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Paper | Special issue | Vol 93, No. 2, 2016, pp.545-556
Published online, 7th January, 2016
DOI: 10.3987/COM-15-S(T)37
Mechanistic Aspects of the Mild-Condition Phthalimidine Synthesis with Use of 1,2,3-1H-Benzotriazole and 2-Mercaptoethanol as Dual Synthetic Auxiliaries

Ichiro Takahashi,* Teruki Kawakami, Hidehiko Kitajima, Kimio Isa, and Shinzo Hosoi

*Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Fukui University, Bunkyo, Fukui 910-8507, Japan

Abstract

The mild-condition phthalimidine synthesis based on Mannich-type condensation reaction between o-phthalaldehyde and p-toluidine was first achieved with use of 1,2,3-1H-benzotriazole (Bt-H) and 2-mercaptoethanol (MET) as dual synthetic auxiliaries. Mechanistic aspects based on reaction condition optimization exercises are described.