3-amino indanone compound synthesis method

A technology of aminoindanone and synthesis method, which is applied in the direction of preparation of organic compounds, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc., to achieve wide substrate adaptability, high conversion efficiency, and reaction yield high effect

Active Publication Date: 2017-08-11
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis of 2,3-non-aryl substituted indanone compounds using C-H bonds has not been reported. Inspired by the recent use of imidate as a directing group to synthesize a variety of heterocompounds with different reaction substrates, our subject For the first time, the group developed a one-step synthesis of 2,3-difunctionalized indanone using rhodium-catalyzed imidate and a series of electron-withdrawing alkenes. The method has mild conditions and wide reaction adaptability. - Difunctionalized indanones provide a simple and efficient method

Method used

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  • 3-amino indanone compound synthesis method
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  • 3-amino indanone compound synthesis method

Examples

Experimental program
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Effect test

Embodiment 1～11

[0035] Add imine (0.2mmol), olefin compound (0.4mmol), pentamethylcyclopentadiene rhodium dichloride (0.02mmol), manganese acetate (0.2mmol) and 1ml of organic solvent, mixed and stirred evenly, after the reaction was completed according to the reaction conditions in Table 2, cooling, suction filtration, silica gel mixing sample, purified by column chromatography to obtain the corresponding 3-aminoindanone compound (I), the reaction process is as follows Show:

[0036]

[0037] Table 1 Raw material ratio of Examples 1-11

[0038]

[0039]

[0040] Table 2 Reaction conditions and reaction results of Examples 1 to 11

[0041]

[0042] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, n-Bu is n-butyl, 2-naphthyl is 2-substituted naphthyl, CF 3 is trifluoromethyl, Ph is phenyl, and 2-thiophene is 2-substituted thiophene.

[0043] The structure confirmation data of some compounds prepared in Examples 1-10:

[0044]

[0045] butyl 3-am...

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Abstract

The invention discloses a 3-amino indanone compound synthesis method which includes the steps: adding an imine derivative, an olefin compound, pentamethyl dichloride rhodium cyclopentadiene and manganese acetate into an organic solvent; performing heating reaction under air conditions; performing post-treatment after complete reaction to obtain a 3-amino indanone compound. According to the method, simple and easily obtained raw materials are synthesized at one step to obtain the 3-amino indanone compound, conversion efficiency is high, and atom economy is good. Besides, the synthesis method is simple in operation and high in reaction yield, and a substrate is wide in adaptability.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 3-aminoindanone compounds. Background technique [0002] Indanones are a class of important structures that widely exist in natural products and drug molecules, and are also widely used in organic light-emitting materials and dyes. Traditional methods for synthesizing indanones usually require substrate pre-functionalization, more reaction steps and harsher reaction conditions, and 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 development. [0003] Transition metal-catalyzed C-H bond activation is a synthetic strategy developed in the last decade to achieve atom economy, reduce reaction steps, and synthesize complex compounds. The synthesis of indanones via C–H bond activation has been reported in the past few years. For e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/10C07C229/50C07D333/78C07C231/12C07C237/24C07F9/40C07C315/04C07C317/30
CPCC07C227/10C07C231/12C07C315/04C07D333/78C07F9/4018C07F9/4075C07C229/50C07C237/24C07C317/30
Inventor 张玉红吕宁宁陈铮凯刘岳刘占祥
Owner ZHEJIANG UNIV
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