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Synthesis 1989; 1989(7): 550-552
DOI: 10.1055/s-1989-27315
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Aromatic Nucleophilic Nitrogen-Nitrogen Exchange Reaction of N,N-Dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine with Amino Acid Derivatives: A Facile Synthesis of Fluorine-Containing 1H-Benzo[g]indolines and 1H-Benzo[g]indoles

Masaru Hojo* , Ryōichi Masuda, Etsuji Okada, Hiroshi Miya
  • *Department of Industrial Chemistry, Faculty of Engineering, Kobe University, Rokkodai, Nada, Kobe 657, Japan
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Publication Date:
17 September 2002 (online)

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Aromatic nucleophilic nitrogen-nitrogen exchange reaction of N,N-dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine 1 with some amino acid derivatives gives the corresponding N-[2,4-bis(trifluoroacetyl)-1-naphthyl]amino acid derivatives 2a-d in excellent yields. Basecatalyzed cyclization affords fluorine-containing 1H-benzo[g]indolines (2,3-dihydro-1H-benzo[g]indoles) 3a-d in high yields. Further conversion of 3a into 1H-benzo[g]indoles 4,5 is also described.

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