Synthesis of Novel 8-Hydroxyquinoline-Containing Diaz-18-Crown-6 Ligands and Analogues.
Abstract
Ten new analogues of 5-chloro-8-hydroxyquinolin-7-ylmethyl-and -5-chloro-8-hydroxyquinolin-2-ylmethyl-substituted diaza-18-crown-6 ethers 1 and 2, respectively (Figure 1) were synthesized via a one-pot or stepwise Mannich reaction, reductive amination, or by reacting diaza-18-crown-6 with 5,7-dichloro-2-iodomethyl-8-quinolinol in the presence of N,N-diisopropylethylamine (Schemes 1 and 2). The Mannich reaction of N,N'- bis(methozymethyl)diaza-18-crown-6 with 4-chloro-2-(1 H-pyrazol-3-yl)phenol gave the - NCH2N-linked bis(3-(5-chloro-2-hydroxy)pyrazol-1-ylmethyl)-substituted diazacrown ether (14) in a 98% yield. The reaction of bis-N,N'-methoxymethyldiaza-18-crown-6 with 2.2 equivalents of 10-hydroxybenzoquinoline gave only the monosubstituted diazacrown ether ligand (8). The yields of the new products are given in the schemes.
Document Details
- Document Type
- Technical Report
- Publication Date
- Nov 03, 1999
- Accession Number
- ADA370492
Entities
People
- Guoping Xue
- Jerald S. Bradshaw
- Krzysztof E. Krakowiak
- Ning Su
- Paul B. Savage
- Reed M. Izaft
Organizations
- Brigham Young University