Synthesis of a Series of Novel Chiral Aromatic Heterocyclic Macrocycles Containing L-Amino Acid and 2,5-Bisphenyl-1,3,4-triazole Subunits

Abstract

An array of novel chiral aromatic heterocyclic macrocycles, which may show potential enantiomeric recognition to variable D- and L-amino acids, were synthesized in acceptable yield. The desired macrocycles 3a–c and 4a–c were obtained via the condensation reaction of chiral diamine intermediates 2a–c with 2,5-bis(o-chloroformylphenyl)-1,3,4-triazole 5 in a presence of Et₃N in a highly diluted dichloromethane solution at room temperature.

Keywords:

• 2,5-Bisphenyl-1,3,4-triazole
• chiral macrocycles
• enantiomeric recognition