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Paper | Regular issue | Vol 43, No. 2, 1996, pp.305-315
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7239
Novel Rearrangement of cis-N-Alkyl-3-phenylaziridin-2-yl Phenyl Ketone Tosylhydrazones with Ethlyl Ether-Boron Trifluoride. Preparation of 1,2,5,6-Tetrahydro-1,2,3-triazine Derivatives

Motonobu Morioka, Masahiko Kato, Hiroshi Yoshida, and Tsuyoshi Ogata*

*Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, Hamamatsu-shi 432, Japan

Abstract

1-Alkyl-4,6-diphenyl-1,2,5,6-tetrahydro-2-tosyl-1,2,3-triazine derivatives (8a-g, i-k) which had a new skeletal ring were obtained in moderate yield (77-49 %) by the rearrangement of cis-N-alkyl-3-phenylaziridin-2-yl phenyl ketone tosylhydrazones (3a-g, i-k) with ethyl ether-boron trifluoride (1/1) (7) in chloroform under room temperature. The starting materials (3a-l) were prepared in good yield (88-39%) by the condensation of cis-N-alkyl-3-phenylaziridin-2-yl phenyl ketones (1a-l) with tosylhydrazine (2) in chloroform in the presence of PPE (polyphosphoric acid ethyl ester) hydrolysate as a catalyst.