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Synthesis 1990; 1990(12): 1135-1137
DOI: 10.1055/s-1990-27114
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A Facile and Convenient Synthetic Method for Fluorine-Containing Benz[c]acridines and Dihydrobenz[c]acridines from N,N-Dimethyl-1-naphthylamine

Masaru Hojo* , Ryoichi Masuda, Etsuji Okada, Takeshi Tomifuji, Naonori Imazaki
  • *Department of Industrial Chemistry, Faculty of Engineering, Kobe University, Kobe 657, Japan
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Publication Date:
02 May 2002 (online)

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Aromatic nucleophilic nitrogen-nitrogen exchange reaction of N,N-dimethyl-2, 4-bis(trifluoroacetyl)-1-naphthylamine (1) with p-substituted anilines gives the corresponding N-aryl-2,4-bis(trifluoroacetyl)-1-naphthylamines 2 in high yield. Acid-catalyzed cyclization of 2 affords selectively fluorine-containing benz[c]acridines 3 in almost quantitative yield, while the base-catalyzed cyclization gives fluorine-containing 7,12-dihydrobenz[c]acridines 4 in fair yield.