Facile titanium(IV) chloride and TBD-mediated synthesis of N-aryl-substituted azacycles from arylhydrazines

Abstract

A novel practical synthesis of N-aryl-substituted azacycles from arylhydrazines is described. In this method, target azacycles were prepared via reaction of arylhydrazines with cyclic ethers in the presence of both titanium(IV) chloride and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as key combined reagents. Using this synthetic protocol with titanium(IV) chloride and TBD, reaction of arylhydrazines with cyclic ethers successfully afforded various N-aryl-substituted azacycles in high yield. This facile synthetic method using arylhydrazines will be a promising guide for the synthesis of azacycles from arylhydrazines.