Facilitating Students’ Review of the Chemistry of Nitrogen-Containing Heterocyclic Compounds and Their Characterization through Multistep Synthesis of Thieno[2,3-b]Pyridine Derivatives

• Hanlin Liu ^[1] ; Vladimir Zaplishnyy ^[1] ; Lana Mikhaylichenko ^[1]
  1. [1] University of Toronto

     University of Toronto

     Canadá

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 93, Nº 10, 2016, págs. 1785-1787
• Idioma: inglés
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• Resumen

  • A multistep synthesis of thieno[2,3-b]pyridine derivatives is described that is suitable for the upper-level undergraduate organic laboratory. This experiment exposes students to various hands-on experimental techniques as well as methods of product characterization such as IR and 1H NMR spectroscopy, and mass-spectrometry. It also provides an opportunity for students to review important theoretical topics such as nucleophilic substitution, tautomerization, acidity of methylene-active compounds, base-promoted alkylation, and cyclization.