Studies On Silver(?)-Catalyzed Nitrogenation Of 2-arylphenylacetylene

A wide range of alkynes exist in nature and alkynes are found in various natural products,bioactive compounds and organic materials^[1].Because they can be readily converted into a variety of other functional groups,alkynes are versatile intermediates in organic synthesis^[2].In recent years,significant attention has been placed on the nitrogenation of the alkyne via carbon-carbon triple bonds?C?C?using trimethylsilyl azide?TMSN₃?as nitrogenating agent.However,in this paper,we describe both carbon atom of the alkyne are incorporated in the final phenantridine products,without the cleavage of the carbon-carbon triple bond.The main contents of the paper are as follows:1)The review of the paper is divided into three parts:?1?the progress of the research on silver-catalyzed free radical cyclization reaction of alkyne;?2?the progress of the research on nitrogenation of alkyne;?3?the progress of the research on the synthesis of phenanthridine compounds.In this paper,the silver-catalyzed nitrogenation of 2-arylphenylacetylene has been achieved.The reaction underwent hydroazidation,free radical addition and cyclization.Using the catalytic system designed in this article,we successfully synthesized twenty-six sulfonylated-substituted phenanthridine compounds and characterized their structures by ¹H-NMR,¹³C-NMR and MS,respectively.This paper provides a new method for the synthesis of 6-substituted phenanthridines by 2-arylphenylacetylene in one pot.