Synthetic method of nitrogen-containing spiro compound

A synthesis method and compound technology are applied in the synthesis field of nitrogen-containing spirocyclic compounds, which can solve problems such as reaction conditions of multiple reaction steps, and achieve the effects of wide substrate adaptability, simple experimental conditions and simple operation.

Active Publication Date: 2018-01-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The traditional method of synthesizing nitrogen-containing spirocyclic compounds usually requires pre-functionalization of the substrate, and at the same time requires more reaction steps and harsher reaction conditions, and the traditional transition metal-catalyzed activation of the oxidized C-H bond often A large amount of oxidant is required, so these traditional reactions will inevitably produce a large amount of spent alkali, spent acid and metal waste

Method used

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  • Synthetic method of nitrogen-containing spiro compound
  • Synthetic method of nitrogen-containing spiro compound
  • Synthetic method of nitrogen-containing spiro compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1~15

[0040] Add imine (0.3mmol), maleimide compound (0.2mmol), diiodide pentamethylcyclopentadiene-cobalt carbonyl (0.02mmol), trifluoro Silver methanesulfonate (0.04mmol), nitrobenzene (0.2mmol) and 1mL of organic solvent were mixed and stirred evenly. After the reaction was completed according to the reaction conditions in Table 2, it was cooled, filtered with suction, mixed with silica gel, and purified by column chromatography to obtain Corresponding nitrogen-containing spiro compound (I), the reaction process is shown in the following formula:

[0041]

[0042] The raw material proportioning of table 1 embodiment 1~15

[0043]

[0044] The reaction condition and reaction result of table 2 embodiment 1~15

[0045]

[0046]

[0047] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, 2-naphthyl is 2-substituted naphthyl, CF 3 is trifluoromethyl, Ph is phenyl, and 2-thiophene is 2-substituted thiophene.

[0048] a with AgSbF 6 Instead o...

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Abstract

The invention discloses a synthetic method of a nitrogen-containing spiro compound. The method comprises adding an imine derivative, a maleimide compound, diiodide pentamethyl cyclopentadiene cobalt carbonyl, silver trifluoromethanesulfonate and nitrobenzene in an organic solvent, performing heating for a reaction in a vacuum-pumping condition, and after the reaction is completed, performing post-treatment to obtain the nitrogen-containing spiro compound. According to the method, simply-available raw materials are adopted to synthesize the nitrogen-containing spiro compound in one step. The method is high in conversion efficiency and good in atom economy. The synthetic method is simple to operate, high in reaction yield and wide in substrate adaptability.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a synthesis method of nitrogen-containing spirocyclic compounds. The method adopts transition metal Co as a catalyst, and performs oxidation-type C-H bond activation under the condition of not adding an oxidizing agent. Background technique [0002] The skeleton of the spirocycle is an important structure that widely exists in natural products and drug molecules. Traditional methods for synthesizing nitrogen-containing spirocyclic compounds usually require pre-functionalization of the substrate, and at the same time require more reaction steps and harsher reaction conditions, and traditional transition metal-catalyzed activation of oxidized C-H bonds often A large amount of oxidant is required, so these traditional reactions will inevitably produce a large amount of spent alkali, spent acid and metal waste. It is imperative to seek new and different approaches to deve...

Claims

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Application Information

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IPC IPC(8): C07D471/10
Inventor 张玉红吕宁宁刘岳刘占祥
Owner ZHEJIANG UNIV
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