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Paper | Regular issue | Vol 43, No. 8, 1996, pp.1759-1765
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7508
Anomalous Bamford-Stevens Reaction of cis-N-Alkyl-3-phenylaziridin-2-yl Phenyl Ketones. Preparation of 1,6-Dihydro-1, 2,3-triazine Derivatives

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

*Department of Applied Chemistry, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Shizuoka, Japan

Abstract

The Bamford-Stevens reaction of cis-aziridinyl ketone tosylhydrazones (1a-k) yielded 1,6-dihydro-1,2,3-triazine derivatives (3a-k) without eliminating the nitrogen molecule. The reaction was induced using a slight excess of sodium hydride (2) or sodium ethoxide. When a large amout of sodium ethoxide was used, 1-isopropylamino-3,5-dephenylpyrazole (4a) was formed from the corresponding substrate (1a).