Mizuki Hatakenaka

A FACILE SYNTHESIS OF FLUORINE-CONTAINING 1,7-PHENANTHROLINES BY THE CYCLIZATION OF N-PROPARGYL-6,8-BIS(TRIFLUOROACETYL)QUINOLIN-5-AMINE WITH VARIOUS ACTIVE METHYLENE COMPOUNDS

The reaction of N-propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine (1) with various active methylene compounds gave the novel fluorine-containing 1,7-phenanthroline derivatives (3). Furthermore, changing the electron-withdrawing groups on active methylene compounds induced interesting alternation of the reaction site wherein the enolate anions attack first and led to construction of the different nitrogen-containing heterocyclic systems, 1,7-phenanthrolinone (4) and 1,4-dihydro-1,7-phenanthroline (5).