Synthesis of indole fused heterocyclic compounds

Kaptı, Tolga
Nitrogen containing heterocyclic compounds show wide range of biological activities so their syntheses have always been attractive area in organic chemistry. Indole derivatives, which are one of the important example of these biological active compound, are precursors to many pharmaceuticals. The aim of this research is to develop new synthetic methodologies leading to the synthesis of new derivatives of pyrimidoindole and quinoline, which have been found to show important biological activities. In this study, an indole derivative was used as a starting compound which was obtained using reaction of Fischer indole cyclization reaction. Reactive molecules such as acyl azide and isocyanate were used as key step reactants and also Curtius rearrangement reaction was used to converte acyl azide to isocyanate. Isocyanates were converted into the corresponding urethane or urea derivatives by treatment with different alcohols and amines, respectively. To reach target pyrimidoindole skeleton, these urea derivatives were used for the intramolecular cyclization. In the second part of this study, ozonolysis reaction were studied on the starting indole compound for obtaining quinoline skeleton
Citation Formats
T. Kaptı, “Synthesis of indole fused heterocyclic compounds,” M.S. - Master of Science, Middle East Technical University, 2013.