Study On The Visible-Light-Photocatalyzed C5-H Nitration Of 8-Aminoquinoline Amides

In this thesis,visible-light-photocatalyzed C5-H nitration of 8-aminoquinoline amides was developed.The main results obtained are as followed:1.The reaction of 8-aminoquinoline amides with Cu(NO3)2?3H2O as a nitro source was performed in DCE at room temperature under air for 10 h using K2S2O8 as an oxidant,and Acid Red 94 as the photoredox catalyst,successfully affording the target compounds in moderate to good yields.The reaction featured the simple photocatalytic system,preceeding at room temperature and easy to operate,avoiding the shortcomings of traditional heating methods.Futhermore,the photoredox catalyst Acid Red 94 is a type of organic dyes with a lower cost than transitional metal salt.2.In order to obtain the mechanistic information about thistransformation,control experiments were carried out.No desired product was observed when the benzamidesand benzoate were participated in this reaction under the standard conditions.These results showed that the formation of a chelated complex between 8-aminoquinoline and the copper salt was crucial tothe remote C-Hnitration.The addition of TEMPO to the reaction mixture resulted in inhibition of corresponding nitration products,suggesting that radical steps might be involved in this reaction.