Synthesis of New Multibenzo Oxygen–Sulfur Donor Macrocycles Containing Lactams at Room Temperature

Abstract

Some new oxygen–sulfur, multibenzo macrocyclic ligands containing amide groups have been prepared using the macrocyclization process with the reaction of 2,2′-thiobis-[4-methyl(2-aminophenoxy)phenyl ether] as a symmetrical diamine with appropriate dicarboxylicacid dichlorides in moderate yields. This macrocyclization led to the formation of di- and tetramide macrocycles. These reactions were routinely carried out at ambient temperature in CH₂Cl₂ as solvent in high dilution without template effect conditions. It is found that sulfur the atom affects the rigidity of the macrocycles and diastereotopicity of nuclei in the ring of these series of macrocyclic compounds.

Keywords:

• Diamide
• diamine
• dicarboxylic acid dichloride
• lactam
• macrocycle

Acknowledgments

We thank the Research Council of the Tarbiat Moallem University for financial support. We wish also to thank Prof. R. Gleiter and Ms. Birgit Esser from Heidelberg, Germany, for FAB-mass analysis of macrocycle 3.