Synthesis 1990; 1990(6): 481-483
DOI: 10.1055/s-1990-26911
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A Convenient and Facile Synthesis of Fluorine-Containing 1H-,2H-Benz[g]indazoles and Naphthisoxazoles by Aromatic Nucleophilic N-N Exchange Reaction of N,N-Dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine with Hydrazines and Hydroxylamine

Masaru Hojo* , Ryōichi Masuda, Etsuji Okada
  • *Department of Industrial Chemistry, Faculty of Engineering, Kobe University, Kobe 657, Japan
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Publication History

Publication Date:
17 September 2002 (online)

N,N-Dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine (1) undergoes an aromatic nucleophilic N-N exchange reaction with hydrazines followed by cyclocondensation to afford the corresponding fluorine-containing 1H- and 2H-benz[g]indazoles 2, 3 in excellent yields. This reaction can be extended to the synthesis of 5-trifluoroacetyl-3-trifluoromethylnaphth[1,2-c]isoxazole (5) using hydroxylamine.