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Synthesis 1993; 1993(12): 1257-1260
DOI: 10.1055/s-1993-26038
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A Simple Synthetic Method for Tetraaza[3.3.3.3]meta- and paracyclopanes by Alkylation of N-Substituted Trifluoroacetamide

Teruo Shinmyozu* , Nobuhiko Shibakawa, Ken'ichi Sugimoto, Hiroko Sakane, Hiroyuki Takemura, Katsuya Sako, Takahiko Inazu
  • *Department of Chemistry, Faculty of Science, Kyusyu University, Hakozaki 6-10-1, Higashi-ku, Fukuoka 812, Japan
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Publication Date:
29 April 2002 (online)

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A simple and practical synthesis of the title compounds 1b and 2b is described. Alkylation of N-substituted trifluoroacetamides (5a and b) with appropriate dibromides (6 and 9) in the presence of sodium hydride in N,N-dimethylformamide at 100°C, or powdered potassium hydroxide in refluxing acetone, followed by removal of the trifluoroacetyl group and N-methylation of the resultant amines provides the desired 1b and 2b in 21 and 19 % overall yields, respectively, along with their lower and higher homologs.