Azafluorenone derivative and preparation method and application thereof

Abstract

The invention belongs to the technical field of organic synthesis and particularly relates to a polyfunctional-group-substituted azafluorenone derivative and a preparation method and application thereof. The structural formula of the azafluorenone derivative is shown as a formula (I), wherein Ar is an aryl group, the aryl group comprises an aromatic heterocyclic group, a phenyl group or aromatic fused ring group, R1 is selected from hydrogen, an ether group, halogen, acetyl, an ester group, trifluoromethyl or sulfuryl, and R2 is selected from hydrogen, alkyl, aryl, halogen, an ether group, trifluoromethyl, acetyl, an ester group or sulfuryl. By taking an aryl imido ester compound and olefin as substrates and under a metal catalysis effect, a cascade reaction of multiple times of aromatic ring carbon hydrogen bond activation based on aryl imine ester guidance and oxygen oxidation of alkyl carbon-carbon is achieved, and accordingly the poly-substituted azafluorenone derivative is rapidlyand modularly constructed. The azafluorenone medicine has a good application prospect in the development of organic photoelectric materials.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an azafluorenone derivative and a preparation method and application thereof. Background technique [0002] The field of modern organic synthesis not only pursues the synthesis of target compounds, but people have paid more attention to how to obtain target molecules in a simple, efficient and elegant manner. In this context, the use of more inert chemical bonds such as carbon-hydrogen bonds and carbon-carbon as substrates avoids cumbersome steps such as the synthesis, isolation, or pre-introduction of active functional groups of intermediate molecules, and becomes a new attractive synthetic method. Strategy. [0003] Although carbon-hydrogen bonds and carbon-carbon bonds have higher activation energies, and the number and types of carbon-hydrogen bonds that need to be considered when facing selective activation of such inert bonds (such as primary carbon-h...

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Problems solved by technology

Although azafluorenones have achieved significant progress in the use of classical synthetic methods, there are still problems such as harsh reaction conditions, corresponding relatively complex precursors that must be synthesized in advance, and cumbersome steps.

In summary, the strategy of using simple and easy-to-obtain raw materials and green synthetic methods to modularize the synthesis of multi-substituted azafluorenones has yet to be developed, and the development of new simple and easy-to-obtain substrates and expand the applicability of substrates for nitrogen The green and efficient synthesis of heterofluorenones has always been the goal of organic chemists

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