TBAF-Catalyzed Cascade Synthesis Of 1H-[1,2,3] Triazolo [4,5-c] Quinoline Derivatives

Trizole compounds are an important class of heterocyclic compounds with biologically activity.Recent years,it has been discovered that trizole-fused heterocyclic compounds have the unique effects in medicinal chemistry,materials chemistry,biochemistry and others.Therefore,reserachers pay more attention to constructing trizole-fused heterocyclic compounds.In 1930s,1,2,3-triazole compounds were originally synthesized.To date,synthetic chemists have successfully developed a variety of methodologies of preparation of triazole compounds,such as Cu?Ag?-catalyzed azide-alkyne cycloaddition?Cu AAC,Ag AAC?,etc.Based on these methodologies of trizole syntheses,researchers have developed more methods to synthesize trizole-fused heterocyclic compounds.In this thesis,we explored a TBAF-catalyzed cascade reaction between?-?2-aminophenyl?-?,?-ynones and TMSN₃.With the newly developed method,various of 1H-[1,2,3]triazlol[4,5-c]quinolines were synthesized.The detailed research was as followes.A new method of synthesizing of 1,2,3-trizolequinoline compounds has been developed based on the azide-alkyne dipolar cycloaddition.The reacton used?-?2-aminophenyl?-?,?-ynones as substrates,1.1 eq.of TMSN₃as azide source,5.0mol%TBAF as the catalyst.Then the mixture reacted in 30 ^oC DMF solution for 8 h,and the resulted trizole-fused quinoline derivatives were obtained as the cascade reaction products.Finally 33 functionalized 1H-[1,2,3]triazolo[4,5-c]quinolines were successfully synthesized via this cascade reaction,and the yields of most products ranged from 73%to 95%.Among those 33 compounds,4-alkyl-1H-[1,2,3]triazolo[4,5-c]quinolines were unreported.Compared to the leterature methods,our newly developed metal-free catalyzed methodology possessed the characteristics of the wider substrate ranges,the milder reaction conditions,the easier operation and the more safety.It belived that the new method can provide an important reference value for the future research.