preparation method thereof
  • Spiro[3,5'-pyrrole[2,1-a]isoquinoline-oxindole] compound and preparation method thereof

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Experimental program
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preparation example Construction

[0028] The concrete steps of preparation method are as follows:

[0029] The operation steps of synthetic representative compound 3a:

Embodiment 1

[0031]

[0032] Weigh 3-pyrrole oxide indole 1a (59.4mg, 0.3mmol), 2-bromobenzyl bromide 2a (90.0mg, 0.36mmol), Na 2 CO 3 (0.75mmol, 79.5mg), Pd(TFA) 2 (10mol%, 10.0mg) and PPh 3 (20mol%, 15.7mg) in a hard reaction tube, and then 2.5mL DMF was added, and the reaction solution was stirred and reacted at 140°C for 24h. After the completion of the reaction monitored by TLC, 10.0 mL of water was added to the reaction solution, and extracted with ethyl acetate (6×6 mL). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The final residue obtained was separated and purified by column chromatography (petroleum ether / ethyl acetate=5:1) to obtain the target compound 3a (yield 72%).

Embodiment 2

[0034] Weigh 3-pyrrole oxindole 1a (39.6mg, 0.2mmol), 2-bromobenzyl bromide 2a (50.0mg, 0.2mmol), Na 2 CO 3 (0.5mmol, 53.0mg), Pd 2 (dba) 3 (10mol%, 18.3mg) and PPh 3 (20mol%, 10.5mg) in a hard reaction tube, and then 2.0mL DMF was added, and the reaction solution was stirred and reacted at 140°C for 10h. After the completion of the reaction monitored by TLC, 10.0 mL of water was added to the reaction solution, and extracted with ethyl acetate (6×6 mL). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The final residue obtained was separated and purified by column chromatography (petroleum ether / ethyl acetate=5:1) to obtain the target compound 3a (yield 53%).

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Abstract

The invention discloses a spiro[3,5'-pyrrole[2,1-a]isoquinoline-oxindole] compound, which is prepared through adding 3-pyrrole oxindole and 2-bromomethyl aryl bromide into an organic solvent; then adding a metal palladium catalyst, phosphine ligand and inorganic base; performing chemical reaction under a heating condition; processing to obtain a pure product of the compound disclosed by the invention after reaction finishes. A preparation method is shown in the specification. The preparation method disclosed by the invention utilizes 3-pyrrole oxindole easy to prepare and 2-bromomethyl aryl bromide commercially easy to obtain as raw materials, series of varieties of spiro[3,5'-pyrrole[2,1-a]isoquinoline-oxindole] compounds of novel structures can be obtained through nucleophilic substitution / C(sp2)-H arylation one-pot cascade reaction, and the preparation method has the characteristics of a wide substrate application range, convenience to operate, simple aftertreatment, relatively high yield and the like.

Description

technical field [0001] The invention relates to the fields of heterocyclic compounds and organic chemical synthesis, in particular to a spiro[3,5'-pyrrole[2,1-a]isoquinoline-oxindole] compound and a preparation method thereof. Background technique [0002] Synthesis of structurally diverse nitrogen-containing heterocyclic compounds using simple and readily available starting materials has always been the focus of attention in the field of organic chemistry. The indazine skeleton containing pyridopyrrole ring is the core structural unit of natural alkaloids, and the compounds containing this heterocyclic skeleton often have good biological activity and potential pharmaceutical value. At present, indolizine derivatives are mainly obtained by extraction and separation from natural products or artificial synthesis. Among them, artificial synthesis methods are increasingly important, mainly including intramolecular cyclization reactions based on pyrrole or isoquinoline skeletons...

Claims

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Application Information

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IPC IPC(8): C07D471/20C07D491/22C07D495/22
CPCC07D471/20C07D491/22C07D495/22
Inventor 崔宝东张廷磊陈永正韩文勇
Owner ZUNYI MEDICAL UNIVERSITY
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