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Synthesis 1992; 1992(6): 536-538
DOI: 10.1055/s-1992-26156
short paper
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Facile and Convenient Synthetic Methods for Fluorine-Containing Benzo[c]thioxanthenes and Benzo[c]xanthenes from N,N-Dimethyl-1-naphthylamine

Etsuji Okada* , Ryoichi Masuda, Masaru Hojo, Naonori Imazaki, Koichi Takahashi
  • *Department of Industrial Chemistry, Faculty of Engineering, Kobe University, Kobe 657, Japan
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Publication Date:
17 September 2002 (online)

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Aromatic nucleophilic N-S and N-O exchange reactions of N,N-dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine (1) with thiophenols and phenols gave the corresponding 2,4-bis(trifluoroacetyl)-1-(arylthio)naphthalenes 2 and -1-(4-methoxyphenoxy)naphthalene (5) in moderate to excellent yields. Acid-catalyzed cyclization reactions of 2 and 5 afforded fluorine-containing 7H-benzo[c]thioxanthenes 3,4 and 7H-benzo[c]xanthenes 6,7, respectively, in high yields.