Accession Number:

ADA370492

Title:

Synthesis of Novel 8-Hydroxyquinoline-Containing Diaz-18-Crown-6 Ligands and Analogues.

Descriptive Note:

Technical rept.

Corporate Author:

BRIGHAM YOUNG UNIV PROVO UT DEPT OF CHEMISTRY AND BIOCHEMISTRY

Report Date:

1999-11-03

Pagination or Media Count:

5.0

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- bismethozymethyldiaza-18-crown-6 with 4-chloro-2-1 H-pyrazol-3-ylphenol gave the - NCH2N-linked bis3-5-chloro-2-hydroxypyrazol-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.

Subject Categories:

  • Inorganic Chemistry
  • Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE