Four Novel 30-Membered Imine and Amine Macrocycles Derived from Ortho-Aminophenyl Diamines

Abstract

Two novel macrocyclic tetra-imine-diphenol Schiff base (H₂L₁ and H₂L₂) were synthesized by [2 + 2] cyclocondensation of ortho-aminophenyl diamines [1,2-bis(2′-aminophenoxy)benzene (I) and 1,2-bis(2′-aminophenoxy)-4-t-butylbenzene (II)] with 2,6-diformyl-4-methylphenol. Two novel tetra-amine-diphenol macrocycles (H₂L₃ and H₂L₄) have been obtained by reduction of the imine analogs with NaBH₄ in MeOH/CHCl₃.

Keywords:

• ortho-Aminophenyl diamines
• Schiff base macrocycles
• tetra-amine-diphenol macrocycles

ACKNOWLEDGMENTS

We are grateful to the Departments of Chemistry of Bu-Ali Sina and Tarbiat Moalem Universities and to Sharif University of Technology for the support of this work.