Title:A Practical Synthesis of Macrocyclic Schiff Base Bearing Hydroxyethyl
Pendants Utilizing Solubility Discrepancies
Volume: 19
Issue: 9
Author(s): Runlai Li*, Shu’an Li, Tian Xia, Chunwei Ji, Na Gu, Linzhe Li and Zhenming Zhang*
Affiliation:
- College of Polymer Science and Engineering, Sichuan University, Chengdu, China
- School of Chemical Engineering,
Jiangsu Ocean University, Lianyungang, China
Keywords:
Macrocyclic Schiff bases, pendants, [2+2] condensation, solubility discrepancies, macrocyclic synthesis, hydroxyethyl.
Abstract: Six macrocyclic Schiff bases bearing hydroxyethyl pendants have been synthesized in high
yields via [2 + 2] condensation between the rigid dialdehydes and 2-[bis(2-aminoethyl)amino]ethanol
or 1-[bis(2-aminoethyl)amino]-2-propanol at 0°C for 12 hours in the CH3CN/H2O mixture. Solubility
discrepancies between macrocyclic products and raw materials in selected solvents enable a facile separation
and high yields, avoiding any intractable chromatographic purification. This straightforward
synthetic protocol provides a relatively facile resolution with potential widespread applications for the
synthesis of Schiff bases.