Synthesis of Bis-8-Hydroxyquinoline-Armed Diazatrithia-15-Crown-5 and Diazatrithia-16-Crown-5 Ligands
Abstract
The synthesis of a series of diazatrithia-15-crown-5 and diazatrithia-16- crown-5 ligands containing two 8-hydroxyquinoline side arms are reported. The ligands were prepared by a two-step process. First, diazatrithiacrown ethers 11 and 12 were prepared by treating bis(alpha-chloroamide) 5 with various dimercaptans followed by reduction using a boron-THF complex. Hydroxymethyl-substituted macrocycle 12 was rearranged to hydroxy-substituted diazatrithia-16-crown-5 in refluxing aqueous HCl. Macrocyclic diamines 11-13 were converted to either 5-chloro-8-hydroxyquinolin-7-ylmethyl-substituted diazatrithiacrown ethers 14-16 by a Mannich aminomethylation reaction or to 8- hydroxyquinolin-2-ylmethyl-substituted diazatrithiacrown ethers 17-19 by reductive amination using 8-hydroxyquinoline-2-carboxaldehyde.
Document Details
- Document Type
- Technical Report
- Publication Date
- Apr 17, 2001
- Accession Number
- ADA389138
Entities
People
- Jerald S. Bradshaw
- Krzysztof E. Krakowiak
- Paul B. Savage
- R. T. Bronson
- Reed Izatt
Organizations
- Brigham Young University