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Paper | Special issue | Vol 93, No. 2, 2016, pp.557-571
Published online, 7th January, 2016
DOI: 10.3987/COM-15-S(T)38
Application of the Mild-Condition Phthalimidine Synthesis with Use of 1,2,3-1H-Benzotriazole and 2-Mercaptoethanol as Dual Synthetic Auxiliaries. Effective Synthesis of Phthalimidines Possessing a Variety of Substituents at 2-Position

Ichiro Takahashi,* Teruki Kawakami, Etsushi Hirano, Mako Kimino, Shigeki Kamimura, Takayuki Miwa, Takanori Tamura, Ryo Tazaki, Hidehiko Kitajima, Minoru Hatanaka, 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 1:1 condensation reaction between o-phthalaldehyde with a variety of primary amines in the presence of excess 2-mercaptoethanol and 1,2,3-1H-benzotriazole as “dual synthetic auxiliaries” in MeCN for 13 h at room temperature afford 2-substituted phthalimidines (2,3-dihydroisoindol-1-one) in fair to good isolated yields.