1219604-19-9Relevant academic research and scientific papers
A concise synthesis of fluorine-containing benzo[h]quinolines and benzo[h]quinolones by selective pyridine and pyridinone rings formation reactions of N-propargyl-2,4-bis(trifluoroacetyl)-l-naphthylamine with various active methylene compounds
Okada, Etsuji,Shibata, Dai,Tsukushi, Norikado,Dohura, Masato,Ota, Norio,Adachi, Satoru,Medebielle, Maurice
experimental part, p. 357 - 370 (2010/09/05)
N-Propargyl-2,4-bis(trifluoroacetyl)-l-naphthylamine (3) underwent nitrogen-containing heterocyclic ring-formation reactions with a variety of active methylene compounds in the presence of sodium alkoxides. This annulation reactions with dialkyl malonates were highly dependent on reaction temperature to give selectively the corresponding fluorine-containing benzo[h]quinolines (5) at high temperature and 1H-benzo[h]quinolin-2-ones (7 and 8) at low temperature. Furthermore, changing the electron-withdrawing groups of active methylene compounds led to alternation of the reactive site wherein the reagents attack first and to the formation of the different nitrogen-containing heterocyclic systems, pyridine (9), dihydropyridine (11 and 13) and pyridone (12).
