2-Benzyliden-2H-thieto[3,2-b]quinoline: A new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline

Makhluf J. Haddadin, Claudia El-Nachef, Hawraa Kisserwani, Yara Chaaban, Mark J. Kurth, James C. Fettinger

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

Synthesis of the strained 2H-thieto[3,2-b]quinoline ring system is reported for the first time. Treatment of (Z)-2-benzyliden-2H-thieto[3,2-b]quinoline derivatives of this heterocycle with base, at reflux in ethanol, causes a novel rearrangement to 2-phenylthieno[3,2-b]quinolines. Indeed, the one-pot reaction of 2-aminobenzaldehydes and (Z)-2-benzylidenethietan-3-one in refluxing basic ethanol leads directly to 2-phenylthieno[3,2-b]quinolines in good yields.

Original languageEnglish (US)
Pages (from-to)6687-6689
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number51
DOIs
StatePublished - Dec 22 2010

Keywords

  • Base-mediated rearrangement
  • Friedländer reaction
  • Thieno[3,2-b]quinoline
  • Thieto[3,2-b]quinoline

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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    Haddadin, M. J., El-Nachef, C., Kisserwani, H., Chaaban, Y., Kurth, M. J., & Fettinger, J. C. (2010). 2-Benzyliden-2H-thieto[3,2-b]quinoline: A new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline. Tetrahedron Letters, 51(51), 6687-6689. https://doi.org/10.1016/j.tetlet.2010.10.039