The Research Of A New Type Of β-substituted Indole Derivatives And The Total Synthesis Of 4’-methoxy-Ochnaflavone

Indoles is an important component of heterocyclic chemistry, it is widely used in the field of pesticides, pharmaceuticals, perfumes and dyestuff. β-substituted indole derivatives have a unique structure, showing some special biological activity, which has attracted a wide interest from scientists. IAs a matter of fact, the synthesis of these compounds containing thiocyanate structure is highly desirable because they might exhibit interesting pharmacological activities. And the study will promote the progress of β-substituted indole derivatives.Here,we chose indole, m-nitrobenzaldehyde and potassium thiocyanate as the model substrates reporting a three-component one-pot reaction for the synthesis of 3-(alkyl (thiocyanato) methyl)-1H-indole, a new type of β-substituted indole derivatives. By trying different Lewis acid, varing the reaction solvent, time and temperature, we approached the optimal reaction conditions:free-catalyst, ethanol as the solvent, at room temperature react for 12 h. With the optimal condition in hand, we expored the substrate aldehyde, getting a conclusion:Aromatic aldehydes can react more easily than alkane aldehydes; Benzene ring containing electron-withdrawing groups can facilitate the reaction process; Contrarily, the more the electron-donating group is, the lower the yield is. The method of three-component one-pot is applied in this experiment, it shows some significant advantages:simple operation, catalyst-free and environment friendly.Bioflavonoids have many important pharmacological and biological activities such as anti-tumor, anti-viral, anti-inflammatory, antioxidant and blood system. The formation of bioflavonoid is diverse, in the view of the molecular structure, we can divide them into two coupling forms of C-O and C-C; in the view of the synthesis method, biflavone can be formed by the condensation of two flavonoid molecules and can also be obtained through the cyclization reaction of double chalcone. Here, we set 4’-methoxy-Ochnaflavone as target molecule, selecting some simple and easily available 2,4,6-trihydroxyacetophenone and hydroxybenzaldehyde as he starting materials. Going through brominated、Ullmann coupling reaction、Methoxymethylated、methylation、aldol condensation、cyclization and deprotection steps, we try to explore the synthesis of biflavone 4’-methoxy-Ochnaflavone...