Access to cyclobutene-fused azepines through au-catalyzed cycloisomerization of stable alkyne tethered ketene N,N -acetals

Abstract

A base promoted reaction between N-protected propargyl amines and 3-bromopropiolate readily provides an array of novel stable alkyne-tethered ketene N,N-acetals in good yields. A wide range of structurally complex cyclobutene-fused azepine heterocycles are synthesized through the gold-catalyzed intramolecular cycloisomerization of ketene N,N-acetals for the first time. A plausible reaction pathway is deduced on the basis of the 1H NMR studies. © 2014 American Chemical Society.