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Note | Regular issue | Vol 45, No. 6, 1997, pp.1173-1181
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7781
Thermal Rearrangement of cis-N-Alkyl-3-phenylaziridin-2-yl-phenyl Ketone Tosylhydrazones in Dimethoxyethane. Preparation of 5-Alkylamino-2-pyrazoline 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

Thermal rearrangement of cis-aziridinyl ketone tosylhydrazones (4) in refluxing dimethoxyethane produced 5-alkylamino-3,5-diphenyl-1-tosyl-2-pyrazolines (5) in good to excellent yields. The reaction of cis-1-isopropyl-3-phenyl-aziridin-2-yl phenyl ketone tosylhydrazone (4a) in refluxing chloroform in the presence of acetic acid yielded 3,5-diphenyl-1-tosyl-pyrazole (6a). Under the similar conditions, 5-isopropylamino-3,5-diphenyl-1-tosyl-2-pyrazoline (5a) was rearranged into 6a. The rearrangement from 4 to 5 was assumed to be initiated with ionic cleavage of the bond between ring nitrogen and C2 carbon.