The Tandem Cyclization Reaction Of O-Cyanoanilines With Diaryliodonium Salts:a Modular Synthesis Of Quinazolinimine And Acridine Derivatives

Diaryliodonium salts ususlly use as a low toxic, low pollutional, and highly active reagents in the organic synthesis chemistry. Diaryliodonium salts, Ar2I+ X-have been paid much attention due to their powerful arylation even for many weak nucleophiles to synthesize valuable aromatic compounds. The recent findings demonstrated that diaryliodonium salts could be employed as C2-building blocks in organic reactions, which extended their wider application in the synthesis of arenes and hetero-arenes. During the study of synthesizing nitrogen-containing heterocycles with diaryliodonium, we find that the diaryliodonium could induce a tandem cyclization reaction. And the tandem cyclization reaction is always efficient. The o-cyanoanilines have two active functional groups, which could both react with diaryliodonium salts. During we have a study on the tandem cyclization reaction, we have found a interesting reaction, we can use the o-cyanoanilines and diaryliodonium Salts to produce two different productions by control the reaction condition.Our work is us the o-cyanoanilines and diaryliodonium Salts as the substrates. At the condition of the Cu(OTf)2 as the catalyst, DCE as the solvent, we could produce Quinazolinimine and Acridine Derivatives control the reaction condition. We have respectively produced 36 quinazolinimine derivatives and 12 acridine derivatives. The reaction possesses numerous advantages, such as the reaction condition is mild, yields is very high, and have a good reaction selectivity.This article have reported a method to produce two different products by control the condition of the reaction. At the end we have proposed the two reaction pathways, respectively. We have put attention to the electronic effect of substituents. Then we try to use the 13C NMR,1H NMR, HRMS to confirm our compounds’ structures are corrected.