Original scientific paper

Lariat Ethers with Pendant Phenanthridine Units. Synthesis and Complexation of Na- and K-Picrate.

Sulejman Alihodžić ; Laboratory for Supramolecular and Nucleoside Chemistry, Department of Organic Chemistry and Biochemistry, Rudjer Bošković Institute, P.O.B. 1016, HR–10001, Zagreb, Croatia
Mladen Žinić ; Laboratory for Supramolecular and Nucleoside Chemistry, Department of Organic Chemistry and Biochemistry, Rudjer Bošković Institute, P.O.B. 1016, HR–10001, Zagreb, Croatia

Abstract

Lariat ethers 12 and 13 with appended phenanthridine fluorophoric units have been prepared as potential fluorescent chemosensor molecules for alkaline metal salts possessing aromatic anions. The starting 8-ethyloxycarbonylamino-6-methylphenanthridine (1) was converted via 2, 3, 6 and 7 to N-(2-tosylethyl)-derivatives 4 and 8 suitable for N-alkylations of diaza- and aza-18-crown-6. However, the alkylations failed, giving the 2-oxazolidinone derivative 5 formed by intramolecular cyclization of phenanthridine N-carbamate derivatives 4 and 8 in basic conditions. The phenanthridine derivative 10 having benzyl instead carbamate protection on 8-amino group successfully alkylated mono- and diaza-crown ethers, giving lariats 12 and 14. Subsequent removal of benzyl protection groups in acidic conditions gave lariats 13 and 15. Lariat 12 was found to form unique Na- and K-picrate complexes with the metal cation bound in the crown cavity and picrate anion intercalated between phenanthridine units.

Keywords

crown ethers; lariate ethers; phenanthridine; complexes; sodium picrate

Hrčak ID:

132300

URI

https://hrcak.srce.hr/132300

Publication date:

1.12.1999.

Visits: 857 *