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Synthesis method of nitrogenous heterocyclic quaternary salt compounds

A synthesis method and compound technology, which is applied in the field of synthesis of nitrogen-containing heterocyclic quaternary salt compounds, and can solve problems such as difficult access to quaternary ammonium salts

Inactive Publication Date: 2019-04-12
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, quaternary ammonium salts are relatively difficult to obtain, so it is of great research and application value to find a synthetic method for nitrogen-containing heterocyclic quaternary salt compounds with mild conditions, novel high-efficiency, and easy access.

Method used

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  • Synthesis method of nitrogenous heterocyclic quaternary salt compounds
  • Synthesis method of nitrogenous heterocyclic quaternary salt compounds
  • Synthesis method of nitrogenous heterocyclic quaternary salt compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] Above-mentioned reaction condition optimization experiment is shown in the following table:

[0032]

[0033]

[0034] Reaction conditions: 1a (0.2mmol), 2a (0.3mmol), [Cp*Rh(OAc) 2 ] (8mol%), organic solvent (2.0mL), additives and oxidizing agents. Wherein the label 3 adopts 2a as 0.2 mmol.

[0035] Under the protection of inert gas, add [Cp*Rh(OAc) 2 ] (8mol%), AgSbF 6 (0.2mmol), AgOAc (0.3mmol) and DCE (2.0mL), stirred for ten minutes under backlight conditions, then added compound 1a (0.2mmol) and compound 2a (0.3mmol), placed in 100 ° C oil bath for reaction, in After the reaction was complete (24 hours), the sealed tube was removed from the oil bath and cooled to ambient temperature. The reaction was filtered through celite, eluted with DCM:MeOH=10:1 and concentrated. The crude product was then transferred to a tube with a magnetic stir bar, then DCM (2.0 mL), water (2.0 mL) and NaSbF were added at room temperature 6 (100mg). After stirrin...

Embodiment 2

[0038]

[0039] Under the protection of inert gas, add [Cp*Rh(OAc) 2 ] (8mol%), AgSbF 6(0.2mmol), AgOAc (0.3mmol) and DCE (2.0mL), stirred for ten minutes under the backlight condition, then added compound 1a (0.2mmol) and compound 2b (0.3mmol), placed in 100 ° C oil bath for reaction, in After the reaction was complete (24 hours), the sealed tube was removed from the oil bath and cooled to ambient temperature. The reaction was filtered through celite, eluted with DCM:MeOH=10:1 and concentrated. The crude product was then transferred to a tube with a magnetic stir bar, then DCM (2.0 mL), water (2.0 mL) and NaSbF were added at room temperature 6 (100mg). After stirring the reaction mixture for 10 minutes, the organic layer was separated and the aqueous layer was extracted twice with DCM. The organic layer was evaporated and purified by silica gel chromatography (DCM:MeOH=15:1) to give the product 3ab.

[0040] 3ab, 69.0mg, 62%. 1 H NMR (400MHz, CD 2 Cl 2 )δ10.19(d,J=...

Embodiment 3

[0042]

[0043] Under the protection of inert gas, add [Cp*Rh(OAc) 2 ] (8mol%), AgSbF 6 (0.2mmol), AgOAc (0.3mmol) and DCE (2.0mL), stirred for ten minutes under the backlight condition, then added compound 1a (0.2mmol) and compound 2c (0.3mmol), placed in 100 ° C oil bath for reaction, in After the reaction was complete (24 hours), the sealed tube was removed from the oil bath and cooled to ambient temperature. The reaction was filtered through celite, eluted with DCM:MeOH=10:1 and concentrated. The crude product was then transferred to a tube with a magnetic stir bar, then DCM (2.0 mL), water (2.0 mL) and NaSbF were added at room temperature 6 (100mg). After stirring the reaction mixture for 10 minutes, the organic layer was separated and the aqueous layer was extracted twice with DCM. The organic layer was evaporated and purified by silica gel chromatography (DCM:MeOH=15:1) to give the product 3ac.

[0044] 3ac, 82.0mg, 78%. 1 H NMR (400MHz, Acetone-d 6 )δ10.73(d,...

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Abstract

The invention discloses a preparation method of nitrogenous heterocyclic quaternary salt compounds,and belongs to the field of organic synthesis. In an organic solvent, Rh(III) serves as a catalyst,inthe presence of an additive and an oxidizing agent, substituent 8-methylquinoline and eneyne react at a heating condition, and subsequently, hexafluoroantimonate is added to react to obtain nitrogenousous quaternary salt. According to the preparation method of the nitrogenous heterocyclic quaternary salt compounds, substituent 8-methylquinoline serves as a substrate and reacts with preliminarilyprepared 1,3-eneyne to directly build carbon-nitrogen bonds and carbon-carbon bonds,and the nitrogenous heterocyclic quaternary salt compounds are efficiently synthesized. The preparation method has relatively mild reaction conditions, a wide substrate range, high efficiency and excellent regioselectivity.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of a nitrogen-containing heterocyclic quaternary salt compound. Background technique [0002] Nitrogen-containing heterocyclic quaternary salt compounds are ubiquitous in natural products and bioactive molecules. They are also found in a large number of medicines used to fight various diseases. Nitrogen-rich heterocyclic compounds have profound effects on human health. Despite numerous synthetic approaches, the diversification of heterocycles, step-by-step economics, and general synthetic approaches remain limited. [0003] Advances in transition metal-catalyzed C–H functionalization have significantly simplified the synthesis of a plethora of heterocyclic molecules. In many cases, heteroatom directing groups participate in cyclization reactions in addition to providing chelation assistance, which requires sufficient interaction between the metal c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06
CPCC07D471/06
Inventor 崔艺馨于艳江白大昌
Owner HENAN NORMAL UNIV
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