Study On The Synthesis Of Triarylmethane Derivatives Containing All-carbon Quaternary Carbon Centers Using δ-Cyano-p-Methylenebenzoquinone

Objective: Triarylmethane derivatives are widely present in natural products and pharmaceutical active molecules due to their high biological activity.Among them,anti-tuberculosis drugs and anticancer drugs and potassium ion channel inhibitor drugs are widely used.At present,the construction of asymmetric triarylmethane containing tertiary stereocenters has been extensively studied.The effective preparation of triarylmethane derivatives containing quaternary carbon stereocenters with higher molding value has not yet been developed.Therefore,this article will construct triarylmethane derivatives containing a quaternary stereo center through a simple and stable method.Method: In order to obtain triarylmethane derivatives containing quaternary stereocenters,we explored the new reactivity of m-benzoquinones(p-QMs)and,under certain conditions,allowed them to be generated in situ instantaneously compared to previous methods.For a faster intermediate,we install an electron-withdrawing group at the delta position of the methylene outside the ring to adjust the electron density distribution of the molecule,enhance the stability of the resulting p-QM by reducing its polymerizability,and will be highly The modified cyano group is placed in the δ position for investigation.results: Placing the electron-withdrawing cyano group in the cyclic methylene δposition of p-QMs is conducive to enhancing its stability.The range of these valuable structural units for 1,6-conjugated addition reactions has also been significantly expanded.By using pre-synthesized δ-CN-δ-aryl substituted p-QMs as substrates,a variety of electron-rich aromatic hydrocarbons participate in the aromatization process,thus providing a variety of carbon-rich quaternary stereo centers triarylmethane.Using the convertible nature of the nitrile moiety,other tri-and tetraarylmethanes of valuable functional groups that are difficult to prepare can be easily obtained.Through computational studies,the following hypothesis is supported: the installation of an electron-withdrawing cyano group at the delta position of the exocyclic methylene group will adjust the electron density distribution of the molecule and improve the thermal stability of the generated p-QM by reducing the polymerizability.Conclusions: The successful synthesis of various triarylmethanes with all-carbon quaternary stereocenters provides new synthons for the development of new drugs.Next,the laboratory will focus on the ongoing research to explore the reactivity and corresponding variants of pre-synthesized p-QM with other valuable electron donors at the delta position.