Synthesis of Iodo-substituted spiro-fused pyridine derivatives

Teke, Ecem
Spiro cyclic molecules have gained significance because of their biological activities and electronic properties. Spiro frameworks are present in importance natural products and optoelectronic materials. Moreover, due to steric strain, the presence of a spiro carbon atom induces easy rearrangements that can lead to different cyclic products. Although there are some methods to synthesize spiro compounds, the synthesis of iodo-substituted spiro-fused pyridines have not been studied. Accordingly, in this thesis, a new method for the synthesis of iodo-substituted spiro-fused pyridines have been developed via electrophilic cyclizations. After preparation of 5-alkynyl-4-(4-methoxyphenyl)pyridines, these derivatives were subjected to electrophilic cyclization in the presence of moleculer iodine and NaHCO3, which afforded iodo-substituted spiro-fused pyridines. The reaction conditions have been optimized and the limitations, scope and mechanism of these cyclizations have been studied.
Citation Formats
E. Teke, “Synthesis of Iodo-substituted spiro-fused pyridine derivatives,” M.S. - Master of Science, Middle East Technical University, 2014.