Synthesis and characterization of a new biscrown compound formed from diamide crown ligands

Abstract

Diamide macrocycles are valuable intermediates for the synthesis of aza crown compounds as well as more complex ligands such as various cryptands and cryptohemispherands. Their versatility in many fields, such as chemistry, biochemistry, biophysics, biology, agriculture, industry, medicine, molecular diagnosis, sensors, and phase transfer catalysts, has captured the interest of many. In the first step, 2,4-dimethylphenol was converted to the oxythiobis [4,6-dimethylphenyl] (1) by reacting with thionyl chloride. Then, oxythiobis [4,6-dimethyl phenoxy methyl acetate] (2) was obtained from the reaction of oxythiobis [4,6-dimethylphenyl] (1) with methyl chloroacetate. The reaction of oxythiobis [4,6-dimethyl phenoxy methyl acetate] (2), with a diethylenetriamine, produced the tri-aza dibenzo sulfoxide macrocyclic diamides (3). Bis [tri-aza dibenzo sulfoxide macrocyclic diamides] (4) was prepared from the reaction of tri-aza dibenzo sulfoxide macrocyclic diamides (3) with a suitable active compound such as diacid or dichloride. The structures of all synthesized compounds were characterized by ¹H NMR, ¹³C NMR, FT-IR, and mass spectra.