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Communication | Special issue | Vol 79, No. 1, 2009, pp.395-401
Published online, 20th November, 2008
DOI: 10.3987/COM-08-S(D)46
An Efficient and Selective Synthetic Method for Fluorine-Containing Benzo[h]quinolines and 1H-Benzo[h]quinolin-2-ones from N-Propargyl-2,4-bis(trifluoroacetyl)-1-naphthylamine

Etsuji Okada,* Dai Shibata, Norikado Tsukushi, Masato Dohura, and Maurice Médebielle

*Department of Chemical Science and Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan


N-Propargyl-2,4-bis(trifluoroacetyl)-1-naphthylamine (3) underwent nitrogen-containing heterocyclic ring-formation reactions with active methylene compounds such as dialkyl malonates in the presence of sodium alkoxides. This ring closure reactions were very 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.