Synthesis Of1,7-diyne Ether(amine) And Its Application In The Synthesis Of Chromene And Phenanthridine Derivatives

Allenes which contain two cumlated C=C double bones, have shown a variety of unique chemcial reactivity and selectivities in organic synthesis. In recent years, much attention has been paid to allene intermediates generated during the reaction, which could avoid of its preparation and storage but could take full advantage of its high reactivity and selectivities during the reaction.Using 2-iodoanline and 2-iodophenol as the readily starting materials, coupling with the terminal alkynes firstly, then reacted with propargyl bromide, subsequently coupling with 3-iodocyclohex-2-enone, 1,7-diyne ether and 1,7-diyne amine were prepared in moderate yields.The series of 1,7-diyne ether and 1,7-diyne amine were used to the synthesis of chromene and phenanthridine derivatives by the base-promoted isomerization. Chromene and Phenanthridine derivatives were obtained using EtOH as the solvent and Et3N as the base at 80℃in moderate yields.