Synthesis of Novel Isoquinolino[5,4- ab ]phenanthridine Derivatives via Pictet-Spengler Reaction

Min Chen Tsai, Pei Yu Huang, Liang Sheng Syu, Tzenge Lien Shih

Research output: Contribution to journalJournal Article peer-review

1 Scopus citations

Abstract

The reaction of 5-amino-2-[2-(dimethylamino)ethyl]-6-phenyl-1 H -benzo[ de ]isoquinoline-1,3(2 H)-dione with a series of aldehydes in acidic media (phosphoric acid, trifluoromethanesulfonic acid, and trifluoroacetic acid) is described. This key step is based on the Pictet-Spengler reaction to synthesize ten novel isoquinolino[5,4- ab ]phenanthridine derivatives. The most effective acid is phosphoric acid and optimized yields were obtained. The frameworks of target compounds are unique and have never been reported.

Original languageEnglish
Pages (from-to)1377-1382
Number of pages6
JournalSynthesis (Germany)
Volume51
Issue number6
DOIs
StatePublished - 2019
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2019 Georg Thieme Verlag. All rights reserved.

Keywords

  • Pictet-Spengler reaction
  • Suzuki-Miyaura cross-coupling reaction
  • homophthalimide
  • isoquinoline-1 3-dione
  • naphthalimide
  • phenanthridine

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