Polysubstituted indole derivatives are a kind of very important nitrogen-containing heterocyclic compounds, which widely exist in many natural products and drug molecules in nature. They have unique biological and pharmaceutical activities. They are not only very important fine chemical intermediates, but also widely used in the fields of pesticides, medicines, dyes, feeds, spices, foods and additives, so their chemical synthesis has always attracted the vast number of organic chemists. Therefore, it is of great academic significance and application value to design new reaction substrates and develop new synthesis methods for the synthesis of polysubstituted indoles and their derivatives. This paper mainly focuses on the simple use of special reaction substrates. In the first part, the cycloaddition reaction between 3- indolemethanol and conjugated diene was successfully carried out under the catalysis of Lewis acid bromide, and a method for efficiently and rapidly synthesizing new compounds containing indole seven-membered ring skeleton was developed. Part II: The Friedel-Crafts alkylation of 3- indole methanol catalyzed by Bronsted. The Friedel-Crafts alkylation of 3- bis-indole-methanol with a variety of heterocyclic aromatic hydrocarbons was successfully realized with indigo -3- indole-methanol as the substrate, catalyzed by Bronsted acid such as (R)- camphor sulfonic acid, and a series of 3- bis-indole-methanol derivatives with potential biological activities were synthesized. Part III: Study on cycloaddition reaction of benzoquinone intermediates. Using 2- hydroxymethylphenol as the substrate, under the catalysis of Bronsted acid, a series of diolefins and monoolefins were used to generate in-situ phthaloquinone intermediates. The relative configuration of the product was determined by two-dimensional NMR spectra H, H-Cosy and NOESY. The stereoselectivity of the reaction was explained by theoretical calculation, and the product was derivatized. The innovation of this reaction is that cyclopentadiene and some diene compounds are used as dienophiles in the reaction, while the in-situ o-QM intermediate is used as dienophiles. This reaction successfully developed a simple and rapid method to construct 2- alkenyl chroman compounds, and updated the application mode of cyclopentadiene.

Methanol poisoning can usually be detoxified with ethanol. The principle is that the metabolite of methanol is toxic, so it can be detoxified by inhibiting metabolism. The metabolism of methanol and ethanol in human body is the same enzyme, and this enzyme has greater affinity with ethanol.