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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

A Practical Synthesis of Macrocyclic Schiff Base Bearing Hydroxyethyl Pendants Utilizing Solubility Discrepancies

Author(s): Runlai Li*, Shu’an Li, Tian Xia, Chunwei Ji, Na Gu, Linzhe Li and Zhenming Zhang*

Volume 19, Issue 9, 2022

Published on: 24 January, 2022

Page: [719 - 724] Pages: 6

DOI: 10.2174/1570178619666211230124256

Price: $65

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.

Keywords: Macrocyclic Schiff bases, pendants, [2+2] condensation, solubility discrepancies, macrocyclic synthesis, hydroxyethyl.

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