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A Convenient and Efficient Method for the Preparation of Unique Fluorophores of Lariat Naphtho‐Aza‐Crown Ethers
Author(s) -
Sharghi Hashem,
Ebrahimpourmoghaddam Sakineh
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890148
Subject(s) - chemistry , diethylenetriamine , mannich reaction , amine gas treating , phenol , yield (engineering) , phenols , solvent , acetone , organic chemistry , resorcinol , crown ether , ether , naphthalene , polymer chemistry , nuclear chemistry , ion , materials science , metallurgy , catalysis
New naphtho‐aza‐crown ethers containing different phenolic side‐arms attached through the ortho ‐position of the phenol have been prepared under solvent‐free conditions. The starting macrocyclic naphtho‐aza‐crown ether 2 was obtained by treatment of naphthalene dicarboxylic acid diester 1 with diethylenetriamine in EtOH at room temperature for two days without stirring in 77% yield ( Scheme 1 ). Phenolic ligands ( 3 – 14 ) were synthesized by the Mannich reaction of the secondary macrocyclic amine 2 with the substituted phenols using nontoxic and inexpensive CaCl 2 . This procedure was applied successfully for the synthesis of Mannich bases from simple secondary amines. The CaCl 2 powder can be reused up to three times after simple washing with dry acetone.