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Synlett 1996; 1996(4): 353-355
DOI: 10.1055/s-1996-5438
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Novel Phthalimidine Synthesis. Mannich Condensation of o-Phthalaldehyde with Primary Amines using 1,2,3-1H-Benzotriazole and 2-Mercaptoethanol as Dual Synthetic Auxiliaries

Ichiro Takahashi* , Teruki Kawakami, Etsushi Hirano, Hiroshi Yokota, Hidehiko Kitajima
  • *Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Fukui University, Bunkyo 3-9-1, Fukui 910, Japan, (Fax) 81-776-27-8761, (E-mail) ichiro@acbio.acbio.fukui-u.ac.jp
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Publication Date:
31 December 2000 (online)

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The 1:1 condensation reactions of 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-ones) in fair to good isolated yields.

phthalimidine - Mannich condensation - dual synthetic auxiliaries