Download PDF
Synthesis 1990; 1990(6): 481-483
DOI: 10.1055/s-1990-26911
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.

      >