Synthesis of Novel Indole-Based Heterocycles

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Creative organic synthesis is a cornerstone for feeding the demands of numerous research areas (such as pharmaceuticals, agrochemicals, material sciences, catalysis, photochemistry, fragrances and pigments) where novel molecular frameworks with interesting properties and topology are constantly sought. It is crucial for synthetic chemists to develop and fine-tune reaction methodologies that enable efficient and green synthesis of the desired skeletons. The indole core is a prevalent substructure in many natural products and biologically active compounds. Due to its biological importance, indole based compounds attract special attention as a building block for the development of therapeutic agents by medicinal chemists. A plethora of bioactivities surrounding the indole-core continue to be a driving force in the development of new methodology to find useful compounds and increase the heterocyle diversity. Thus, the need for development of efficient and practical syntheses of indoles bearing a variety of substitution patterns is of great significance. The objective of my research program is to explore and develop novel and efficient synthetic methodology of indole heterocycles bearing a variety of substitution patterns. The long-term goal is to use the developed methodology to enrich the heterocycle diversity around indole nucleus to find commercially useful chemicals. The proposed research program will lead to novel indole-based molecular architectures with interesting biological properties and 3-D topology. These molecules could also serve as building blocks for synthesizing compounds of desired frameworks. Particular attention will be given to incorporating green properties (such as, clean and quantitative conversion, mild conditions, catalyst recycling, atom economy, one-pot cascade reactions, and low waste production) to methodologies developed in my laboratory in order to advance their practical and commercial importance. Approximately 25-30 students (HQP) will be trained over the tenure of the grant. The training received by HQPs will better prepare them to contribute to research activities in industry, government, and university laboratories across Canada.