APPLICATION OF SOLID PHASE HETEROCYCLIC SYNTHESIS USING ORGANOMETALLICS

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Solid phase synthesis of heterocyclic compounds was investigated using organometallic reagents. Among them, nitrogen heteroaromatics such as indoles, pyridines were chemoselectively metalated using various organometallic reagents and it was found that mesityllithium works as a chemoselective deprotonating agent for solid phase metalation. Scope and limitation was disclosed for the solid phase deprotonation and the reactions with various electrophiles were also examined. Stabilization of the intermediary immobilized oragnometallic species was examined using spectroscopic measurements. As an application of the metalation, the combination with palladium catalyzed reactions was studied and new indole cyclizations using intramolecular palladium catalyzed coupling reaction were also developed. Approaches for high throughput synthesis were investigated using a automated synthesizer and the usefulness of the polymer supported chemistry was demonstrated.