A Convenient and Efficient Method for the Preparation of Unique Fluorophores of Lariat Naphtho-Aza-Crown Ethers

✍ Scribed by Hashem Sharghi; Sakineh Ebrahimpourmoghaddam

• Book ID: 102259823
• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: German
• Weight: 191 KB
• Volume: 91
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200890148

✦ Synopsis

Abstract

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.